
Holiday rentals with a pool in Islamorada
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Top-rated rentals with a pool in Islamorada
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Popular amenities for Islamorada rentals with a pool
House rentals with a pool

Tiny Home on Waterfront | Bay Views | Deck | Pool
Great great getaway place to relax. Right on the waterfront. You can get your boat, Jet ski and enjoy your stay. I loved watching sunrise with my cup of coffee.

Cancellation Deal: 08/02 thru 08/09
Had a wonderful stay, would recommend to anyone looking for a convenient, beautiful spot in Marathon. Eddie was an excellent host!

Movie Theater | HotTub | Pool | Boat/RV/EV Parking
We almost stayed at a hotel, but I saw Christian’s place pop up and it looked like a fun place for the family. It is so awesome! It is exactly as described.and more . He uses every inch of that awesome property for something fun. It’s also a close drive or bike ride to so many things. We took almost all of his suggestions on places to eat and things to do and they were right on. The last night we all chilled outside and projected the Goonies on the outdoor screen and had some good relaxing family time. He is an excellent host and is so helpful. We are all so happy we chose his Airbnb.. Thank you so much, Christian! You are one of a kind and your place is so cool.

Newely Renovated 3/2-private pool/dock/cabana club
Absolutely amazing place to stay! Dennis is amazing and had several great recommendations for us to eat and do! The dock out back was beautiful and we were even able to see manatees! The pool was a GREAT addition and my family wouldn’t have wanted to explore the Keys any other way! The neighbors are also friendly and great to talk to! Overall beautiful place! My family and I would stay again!

Beach House, Private Pool & Dock, Gulf Sunset view
Our 7 day stay was the most relaxing vacation we’ve had in years. The location was somewhat remote but only a short drive into Marathon. We hope to come back soon!!!

Grand Blue Arenas/ 120'Dock/Mini golf/GameRoom
We had an absolutely amazing stay at this beautiful home in Marathon Keys! From the moment we arrived, it was clear that this property is extremely well-maintained and spotless. The house was immaculately clean, which made settling in with kids feel effortless and comfortable.The two-story layout was perfect for our family, offering plenty of space for everyone to spread out and relax. The home is definitely kid-friendly and family-oriented, with thoughtful touches throughout. The pool was a huge hit with both the kids and adults, and we had so much fun spending our evenings enjoying it! The kitchen was gorgeous and fully equipped with high-quality appliances, which made cooking meals together easy and enjoyable. We brought both a 22-foot bay boat and a 22-foot pontoon, and docking was a breeze. Overall, this home was the perfect place for our family getaway. We made unforgettable memories here and would absolutely return. Highly recommended for families looking for a home in the Keys!

Anglers Terrace, Condé Nast Traveler's Best Airbnb
The house was beautiful!We thoroughly enjoyed all the outdoor spaces.With 4 bedrooms and an 8 month old, the house offered many spaces for everyone to be comfortable. The beds were comfortable and we were all well rested. The rooftop area for grilling and chilling was amazing. The outdoor seating area off the main level was where we celebrated Father’s Day dinner. Morning snuggles were spent in the seating area off the den.The pool area was where we laughed and swam and had many a cocktail. We loved our week as a family there and had no reason to leave except for a few dinners out.Andy was very responsive, dropped off bagels one morning and a great resource for recommendations. Highly recommend Anglers Terrace as we loved our week there!

Private Pool! Luxury Paradise Pointe, Pet Friendly
Amazing Stay in the Florida Keys! We had an absolutely incredible time at this home in the Florida Keys! Everything about our stay was perfect. The house was clean, comfortable, and had everything we needed for a relaxing getaway. The highlight was definitely the pool — it was beautiful, well-maintained, and the perfect spot to unwind after a day of exploring. The outdoor space was peaceful and made it feel like our own private paradise. Loved the tv out by the pool! We couldn’t have asked for a better place to stay. The location was great, the home was even better than expected, and we left feeling completely refreshed. Highly recommend and would definitely stay here again!
Condo rentals with a pool

1BR - Key Largo Sun & Sand Hideaway
Stayed at Vanessa’s place twice while visiting the Keys. Quiet, clean and private. A great host and would definitely stay again next time a visit. Easy access to everything off the highway and great amenities with the pool and beach nearby. 10/10.

Reel Large END Unit in Ocean Point Suites
Something for the whole family to do right at location. Pool was great.

Gorgeous lagoon-front 2BR Townhouse with 2 pools
This place was just what we needed. It was the perfect size for our 4 plus a dog for 2 nights. It’s located in a nice community and close to a lot. I would stay here again!

Ocean Views at Ocean Pointe
We had a fantastic stay at this condo in Tavernier! The location was ideal—close to everything we wanted to see and do in the Keys. The unit was clean, comfortable, and well-stocked, with a beautiful view of the ocean that made every morning feel like a dream. The host was extremely responsive and made everything easy from check-in to check-out. Highly recommend this place—we’d love to come back!

Slip, Ramp, Pool, Trailer Parking, Bait Freezer
Absolutely perfect for a honeymoon getaway, quiet perfect amount of space for us, the set up was great with 2 bathrooms and a huge walkin closet, the couches were super comfy, the TV was big enough to see from across the room, we enjoyed everything about it. Got to meet some of the neighbors and they were all very welcoming and enjoyed talking to them. Scott had some great local recommendations and we enjoyed everything.

Studio with Balcony, Kitchen, Open Living Space
My husband and I chose this place for part of our honeymoon, and we were so happy we did! We absolutely loved it, even more than the resort we paid double the price for in Key West. Our room was clean and very comfortable. The pool area was equally clean, never too crowded, and offered a really peaceful atmosphere. Having a full kitchen was a huge benefit for us, it allowed us to save money on meals and enjoy some home-cooked food. We were also incredibly lucky to have a beautiful view of the water from our room. We loved waking up each morning, making breakfast in our kitchen, and eating it on our little patio while enjoying the view. There’s lots of cool stuff to do in Islamorada, and the location of this place made it easy to explore everything. We had such a wonderful experience and would love to return someday!

Modern and Coastal 3212 is Across from Pool
This is the perfect place to stay to explore the areas of Key Largo and Islamorada. The unit is very clean and nicely decorated. We had no issues and would stay there again. Highly recommend!

Beachside Unit 28 - Private Beach, Pool & Paradise
The place was exactly as described the only complaint I have is the bed is firm but it didn’t bother my wife at all . The rainfall shower head was a 10/10 after a long day in the heat ! The onsite grills were awesome we grilled 2 of our 4 nights since it was so convenient.
Quick stats about holiday rentals with a pool in Islamorada
Total rentals
610 properties
Nightly prices starting at
$108 AUD before taxes and fees
Total number of reviews
3.2K reviews
Family-friendly rentals
420 properties are a good fit for families
Pet-friendly rentals
260 properties allow pets
Rentals with dedicated workspaces
340 properties have a dedicated workspace
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- Everglades National Park
- Sombrero Beach
- John Pennekamp Coral Reef State Park
- Zoo Miami
- Bahia Honda State Park
- Coral Castle
- Cannon Beach
- Biscayne National Park
- Conch Key
- Calusa Beach & Loggerhead Beach
- Everglades Alligator Farm
- Theater of the Sea
- Long Beach
- Cocoa Plum Beach
- EAA Air Museum
- Sea Oats Beach
- Monkey Jungle
- Far Beach
- Horseshoe Beach
- Windley Key Fossil Reef Geological State Park
- Long Key State Park
- Keys' Meads