
Vacation 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

Sandbox
⭐️⭐️⭐️⭐️⭐️ Absolute Paradise in the Heart of the Keys! Our stay at this vacation house in Marathon was nothing short of incredible. From the moment we arrived, we felt like we had found our own private slice of paradise. The house was spotless, beautifully decorated, and had all the comforts of home—plus the added bonus of breathtaking ocean views and island vibes. The location couldn’t have been better. Tucked away in a peaceful part of Marathon, we were just minutes from everything—the beach, boat rentals, amazing restaurants, and the iconic Seven Mile Bridge. The property itself was incredibly well-equipped: a fully stocked kitchen, super comfortable beds, high-speed WiFi. What really made this place stand out was the outdoor space. The private dock was perfect for fishing and sunset cocktails, and the pool made it hard to ever want to leave. We even spotted dolphins just off the dock one morning—unreal! The hosts were friendly, responsive, and went out of their way to make sure we

Discount Available! 100' Dock, Lots of Amenities!
We came down for a weeks vacation brought two boats, plenty of space on the docks. Communication with Meredith was great. Great location.

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!!

4BR 3B, Heated Pool & Spa, 60' Dock
Our stay in Marathon couldn’t have gone any better! I traveled with my three 20-something sons and their wives/significant others. The layout of Gerardo’s home was perfect for our needs. We had plenty of room, places to enjoy together, and space where everyone could find some peace and quiet. The location was ideal. We were within an easy driving distance of all excursions and restaurants and could even walk to Island Fish Company, which was one of our favorites. Gerardo was extremely responsive. He checked in prior to our arrival and touched base a couple of times to make sure there was nothing we needed. An excellent home I recommend to others with no hesitation!!

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.

NEW! Oceanside Casa Largo Modern Tropical Getaway
amazing stay at Martha's place. it's prestine. she's super responsive and very kind. I'd stay at any of her places because she's on top of it.

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!
Condo rentals with a pool

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

Your Happy Place - Oceanfront
Sandra's place was very nice and clean. She was very reponsive with any and all questions. The accomodations are as listed. I enjoyed the peace and quiet. I most enjoyed relaxing on the balcony listening to the ocean. All you need is you, clothes, and the memories you will make. The rest is provided. However I will note that I was expecting a "real" beach and it was more of a lagoon. although still nice. Thanks Sabdra I would definitely book again. 🙂

2BR - Key Largo Sunshine Getaway
We had a great stay at this location. Vanessa was very friendly and responsive. We arrived at the location earlier than expected and she kindly allowed an early check-in. We did have a need for AC maintenance during our stay and Vanessa was quick to respond and had contracted professionals that were able to resolve the issue in a timely manner. The accomodations were as described and the grounds were peaceful and very well maintained.

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
Host was extremely helpful and communicative. Check in was a breeze and all the amenities needed for a pleasurable stay. Bonus outdoor bait freezer!

BEAUTIFULLY DESIGNED OCEANFRONT CONDO
We really enjoyed our stay Beautiful condo extremely clean clear instructions wonderful place to stay pool and hot tub area are amazing. You can swim anytime which is really nice. Most places the pool closes at dusk. There is a nice poolside little restaurant and also a restaurant right by the beach area really convenient would go back there anytime

Tiki Time! Ocean Pointe Top Floor King 1 Br/1Ba
amazing place! so cute and very central to where we needed to be. so many amenities and the pool is amazing. the only thing I would say is the mattress is hard as a rock, so my husband and I had to sleep on the pull out couch for any rest.

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!
Quick stats about vacation rentals with a pool in Islamorada
Total rentals
610 properties
Nightly prices starting at
G$14,637 GYD 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
- Conch Key
- Biscayne National Park
- Calusa Beach & Loggerhead Beach
- Theater of the Sea
- Everglades Alligator Farm
- EAA Air Museum
- Cocoa Plum Beach
- Long Beach
- Monkey Jungle
- Far Beach
- Horseshoe Beach
- Windley Key Fossil Reef Geological State Park
- Long Key State Park
- Keys' Meads