If you desire to visit a place with blue waters, amazing wildlife, tasty seafood, fun encounters, and gorgeous sunsets in Florida, then make Islamorada a priority. In this oasis of breathtaking scenery, you can let go and enjoy every minute of your vacation. The picturesque village is a water sports paradise with so many exciting things to do. Visit Robbie’s Marina of Islamorada and engage in offshore fishing, snorkeling, kayaking, and feeding tarpons. Hire a glass-bottom boat on the same site to explore the coral reefs and fish species. At Theater of the Sea, you can swim with dolphins. The conservation park was established in 1946 and is home to nurse sharks, sea lions, turtles, and dolphins.
To help you relax in comfort and explore the village with ease, you need to find a place to stay first. Luckily, you can find many fantastic Airbnbs in Islamorada. Some of these rentals even have a boat dock. For more suggestions, check out this list of the best vacation rentals with boat dock in Islamorada, Florida.
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 June 28, 2025.
1. Spacious townhouse with pool (from USD 286)
Looking for one of the best places to stay in Islamorada with a boat slip? Then check out this Airbnb vacation rental in Islamorada.
Immerse yourself in relaxing vibes by residing in this chic and spacious townhouse for four guests. You’ll fall in love with its modern conveniences. In the living room, you’ll find an HDTV and in the kitchen, there’s a Samsung refrigerator. Watch manatees swim by from the deck or take quiet walks on the private beach area for a relaxing time.
The boat slip in front of the townhouse is available for rent. Besides that, you can take full advantage of the heated swimming pool, fish cleaning station, and tennis court while staying in the rental.
Islamorada, Florida, United StatesAccommodates: 4
Top guest reviews
Host:
claire was a wonderful host and she has a lovely homeclaire is a wonderful host that exceeded expectationsclaire is a very good host and answered very quick when i had questionsclaire was an amazing host that was quick to respond and clarify any questions i hadhighly recommend this rental and this hostLocation:
the location is perfectnice townhome with great locationgreat central location in the keysso close to our new favorite restaurantsthe location of claire’s place was perfectCleanliness:
very clean space beautiful townhomethe place was very clean and nicely decoratedthe condo was very clean spacious and well stockedthe townhouse was extremely clean and comfortablethe pool was beautiful clean and refreshingRead more reviewsAmenities & Room:
also the pool is huge heated and with plenty of lounge chairs
2. Bay Harbour Starfish (from USD 459)
Bay Harbour Starfish, a luxurious three-bedroom condominium, is spacious enough for six guests. As it’s set facing the Atlantic Ocean, you wake up to lovely water views each morning. Also, it has a 30-ft (9-m) boat slip where you can park your boat.
Watch boats ply by while dining on the screened-in patio. Make good use of the heated pool and hot tub if you’re looking to soothe your body after a day’s travels. A well-equipped gym is available on the property as well.
Islamorada, Florida, United States
Top guest reviews
Host:
lee was super helpful and a great hostfirst off the owners were super helpful and responsivethe landlord was very helpful throughout the process and always responded quicklythank you to the owners for allowing their beautiful condo to be rentedthe owners were in communication prior to our trip and made the experience excellentLocation:
we enjoy the location but especially enjoy the complexit is in a beautiful locationwe were close to all the great restaurants and sight seeingthe location is quiet peaceful & beautifulthe property is very nice and in great locationCleanliness:
clean and new insideimmaculate condo - fresh clean and luxurious decorthe place is super clean and beautifulcondo was beautiful clean and had everything we neededthe pool was very quite and clean as wellRead more reviewsAmenities & Room:
very nice condo decor furniture and bedseverything in this condo is first class with excellent quality furniture beds kitchen appliances and moreeverything in this condo is first class with excellent quality of furniture beds kitchen appliances and morethere were plenty of lounge chairs tables and umbrellas to relax and stay out of the sunwe enjoyed the extras = bicycles fishing poles and beach/pool toys
3. Happy Tarpon (from USD 500)
Happy Tarpon is tucked away in central Islamorada. Measuring 2,400 sq. ft. (223 sqm), this house rental with a dock in Islamorada is sizeable enough to accommodate up to 6 people. Among its features is a deep-water dock. A 28-ft (8.5-m) boat can be parked at the dock. Next to the boat dock is a fish cleaning table that’s supplied with fresh water.
That’s not all, a heated pool, free Wi-Fi, and a full kitchen are other amenities provided here.
Islamorada, FL, US
4. Stylish abode with bicycles (from USD 210)
Tucked away in a quaint community, this house for 10 people lets you enjoy a mix of luxury and relaxation. It gives you access to a private community beach where you can swim and get a tan all day long. If you enjoy cooking, there’s a fully updated kitchen with a dishwasher, coffeemaker, and stove at your disposal.
That’s not enough, the property has a boat dock, two bathrooms, and fast Wi-Fi. The young guests will especially take delight in the bicycles, foosball table, Xbox 360, and mini basketball hoop offered on the property.
Islamorada, FL, US
5. Peaceful condo with stunning views
Stay in this three-bedroom condo where you can wake up to lovely views of the marina and ocean every day. Furthermore, you’ll be in a quiet gated community with welcoming neighbors. If you’re bringing your boat, there’s a 30-ft (9-m) boat slip ready for use.
To help you relax, a community pool, hammock, and picnic table are provided. Being a monthly rental, this condo is perfect for a long-term vacation in Islamorada.
Accommodates: 6
Minimum Nights: 30
Refund Policy : 100% refund if you cancel at least 60 days before check-in.
Top guest reviews
Read more reviewsLocation:
perfectly located in central islamorada near dining and musicthis property was the absolute perfect location in islamoradagreat location in islamorada with nice ocean view
6. Modern dwelling for six guests
If you love staying in the lap of luxury, then this house will not disappoint. It’s situated in a safe, gated community, and is ideal for kids. With high-speed Wi-Fi, all of the six guests staying here can stream and download videos with ease.
The house’s privately owned boat dock is available for hire. Aside from that, the house features a gas barbecue grill, bikes, and three televisions.
Accommodates: 6
Minimum Nights: 7
Refund Policy : 100% refund if you cancel at least 60 days before check-in.
Top guest reviews
Host:
great response from ownerthe management is very responsivethe owner was easy to communicate with and extremely kind and helpfulproperty staff was on top of everything and made sure the trip was a joyand jo was a great host very responsive and helpfulLocation:
beautiful location and perfect house for our christmas 2019 weeklong staygreat house great location and great timethe neighborhood pool and beach are close by and excellent for young childrentotally happy with the location we barely left islamorada lots of restaurant options close byexcellent location in the keysCleanliness:
very clean and well equipedvery clean and well equipped toovery clean organized everything you needit's modern clean and comfortablepool was also spotlessly clean and a wonderful temperatureRead more reviewsAmenities & Room:
we loved the porches and the well-stocked kitchen was great for dinner prepcomfortable beds and well equipped and organized kitchensafe gated community with nice pool and the townhouse was comfortablebut also have great views of the ocean nice pool and quiet and restful location
Islamorada: a must-visit destination in Florida
A trip to Florida is incomplete without visiting Islamorada. From delicious seafood to fun outdoor adventures, the village is prepared to make your holiday special. Check out any of the above vacation rentals if you want to enjoy a blend of restful stays with thrilling water sports.
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