Islamorada is an incorporated village situated in Monroe, Florida. The name is of Spanish origin and it literally means “Island Home.” Although there are times that it is also called “Purple Isle.” It boasts beautiful and awe-inspiring coral reefs that will surely leave any visitor’s mouth agape. Having numerous islands composing the whole village, it does not lack seafood varieties. Visitors may rent a boat to partake in fishing activities as well as indulge in the delectable and sumptuous feasts that the sea offers. Popularised as the Sport-fishing Capital of the World, Islamorada boasts the world’s largest fishing fleet per square mile (11 square feet). Whether you’d like to snorkel or catch the sight of dolphins, be prepared to go wet and wild. If you want a peaceful and comfortable vacation, keep reading and book one of the best Vrbo vacation rentals in Islamorada, Florida.
What to look forward to:
- Theater of the Sea has animal interactive programs to keep visitors of all ages engaged, along with fun shows where you can watch animals and birds such as dolphins, sea lions, and parrots put on a show. You can also swim with dolphins, stingrays, sea lions, and much more.
- The village also has many parks and beaches to explore, which you can find a list of on Islamorada's official government website. The list mentions amazing options such as Anne's Beach, which has a shallow swimming area safe for kids and dogs.
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 26, 2025.
1. Luxurious apartment with ocean views
Best for: Families with kids, beach lovers, group stays
Are you looking forward to a luxurious vacation by the ocean? Then you’ll love this gorgeous apartment for rent near Islamorada. The unit offers spectacular views of the ocean, which you can enjoy from the balcony.
The kitchen has all the essentials you’ll need to cook lavish meals. Enjoy the taste of home-cooked food as you relish the view from the glass doors in the dining area. Lay back on the living room couch after a hearty meal or go for a dip in the pool. The property also has exercise equipment, perfect for fitness enthusiasts who are hesitant about fully letting go on the holidays.
Tavernier, Florida, United States
48.98 km (30.5 mi) from Everglades National Park
2. Quaint cottage on the beach
Best for: Beach lovers, watersports enthusiasts, pet parents, families with kids, couples
This place to rent in Islamorada, Florida, is ideal for small families looking forward to a summer vacation by the beach. Enjoy the spectacular sea views as you rest on the sun loungers and enjoy getting a tan on the beach. Spend quality time with your loved ones as you enjoy delicious meals cooked in the fully equipped kitchen. On lazy days, spend the afternoons relaxing on the living room couch as you scroll through your socials with the high-speed internet available.
To have fun, book nearby water activities, such as snorkeling, swimming, and kayaking. Or, you can go out and explore all the must-try eateries around this neighborhood.
Islamorada, Florida, United States
48.69 km (30.3 mi) from Everglades National Park
Top guest reviews
Host:
Carmen was awesome to work with Always very quick to respond to any questionsThey answered all our questions very quickThey are the absolute best genuine people we have met :)We spoke with Carmen and the neighbors both very nice and welcoming's since she also has a boat rampLocation:
it has everything you need and in a great locationIslamorada is a beautiful area with delicious restaurants and lots of shopsThe owners Carmen and Pablo are very nice peopleWe're in the keys 3 to 4 times a year and this place has become our first pickThe location is perfect Easy access to the marinas for fishing charters and other attractions Carmen and PabloCleanliness:
Everything was clean and well maintainedThe property was very clean spacious and provided everything we needed for our relaxing vacationLoved our stay so clean and well keptWas newly renovated clean and smelled amazingThe view and location was awesome and secure The property provide a large boat dock and slip which we were excited aboutRead more reviewsAmenities & Room:
Downstairs is one bedroom upstairspretty much anything you needHaving a large truck also made it difficult to back boat to slip due to one palm tree which is in line with boat slipThere is a full size kitchen and a washer/dryerbut is was our own private paradise
3. Child-friendly property in front of the ocean
Best for: Families with kids, beach lovers, group stays
This two-bedroom property can hold up to four individuals, making it the perfect Vrbo rental for families in Islamorada. It is close enough to the ocean that guests may enjoy various water sports and satisfy their inner surf dudes. Workout maniacs would love the place as it has a state-of-the-art workout gym.
In addition, it has a sauna that can help relieve the muscles after a long and strenuous workout. Guests are also free to bring their boat or even rent one as the place has a free dockage for such.
Islamorada, Florida, United States
48.46 km (30.2 mi) from Everglades National Park
Top guest reviews
Host:
Great condo Close to pool ocean and boat slipall Pat as well as her family were very quick to help with anything that came up or answer any questions that we hadWe took so many excursions even a garden tour and still have lots left for next yearPat left us was invaluableWe rented our condo for February to avoid winter We wanted to be on the ocean with swimming pool and hot tub with beautiful gounds and a gate for safetyLocation:
Five star condo property in Islamoradait stays cool Unit itself is like a well loved family cottage that has everything neededAs it does not get afternoon sunRead more reviewsAmenities & Room:
Although the unit is not the best location in terms of the water it is fine
4. Newly renovated villa by the bay
Best for: Pet parents, families with kids, outdoor enthusiasts, beach lovers, group stays
This renovated villa has two bedrooms which can accommodate up to six individuals. It has a fully equipped kitchen, a full-size washing machine and dryer, a cable television, and a dining room. What’s better is that it is only 30 feet (9 m) away from the water. That means that the guests may enjoy the cool sea breeze while contemplating about life. In the evening, guests will be greeted with the mesmerizing view of the Everglades and the golden crown of the sunset. At night, they may enjoy cooking and feasting on grilled delicacies as the property has an enclosed patio with an outdoor grill and dining.
Islamorada, Florida, United States
48.54 km (30.2 mi) from Everglades National Park
Top guest reviews
Host:
Mr Mitchell was a great hostMarina super convenient for those with boatsWe met some fantastic people and of course the fishing was awesome and let me not forget to mention the fresh key limes for my pies Looking forward to the same time next yearWe can't wait for next yearand it's also well prepared for those who like to fish or have a boatLocation:
Tackle is also within walking distanceThank you Bob and Pyllis for another great timeYou are secluded from the busy world and it is the perfect place to de-stressWe had a manatee swim up to the dock for a drink of fresh water--a great surpriseBut why would anyone want to leave this adorable house and patio????Cleanliness:
The views are amazing and the villa is updated and cleanRead more reviewsAmenities & Room:
The boat basin is perfectSunset Happy Hour is a never miss for meThe other renters were fun to be withThe Bayview Villa is everything you will need in the KeysNot only are the accommodations outstanding
5. Private villa facing the Everglades
Best for: Nature lovers, pet parents, families with kids, couples
This two-bedroom villa can house up to four people. Located in the lush tropical hammock in a quiet residential area, visitors are sure to have a peaceful, quiet, and relaxing vacation. Only approximately 50 feet (15 m) away from the water, watching the waves crash onto each other can be a good way to pass time. It also has its own wading beach and marina, complete with night lights, power, and water. Entertainment includes cable television, a VCR, and a fully equipped kitchen.
Islamorada, Florida, United States
48.55 km (30.2 mi) from Everglades National Park
Top guest reviews
Host:
hammer head sharks sea horsesMr Mitchell was a wonderful hostThe hosts were very gracious and always available for any questions Thanks for a nice stayThe property well taken care ofThe marina was nice calm easyLocation:
There are so many restaurants and stores within walking distance or more less than a 5 minute drive awayThis home is in a great location and just steps from the waterIn 35 minutes we were at K-Mart in Key Largo and 15-20 minutes to Win-Dixie in Tavenier (which I found to be cheaper than Publix and maybe better stocked )The location of the villa in Islamorada is amazing you can walk to numerous shops bars and restaurants We loved being able to moor our boat in the marina and enjoyed many peaceful afternoons rela...This vacation was by far the bestCleanliness:
It is kept very clean andThe villa was very clean and updatedThe house was "cozy" for a family of 4 full grown peopleThe 1 bedroom villa was clean and spacious and very comfortableRead more reviewsAmenities & Room:
The villa is very comfortable and had all the amenities of homebut it was very comfortableThe landscaping was immaculate and the other visitors on the property were all so niceThat was a game changer for us to be able to turn the key and goYou can fish off the pier
6. Waterfront home with heated pool
Best for: Beach lovers, pet parents, families with kids, group stays
This spacious, 176-square-metre (1,900-square-foot) home welcomes 10 guests to explore its beauty. Natural light bathes the rooms allowing guests to enjoy a cheerful start to the day. Guests are invited to take a splash in the heated, outdoor pool or laze on the sun beds. Guests also have unrestricted use of a kayak and two cruiser-style bicycles. After a fishing expedition or a stroll along the beach, simply take an outdoor shower before entering the premises.
Offers are available for monthly stays and a cleaning fee applies.
Islamorada, Florida, United States
48.06 km (29.9 mi) from Everglades National Park
Top guest reviews
Host:
the owner could not be more accommodating and friendlyhighly recommend this house and the owner it's just a perfect getawayunbelievable house like new great owner very easy to work withmichael is a great host tooLocation:
beautiful house great pool best locationbest location for getting to the gulf or ocean by boatthe pool was definitely and added plus and the location for canal docking are just perfectthe location is perfect with access to the ocean and the bay very quicklyCleanliness:
the home is beautiful very clean and wonderfully maintainedRead more reviewsAmenities & Room:
the beautifully renovated fully stocked kitchens on both floors came in handyboth kitchens were beautiful and stocked with everything we needed2 kitchens offer great optionsthe pool was the best entertainment for our family
7. Two-storey home with private plunge pool
Best for: Watersports enthusiasts, luxury travelers, beach lovers, pet parents, families with kids and infants, group stays
There’s plenty to do when you check into this property, which is situated directly on the bay in Coral Cove. The secluded house is less than 1.6 kilometres (1 mile) away from dining and retail options. To make the best use of the fully equipped kitchen, guests can grab their grub from the local grocery store, The Trading Post, which is approximately 61 metres (200 feet) away.
Guests bringing a boat will have to request a dock space in advance for a fee. The property features a private patio and a heated, plunge pool that looks over the bay. Paddleboards and beach cruisers are also provided so that guests can conveniently explore the area.
Stay for a month to enjoy discounts! Do note that a cleaning fee applies.
Islamorada, Florida, United States
48.75 km (30.3 mi) from Everglades National Park
Top guest reviews
Host:
giovanna was a wonderful host thoughtful communication was helpful and she has thought of it allgiovanna was the perfect hostthe house is beautiful and giovanna is a fabulous hostwe met some of the neighbors who were very polite & friendlyour host giovanna was very accommodating and had excellent communication skillsLocation:
wonderful property located in an excellent location on islamorada with several restaurants and stores within walking distancethe location is also greatwe loved the location and the settingi highly recommend this locationthe location is perfect and the house is immaculateCleanliness:
the property was exceptionally clean and was turn-keythe house itself was beautiful clean and well keptthe house is beautifully decorated and spotlessthey house is extremely clean and decorations are well thought outRead more reviewsAmenities & Room:
the open water views from the dock and pool area are fantasticboth pools are beautifully maintained & we used them frequentlythe beds sheets pillows are high end and very comfortable
8. Beautiful home on a dock
Best for: Luxury travelers, beach lovers, families with kids, group stays
Fancy steering your boat to check into your vacation home? Located on an 18-metre (60-foot) deep water dock in Plantation Key, this property allows you to do just that. The property also includes a porch and a wrap-around balcony. The most alluring feature is the hot tub on the deck that overlooks the waters. Founder’s Park is just 3.4 kilometres (2.1 miles) away, where you’ll find entertainment on the beach, pool, marina and dog park.
Book a stay of at least 28 nights to enjoy a monthly discount. Do note that administrative and cleaning fees apply.
Plantation Key, Florida, United States
48.37 km (30.1 mi) from Everglades National Park
Top guest reviews
Host:
the home has all the amenities and the owners were easy to reachLocation:
close to great restaurants and the grocery storelots of shopping and great food close by as wellthe location by land and water were greatthis was a beautiful quiet relaxing location to come back to after a day of scuba divingCleanliness:
the house was clean comfortable and well stockedRead more reviewsAmenities & Room:
exactly as pictured very relaxing spacious good beds good linens fully stocked kitchen great viewthe hoses fish cleaning station and ample room on the deck made every adventure smooth
9. Boutique home with access to private beaches
Best for: Families with infants, watersports enthusiasts, beach lovers, group stays
Checking into this property grants you exclusive access to the gated community located in Anglers Reef. With 52 villas and 30 boat slips, you’d be living in luxury amongst fellow water enthusiasts. Shared amenities include a heated swimming pool, two private beaches and landscaped gardens that look over the magnificent Atlantic Ocean. Hosts have kindly provided free wifi, beach towels, as well as booklets on dining and attractions so that you can plan your stay with ease.
There’s a monthly discount to score and a cleaning fee applies.
Islamorada, Florida, United States
48.44 km (30.1 mi) from Everglades National Park
Top guest reviews
Host:
gorgeous house and the owners were greatour initial booking contact with the owners was easy and we always received quick responsethe owners were incredibly helpful and responsive with the bookingCleanliness:
the property - the house is very well laid out and is beautifully designed and spotlessly cleanthe unit itself is very nice and cleanRead more reviewsAmenities & Room:
all appliances worked well furniture is comfy and the beds were outstandingbeautiful condo 100 feet from the pool and beach
10. Luxury villa in the heart of Florida Keys
Best for: Families with kids and infants, watersports enthusiasts, group stays
Situated in Angler’s Reef, a luxurious gated community in the centre of Florida Keys, this home welcomes up to eight guests for a restful stay. The first- and second-storey feature wrap around balconies, where guests can enjoy breathtaking sea views and the soothing ocean breeze. The kitchen is fully equipped and laundry facilities are provided. You can bring your own boat and dock it in the boat slip. Otherwise, you’ll have access to kayaks loaned by the community on a first-come-first-served basis.
Monthly discounts are available for long-term stays. A cleaning fee and property damage insurance apply.
Islamorada, Florida, United States
48.47 km (30.2 mi) from Everglades National Park
Top guest reviews
Host:
the owner was wonderful and very helpfulowner and property manage were extremely helpful and quick to respondLocation:
very enjoyable location and the accommodations were perfectthe location right at the pool and marina front made it even betterthe location of anglers reef gave us great access to the ocean and bayCleanliness:
you have a beautiful and very clean homethe house was very comfortable and cleani’m not on vacation to clean a house in better condition than when i arrivedhome had everything we needed clean and well stockedRead more reviewsAmenities & Room:
we love this community because of the view pool & the relaxing atmospherelovely property nice views of ocean and poolour kids enjoyed the pool and the 'old school' video game table on the main levelthe pool was well maintained and our family enjoyed the time togetherthe pool was warm & wonderful too
11. Cosy flat at Futura Yacht Club
Best for: Beach lovers, families, group stays
Located in the private community of Futura Yacht Club, this unit welcomes guests for month-long stays. The club features a heated, outdoor pool and a tennis court. Within the unit, you’ll find a balcony, from where you can look over the garden while sipping on a cuppa. A fully equipped, private kitchen is at your disposal, but you’d have to use the communal washer and dryer located on your floor.
Monthly stays are entitled to a discount and a cleaning fee applies. Make your reservations early as this rental unit is a favourite with vacationers!
Tavernier, Florida, United States
49.04 km (30.5 mi) from Everglades National Park
Top guest reviews
Host:
joe the owner was super accommodatinggreat communication with the property owner and the boat dockage was top notch will definitely stay againLocation:
the location is perfectgreat location and quiet complexhave free access to founders park beach which was also beautifulwe were in town to visit with friends and wanted a comfortable conveniently located place to stayperfect location to explore the keys and relaxCleanliness:
condo was very clean and comfortablethe condo was very clean and was also very well stockedthis was such a clean and well appointed place to stayproperty was quiet and cleanclean all the essentials and lovely groundsRead more reviewsAmenities & Room:
the condo was very well appointed and the bed was so comfortablethe boys enjoyed fishing off the dock every night followed by a swim in the beautiful poolthe condo was nice and cozy and maintained really well
12. Bayside house in the heart of Islamorada
Best for: Families, beach lovers, group stays, luxury travelers
This luxurious oceanside retreat is ready to accommodate up to 10 guests, with 5 bedrooms and 4 baths allowing everyone to feel at ease. It comes with mod-cons such as a large-screen TV, two-door fridge, and central air conditioning, perfectly complementing the house’s chic interior.
With a full kitchen at your disposal, preparing delicious meals for everyone is a breeze. At the backside of the property, there’s a gorgeous pool area where you will be treated to stunning views of the sea and sun as you take a dip in the swimming pool.
Islamorada, Florida, United States
48.57 km (30.2 mi) from Everglades National Park
Top guest reviews
Host:
the home owners couldn’t be more courteous and attentive when ever we contacted themshe is extremely responsive and made us feel that she was always a text or call awaythe owners were great and very prompt in respondingthe owners were fantastic to deal with and extremely responsiveour group which was three couples thoroughly enjoyed the updated waterfront home and the owners attention to detailLocation:
great location walking distance to many great restaurants and storesexcellent property and great locationthe house is conveniently located close to all of the best restaurants and barsvery convenient location bedrooms are spacious and our group of 10 slept very comfortablyCleanliness:
the house was very clean and extremely well stocked (kitchen towels extra linens cleaning supplies puzzles)it is so classy and clean and stylisheverything was great the property was very clean and has clearly been renovated recentlythis property is absolutely beautiful clean everything you need and morehouse is tastefully decorated in a clean upscale beachy decor and very comfortable for all ages 1-64Read more reviewsAmenities & Room:
the heated pool came in handy as the nights got very cool during our staywe fished watched the manatees and loved the heated pool
13. Lovely cottage with an expansive deck
Best for: Pet parents, families with kids and infants, group stays
With a spacious deck and docking area for a boat, this cottage is designed for guests who love the outdoors. The swimming pool is kept pristine and has sun loungers by its side, so you can top up your tan. The second-floor has a terrace where you can enjoy your meals while taking in the canal and pool views.
Upstairs, there’s also a fully equipped kitchen and a plush living area with a TV. The four bedrooms can fit a total of eight guests, and the three bathrooms provide enough room for everyone to keep fresh and clean.
Islamorada, Florida, United States
50.07 km (31.2 mi) from Everglades National Park
Top guest reviews
Host:
very pet friendly home with fenced in yardLocation:
quick walk to fresh seafood marketRead more reviewsAmenities & Room:
recently remodeled with coastal decor great furnishings and a pool which was invaluable with the kids( ceiling fans throughout house and maintenance on the wood deck) beach privilege on bayside was enjoyable
14. Gorgeous oceanfront house with five bedrooms
Best for: Watersports enthusiasts, families, group stays, beach lovers
This sleek and stylish oceanfront house can sleep 10 people in its 5 bedrooms. Each room boasts incredible views of the ocean. When not at the private beach, which is steps away from the property, cool off in a private pool. It can also be heated for extra relaxation.
When you aren’t going for a swim, you can even sit back and sunbathe poolside on the comfy lounge chairs. Active guests can fish or kayak from the private observation dock, or just enjoy the views. Three kayaks and two paddle boards are available in the house.
Islamorada, Florida, United States
49.75 km (31.0 mi) from Everglades National Park
Top guest reviews
Host:
the owner was gracious and helpful with all of our questionsowners were easy to work withchausey is an awesome hosteverything was as expected from the listing and the host was helpful and easy to work withLocation:
a wonderful location to rest relax and recoverwe loved the house and locationthe location the layout both inside and out and the access to fun activities were all huge benefitsexcellent location with magnificent viewsRead more reviewsCleanliness:
light bright and clean it has everything you need for a great beach vacation
15. Happy Tarpon
Best for: Families with kids and infants, watersports activities, group stays
Happy Tarpon is an inviting and spacious house, with a large yard and a boat dock. Active guests can indulge in boating, fishing, canoeing, and other outdoor activities nearby. The house also has an outdoor swimming pool, which is easily accessible from the living area and kitchen. The pool is heated, so you can enjoy a swim at any time of the year.
For those less athletically inclined, there’s a sunning deck for relaxing and cable TVs and wireless internet access to keep you entertained. Inside, you’ll also find three bedrooms and three bathrooms, allowing up to six guests to stay here. The kitchen is fully equipped for cooking and baking needs.
Islamorada, FL, US
16. Perfect Escape
Best for: Families with kids, group stays
If you want the perfect escape from the urban grind, the aptly named Perfect Escape residence is your ideal spot. With four bedrooms and four bathrooms, up to eight guests can sleep soundly here.
A large cabana, sun loungers, and a living room are all perfect spots where you can spend quality time with your family. You can splash around with your loved ones in the private pool, which can also be heated for an extra cost of 250 USD per week. For more water fun, a boat is also available for rent on site — just be sure to contact the owners in advance for arrangements.
Islamorada, Florida, United States
48.45 km (30.2 mi) from Everglades National Park
Top guest reviews
Host:
everyone was very friendlythe owner was so easy to work witharlene was very responsive to questions prior to and throughout our stayarlene was super responsive to any questions and or needsthe set up is perfect for multiple families and the owner is very responsive with any questionsLocation:
great house to stay and perfect location just minutes from the atlanticgreat location and convenient to have dock for boatgreat location with a boat rental company very closethe house and the location couldn’t be betterCleanliness:
upon arrival everything was super cleanone dish rag and one hand towel per bathroom was inconvenient since clean ones are needed dailythe house was clean and there was ample parking for three cars and a boat trailerthe house was spotless everything works well and arlene was a terrific and extremely accommodating hostRead more reviewsAmenities & Room:
the balcony had amazing views of the pool and waterexcellent location nice pool gated yard and plenty of dock space that has recently been redonefantastic place for family and friends with a pool
17. Luxury home with magnificent ocean views
Best for: Group stays, luxury travelers, families, beach lovers
Live the resort life at this property! This elegant home is great for 12 guests and features amenities to keep everyone entertained. The property comes with a heated pool, sunset deck, hot tub, fire pit and outdoor grilling area for guests to make the most of the scenic views around it. From the dock area, guests also have quick access to the ocean. Additional services such as daily housekeeping and a personal chef can be arranged for a fee.
Discounts apply for a stay of at least 28 nights. Charges apply for pool maintenance and cleaning.
Tavernier, Florida, United States
48.62 km (30.3 mi) from Everglades National Park
Top guest reviews
Location:
the secluded waterfront location is ideal for boating and water sports and close to restaurants and shopsbeautiful modern house in a great locationRead more reviewsAmenities & Room:
indoor kitchen has only the finest appliances and a huge island that seated all 7 of usbeds were all comfortable and pantry and cupboards were stocked with basic necessities
18. Southern Diversion
Best for: Families with kids and infants, beach lovers, group stays
The first thing you notice when you arrive at this estate is the lush façade lined with beautiful palm trees and a well-manicured pavement leading to the house. Relax on the enclosed balcony and enjoy 180-degree views of the Atlantic Ocean.
The house is situated on a beautiful beach equipped with lounge chairs, where you can relax and watch the sun go down. Between the beach and the house, there’s a nice pool area for unwinding. The home is suitable to sleep up to 16 guests.
Islamorada, Florida, United States
48.45 km (30.2 mi) from Everglades National Park
Top guest reviews
Host:
The caretaker John was very helpfulThey could use some more pool towels Owner not the easiest to work withthe groundskeeper was super-helpful and available whenever we needed himwell-kept responsive owner to questions and requests and a great conciergeI P experience and was very helpful in explaining the dock lift channel to bring our boat inLocation:
Conveniently located to good restaurantsThe house is in the perfect location being close to restaurants and activitiesThe dock was a perfect This area of the island has plenty of restaurants activities bars and shoppingThis property is directly across the street from an amazing spaVery close to great dining and convenient to shopping and the tackle shop We will definitely return for another stay but longerCleanliness:
The house was exactly as describedThe pool was lovely as were the views from this spacious propertyThe four bathrooms were greatthe house is very well appointed clean large and roomyWe were able to accommodate approximately fifty guests caterers a bandRead more reviewsAmenities & Room:
towels - everything you will need for outsideOur family came here to celebrate our parents 40th wedding anniversary and it was amazingThe house had plenty of room for all our extended family including a bunch of young kiddosThe bunk room was perfect for all the cousins to sleep inThe property was just beautiful - from the tree lined drive up to the front of the home to the postcard-like views of the ocean out back
19. Beachfront home for eight
Best for: Beach lovers, families, pet parents, group stays
This peaceful, beachfront home offers you the opportunity to spend your evenings on the beach with your four-legged friend. It’s pet-friendly, and located right in front of a sandy beach. The house is furnished with a 60-inch smart TV in the living room and a 40-inch smart TV in each bedroom. Furthermore, you’ll get to enjoy breathtaking ocean views from every angle of the house. The house has free Wi-Fi and air conditioning as well.
Islamorada, Florida, United States
48.65 km (30.3 mi) from Everglades National Park
20. Tipsy Turtle
Best for: Families with kids and infants, beach lovers, group stays
Known as Tipsy Turtle, this cozy home has two beautifully appointed bedrooms that can sleep up to six people. Located just a stone’s throw away from the private beach, the home has four balconies, where you can enjoy a glass of wine with the ocean vista and soak in the essence of Islamorada.
When dinner beckons, you can either cook on site in the fully functional kitchen, or head to the oceanfront restaurants, which are just a five-minute walk away. It also features a plush living area with a TV, a wonderful dining room, and guests have access to the community pool with views of the Atlantic Ocean.
Islamorada, Florida, United States
48.51 km (30.2 mi) from Everglades National Park
21. Two-bedroom condo with a balcony
Best for: Families with kids and infants, group stays, beach lovers
Looking for a place that’s close to the beach where you can stay for a week? Check out this idyllic rental nestled in a lush forest, just a short walk from the beach. Its balcony offers striking views of the vast turquoise waters. While here, take advantage of the free wireless internet connectivity to update your socials and to connect with your family back home. The property has a lovely beach surrounded by lounge chairs and palm-thatched shades.
Tavernier, Florida, United States
48.97 km (30.5 mi) from Everglades National Park
Top guest reviews
Host:
She returned all emails and text messages very quickly and answered all questionsWe had great communication with the ownerthat make them balance outHopefully she will have us back in the futureWe met several really nice people at the poolLocation:
Perfect location for a quiet getaway Off the main highway just enoughThe location was just perfect alsoMany restaurants and shops Overall wonderfulIt's a great location/walk along long white sugary sandy beachesCleanliness:
It was very clean and brightVery nicely furnished and very cleanThe owners also had plenty of informational notebooks and pamphlets to assist with "Things-to-Do" and/orThe unit is very clean and well appointed and Donna is a pleasure to work withThe condo itself is extremely clean very comfortable and boyRead more reviewsAmenities & Room:
Bed was very comfortable plenty of towels in bathroom pool at condo isThe beds provided excellent sleep and sweet dreamsThe pool is immaculate and the charcoal grills on the beach were greatEverything was pretty much as advertisedbut both have features (en suite bathroom in one; big sliding door to balcony in the other)
22. Gorgeous abode with two beaches
Best for: Watersports, families with kids, beach lovers, group stays
Marvel at the red-hued sunsets while chilling on the balcony while sipping your favorite wine. Nestled in the welcoming community of Anglers Reef, this house has two nicely decorated bedrooms and three bathrooms. From here, guests can walk to the nearby local bars, restaurants, and Snake Creek Marina.
Guests will enjoy access to the two beaches — North beach which is a short stroll away, and South beach, which has a kayak for those who want to explore the waters. There’s also a resort-style pool that invites you in for a relaxing dip.
Islamorada, Florida, United States
48.5 km (30.2 mi) from Everglades National Park
23. Two-bedroom home with a heated pool
Best for: Beach lovers, watersports enthusiasts, families, group stays
With a maximum occupancy of up to six guests, this home is ideal for a family getaway. The rental is situated a few steps away from a private beach, where you can go for leisure walks. Take advantage of this location to bring your kayak or boat for a wonderful adventure. Here, you will have plenty of entertainment, thanks to the three large flat-screen TVs in the house. The home has high-speed Wi-Fi, and a heated pool to relax in.
Islamorada, Florida, United States
48.41 km (30.1 mi) from Everglades National Park
24. Sunrise Haven
Best for: Pet parents, watersports enthusiasts, beach lovers, families with kids, group stays
This elegant condo, within a resort, is an ideal space for a family or group of six people. Once you’ve explored the condo, which comes with three bedrooms, a full kitchen, a spacious living room and a great room with a HDTV, stereo system and a wet bar, turn your attention outside. All the rooms of this condo have a balcony and large windows boasting stunning views of the ocean or pool.
Guests have access to the community pool, a hot tub and a pristine beach, which are mere moments away. Stand-up paddle boards and kayaks are available for guests’ use. Several restaurants, arts district, and the marina are easily accessible from here. Feel free to come with your furry friend as the condo welcomes up to 2 dogs less than 23 kg (50 lbs).
Islamorada, Florida, United States
49.27 km (30.7 mi) from Everglades National Park
Top guest reviews
Host:
steven is an excellent communicator and an extremely kind landlordthe property manager jeff was very responsivethe owners were very responsive and a pleasure to work withjeff the owners son was really nice and pleasant to work withowners communicated well throughout the booking process and were even available during our stay with any help neededLocation:
a terrific location and great propertysuper convenient location to dining and shopping and several marinas with chartersthe location is close to lots of good restaurantsthis is a great place to stayCleanliness:
nice experience clean and all facilities worked wellthe condo was clean and well equipped and pool was great for our kidsRead more reviewsAmenities & Room:
loved the pool (although the water temperature was way too warm) and easy access to everythingpool and hot tub were warm and beautiful
25. Rental with a private oceanfront
Best for: Nature lovers, beach lovers, pet parents, families with kids, group stays
Elegance and sophistication, that’s the aura exuded by this four-bedroom home. Sitting in the Islamorada’s Millionaire’s Row, this accommodation will make you feel like one of the rich and famous. The beach is right outside the house and you need not worry about bumping into other beach goers as it’s exclusive to this house. Settle in and take advantage of the swimming pool which is set amidst lush tropical trees. You also get a well-fitted kitchen that boasts elegant, silver appliances. The living room is spacious, cozy and a perfect place to relax at the end of the day. You can hang out here and watch the television or sit outside on the deck and be awed by the spectacular view.
Tavernier, Florida, United States
48.98 km (30.5 mi) from Everglades National Park
Top guest reviews
Host:
The pool was a huge hit with our kids and usthe owner was helpful answering any anddock for fishing or keeping a boat clean almost new pool and spa laundryAll questions and concerns were quickly responded to and taken care ofWe caught many mangrove snappers from the great dock and made yummy fish tacos two different nightsLocation:
It's near to many great restaurantsJust a great vacation and the perfect location to good restaurants and charter boatsThe boys took the paddle boards out on a very calm seawe felt secluded yet close to everythingWe all enjoyed the salt water swimming poolCleanliness:
The house was incredibly clean and well stocked with plenty of towels and beach towels as wellThe house had everything we needed and the property is truly privateThe ocean views and sunrises were outstandingRead more reviewsAmenities & Room:
The house was just like the pictures and very comfortable for all seven of usThe downstairs suite was so private and the upstairs three bedrooms were laid out to perfectionThe kitchen was well stocked and all appliances worked great as did the air conditionerThe driveway to the house sets the stage and the expansive yard to the oceanThe kids loved fishing off the dock while we lounged in the spa
26. Tiny paradise complete with pool
Best for: Families, couples
This listing is located beneath the owner’s apartment. Despite its location, the guests have total autonomy on the property and complete privacy as the owners prefer not to meddle with the guests’ activities. The house itself has a mini kitchenette and refrigerator. What’s best, however, is the pool, spa, barbecue grill, and Tiki hut that is available for the guests to use.
185 Plantation Dr
48.72 km (30.3 mi) from Everglades National Park
27. Penthouse overlooking the serene blue waters
Best for: Beach lovers, families, group stays
This property is a penthouse with two bedrooms and it can sleep up to four persons. That being said, its high location gives the best sightseeing view of the blue and fresh waters of Islamorada. It is perfect for boaters as the listing also features deep water dockage and an on-site boat ramp. Also, storage for the boat trailers is provided with no extra expense. In addition to that, the owner is kind enough to offer to hook up the guests with charter boats and the best of the best boat captains.
48.65 km (30.3 mi) from Everglades National ParkTop guest reviews
Host:
Love the pool marina and gardens of the propertyIt is huge and also nice and warmThe Yacht club property was great with pool and marinawe rented a boat and dock in marina and had a great time againThe owner is very nice and very easy to work with Very close to everything Will definitely be backLocation:
bars and shops to choose from in areaReally liked the security of a gated communityWe especially loved the picnic and BBQ areaLocation was easy for walking to restaurants or driving in either directionThe pool is a short walk from the building which is good for Senior citizensCleanliness:
The premises were well kept with good facilities and lovely sea viewsRead more reviewsAmenities & Room:
The kitchen was amazing with real chinaCondo was comfortable with a beautiful viewEverything was spotless and the beds and the furniture were all comfyEverything that you need was in the unitThe unit has all of the updated amenities to enjoy comfort and relaxation
28. Private and gated townhouse
Best for: Families, outdoor enthusiasts, group stays, beach lovers
This townhouse listing is located in the Florida Keys. It is part of the Exclusive Bay Club that provides daily free access to amazing amenities and facilities. Guests may access and use two tennis courts, a swimming pool, a clubhouse, a private beach area and a fishing dock. In addition to that, all of these are within the gated vicinity of the neighborhood. The townhouse itself has a fully equipped kitchen, a flat screen television in every room, and a barbecue grill and picnic tables.
49.08 km (30.5 mi) from Everglades National ParkTop guest reviews
Host:
We contacted the manager and hopefully they will be available for the next guestWe felt very welcome by everyone in the complexcoffee machines are all in good order More small appliances in stocknice and warm Garbage is picked up promptly People are very friendlyKitchen - more than enough dishes and utensils and of good quality Fridge stoveLocation:
The location was perfect for attractionsThe best beaches were closeplus there is plenty of activities and shopping within 15 minutes either directionA dock and beach are a 2 minute walk from your front doorWe spent the month of March 2019 in this townhouse at the Executive Bay ClubCleanliness:
but we didn't use Tennis rackets and ballsplace was clean and very efficientIt was clean and niceand we were very comfortable thereThe tennis court is right beside the unitRead more reviewsAmenities & Room:
The down stairs bathroom with a small shower was adequateThere is only one pot in the kitchenIt was also nice that there were some chairs and an umbrella for the beachThe back padio was a plus and a wonderful spot to set outside and enjoy the suroundings however follage that surounds the padio is in need to trimming and cleaning up Spiral stairs to the second ...We have twin 7 yr olds and a 8 month old
29. Tropical bungalow with a whole list of activities
Best for: Couples
This two-bedroom tropical bungalow can house up to four individuals. It is situated in the perfect location to experience everything Islamorada has to offer. The owners are even kind enough to patch up a whole list of activities, restaurants, and places to go to. It is also freshly renovated after typhoon Irma struck. It is, however, important to take note that pets are not allowed in the property.
49.96 km (31.1 mi) from Everglades National ParkTop guest reviews
Host:
They also have an excellent binder with great reviews of things all around the Keys for you to enjoy Very very thoughtful and responsive ownersThat heated pool is the bestWe met some of the residents and they were very nice and had good advice for local restaurants Would definitely recommend this cottageWe absolutely adored the swimming poolThe owners Bill and Maggie were very responsive to all of our questions we had along the wayLocation:
We felt very safe at this location and were within 30-45 minutes of many things to do and within probably 60-90 minutes of Key West depending on trafficIt really was a home from home which was in a quiet area and local to shops and great restaurantsThe house was just want we were looking forHaving a washer and dryer was a huge bonus and allows you to pack a little less than you normally would We took advantage of the bikes that Bill and Maggie provided taking daily bike rides to diff...We rented two additional bikes and rode to Robbie's a number of times forCleanliness:
The bungalow was neat and clean and the owners were a joy to work withwhich I think we occupied each eveningThe neighborhood was nice and cleanThe community is very clean and quiet Will definitely be back for another visitPersonally we went kayaking and parasailing--both which were amazingRead more reviewsAmenities & Room:
The living room was comfortablevisiting bahia honda state parkIt had everything we needed to make our vacation comfortable cozy and easyThe home is immaculate and has everything you could possibly need Very tastefully decorated with comfortable beds and nice linensWe loved the kitchen & grill for cooking
30. High-end condominium with oceanfront views
Best for: Waterports enthusiasts, families, group stays
This two-bedroom condominium unit can accommodate up to six individuals. It boasts of having a high-end interior design and appliances. It has a kitchen, fully equipped with high-end appliances and cookware. Furniture is also, of course, upscale; it has a pottery-barn sofa and Prana mattress among others. The location is just a walking distance away from luxurious restaurants, thrilling water activities, as well as, the shopping district. To top it all off, it has a swimming pool that is heated up during the winter season.
49.25 km (30.6 mi) from Everglades National ParkTop guest reviews
Host:
The owner Sandy was very helpful to us with anything we neededOwner Sandy is awesome Condo is awesomeBeautiful condo and the owner is so easy to work with Definitely will stay againMost are done in fairly cheap beachyLocation:
Although there is still quite of bit of damage to the keys from the previous hurricane we did not have a problem finding plenty of places to go out to eat and there was plenty of staff around to he...which is only a half mile away there are numerous things over there to take advantage of such as 1 Heated olympic swimming pool 2 tennis courts 3a sandy beach on the bayIt is so nice that many days you can be content just to sit around the condo The condo has a very nice albeit small pool Because of the small size it is generally very warm which is really nice ...Read more reviewsAmenities & Room:
Other tenants / owners are awesomeThe view out the front of her condo is mesmerizing Also to watch the sunrise in the early morning is just spectacular
31. Tropical property near the ocean
Best for: Watersports enthusiasts, beach lovers, families, group stays
Situated near the ocean, this tropical bungalow gives off the feeling and atmosphere of being disconnected from the toxicity of life. Despite that, it is near luxurious restaurants, pubs, marinas, and shopping centers. It is only two blocks away from the ocean where guests may enjoy fishing, boating, kayaking, and other water activities.
49.95 km (31.1 mi) from Everglades National ParkAccommodates: 4
Minimum Nights: 7
Refund Policy : 100% refund if you cancel at least 30 days before check-in.
Top guest reviews
Host:
We like having personal recommendations to guide us while on vacation" The owner Caitlin was very attentive to any questions we had with speedy responsesgreat clean new fun great poolso we checked out many of the places suggested in the welcome packetAll info regarding the home was honest and accurate Couldn't ask for better weather which always helps a reviewLocation:
Outdoor activities and restaurants are close byand we enjoyed it several timesThe bottle of Prosecco was a nice surpriseMy family enjoyed the activities snorkeling parasailingThe location is very close to all restaurants food stores and fun places to visit Recommend you visit Founders ParkCleanliness:
well decorated and up to date) and perfectly appointed; towels linensOur bungalow was we clean and had everything we neededIt was very clean and comfortableI loved the simplistic beachy feel of the cottage and found the place to be clean and well equippedRead more reviewsAmenities & Room:
It was very nicely equipped with a functional kitchen and modern bathroom with showerIt was wonderful and had everything we needed includedThe unit itself was also smaller than we were expectingyou wont be sorryupdated and pool was nice Home can be a little noisey at night because of the highway
The village of islands
Islamorada is quite famous as the sport-fishing capital of the world and welcomes guests to stay at an all-inclusive resort nearby. Unsurprisingly, the village is the place to be for people who love the ocean or enjoy playing around in the water.
Consisting of various islands and bays, this destination is just perfect for all kinds of tourists- both casual goers and hardcore ocean lovers. If you’re planning to visit and looking for where to stay in Islamorada, be sure to keep this list handy!
Frequently asked questions about the best Vrbo vacation rentals in Islamorada, Florida
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