
Holiday rentals with a pool in Islamorada
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Top-rated rentals with a pool in Islamorada
Guests agree: these homes with a pool are highly rated for location, cleanliness and more.
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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!

Vaca Vista 3
What a wonderful place to vacation. My entire family had a fabulous time. A bonus was seeing the manatees in the canal. The home was very clean and was very spacious. We all highly recommend this home!!

Million Dollar View
This home was everything we expected and more. Stunning location with absolute privacy. The extra long dock was amazing, the pool was fantastic, and the grounds were meticulous. It’s literally your own private resort. Roman, the host, was very quick with communication. He and his wife actually met us when we checked in to see if we had any questions and provided us with an arrival gift. If you have looked at the listing and are thinking of renting it, do it. You will not be disappointed at all. Excellent value all around.

Endless Summer
We very much enjoyed our stay, the house was as expected based on previous reviews & pictures. The location was perfect for us to access from Key Largo to Key West easily. The pool was nice & the kids had fun snorkeling off the back dock & looking for all kinds of wildlife both on land & in the water with their flashlights after dark. We found the sunsets at the house to be better than what we experienced in Key West. If you need beach chairs and/or beach umbrella, we recommend you rent those.

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!

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!

Captain's Retreat: Disneyland for Boaters
⭐️⭐️⭐️⭐️⭐️ Incredible Stay in Marathon, Florida! From the moment we arrived, this home blew us away. The pool was absolutely stunning—perfectly maintained, crystal-clear, and the true highlight of our trip. Whether we were lounging during the day or enjoying an evening swim under the stars, it felt like our own private resort. The house itself was exceptional. Every room felt thoughtfully designed and meticulously decorated, with beautiful coastal touches and upscale finishes that made the space feel both luxurious and welcoming. You can really tell the owner put a lot of care into every detail—from the cozy bedding and well-stocked kitchen to the smart layout and stylish accents throughout the home. The amenities were top-notch: great AC, comfortable beds, high-end appliances, outdoor seating, grill area, shuffleboard, pool table and even beach towels and gear available for guest use. It was clear that nothing was overlooked. If you’re looking for a peaceful, beautifully
Apartment 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
very kind and flexible hosts. Let us check out an hour after checkout time and we're also very communicative, friendly and service oriented. definitely recommend

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!

Tequila Sunrise
Exactly what we were looking for. Clean, cozy and great location with an amazing view of the ocean and sunset. Pool area with hot tub was clean and a nice bonus, as well as the small beach and pier. Highly recommend and would definitely book again

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.

Sugar Cane - Florida Keys tropical retreat
Great stay in the Keys, easily accessible to all that the area has to offer. Nice amenities in the community as well. Would stay again!

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!
Quick stats about holiday rentals with a pool in Islamorada
Total rentals
610 properties
Nightly prices starting at
₹6,060 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
- Theater of the Sea
- Everglades Alligator Farm
- Long Beach
- Cocoa Plum Beach
- EAA Air Museum
- Sea Oats Beach
- Far Beach
- Monkey Jungle
- Horseshoe Beach
- Windley Key Fossil Reef Geological State Park
- Long Key State Park
- Keys' Meads