Florida is a world-renowned tourist destination, but have you ever heard of Islamorada? This little hamlet is hidden away in the Florida Keys, a location that allows it access to the attractive coral reefs in the area. Being a small village, Islamorada is a wonderful getaway destination for those seeking a serene vacation, devoid of the general rush of the city. It’s characterized by lush tropical forests that surround the stunning holiday homes. Attractions in this area include the Lignumvitae Key Botanical State Park and the Windley Key Fossil Reef Geological State Park. Escape the crowded cities of Florida and settle down in Islamorada. Here are our suggestions for vacation rentals in this destination. Check them out below.
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 March 22, 2024.
1. Private oceanfront house (from USD 928)
Eight guests can stay in this house, one that’s suited for a group of friends on a vacation or even a family visiting Islamorada. If you stay here, you’ll be in a serene, tropical setting in the heart of La Jolla Resort. At your disposal will be two acres (0.8 hectares) of lush lawns and exquisite tropical trees. The house itself has three bedrooms, with a total of four beds set to offer comfort to all guests staying here. The deck area outside is aptly placed to offer a breathtaking view of the ocean, visible just beyond the trees. And, of course, you get all the homely facilities from a spacious living area to a well-equipped kitchen.
Top guest reviews
Read more reviewsLocation:
great location and roomy accommodations for our groupwonderful location beautiful scenery and great service
2. Three-bedroom oceanfront house (from USD 1028)
This is another house that’s nestled in La Jolla Resort, offering all the benefits similar to the house above. These include proximity to the stunning beach, an unfettered view of the ocean, a serene tropical garden in the compound and a luxurious home for you and your friends. This house can host eight guests. But unlike the house in the listing above, this one has a covered deck, shading you from the sun but still offering an excellent view of the ocean. Inside there’s a luxurious living room, a spacious dining area and a fully equipped kitchen, a major selling point for those intending to prepare their own meals.
Top guest reviews
Host:
staff were very nice and were helpfulRead more reviewsLocation:
great location close to everything
3. A private oceanfront cottage (from USD 225)
Stay in this private cottage that places you right at the beach. With the ocean outside your front door, you have all the reasons to spend all your time on the fine golden sands of the beach. This cottage has just one bedroom, but it still can host up to four guests. The interior is just like any other home, with a cozy living room and a spacious kitchen/ dining area. And, yes, you can prepare meals if you choose to, in this fully equipped kitchen. The bedroom has a queen bed and a large-screen television is mounted on the wall adjacent to it so you’ll be able to fall asleep while watching your favorite show.
Top guest reviews
Amenities & 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 paradiseCleanliness:
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 aboutHost:
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 rampRead more reviewsLocation:
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 Pablo
4. Five-bedroom house (from USD 1499)
If listing four above still isn’t large enough for your party, then consider this five-bedroom house. This one can host a whopping 16 guests, meaning no one will be left behind. Have fun exploring Islamorada which is a short walk from the house. You also get a private beach area that stretches for 60 meters (200 feet). Other than the house, which is quite well decked out, you also get access to a heated pool and WiFi connectivity. This beautiful wood-clad mansion is such a welcoming rental, offering delightful views of the ocean at all times of day.
Top guest reviews
Amenities & 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 backCleanliness:
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 bandHost:
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 inRead more reviewsLocation:
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 longer
5. Beautiful Islamorada home (from USD 745)
With a look that blends in well with the tropical landscape and a magnificent view of the ocean right from the house’s balcony, this vacation rental argues a good case as a prime home for those visiting Islamorada. It has four bedrooms and three bathrooms and can comfortably accommodate eight guests. The kitchen is meant for culinary aficionados. Spacious and well-equipped, there is nothing you can’t cook here. Of course, there’s also a large living space that’s adorned with chic furniture, a perfect place to relax after a long day. You also get a swimming pool so you have all the reason to spend time in the water.
Top guest reviews
Amenities & 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 tooCleanliness:
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 stockedHost:
the owner was wonderful and very helpfulowner and property manage were extremely helpful and quick to respondRead more reviewsLocation:
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 bay
6. Mitchell’s bay-view villa (from USD 325)
Surrounding this house are breathtaking views. On one side is the Florida Bay and the other the stunning Everglades. In the evenings, this picturesque view is colored by a stunning sunset hue. This is a representation of what paradise is, and it’s all at your disposal when you stay in this two-bedroom villa. Another reason you should book this house is that it’s just 9 meters (30 feet) from the soothing ocean waters. If you’re not yet convinced, then you’ll be glad to know that there’s a marina on the property as well as a wading beach. The house can sleep six with two bathrooms.
Top guest reviews
Amenities & 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 outstandingCleanliness:
The views are amazing and the villa is updated and cleanHost:
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 boatRead more reviewsLocation:
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????
7. Rental with a private oceanfront
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.
48.98 km (30.5 mi) from Everglades National ParkAccommodates: 8
Minimum Nights: 7
Refund Policy : 100% refund if you cancel at least 60 days before check-in.
Top guest reviews
Amenities & 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 spaCleanliness:
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 outstandingHost:
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 nightsRead more reviewsLocation:
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 pool
8. Executive Bay townhome
Islamorada’s heavenly beaches are a major reason you should visit and this townhome offers a quick and easy access to one such beach. Found in Executive Bay Club, the vacation rental is only a stone’s throw from the ocean. In fact, you need only stroll a few minutes to be on the fine golden sands. If you hardly ever get enough of the water, you can spend time in the pool on the property. And when you need to get your blood flowing, try a game of tennis in one of the two tennis courts available. This townhome boasts two bedrooms, each one elegantly furnished, offering a comfortable sleep for up to six guests. All the creature comforts of a modern home are available here, from a flat-screen TV in each of the bedrooms and the living room to laundry facilities.
Islamorada, Florida, United States
48.65 km (30.3 mi) from Everglades National Park
9. Oceanfront house at the pier
Can’t get enough of the ocean? Then check out this four-bedroom house that is the perfect place for a large group of travelers. If you’re planning a getaway with your extended family or your colleagues, then go ahead and book this lovely home. From inside the house, you’ll be constantly marveled by the view of the ocean, a view that only gets better from the deck outside. Being a modern home, you won’t lack in amenities like a beautifully furnished living area, a spacious kitchen and even WiFi. On top of these, you’ll also have access to a swimming pool on the property as well as a tennis court.
Islamorada, Florida, United States
48.79 km (30.4 mi) from Everglades National Park
A dream vacation
Enjoy a dream vacation in Islamorada by booking yourself one of the vacation rentals above. You’ll be within easy reach of the beach and with plenty of amenities to ensure you live in comfort. Explore Islamorada and gather an unforgettable experience.
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