Key West is home to the southernmost point in the United States, and it’s a popular vacation destination for those looking to enjoy the island’s many draws. Because this island is so small, it can be hard to find affordable and unique accommodation. Here is a list of different Vrbos in Key West, Florida. There are different amenities and features for all budgets, so there is something unique for every traveler!
Popular picks in Key West
Beach bummers can spend some time on Smathers Beach, which attracts a lot of visitors during spring. It’s the largest public beach in the city and has several amenities such as Jet ski rentals, a beach volleyball net, and restrooms.
Families visiting with kids can take their little ones to Key West Aquarium to explore the rich marine life of this city. The aquarium also offers a Touch Tank Tuck-In Tour where the guide will help you interact with Sea stars, sea cucumbers, and other animals.
Take a guided tour to explore the Hemingway Home and Museum where you can also spot the six-toed cats!
We handpicked these listings carefully, considering (wherever possible) Superhost status, recent guest reviews, location, accommodation type, prices, availability of dates, decor, and amenities. The image galleries get refreshed with the latest updates regularly. They were last updated on October 20, 2025.
1. Cozy room rental with a private pool (from USD 273)
Take your special one on a romantic getaway to this cozy room rental located just a few minutes from the beach. This open-plan living space has a queen-size bed, one full bath, and a compact kitchenette with basic tools and appliances to easily prepare delicious meals. There is also a table for two across your bed and a flat-screen TV for your entertainment.
One thing that you will love about this place is the private pool that you can enjoy during your stay. There are also some sun loungers beside where you can relax and get tanned.
Key West, Florida, United States
287 meters (0.2 ft) from The Hemingway Home and Museum
Top guest reviews
Host:
ken was a great hostken was very gracious owner and helpful throughout2 bikes ken is an excellent host and a great communicatorthe owner was responsive and accommodating and the property was in a great locationLocation:
loved the location of this propertygreat rental in a great locationperfect location and size especially as we were always out and aboutCleanliness:
the room is very clean and has everything you needthe room was clean and ready when we arrivedthe place was clean and we could walk to our favorite spotsthe room was clean and not too far from the best places in key westRead more reviewsAmenities & Room:
it would have been perfect if the wifi was stronger at the poolyou do need to bring your own coffee pool is good for a dip rather than a swimken has thought of everything: beach chairs pool towels umbrellas in case it rains and our favorite
2. Pet-friendly studio rental with a porch (from USD 319)
Pack your bags and head to this charming studio in Key West to enjoy a sunny getaway. This living space is ideally located close to the beach restaurants, shops, and vibrant nightlife. It houses one king-size bed that sleeps two guests comfortably, a seating area that can also be used for dining, and a kitchen that is complete with modern appliances for you to make delectable meals.
There is also a covered porch with a table for two where you can have morning coffee together or grab some drinks at night. This property allows pets for a fee of 90 USD, so your furry pals can tag along.
Key West, Florida, United States
248 meters (0.2 ft) from The Hemingway Home and Museum
Top guest reviews
Host:
really all you need Decorated cute and close to many things including Duval St (very close)The Simonton Studio was absolutely perfect for usProperty manager was very easy to communicate with and very helpfulWalk to Duval Street and all it has to offer Definitely will be backWe stayed in Simonton Studio for our honeymoon and absolutely loved itLocation:
But the LOCATION was perfect Walking distance to just about everythingThe location is great for walking or biking everywhere plus is on same street as free bus loop around town Also went to several amazing restaurants in the immediate area for dinnerit did not disappoint Lots to do just walking/biking distance from property- Pam provided tons of info too which was so greatThe bikes were a huge plus You could walk or bike anywhereThis was our first time in Key West and this location was perfect and central to everythingRead more reviewsAmenities & Room:
The bed was comfortable and the place was just the right sizePam was easy to contact and provided great advice on places to see and things to doWe brought stuff to cook for some meals and used the kitchen for most breakfasts so we could splurge on lunches and dinnersThis cute little place had everything anyone would need while vacationing in Key WestThis studio unit is very well appointed with lovely king bed nice bathroom and has fully equipped kitchen
3. Charming retreat with a plunge pool
This charming home is your gateway to a relaxing getaway in the Keys. It’s great for families or small groups of friends looking for a comfy place to stay close to some major attractions. The renowned Duval Street, for instance, is just within walking distance from the property, and it’s where you can find some of the best shopping, dining, and entertainment spots in the region.
Puerta Coralina, as the property is called, is big enough to accommodate a group of up to six. Interior areas include two bedrooms, a living area, three full baths, a dining area, and a kitchen—all fully furnished and equipped for guest comfort and convenience. The outdoor areas, on the other hand, include a beautiful front porch and a fenced backyard with a furnished deck and a plunge pool.
Key West, Florida, United States
851 meters (0.6 ft) from The Hemingway Home and Museum
Top guest reviews
Host:
the property manager was responsive quickly to our needsLocation:
centrally located in key west and in easy walking distance of all our favorite spotsit is in a great location if you plan on exploring key westlove this place super quiet neighborhood house is very comfortablewonder property location and manager was greatCleanliness:
great location very clean and plenty of roomRead more reviewsAmenities & Room:
pool was warm which was perfect for cooler weather great lounge chairs upstairs and on the back porchand the back deck and pool were wonderful to return togreat tvs and wifi to enjoy the olympics when we weren’t out and aboutwe enjoyed its outdoor areas too including the pool patio front porch and upstairs deck
4. Cozy abode with views of Truman Waterfront Park (from USD 578)
Perfect for couples or small groups of friends looking to have a relaxing vacation, this fully furnished home is a comfortable accommodation for Key West visitors. This rental features a private balcony that provides a stunning view of Truman Waterfront Park. It can comfortably sleep up to four people via its two bright and spacious bedrooms. The kitchen comes with all the essentials to ensure easy food preparation.
Its location is also great as you’re a short stroll away from Duval Street, the world-famous commercial area where you can find lots of dining, shopping, and entertainment hubs. Fort Zachary Taylor Historic State Park Beach is also just a few minutes away by foot or bike, providing easy access to beautiful sceneries and lots of outdoor recreation.
Key West, Florida, United States
516 meters (0.4 ft) from The Hemingway Home and Museum
Top guest reviews
Host:
We were super close to Duval street with all the good attractionswas very easy to help and answered any questions we had One suggestion--move the bathroom mirror down some It works for tall people but not for us petite onesThe pool is was very nice and refreshingEveryone we talked to in the community was very friendlyHighly recommend this rental Unit was very clean well stockedLocation:
It is within a few blocks of Duval Street where a lot of restaurants shopping and bars areYou can walk to shops restaurants and of course the barsVery close walk to everything while still far enough for peace and quietnessthere was a playground 3 min away and Duval street is only a few blocks awayCondo is close to everthing we walked 95 percent of the timeCleanliness:
It was decorated very nicely and very comfortableThe house was very nicely decorated and included everything we neededThe common pool was heated in Dec which was greatIt is very comfortable and cleanlocation is great rental is clean and comfortable and enjoyed the poolRead more reviewsAmenities & Room:
the bedrooms had mirror sliding doorsThe kitchen had everything we neededWe did take Lyft one night for our anniversary because it was so hot and humidThe plants and flowers in the courtyard are beautiful and makes you feel like you are secludedCondo was immaculate Washer and Dryer in condo and easy to use Fastest Wifi
5. Lovely paradise with a private pool (from 880 USD)
This lovely home is named after Ernest Hemmingway’s fishing boat “Pilar,” and it truly is a secret paradise. With three bedrooms and three bathrooms, it’s great for families and large groups. The living room has wide doors opening to the beautifully decorated backyard. There is a private pool, hammock, and outdoor seating perfect for entertaining guests. Though located in a quiet gated community, this house is within walking distance of Duval Street and other attractions.
Pilar's Secret
Price: from 880 USD
Number of Guests: 8
6. Colorful oasis with a lazy river pool (from USD 400)
This home is picturesque Key West style, and its bright colors are perfect for a happy vacation in this island paradise! This house even has its own heated lazy river pool for relaxing! The Old Town Key West enchanting garden home is located in one of the last remaining authentic Old Key West neighborhoods, and it’s walking distance from the Hemmingway House and Duval Street. Live like a local in this charming Key West vacation rental.
134 meters (440.4 ft) from The Hemingway Home and MuseumAccommodates: 4
Minimum Nights: 28
Refund Policy : 100% refund if you cancel at least 60 days before check-in.
Top guest reviews
Host:
susan is a super hostonce you meet your host susan you will fall in love with hershe is very accommodating quick to respond and simply a delight to work withwe quickly fell in love with john's bungalow and the owners (susan and bruce)we can't say enough about the owners susan and bruce who now are dear friends of oursLocation:
the location is fantasticthe property is centrally located within walking distance of all of old town restaurants and entertainmenti love this spot great things to walk / ride bikes to nearbythis is a wonderful home located on a quiet street near all the excitement of key westit was close to many attractions and restaurants yet very quite for some down timeRead more reviewsAmenities & Room:
what a delightful bungalow full of old world charm but with modern plumbing and wifi and comfy new bedsat night the lit pool was relaxing and serene
7. Stylish hideaway with a backyard (from USD 150)
This Old Key West style conch house has shining reviews and promises to be the perfect getaway location. With a stunning backyard featuring a large private pool, this house is a bargain find. Located only a block from Duval Street and within walking distance of the Hemmingway House, it would be hard to find a better place to stay on the island.
Key West, FL, US
134 meters (440.4 ft) from The Hemingway Home and MuseumTop guest reviews
Host:
owner was very helpfulthe owners and neighbors greeted us and made us feel so welcomethe property is one of a kind and sheryl is great to work withsheryl was extremely helpful and easy to work withLocation:
the neighborhood is very quiet and easy walking distance from duval stit is in the best location and has everything you need for the perfect key west locationgreat location and perfect for a groupthe location is one of the best and easy walking to duval and many great resturantsthe place is a little piece of paradise inside of paradiseCleanliness:
the house is clean the pool is beautifulthe inside is quaint and clean the pool is absolutely fabulous and the rooms are privatetree tops is adorable clean exactly as pictured and decorated with local art workRead more reviewsAmenities & Room:
the place was great with a very private pool area in the rear
8. Unique houseboat best for couples (from 180 USD)
There are perks to vacationing on a small island, like being able to stay on a one of a kind houseboat. The Stock Island Marina houseboat is a one bedroom one bath condo, perfect for couples or small families looking for a unique way to stay on Key West. There is also an on-site restaurant and a complimentary shuttle service to downtown available for all guests.
Stock Island Marina houseboat
Price: from 180 USD
Number of Guests: 2
9. Well-located haven with oceanfront views
In case you wish to escape from the busyness of Key West, Oceana Vista offers you a reprieve from the comfort of Bay Point. Bay Point is a short 10 miles (16 km) north of Key West and offers peaceful island life. This Oceana Vista rental allows you your own slice of paradise, with 1.5 acres (0.6 hectares) of beachfront views.
Oceana Vista
Price: Depends on dates
Number of Guests: 10
10. Victorian condo with city views (from 180 USD)
Located in a turn of the century Victorian Condo dating back to 1868, this condo in the heart of Old Town Key West is an amazing find. With the ability to sleep four, enjoy the luxury of being close to everything. This condo also has a beautiful wrap around outdoor porch for quiet nights overlooking the city.
The Coral Condo
Price: from 180 USD
Number of Guests: 4
11. Deluxe sanctuary with a pool and a waterfall (from USD 1151)
This vacation rental is the epitome of Key West living. Tucked away in a quiet neighborhood not too far from the busy Duval Street, this home promises an authentic local experience. The living room has a beautiful view of the outdoor space, complete with a waterfall into the pool and an outdoor shower. Experience Key West as a local in the Southard Comfort.
1.14 km (0.8 mi) from The Hemingway Home and MuseumAccommodates: 6
Minimum Nights: 2
Refund Policy : 100% refund if you cancel at least 61 days before check-in.
Top guest reviews
Host:
we met the owner who was so friendly and accomodatingrating details:the property manager was very helpfulrating details:the property manager was very helpfulrating details:the property manager was very helpfulthey were very helpful with checking in and making sure we were ok over our stayRead more reviewsLocation:
location was superb as welleasy access to the free duval loop bus was a plusplenty of room for six adults and the location made for an easy walk to duval streetthe house was in a good location and was as picturedperfect location and very quiet and relaxing after being in main section of town
12. Top-floor condo with ocean views (from USD 560)
This spectacular penthouse condo, also known as Paradise Found, sits on the topmost floor of a residential building. It’s newly renovated and can comfortably accommodate up to six guests! Enjoy the spacious and comfortable bedrooms at this flamingo-colored condo, which is just a few steps from the waves and fine sands of Smathers Beach. Paradise Found’s close proximity to all that Key West has to offer makes it one of the most sought-after rentals in the area. Book your stay now.
Key West, Florida, United States
2.38 km (1.5 mi) from The Hemingway Home and Museum
Top guest reviews
Host:
a site map would be very helpfulLocation:
just gorgeous comfy well maintained and the perfect locationthe location view pool and property maintenance and security are greatCleanliness:
condo was spacious and cleanclean up to date and safecondo was very clean with everything you need for an enjoyable vacationlocation was great condo clean and quietpool is amazing hot tub was always clean and working properlyRead more reviewsAmenities & Room:
nice view of ocean and pool from large balconythe wall unit in the living room was our favoritethe pool and hot tub are amazingour family loved the condo the pool was beautiful and the grounds of the property were gorgeous
13. The Conch Farmhouse (from USD 389)
If you’re looking for style and a great location, look no further than this recently renovated Conch Farmhouse vacation rental in Key West, FL. This house has two beds and one bath and is only a two-minute bike ride from the beach! In addition, this Key West vacation home rental is centrally located near Duval Street and some of the best attractions, so you don’t have to worry about driving!
431 meters (0.3 ft) from The Hemingway Home and MuseumAccommodates: 4
Minimum Nights: 7
Refund Policy : 100% refund if you cancel at least 60 days before check-in.
Top guest reviews
Host:
the owner was wonderful with timely responses to a few questions we hadthe owner was so accessible and helpfulthe owner did a fantastic job with communication and directions for parking etcLocation:
awsome condo in a great locationvery beautiful condo in a great locationthe location was perfect within walking distance to duval restaurants “ftfirst the location was the best - convenient to old town and the amphitheatereverything one needs close to duval and interesting attractions but insulated from noise and trafficCleanliness:
the place was clean and modernthe place was very clean and organizedlocation was great condo and grounds were very clean and quietproperty is attractive very clean well supplied and conveniently locatedthe home was immaculately clean very inviting and relaxingRead more reviewsAmenities & Room:
also the ceiling fan in the four poster bedroom is off balance and makes noise when turned onwe had to choose to omit the fan and sleep in an 80 degree roomfabulous location clean and modern fully equipped from kitchen gear to beach chairscharming very much so not practical when you would like bathroom privacy
14. Beautiful tropical house in Casa Cay West (from USD 687)
This stunning home away from home is located in a newly built gated estate near all the highlights that Key West has to offer. The home has been completely remodeled and features three spacious bedrooms that can sleep up to eight guests. On the ground floor, you will find the living area and dining room which leads to the open kitchen that boasts oak cabinets. From the second floor, you will get views of the landscaped garden and outdoor swimming pool with a tropical feel to it.
Key West, Florida, United States
6.76 km (4.2 mi) from The Hemingway Home and Museum
Top guest reviews
Host:
Judy and her family very welcoming and helpful with anything neededJudy was a great hostJudy was wonderful to work with and made sure check-in and out was easy for usanswered all of our questions and was always just a text awayowner went over and retrievedthe ring great helpLocation:
We got carry outs from pizza place and bakery that were across the streetjet skiing and swimming at the beach during the day Returning to relax at the pool play cards and nap in the late afternoonIt was a lovely place with lots of roomThe location was close to everything you would want and an easy entrance and exitNice property with no surprises Lost power one day for a short time - no big dealCleanliness:
and it was so incredibly cleanClose to Duval clean and adorable housenew in perfect condition Clean and well furnishedRead more reviewsAmenities & Room:
The owners have anticipated every need and equipped the condo accordinglyThere was plenty of space to accommodate 3 couplesThere was plenty of room for 3 couples with outdoor space to enjoy morning coffee3 couple went to Key West to celebrate a 50th birthdayWould have been more convenient if one of the rooms had two twin beds instead of a king bed Generally liked the place and would recommend to others - Thanks
15. Stylish studio in a central location (from USD 385)
This strategically located home is near all the action in the area. This studio is great for solo travelers and couples looking to live like a local while enjoying all the highlights of Key West. There is a queen-size bed, kitchenette, a small breakfast table for two people, and a separate bathroom. You will be one block away from Duval and downstairs there is a Duffy’s and Pisces restaurant.
Key West, Florida, United States
278 meters (0.2 ft) from The Hemingway Home and Museum
Top guest reviews
Host:
Eric was very quick to respond with any questions Very close to duval and other great restaurants bars and shops I would highly recommend and will definitely be backWe contacted the property manager about the ac-Concierge service was also very helpful and booked us some great dinnersWe came during the week and have no problem finding parkingThe rental agency was greatLocation:
Cosy and folly equiped Perfectly located at one street from Duval streetIf you are looking for a great location and price - this is it Takes only a few minutes to walk to Duval and Mallory Squarebut that seems to be the city in generalbut it was not ideait was just a little bit of a bummer for usCleanliness:
It was very clean and absolutely adorableIt was clean and had everything we neededIt looks identical to the picture and was extremely cleantools- plenty of pots and pans and plates and so forthProperty was clean centrally located and had everything we needed for a happy honeymoonRead more reviewsAmenities & Room:
remove the table & benchThe air handler is in the closet - which is right next to the bedNo place to sit and watch tv comfortably without laying in the bedAlso the AC has no control over the fan speedand there is nothing that could be done to improve
16. Lovely unit with a shared pool (from USD 482)
Spend your vacation days in one of the units of Shipyard Condominiums. Only two blocks from Duval Street and the major Old Town Key West attractions, the property never runs out of nearby things to do when you’re exploring the district. Even the beach is within walking distance, so get your swimwear ready.
The unit has a cozy living room with comfy seating and large flat-screen TV so you can watch a blockbuster film in style. The private bedroom is equally comfortable with its snug bed and own flat-screen TV. Do you prefer homecooked meals on most days of your vacation? The galley-type kitchen is sure to be a dependable corner for that as it is equipped with essentials. Your booking also provides you access to a shared pool and an off-street parking space.
Key West, Florida, United States
452 meters (0.3 ft) from The Hemingway Home and Museum
Top guest reviews
Host:
rating details: the property manager was more than helpfulLocation:
enjoyed the location and ability to walk everywherewe really enjoyed being close to everythinglovely condo in a perfect location with everything we needed plus beautiful wood cabinetrywe love the location to restaurants duval and our other favorite placesi was very happy with the locationRead more reviewsCleanliness:
unit could use a deep cleannice apartment clean unit quietthe unit itself was very clean well furnished and very quietthe apartment was clean and furnished with everything we neededthe condo was perfect---clean comfortable stylish and has everything you need
17. Vibrant vacation home for four (from USD 455)
You’ll definitely want to explore the locality when you take refuge in this condo unit located two blocks from the hotspots in Old Town Key West and Duval Street. Take a day out and stroll around shops and museums then taste the local cuisine in the great restaurants. You can also embark on the nearby beach and soak up the sun.
Stepping into the place, you’ll be welcomed by a gorgeous deck perfect for hanging out or alfresco dining. Indoors, the vibrant living room looks cozy with its plush sofa and a flat-screen TV. Free wifi is on-hand to keep your devices efficient. It also highlights a well-equipped kitchen for your skillful cooking and two comfy bedrooms for recharging overnight. Those who plan to rent for at least 28 days can be allowed to stay with their pets.
Key West, Florida, United States
479 meters (0.3 ft) from The Hemingway Home and Museum
Top guest reviews
Location:
such a pretty area and so quiet despite being so close to everythinggreat location quiet clean with a nice poolRead more reviewsCleanliness:
the condo was clean and looks like the decor was recently updated
18. Oceanfront penthouse with a patio (from USD 1342)
Boasting of a wonderful uninterrupted view of the gulf and the docked cruise ship, featuring luxurious and elegant interior design and modern pieces of furniture and appliances, Gulfside Vistas is a stylish and relaxing place to stay in Truman Annex. This Vrbo accommodation rental houses two cozy bedrooms with spacious wardrobes and three lovely private bathrooms, ideal for six people. Aside from that, the lounge area is so relaxing that you would just want to lie all day. There is also a modern and fully equipped kitchen and a dining area in a mini bar type setting. A patio is right outside the penthouse where you can have quality time in and sip cocktails as you watch the beautiful sunset.
Key West, Florida, United States
830 meters (0.6 ft) from The Hemingway Home and Museum
Top guest reviews
Host:
He was also there to help with an easy departureHe was always quick to respond to texted messages regarding questions and needs while at the propertyhe met us upon arrival to greetrep met us at the property and was great Excellent recommendations for foodthe contact person is greatLocation:
Last Key Realty provided SUPERIOR customer serviceTucked inside Truman Annex in a gated community sits this amazing vacation condoViews are magnificent from every room in the condo Close to Duval and Mallory Square for nightlife but peaceful and quiet within the complex Close to Fort Zachary for swimming every day in the...The property and location felt posh - not what we usually rent Shel from Last Key RealtyClose proximity to restaurants and attractions but the neighborhood (Truman Annex) is quietCleanliness:
Pool clean and very quiet pool areaThe property was clean and well appointedI can't say enough about Key WestProperty was clean and close to walking distanc to attractions and main strip- Duval StreetRead more reviewsAmenities & Room:
The condo is in need of repairsThere are two bedrooms one with twin beds and each bedroom has its own bathroom (the one for the kids room is in the hall right outside the bedroom door)The concierge service was helpful SamThe kitchen was well stocked in dishes pansThere is also another powder room and a laundry room
19. Fabulous stay in a gated community (from USD 523)
Situated in a prestigious gated community in Key West, nesting in the Foundry, this stylish Vrbo accommodation will make your Truman Annex vacation more lovely and delightful. Its location is ideal for tourists as it is proximate to the popular Duval Street, Mallory Square, and other city destinations. It can accommodate up to six guests, featuring two lovely bedrooms and three private bathrooms. The furnishing is very cool and airy which makes it more relaxing for the guests. It showcases a high ceiling that makes the place well lit and ventilated. Plus, the lounge area makes you feel at home. Also, included in this accommodation is a fully equipped kitchen and a spacious dining area.
Key West, Florida, United States
758 meters (0.5 ft) from The Hemingway Home and Museum
Top guest reviews
Host:
He was there to get us settled in and show us where everything was stored even gaveVery helpful friendly and quick to respond when we had any questions or concernsThey were super responsive to any issues and their Concierge ServiceThe concierge service helped us find the best day trips and were there for any and all questionsHe helped us with picking the best places to eat and visitLocation:
Truman Annex was within walking/biking distance to everythingThe instant we walked into the propertyIt's in a quite community but a stone's throw away from Duval Street and the wharf areaIt really has the Key West feel There is a note on the thermostat to not set it below 70The property had everything we needed making it convenient for families that travel from afarCleanliness:
The washer and dryer was used often it eliminated over packingVery clean nice and close to everythingThe property was clean and well maintained Just about everything we needed was available for our use:Villa Bahama was well appointed clean and a beautiful town homeRead more reviewsAmenities & Room:
the bed in the master bedroom was a sleeper's bedplenty of towels pillows blankets beach towels and chairs and a well equipped kitchenI also wish there were overhead lights in the bedroomsHe likes it cold at nightThe only thing we missed was music by the pool
20. Charming Vrbo accommodation (from USD 589)
This charming fully furnished accommodation in Truman Annex is the perfect spot for tourists as it is close to the city’s landmarks, restaurants, cafes, retail shops, and other tourist destinations. Plus, going home to this Vrbo accommodation will always be exciting as it is relaxing and has a homey ambiance. It features a simple, chic, and modern interior design style and well-curated decors and furniture. It houses two lovely bedrooms and three charming private bathrooms. Plus, there is a cute little dining area with a fully equipped kitchen. Their rooms even have a patio where you can bask in the morning sunlight or have some quality time in drinking coffee. On top of that, it is within a short distance walk from the beaches and the state park.
Key West, Florida, United States
770 meters (0.5 ft) from The Hemingway Home and Museum
Top guest reviews
Host:
They responded quickly to fix and took care of usGreat booking experience and useful app added to make our stay very enjoyableI was very happy with the locationI was very happy with the locationI was very happy with the locationLocation:
Great place in a great locationIt is in a lovely locationI recommend this vacation rental Reviewer Comments:Very quite area but within 10 minutes walk from main street with restaurants and barsIt was very tranquil but was walking distance to Mallory Square and Duval StreetA couple of blocks to Mallory Square a couple of blocks to our favorite bars onCleanliness:
The house was clean and well equippedIt was very clean and comfortableThe vacation rental was very cleanThe vacation rental was very cleanThe vacation rental was very cleanRead more reviewsAmenities & Room:
The townhouse was as depicted in the description and picturesThe only floor with window or door screens was the top floorThere is a problem with the air conditioningThe kitchen is somewhat under equipped and guest bedroom could use better lighting (as per the boys) Would stay at property again over all satisfiedThe outdoor furniture comprised of two small rusted chairs a rusted bistro table and two beatup Adirondack chairs that were very uncomfortable
21. Classic condo in Key West's Truman Annex (from USD 202)
If you’re all about the interiors, this classic condominium unit in Key West’s Truman Annex is sure to make it on your list. This unit is quiet yet its colors are loud and will make you feel like you just traveled back in time. With one bedroom and one bathroom, it can accommodate two people. Although there is a minimum stay of seven nights, you won’t even notice as there’s plenty of action from the block on Duval Street. You can also use their bicycles to get around the area for those who are tired of walking.
KEY WEST, Florida, United States
482 meters (0.3 ft) from The Hemingway Home and Museum
Top guest reviews
Host:
the owner sent perfect directions and had a very simple set up to get into the unit even with our late arrivaland she did a wonderful job-againSusan is wonderful and is always available for any questions or concerns that may ariseWhat a great location Susan was very helpfulUnit was close to swimming pool which was niceLocation:
Mallory Square is also within walking distanceThe condo itself has a great locationThe condo is located in a very quiet community just away from the hustle and bustle of KW yet easily within walking distanceIt is within walking distance of so much Only two blocks to Duval StreetIt's a dessert restaurant that is very fun and romanticCleanliness:
The condo was very clean and tidyRead more reviewsAmenities & Room:
nice furniture and updated bathroom/showerfull kitchen laundry cable tvThe apartment is actually larger and more spacious than it appears in the photos with great amenities: keyless entryThe bikes that were included with the condo came in very handyThe deck and pool provided hours of relaxation
22. Condo close to the beach (from USD 322)
Beach lovers are going to love this condominium unit exactly near the beach. The Conch Retreat Condominium is a luxurious building located in the heart and center of Old Town that everything is conveniently near. Guests won’t ever get tired of exploring and walking along the historic district with plenty to see and do. But if they do get tired, they can always use the bikes provided by the property. This accommodation can fit up to four people in two bedrooms and one private bathroom.
Key West, Florida, United States
443 meters (0.3 ft) from The Hemingway Home and Museum
Top guest reviews
Host:
Jean and Lowell for being so great to work withThey keep up on what is going on in the community and participate in local meetings to make sure that they let their guest be aware of events taking placeIf you want to know about the island ask Lowell he knows and cares so much about things that created this paridiseand we absolutely love itWe absolutely love it there and were so sad to have to leaveLocation:
A 20 minute walk to Fort Zachary Taylor State Park and 5 minutes to the downtown strip on Duval StIt is within walking distance of everythingThis is the perfect location Close to everything but quiet retreatRide the bikes everywhere or walkThis gated community is beautifully landscaped quiet and relaxingRead more reviewsAmenities & Room:
The condo pool was warm and there was plenty of lounge chairsThe grounds are meticulously cared for; sitting on the back deck is like visiting a jungleThe condo was very clean with sufficient space for 4 peopleYou don't need to rent a carThe kitchen was fully equipped and we did cook a number of meals in the condo really convenient to the grocery store
23. Grand mansion for eight (from USD 1681)
Traveling with your friends and family? Book this beautiful and lush grand mansion that can sleep up to eight people in six bedrooms and five-and-a-half bathrooms. Although there is a minimum stay of six nights, you’re sure to love this private mansion that you won’t even notice time passing by. Located in an exclusive private residential community, Truman Annex, you will never have to worry about crowds in this neighborhood. The entrance is secured and gated and only guests can pass through. It is also fully furnished with all your needs–comfortable beds, private pool, and a beautiful backyard for socializing.
Key West, Florida, United States
584 meters (0.4 ft) from The Hemingway Home and Museum
24. Luxurious abode for six (from USD 474)
Big groups are welcome to stay in this luxurious Boli townhouse in Truman Annex. Those opting for a more private and peaceful vacation in the city will appreciate this gated community. Perfect for a group of six, the townhouse is complete with king-sized beds in two bedrooms, two bathrooms, and a fully equipped kitchen and dining area. They also have a flat-screen television and DVD players (complete with movies) in case you want to stay in. And for those who love the outdoors, there is also a deck with a dining table, hammock, grill, and lounge chair. The pool is just outside the property.
Key West, Florida, United States
530 meters (0.4 ft) from The Hemingway Home and Museum
Top guest reviews
Host:
He was very helpful when we had questionsJohn was very responsive to our questionsThe owner was very nice and very accommodatingWe have coffee out there every morning with the flora and faunaThe pool was so convenient and peaceful too John was great at communicating directions for arrival and departure at the house Overall good experienceLocation:
The location is perfect if you want to walk downtown or drive in any directionCondo was in a great location easy to walk to everythingWe could get to many places by walkingIt was great to walk less than 5 minutes to the busy area but be in a lovely quiet neighborhood to rest our weary headsthe Green Parrot Bar for friday nite sound check and do not miss sunset on Mallory SquareCleanliness:
We find it very clean and invitingThe washer and dryer are another convenience I appreciate as is the internet accessThe Boli is a great; exactly like it's picturedIt is clean quiet and comfortableThe unit is clean and in good repair nicely decorated well stocked and the location was very goodRead more reviewsAmenities & Room:
you own private kitchen living roomNice comfortable big double bedMy only change would be to have a bigger kitchen because I like to cook a lot on vacationbeach towels and a cooler are provided Plenty of room for 4 adultsTownhouse was stocked with extras like kitchen spices cleaners
25. Bright and sunny house near the beach (from USD 438)
If you love bright and open spaces, this sunny townhouse is for you. Perfect for just about four guests, it is complete with two bedrooms, two bathrooms, and a private deck with a lush garden and grill. There is a fully-equipped kitchen and working appliances so that guests can cook up their own meals. There is also a shared pool with lounge chairs perfect for relaxing and socializing with other guests. The best part? the beach is just minutes away. You can go snorkeling and explore the island.
Key West, Florida, United States
501 meters (0.4 ft) from The Hemingway Home and Museum
Top guest reviews
Host:
She made our check in process so nice by meeting us at the property and showing us where things wereThey were always available to help with any of our needsPatty the owner is so sweetPattie is a wonderful and responsive ownerScott and Patty are gracious hostLocation:
The location is perfect and you can walk to just about everything from thereThe place is in a perfect location close to all the great barsComfortable and quite 2Br/2bath townhome within walking distance to everything Key West including the poolFrom the Little White Housemade some suggestions on local restaurants and a lovely sunset sailCleanliness:
Very clean and again location to Duval and Mallory Sq are all walkable Highly recommend this place for a clean and organized condoThe owners Patty & Scott were extremely niceRead more reviewsAmenities & Room:
The only place we have stayed more than onceThe condo had everything you need and its location to the pool is perfectHad everything we needed Love that they supply shampoo conditioner and body wash Less liquids to carry thru TSASeriously stop researching b/cThe condo is off the main drag and is a great location
26. Majestic paradise in the heart of Old Town (from USD 435)
Imagine waking up in this lush and private house located in the heart of Old Town Key West. This paradise isn’t called “majestic” for nothing. If you love the outdoors–greenery, fresh air, and all, you’re definitely going to want to stay here. This house can sleep up to five people in two bedrooms and one bathroom. It has a large courtyard with a wooden sun deck, outdoor grill, and heated swimming pool. Everything else is just walking distance from the property. While you are it, be sure to catch the sunset by the beach!
Key West, Florida, United States
448 meters (0.3 ft) from The Hemingway Home and Museum
Top guest reviews
Host:
The owner was very helpful and provided us with all the information we needed in advance to make check in a breezeThey make sure you have all kinds of info prior to your arrival to make for a great vacationand he was quick to assist with any questions we hadall new inside made us feel right at homecontacted us and shared a tremendous amount of information that was quite helpful when planning our tripLocation:
Great place within walking distance to just about everythingIt is in a perfect location a walks away from beaches and DuvalPerfect location to stay while visiting Key West Walking distancethe minute you walk inThe location is perfect walk to wherever you need to goCleanliness:
The place is neat and cleanRead more reviewsAmenities & Room:
Even the beds and pillows were comfortableThe kitchen was well stocked and the outdoor grill was great for cooking fresh fishbeautiful 2 bedroom condo with everything you need great locationThe washer & dryer are much needed for the weather conditions of Key WestYou can leave your car in the gated area and walk all over town
27. Sunshine Daydream
The Sunshine Daydream Private Home is located less than a block from Duval Street, placing you in the heart of the island. The beach is a short three blocks away, but there is a private saltwater pool in the backyard for your enjoyment. This recently renovated home even has an outdoor bamboo shower! You’ll never feel far from the ocean at this Key West vacation house rental!
396 meters (0.3 ft) from The Hemingway Home and MuseumAccommodates: 4
Minimum Nights: 5
Refund Policy : 100% refund if you cancel at least 60 days before check-in.
28. Homey cottage near the beach
Caribbean Suite is a cleverly decorated one-bedroom cottage at Old Town Garden Villas. Ideal for couples and small families up to four, this tropical-themed condo is close to Florida Keys National Marine Sanctuary and is only 0.5 mi (0.8 km) from the beach on foot. If you’re traveling with your dog to Key West, this is where you’ll want to book your stay as it is dog-friendly. Restaurants and shopping centers are close to the cottage, so getting around shouldn’t be a hassle!
235 meters (0.2 ft) from The Hemingway Home and MuseumAccommodates: 4
Minimum Nights: 1
Refund Policy : 100% refund if you cancel at least 30 days before check-in.
Top guest reviews
Host:
staff was super friendlyeveryone was very friendly and respectfuleveryone was friendlythe grounds keepers keep the place in tip top shape and are very friendlyLocation:
location was just where we like to beit’s a great location near duvall streetit was easy to walk to all the restaurantsgreat location to do whatever you went to key west to dolove the quiet of the old town garden villas yet only steps away from the action on duvalCleanliness:
it was very clean and the bed was also comfortablethe apartment was very clean and comfortablethe carribean suite was very clean and comfortablevery clean loved the property amd pool areaRead more reviewsAmenities & Room:
it is a collection of individual units sharing beautiful courtyard and small poolcomfortable chairs tables with an umbrella make conversations with your neighbors easy to dothe caribbean suite is wonderfully decorated with a very functional kitchen and very comfortable furniturethe pool was small but perfect for cooling off in the afternoon
29. Old Town luxurious abode with a private heated pool
If you’re traveling with a large group and need a lot of space, this Old Town luxurious home is a great find. With four bedrooms and three bathrooms, this large home will fit up to eight people! There is a private heated pool in the backyard, and it is within easy walking distance of all the best attractions like the beach and Duval Street.
614 meters (0.4 ft) from The Hemingway Home and MuseumAccommodates: 8
Minimum Nights: 1
Refund Policy : 100% refund if you cancel at least 30 days before check-in.
Top guest reviews
Host:
owners were easy to reach by messaging through the vrbo appallison was very responsive to questionshome owner found this property available for us the staff at compass realty was accommodating helpful and friendlyshe was always very responsive and timely in getting back to us with any questions we might haveLocation:
pool onsite was great perfect location close to duval and many attractionsgreat location nicely suited for families with childreneasy walk to state park for great sunset viewingthis townhome is located very close to duval street and many local attractions in key westsuch a great location- private pool - close to duval- comfortable bed- everything you need and moreCleanliness:
close to everything very clean bright and airyRead more reviewsAmenities & Room:
plenty of space at the dining table and the towel supply was great toovery comfortable for 3 couples
30. Sunset and oceanview apartment
Come and enjoy amazing sunsets over the deep blue ocean water while sipping on a sundowner on your private viewing space. This property is located in a quiet neighborhood a few blocks away from the busy Duval street. There are two spacious bedrooms and one bathroom accommodating a total of four guests. This is a great space for a small family. There are two bicycles available for guests to use, free Wifi and a large outdoor communal swimming pool in the compound.
523 meters (0.4 ft) from The Hemingway Home and MuseumAccommodates: 4
Minimum Nights: 7
Refund Policy : 100% refund if you cancel at least 30 days before check-in.
Top guest reviews
Host:
Susan could not have been more accommodating as a host Very responsive and cheerfulAll in all a good experience and nice condo with all amenitiesand we felt like she truly cared about us having a great vacationReally we cannot say enough about how much Bruce and Susan and their lovely condo made us feel right at homeYou both are great peopleLocation:
Bikes park pass location privacyquiet but only blocks from Duval Great proximity to Santiago's Bodega a first class tapas restaurant in Bahama Village andAlso try Prana Spa for a wonderful massage Flamming Bouy for lobster mac and cheese Nachos at the Rum Barrel and of course the sunset at Mallory SquareIn addition the bikes were greatWe used the park pass daily sometimes 2 or 3 timesCleanliness:
very clean and well appointedIt was very clean and cozyCondo was nicely furnished and cleanRead more reviewsAmenities & Room:
The bikes came in very handyeverything was to die forSusan has everything that you need in the condoThe kids think they need to be included again as wellThe place was just as she described close enuff to everything
31. Luxury home in Coral Hammock
This property is great for family travelers who are looking for a community resort-style home. This estate houses a number of holiday homes that are suitable for groups and families. This home features a gourmet kitchen and there are three bedrooms and three bathrooms. Leading out of the bedrooms on the second floor you will have your own private balcony and a front porch and deck on the lower floor. Kids will love spending time at the shared swimming pool within the estate.
6.81 km (4.3 mi) from The Hemingway Home and MuseumAccommodates: 6
Minimum Nights: 28
Refund Policy :
Top guest reviews
Host:
the owner was very friendly and helped us with anything we neededrating details:the property manager was adequately helpfulwe can not wait to go backhe also recommend things for us to dorating details:the property manager was very helpfulLocation:
anyway, to my surprise, i loved the stock island gated community locationthe condo is in a great locationno issues parkingbeen back about 40 times since, stayed pretty much everywhereawesome imported sandCleanliness:
very clean placethe property was in great condition and was very comfortablethe vacation rental was very cleanthe property was very nice, clean with everything we needed in itunit was clean and adequately appointedRead more reviewsAmenities & Room:
the condo was wonderfulplenty of cooking supplies, it had soaps and towels all hotel qualitybeautiful townhome, each bedroom feels as if you have your own suiteunit had no kitchen perks like oil, seasonings, foil, cling wrap, etcthe facility was quiet and secure
32. Waterfront home at Paradise Harbor
This luxurious five-bedroom home boasting magnificent water views is the epitome of fine living. The home is located on the water’s edge and boasts a garage fit for two vehicles and covered dining area overlooking the stunning private swimming pool on the ground floor. There is also a boat launch space and amazing tropical garden area. Inside, there is a gourmet kitchen and a full entertainment area that includes a lounge and dining area. The in-house elevator takes you to the upper level of the home. This property is great for those looking to impress a group of friends and effortlessly entertain them in this home that sleeps 14 people.
Key West, Florida, United States
1.58 km (1.0 mi) from The Hemingway Home and Museum
Top guest reviews
Host:
He greeted us at the house and gave us a tourHe made us feel welcome and provided very helpful informationthe concierge was very helpful and friendlyLast Key did help us solve the problem and gave us a small creditShel was there to greet us upon arrival and was available whenever we neededLocation:
they are about 7 minutes awayso we had to move into a replacement house for one night butLast Key gave me a nice place at a decent pricea pool that we got plenty use of Would highly recommend this place for a larger group Great location and stunning houseWe've stayed at this house many many times and everything was perfect as usualCleanliness:
It was very clean and ShelThe house is very nicely decorated clean and maintainedand you can't beat the locationThe house was super clean and very roomy and nicewe're very pleased with everythingRead more reviewsAmenities & Room:
There is more than enough room to accommodate a large number of guestsBig town home with lots of room for plenty of peopleRight on the water for easy dockingThe pictures don't do it justiceYou will need to Uber or drive to town or the beaches
33. Spacious vacation home along Admiral's Lane
For those who want a spacious vacation home for up to four guests, this two-story home in the prestigious Admiral’s Lane neighborhood definitely fits the bill. The bright and breezy home features an open layout main floor showcasing a comfy living area, a six-seater dining table, and a well-equipped kitchen space. Free wifi and a cable TV are also included for an entertaining stay. Through the French doors, you’ll be greeted by a large private deck that offers plenty of space to unwind and enjoy a casual meal. The second level houses the two gorgeous bedrooms fitted with plush beds.
For some basking under the sun, you can enjoy the nearby community pool or walk to the pristine beach for a dose of sand and coast. When booking, note that the property has a seven-night minimum stay policy.
763 meters (0.5 ft) from The Hemingway Home and MuseumAccommodates: 4
Minimum Nights: 7
Refund Policy :
Top guest reviews
Host:
rating details: the property manager was very helpfulrating details: the property manager was very helpfulrating details: the property manager was very helpfulrating details: the property manager was very helpfulrating details: the property manager was very helpfulLocation:
great location and lovely propertybeautiful neighborhood and great locationproperty was perfect the location was greatthe location was perfect for walking to duval stthe location is perfect for walking and bike riding the pool is very close by and cleanRead more reviewsCleanliness:
every part of the property was very clean and well keptthe vacation rental was very cleanthe home was clean and well kept
34. Cozy two-level retreat in the Southard Court area
Have an easy-going getaway in Key West with a stay at this two-level home nestled in the Southard Court area of Truman Annex. Its first floor features an open concept interior comprising the living space with a large TV, a dining table for six, and an equipped kitchen for all your cooking sprees. The living room also extends to a back deck where you can do the outdoor grilling. Make your way to the two bedrooms tucked upstairs when capping the night off.
Staying here also means having to enjoy a shared pool right in front of the property. If you plan to arrive by car, you’ll get one parking space reserved for your vehicle. Be aware that you have to stay for at least seven days to be able to book the unit.
484 meters (0.4 ft) from The Hemingway Home and MuseumAccommodates: 5
Minimum Nights: 7
Refund Policy :
Top guest reviews
Host:
the staff was wonderful; very helpful and friendlyrating details: the property manager was very helpfulrating details: the property manager was very helpfulrating details: the property manager was very helpfulrating details: the property manager was very helpfulLocation:
i loved the location to duval and also the location to the poolperfect location for beach and town exploringloved being near fort zach state parkgreat location secure and quiet yet close to all the action on duval streetgreat location walkable to all things key westRead more reviewsCleanliness:
other than that the condo was clean comfortable and well stockednot to mention the character of the condo and how clean it was
35. Classic condo with a shared swimming pool
Located within a short distance from the city’s top tourist destinations, this stylish condo unit is like a homey nest after a busy day touring the city. It is fully furnished, with fabulous interior design, has lovely amenities, and exudes a relaxing and peaceful ambiance. This Vrbo accommodation is ideal for four guests as it has two cozy bedrooms and three charming bathrooms. There is also a fully equipped kitchen with a dining area where guests can prepare their meals. Basic essentials are also provided to guests for added convenience.
770 meters (0.5 ft) from The Hemingway Home and MuseumAccommodates: 4
Minimum Nights: 7
Refund Policy : 100% refund if you cancel at least 30 days before check-in.
Top guest reviews
Host:
but away from the hustle-and-bustle of Duval Street Very cute and well furnishedRead more reviewsLocation:
Great location walking distance to everythingMoved to this property due to Irma Loved the property and great locationWe loved it and the location was greatLoved the location and the decorWe had the best time in this lovely house Location is perfect you can walk everywhere
36. Spacious accommodation for four
If you are looking for a place to stay in Truman Annex, this lovely townhouse can accommodate up to four guests. It is fully furnished, well equipped with fantastic amenities, and exudes a home away from home kind of ambiance. Including two cozy bedrooms, three private bathrooms, a comfy lounge, fully equipped kitchen, and dining space, coming home to this wonderful home after a busy day at the town center will always be a delight. Aside from that, it is located in one of the most prestigious neighborhoods in Truman Annex. The surrounding area of this accommodation is a tourist destination in itself, picture perfect, exquisitely landscaped, and has park-like features.
key west, fl, US
749 meters (0.5 ft) from The Hemingway Home and MuseumTop guest reviews
Host:
mike the owner is great to work withLocation:
the location is perfectthe location was within easy walking distance to restaurants shopping groceries and points of interestsuperior location & very safe areagreat property with a great locationit's an easy walk to duval and all of our favorite spotsCleanliness:
the house itself was very clean and well appointedtownhouse exactly as described & true to photographs; exceptionally clean & well stockedunit is nicely decorated and very cleanthe condo is clean and spacious with comfortable furnitureit's extremely spacious and cleanRead more reviewsAmenities & Room:
the mattress is extremely comfortablewe loved the side courtyard and had breakfast there every morning
37. Stylish townhouse with a pool
Featuring a stylish, fully furnished home, this rental is like a home away. It exudes a relaxing ambiance, and it has amazing amenities that will make your stay worthwhile. It features two comfortable bedrooms, three bathrooms, a spacious and cozy lounge area, a fully equipped kitchen, a lovely dining area, and a patio. Aside from that, this location is perfect for tourists who like city tours and lovely walks as it is close to the popular landmarks in the area. This accommodation also has wifi access, a flat-screen television, and basic essentials are provided to guests.
Key West, Florida, United States
779 meters (0.5 ft) from The Hemingway Home and Museum
Top guest reviews
Host:
they made sure we had information about the property and the surrounding area to feel at homewe have been going to key west for 18 years and have rented in the truman annex 13 timesvery easy checkin/checkout and randy was very responsive when we pointed out a very small problem that needed to be fixedwe rented truman annex foundry #14 and loved every minute of itno matter the time coming home we always felt safe within truman annexLocation:
beach is also a quick bike ride awayclose enough to walk to everythinggreat house in a great locationi loved the location everything was within walking distanceonly a few minutes to mallory square or zachary taylor state parkCleanliness:
the unit was very clean and extremely comfortableit was very clean and decorated so cuteclean, quiet and perfect for usvery cleanlocation is everything and the truman annex is the place to beRead more reviewsAmenities & Room:
the first floor has a nice and comfortable living room area, featuring plenty of comfortable chairs and a large screen tvloved the bedrooms with their own bathroomsthe pool is small but adaquate for cooling off on hot daysthe condo was very spacious and had all the amenities we neededthere were also towels for use at the pool
38. Beach-themed condo with a shared pool access
This two-bedroom condo is an ideal stay for a family of six and is just a few steps from Ernest Hemingway Home and Museum and Duval Square Mall. When you enter the living room, you’ll be greeted by the cutest beach-themed decor and furniture. Slowly sip on your coffee and take in the view from the deck. The rental comes with central air conditioning, a flatscreen television, and free Wi-Fi. You could also swim a few laps at the shared pool and have a picnic with your loved ones at the gazebo!
259 meters (0.2 ft) from The Hemingway Home and MuseumAccommodates: 6
Minimum Nights: 1
Refund Policy : 100% refund if you cancel at least 30 days before check-in.
Top guest reviews
Host:
we enjoyed the propertyand the staff are all friendlyLocation:
location is good being fairly central making everything within walking distancegreat location on duval streetwalking distance to major attractionslocated in a great location we felt safe and secure in this comfortable town homeperfect location very secure and a wonderful place to stayCleanliness:
very clean and lots of spaceproperty was clean and well maintained including the poolhome was clean and well furnishedgreat accommodations unit was exceptionally cleanthe townhouse was clean with very comfortable bedsRead more reviewsAmenities & Room:
pool is shallow but great for a hour or two rest in the afternoon
Enjoy Key West!
The best way to enjoy Key West is like a local! What better way to explore this beautiful island than from your own Key West beachfront rental oasis? Though the island is small, it has a number of vacation rentals perfect for all group sizes and budgets! Once you’ve found your home away from home, check out the top festivals and seafood restaurants in Key West!
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