20 Best Luxury Rentals In Key West, Florida

Francis
Contributing Writer
Updated
| 9 min read

The idyllic Key West, Florida, evokes images of pristine beaches, vivid coral reefs, and opulent conch-style houses. This dreamy sun-drenched island is a traditional retreat for travelers looking to upscale their holiday. Here, you can walk barefoot on the beach and experience an exquisite sunset. Snorkeling and scuba diving are also treasured activities in this destination where captivating reefs and historic shipwrecks abound. Stroll along the enchanting streets of Duval and take part in its lively nightlife. The grand architecture, lush gardens, and educational artifacts of The Hemingway Home and Museum are also worth a visit. To stay in a remarkable home just as luxurious as this travel destination, check out the best luxury rentals in Key West, Florida below.

Popular picks in Key West

We handpicked these listings carefully, considering (wherever possible) host status, recent guest reviews, location, accommodation type, prices, availability of dates, decor, and access to luxury services and amenities. The image galleries get refreshed with the latest updates regularly. They were last updated on October 28, 2025.

1. Secret Villa II (from USD 13347)

Secret Villa II is an exclusive sanctuary found just a block away from Key West’s liveliest area, Duval Street. Travelers are drawn to this palatial house with a curvy heated pool. The natural vegetation surrounding its outdoor area gives it a picturesque quality.

Each of the three bedrooms is spacious and cozy. Two master bedrooms with en-suite baths and king-size beds are found on the second floor while the first-floor bedroom has a sumptuous queen-size bed. The master bedrooms share a porch with delightful views. Meanwhile, the living area is bright and lightly furnished and the kitchen is complete with cooking necessities. Parking is limited to mid-sized cars and small SUVs, but unlimited public parking is also located just a five-minute walk from the property.

Key West, Florida, United States

603 meters (0.4 ft) from The Hemingway Home and Museum
82 reviews   Airbnb superhost icon Superhost Wifi Available
ENTIRE HOME 3 Beds 6 Guests 3 Bedrooms 3 Bathrooms

Accommodates: 6

Top guest reviews
Host:
jim was a great host and responded promptly to all of our questions
he's a wonderful host and takes great care to make sure his guests are happy
he was available for any questions (very responsive) and made wonderful restaurant recommendations
we were greeted by a friendly and helpful host who was there to help with anything we needed
jim was responsive friendly & a pleasure to deal with
Location:
perfect house in an amazing location
wonderful place great location near everything
wonderful place and great location
the location was absolutely perfect so private but so close to everything
fantastic location and house in the heart of key west
Cleanliness:
bathrooms were clean updated and well equipped with soaps hair dryers etc
exceptionally clean and centrally located
clean fully loaded with linens towels kitchen supplies and everything was in perfect working order
it's beautifully appointed and spotlessly clean
the house is extremely clean classy - and full of everything you need
Amenities & Room:
dining table is outside on patio facing the pool only functional if weather is ideal
Read more reviews

2. Dazzling penthouse with three bedrooms (from USD 7418)

You’ll easily fall in love with this gorgeous penthouse near Duval Street. The place features three bedrooms, private porches, a backyard, and a rooftop deck where you can marvel at views of Duval Street. To cool off on a hot and humid day, take a refreshing dip in the private swimming pool with a waterfall. Note that it can get a bit noisy on some nights because a bar next door hosts live music.

Key West, Florida, United States

540 meters (0.4 ft) from The Hemingway Home and Museum
7 reviews   Wifi Available
Entire villa 3 Beds 8 Guests 3 Bedrooms 2 Bathrooms

Accommodates: 8

Top guest reviews
Location:
great location centrally located perfect home base
fantastic place best location in town mark was extremely helpful
best location huge decks pool and mark has done a great job with the interior beautiful
Cleanliness:
this penthouse is awesome clean modern perfect setup in perfect location
Read more reviews

3. Portside Manor (from USD 23800)

With 6 restful bedrooms, 6.5 baths, and a large private pool, this villa that sleeps 12 is ideal for multi-generational gatherings. Nestled in a posh compound in the center of Old Town Key West, this home’s light-toned walls and tropical-style furnishings give a cozy beach house appeal. From here, enjoy kayaking, snorkeling, and dolphin watching since the accommodation is near Key West Historic Seaport.

The wicker armchairs, plush sofas, TV, and tropical ceiling fans give stylish comfort to the roomy living area. For more, the light blue tone of the equipped kitchen is relaxed and quirky. Additionally, an option to have meals in the indoor dining area or on the deck is available.

Key West, Florida, United States

1.14 km (0.8 mi) from The Hemingway Home and Museum
5 reviews   Wifi Available
Entire villa 8 Beds 12 Guests 6 Bedrooms 6 Bathrooms

Accommodates: 12

Top guest reviews
Host:
—and of course the owners were beyond helpful and kind
also a few friendly roosters
Location:
all within a short walk the perfect space in the perfect location
we loved our stay in the heart of key west walkable to everything and also very private
we became friends with our neighbors at kermit’s key lime pie shop and fisherman’s cafe
Amenities & Room:
the second property is a 3 bedroom home (with large beautiful master) and living room with tv
Read more reviews

4. Newly renovated villa with a U-shaped galley kitchen

Located in the center of Key West’s Old Town, this newly renovated villa is unique with an architectural style that dates back to the late 1800s. It provides two bedrooms and two bathrooms and can accommodate four people. It features a U-shaped galley kitchen with top-quality appliances, a living room with a flat-screen TV, well-manicured gardens, and a large swimming pool. It also includes a front porch with outdoor furniture. Fun activities you can do in the area include visiting museums, dining at restaurants, shopping, boating, diving, and snorkeling. You can also catch a movie at a theater nearby.


367 meters (0.3 ft) from The Hemingway Home and Museum
18 reviews   Wifi Available
villa 4 Guests 2 Bedrooms 2 Bathrooms

Accommodates: 4
Minimum Nights: 0
Refund Policy :

Top guest reviews
Location:
wonderful property located close to everything
the place is perfectly located
fabulous location and a beautiful setting
location is great and very private
was a great property and location
Cleanliness:
very clean home and property is well maintained
it is spacious clean and comfortable
100% clean buetifull perfect location
Amenities & Room:
the home was clean well supplied kitchen handy washer/dryer
Read more reviews

5. Chick-A-Pea Cottage

Chick-a-Pea Cottage

CHICK-a-PEA COTTAGE is a traditional Key West cottage. The charm and historic features have been retained, while all the luxuries of today have been added. April 20 - 29, 2018, in Key West is the 36th Annual Conch Republic Independence Celebration! Come join the celebration! #KeyWest #VacationRentals #FamilyFun #GirlsGetaways #Mancations #CouplesRetreats #SoloTravelers #historickwvacationrentals

Posted by Historic Key West Vacation Rentals on Wednesday, April 18, 2018

Timeless charm and contemporary amenities make Chick-A-Pea Cottage a luxuriously comfortable stay for eight guests. The home’s wood walls and flooring suggest a relaxing country vibe while the plush furniture exudes understated elegance. As for indoor recreation, cable TV and Wi-Fi are available in the lounge. You can also cook up simple meals in the complete kitchen. If you need a breath of fresh air, step out to the patio. You can also take advantage of the pool with a waterfall feature and the relaxing poolside cabana. After a swim, have an afternoon siesta on the tropical-inspired furnishings.

The tranquil atmosphere in the lush garden makes it easy to forget that the accommodation is just a block away from Duval Street. Additionally, The Hemingway Home and Museum is only a few steps away.

Key West, Florida, United States

204 meters (0.2 ft) from The Hemingway Home and Museum
cottage 8 Guests 4 Bedrooms 3 Bathrooms

Top guest reviews
Host:
rating details:the property manager was very helpful
rating details:the property manager was very helpful
rating details:the property manager was very helpful
rating details:the property manager was very helpful
rating details:the property manager was very helpful
Location:
the location of this property is great
great location walking distance to bars and restaurants on duval
would definitely rent this same location again
couldn’t ask for a better location and access to everything key west has to offer
it is right on duval street which my kids loved
Cleanliness:
the house was clean and every detail was thought of
immaculately decorated laid out perfectly spotlessly clean everything we could need was provided
the house was clean spacious and very private even though we were steps away from duvall
Read more reviews

6. El Corazon

El Corazon, a high-end five-bedroom home, lives up to every travelers’ expectation of splendid island living. Newly renovated and fully furnished, this accommodation with a serene patio is surprisingly just off Duval Street.

From plush furnishings to artistic decors, each detail of the house is well thought out to provide style and comfort. Even the quarter-turn staircase exudes a rustic charm. The master bedroom with an en-suite bath is conveniently restful. Meanwhile, a Jack and Jill bath connects every two bedrooms and a complete kitchen is provided for meals. Airy and lightly furnished, the living area leads to a lovely porch through a sliding door. During their downtime, guests can delight in the heated dip pool outside. Parking for a mid-size car is also available here.

Key West, Florida, United States

219 meters (0.2 ft) from The Hemingway Home and Museum
PRIVATE VACATION HOME 10 Guests 5 Bedrooms 4 Bathrooms

Top guest reviews
Host:
rating details: the property manager was very helpful
rating details: the property manager was very helpful
rating details: the property manager was very helpful
rating details: the property manager was very helpful
rating details: the property manager was very helpful
Location:
we loved the location and the property
wonderful location with a private walkway to duval yet still very private
it is the perfect location and a gorgeous property
made it very easy to walk to everything
this property is in the perfect location especially when staying with a large group
Cleanliness:
home was very clean and as advertised
it was very clean and the decor was as pictured
house was beautiful clean had everything we needed
the bathrooms are nice size and clean
the house was clean and had every accoutrement we would have needed
Amenities & Room:
little pool perfect for a dip
tvs work great bathroom downstairs is a little small
Read more reviews

7. Havana Daydream

Have the best Key West trip in this high-end waterfront home. Nestled in a gated community in Key Cove, this bright and spacious accommodation affords an expansive view of the coast. This four-bedroom accommodation can sleep eight in total. Plush couches, stylish wicker chairs, and a massive HDTV provide comfort and entertainment in the living area. Meanwhile, state-of-the-art equipment and utensils make cooking a breeze in the gourmet kitchen.

Outside, enjoy the vistas from the porch, or watch the kids play on the lanai or in the heated pool. Location-wise, Smather’s Beach is just 1.1 miles (1.8 kilometers) from the house.

Key West, Florida, United States

3.33 km (2.1 mi) from The Hemingway Home and Museum
PRIVATE VACATION HOME 8 Guests 4 Bedrooms 4 Bathrooms

Top guest reviews
Host:
our host javier garrido was outstanding
rating details: the property manager was very helpful
rating details: the property manager was very helpful
rating details: the property manager was very helpful
rating details: the property manager was very helpful
Location:
we loved the private location and open floor plan
i was happy with the location
i was very happy with the location
i was very happy with the location
i was very happy with the location
Cleanliness:
property was clean & had plenty of towels for bath & pool
reviewer comments: clean and well maintained property
found the home to be clean and spacious for our group
the vacation rental was very clean
the vacation rental was clean
Amenities & Room:
property is comfortable with fantastic views with loaded home
our grandchildren are 13 n 17 and enjoyed their own space n the pool
plenty of space great pool and surroundings
Read more reviews

8. Luxury penthouse located downtown

Upscale your Key West experience by staying in this luxurious rooftop penthouse found above Wyland Gallery in Duval Street. Large glass windows and a 15-foot (4.6-meter) high ceiling add sunlight and airiness to this two-bedroom accommodation. Contemporary furnishings and a flat-screen TV provide comfort in the generously spaced living area. Meanwhile, granite countertops, dark wood cabinets, and stainless steel appliances make cooking in the complete kitchen fun and easy. During a lazy afternoon, you can visit the roomy rooftop terrace with a seating area.

Stroll around and explore the surrounding Duval Street. In addition, the newly built Truman Waterpark is just a 10-minute walk from the penthouse.

Key West, Florida, United States

353 meters (0.3 ft) from The Hemingway Home and Museum
condo 6 Guests 2 Bedrooms 2 Bathrooms

Top guest reviews
Location:
great location in the heart of the entertainment district
overall the rental location and accommodations are very nice
top floor above an art gallery on duval walking distance from bars shops
the location is awesome the rental has everything you could think of
nice central location easy check- in
Amenities & Room:
overall good however 2 out 3 tvs did not work
beautiful property in great old town location with all of the amenities fabulous stay in comfortable setting
Read more reviews

9. Stars and Stripes

This stately house found in the heart of Old Town Key West has eight bedrooms and four full baths. Though the house sleeps 20, each floor is designed to provide a degree of privacy. The third floor has a kitchenette while both the first and second floors have their respective fully equipped kitchens. The bedrooms and full baths are distributed on each floor, too. Each room is adorned with vintage-style furniture such as iron-framed or four-poster beds, dark wood furnishings, stylish sofas, and consoles tables. Meanwhile, the baths have either a claw-footed tub or a deep-soaking tub.

For a refreshing dip, head to the rectangular pool on the patio. Also, enjoy the view from the spacious balcony or drink a cup of coffee on the porch.

Key West, Florida, United States

911 meters (0.6 ft) from The Hemingway Home and Museum
PRIVATE VACATION HOME 20 Guests 9 Bedrooms 4 Bathrooms

Top guest reviews
Host:
rating details: the property manager was adequately helpful
rating details: the property manager was very helpful
rating details: the property manager was very helpful
rating details: the property manager was very helpful
rating details: the property manager was very helpful
Location:
great location - bike/walk anywhere
very convenient and walking distance to all of the popular restaurants and bars
this house is in a great location and very good for a large group
the location is great close to key west bight schooners wharf duval st bars mallory sq etc
location was perfect and surprisingly quiet
Cleanliness:
the rooms were clean and quiet
the house is in good condition and it was clean when we arrived
there was plenty of room it was clean lots of tvs heated pool
Amenities & Room:
the beds and furniture were very comfortable
we had 8 people with us and the house fit perfectly with plenty of room for more
beds were very comfortable
Read more reviews

10. Captain’s Quarters

Complementing its modern amenities, Captain’s Quarters retains the vintage charm of Key West. Clad with Dade County pine from floor to ceiling, the interior conveys a relaxing feel of a mountain lodge.

Classic chandeliers, stylish ceiling fans, armoires, bureaus, and other wood furnishings elevate the interior. Relax on comfy Belgian-style sofas or tropical armchairs in the family room overlooking the pool. The master bedroom’s en-suite bath boasts a gorgeous claw-foot tub while the modern kitchen is spacious and complete. With 4 spacious bedrooms, the accommodation can sleep 10. One of the rooms is actually a cottage with a queen-size bed, pedestal sink, and TV. Outside, the decked patio offers a lagoon-style pool and furniture for picnics.

Key West, Florida, United States

1.05 km (0.7 mi) from The Hemingway Home and Museum
PRIVATE VACATION HOME 10 Guests 5 Bedrooms 3 Bathrooms

Top guest reviews
Host:
rating details: the property manager was very helpful
rating details: the property manager was very helpful
rating details: the property manager was very helpful
rating details: the property manager was very helpful
rating details: the property manager was very helpful
Location:
the location was good
this house and location are perfect
it is also easy to get anywhere in kw from this location
short walk to all activities- loved this quiet home in key west
i was very happy with the location
Cleanliness:
we knew someone would be coming to clean the pool and someone else to clean the grounds
the house was clean
the pool was amazing (and cleaned twice a week)
Amenities & Room:
the dining room did serve as great addition bed room with having an air mattress
amazing stay pool was so relaxing and beautiful beds were incredibly comfortable
perfect house for a larger family beautifully decorated and amazing pool on the backyard
Read more reviews

11. Captain’s Daughter

Tucked into one of Old Town’s quiet neighborhoods, Captain’s Daughter is a five-bedroom upscale cottage with a private pool and a dock. Sleeping 12, each bedroom has plush beds, elegant nightstands, and dressers while 2 of the bedrooms have a private balcony. The master bath even has a gorgeous corner tub. The spacious lounge is cozy while its dining areas are designed to cater to large-group dining. Also, the chef’s kitchen is roomy with state-of-the-art equipment. Wi-Fi, HDTVs, central heating and air-conditioning, and off-street parking are also conveniently available.

The airy patio has garden furnishings, chaise lounges, a barbecue grill, and a heated pool for outdoor activity. Higgs Beach is also just 0.9 miles (1.4 kilometers) away.

Key West, Florida, United States

1.55 km (1.0 mi) from The Hemingway Home and Museum
PRIVATE VACATION HOME 12 Guests 5 Bedrooms 4 Bathrooms

Top guest reviews
Host:
the property mgr & staff were very friendly
rating details:the property manager was very helpful
rating details:the property manager was very helpful
rating details:the property manager was very helpful
rating details:the property manager was very helpful
Location:
the location was perfect
perfect location so we could fish off the dock
it is close to most attractions and is about a 20 minute walk to duvall street
a perfect place for a gathering of family and/or friends
captain's daughter was spotless in a great location quiet neighborhood that within walking distance to duval street
Cleanliness:
the house was very clean
great large home as described clean and well maintained
it was as clean and roomy for the ten people that were in our group
Amenities & Room:
the air conditioning works great and we were very comfortable our entire visit
the beds were super comfortable and the master
easy check-in nice kitchen large rooms plenty of space
each bedroom had a nice full bathroom
the house was amazing and plenty of room for everyone
Read more reviews

12. Villa Bella

Enjoy the peace and quiet in this island retreat tucked away in Old Town. This luxury vacation rental in Key West features a large formal living room, a fully equipped kitchen with skylights and bar seating, and a two-story central staircase. The master’s bedroom, aside from having a magnificent view of the pool, also has a large jetted tub.

Enjoy the outdoors by going for a swim in the pool, lounging around on the deck, or watching a movie in the outdoor seating area with a TV. Or you can go to South Beach or Simonton Beach, both 0.2 miles (0.32 kilometers) away.

Key West, Florida, United States

695 meters (0.5 ft) from The Hemingway Home and Museum
villa 12 Guests 6 Bedrooms 5 Bathrooms

Top guest reviews
Host:
rating details:the property manager was very helpful
rating details:the property manager was very helpful
Location:
i was very happy with the location
i was very happy with the location
Read more reviews

13. Luxurious compound with a swimming pool and a hot tub

This compound, located in the heart of Old Town, comprises a penthouse and a guest house. The island-style furnishings and artwork complete the tropical vibe of this luxury house rental in Key West, Florida, especially with the open floor plans making the buildings look and feel spacious.

Choose your mode of relaxation: swimming in the heated pool with a waterfall, soaking in the hot tub, or enjoying the views in the terraces available for each room. Or, you can watch your favorite movies or shows on the numerous HD flat-screen TVs. If you want to dine outdoors, there is a dining terrace just off the fully equipped kitchen.

key west, fl, United States

493 meters (0.4 ft) from The Hemingway Home and Museum
villa 16 Guests 7 Bedrooms 7 Bathrooms

14. Newly renovated sanctuary with a heated swimming pool

This three-bedroom luxury home in the Florida Keys includes French doors, a heated swimming pool, and a deck. It can accommodate six guests. On the deck, you can unwind with a glass of wine or beer. The place also features a full-service kitchen with a blender you can use for making delicious cocktails.

You can experience the city’s vibrant nightlife by dining at restaurants or drinking at bars. You can also visit museums and art galleries nearby. This villa in Key West is near the beach with many of the most popular beaches, such as South Beach, only a bike ride away.

Key West, Florida, United States

602 meters (0.4 ft) from The Hemingway Home and Museum
villa 6 Guests 3 Bedrooms 3 Bathrooms

Top guest reviews
Host:
owner is super nice
the property manager was attentive and beyond helpful
jim was very helpful when he greeted us upon arrival
the check in process was easy and the site manager was friendly and accessible
the owner is super nice and has become a great friend
Location:
the location was great
excellent location - quiet but very close to duval
great location i cannot stress enough
the house is close to everything which made it the ideal location
close enough to enjoy everything and far enough away for it to be quiet
Cleanliness:
clean new appliances and comfortable
the house was extremely clean with lovely decor
after that it was sparkling clean and we had a great time
great location super clean & beautiful place
we thoroughly enjoyed are vacation the house was very clean well equipped and a perfect location
Amenities & Room:
the linens on the beds were amazing and the furnishings were all high end
the beds were extremely comfortable
very well appointed with all the amenities including pool/beach towels umbrellas a cooler laundry and supplies etc
there was plenty of room to spread out and having the pool right there was a fantastic perk
we all loved lounging by the little private pool and riding the bicycles provided by the owner
Read more reviews

15. Beautiful house with a porch and a verandah

This beautiful house is equipped with 7 bedrooms and is ideal for up to 14 guests. It features an outdoor swimming pool, a pool deck, a large dining room, and a remodeled kitchen with stainless steel appliances and granite counters. Every bedroom is warm and well-furnished with comfortable beds. The place also has a porch and a verandah, which overlooks the pool. You can engage in some fun activities nearby, such as diving, sailing, and visiting museums. The beach, shops, cafes, and art galleries are also close by.

Key West, Florida, United States

848 meters (0.6 ft) from The Hemingway Home and Museum
PRIVATE VACATION HOME 16 Guests 7 Bedrooms 6 Bathrooms

Top guest reviews
Location:
walking distance to pretty much everywhere
good location and plenty of rooms
the location in old town seaport area is so convenient and our favorite area on island
great location enough room for our group of 14
the house was great for our large group and so close to the heart of key west
Cleanliness:
the pool was clean and warm
the pool needed to be clean more often
Read more reviews

16. Private residence with a rooftop deck

Situated in an upscale neighborhood near many tourist sites, this 4-bedroom villa can accommodate up to 10 persons. It is a great hideaway for families or groups of friends. This vacation rental with a private pool also features an outdoor sitting area, a living room with a flat-screen TV, and an open kitchen. It provides a room that leads to a covered lanai with a dining table. It also has a rooftop deck where you can lounge about, dine al fresco, entertain guests, and drink.

Key West, Florida, United States

307 meters (0.2 ft) from The Hemingway Home and Museum
PRIVATE VACATION HOME 10 Guests 4 Bedrooms 4 Bathrooms

Top guest reviews
Location:
the location is great
perfect location for family and friends
a wonderful property in a perfect location
easy walk to get on the conch train
it was in walking distance from all great restaurants and right off of duval street
Cleanliness:
the house is so cute and clean
the house is not only beautiful but clean and centrally located
we had a great time at amelia's hideaway it was clean and in a great location
Amenities & Room:
nice bedrooms and the pull out sofa bed was comfortable
the pool was fantastic and the courtyard was great for hanging out
loved the number of bathrooms (group of 8) the separate sleeping areas and the entertaining areas
we loved the outdoor patio and swimming pool definitely would stay here again
ac worked perfectly as well rooms were decorated nicely and nice bedding
Read more reviews

17. Exquisite home for eight

This exquisite home offers four bedrooms and three and a half bathrooms and can accommodate eight people. One of the rooms is a master bedroom with a king-sized bed, an ensuite bathroom, and a private deck overlooking the garden. The other bedroom comes with a queen-sized bed while the third bedroom is equipped with two twin beds. The place also features dining and living areas and a terrace where you can enjoy your morning cup of coffee or a glass of wine in the evening. It includes a pool area, which is a lagoon-inspired space where you can have a refreshing swim or simply lounge about.

Key West, Florida, United States

685 meters (0.5 ft) from The Hemingway Home and Museum
PRIVATE VACATION HOME 8 Guests 4 Bedrooms 4 Bathrooms

Top guest reviews
Location:
location was great as it was close to duval street and short walk to everything
great house pool and location
we loved the location and the fact that it was not right by duval
close to everything especially by bike pool was great i would definitely stay here again
Cleanliness:
comfortable clean beautiful private backyard pool
this is a great property with great kitchen clean beautiful landscaping and pool
Amenities & Room:
there were 7 adults vacationing together and we all had a blast along with comfortable nights sleep
Read more reviews

18. Historic abode near art galleries

This historic abode is beautiful with a cathedral ceiling and French doors. It provides two bedrooms and two bathrooms and can accommodate six people. It features a front porch with a swing, which you can use for lounging about. It has a swimming pool and a shaded hammock, which is the perfect spot for an afternoon nap. It is near art galleries, restaurants, and shops. For added convenience, guests can request for a professional maid and avail of catering services.

Key West, Florida, United States

391 meters (0.3 ft) from The Hemingway Home and Museum
PRIVATE VACATION HOME 6 Guests 3 Bedrooms 2 Bathrooms

Top guest reviews
Host:
property managers were very responsive
Location:
for places further away i'd recommend renting a bike
great location and house was perfect for our group of four
walking and easy biking distance to just about anything you could want to do
the location of this property was great for our week long stay in key west
the house is on a quiet side street off duval and is in the perfect location
Cleanliness:
house was very clean and comfortable
the house was clean cozy and so cute
the home was clean and stocked with a startling supply of soap and paper products
the home was clean well appointed and was perfect for our family
Amenities & Room:
i would also suggest better lighting in the bathrooms
the size of the pool was perfect for the 4 of us
Read more reviews

19. Chic dwelling with a sitting room

This chic dwelling offers 6 bedrooms and can accommodate up to 15 guests. One of these rooms is a master bedroom with king-sized and two twin beds and a glassed-in porch. It is surrounded by a lush greenery and is well-designed with artworks. It features a sitting room, a galley kitchen, and a swimming pool that is shared with other vacation homes. It also has covered porches with outdoor furniture and a lovely garden. It is near restaurants and yoga studios.


1.3 km (0.9 mi) from The Hemingway Home and Museum
21 reviews   Wifi Available
villa 15 Guests 6 Bedrooms 4 Bathrooms

Accommodates: 15
Minimum Nights: 0
Refund Policy :

Top guest reviews
Location:
the property was close to beaches and the kids loved the pool
close to everything like it says we all had a wonderful experience
Cleanliness:
the pool was nice but we had to clean it everyday
house was nice and clean
house was clean kitchen well supplied overall good
beds were comfortable and the property was pretty clean
Amenities & Room:
most everything was great i didn't realize there were three complete kitchens with the main house and the cottage
if some of these improvements were made i would be comfortable giving it a 5 star rating
Read more reviews

20. Pink House

Pink House is a historic Key West house found just a few steps away from Duval Street. A top-of-mind choice by discerning guests looking to celebrate their next big event, the accommodation’s Victorian features, hardwood floors, and Dade County pine walls make it even more appealing.

The home’s 6 restful bedrooms, 4 well-appointed baths, and 2 spacious living rooms are ample for 14 guests. Each bedroom displays a unique luxuriousness. You can also choose to relax in a living area with either rustic-style or country-style furnishings. Outside, the rectangular pool is surrounded by a stone patio with a lush garden.


736 meters (0.5 ft) from The Hemingway Home and Museum
136 reviews   Wifi Available
House 14 Guests 6 Bedrooms 4 Bathrooms

Accommodates: 14
Minimum Nights: 3
Refund Policy : 100% refund if you cancel at least 60 days before check-in.

Top guest reviews
Host:
property manager was awesome and communicative
don’t know the hosts cost but it’s worth it
the house manager was super friendly and just a text away at all times
the communication with the owner was smooth and they were very friendly
Location:
great location of the house
location was excellent especially close to duval and the bars
this location was absolutely perfect to walk around key west
the location was perfect could walk everywhere
house was perfectly situated in the heart of key west steps from duval street
Amenities & Room:
such a cool old house with plenty of room to spread out
the pool was great and we had everything we needed
the house itself was huge and had a great backyard with dipping pool
great backyard with a pool and 2 different balconies plus a front port and patio
Read more reviews

Have a grand stay in Key West

Key West is no regular tropical island. Picturesque and opulent, its exquisite sandy beaches are just the tip of the iceberg. So ready your travel bags, book your flights, and stay in these luxurious homes for the full experience.

Any must-sees we missed? Tell us about them in the comments section or write a post here to help out fellow travelers!
Disclosure: Trip101 selects the listings in our articles independently. Some of the listings in this article contain affiliate links.

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Francis is a versatile writer, an ardent reader, and a dedicated traveler. His culinary adventures take him to minimalist sushi restaurants, and he finds joy in strolling through Chinatown,...View profile

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