Holiday rentals with a pool in Islamorada

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Popular amenities for Islamorada rentals with a pool

House rentals with a pool

Superhost
Home in Key Largo
4.91 out of 5 average rating, 151 reviews

Tiny Home on Waterfront | Bay Views | Deck | Pool

VikranthRating, 5 stars2 weeks ago
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.
Top Guest favourite
Home in Marathon
4.99 out of 5 average rating, 138 reviews

Cancellation Deal: 08/02 thru 08/09

ShelleyRating, 5 stars1 week ago
Had a wonderful stay, would recommend to anyone looking for a convenient, beautiful spot in Marathon. Eddie was an excellent host!
Top Guest favourite
Home in Marathon
5 out of 5 average rating, 40 reviews

Movie Theater | HotTub | Pool | Boat/RV/EV Parking

AnneRating, 5 stars3 weeks ago
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.
Superhost
Home in Key Largo
5 out of 5 average rating, 4 reviews

Newely Renovated 3/2-private pool/dock/cabana club

OliviaRating, 5 stars3 weeks ago
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!
Guest favourite
Home in Marathon
4.93 out of 5 average rating, 61 reviews

Beach House, Private Pool & Dock, Gulf Sunset view

DanielRating, 5 stars4 weeks ago
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!!!
Superhost
Home in Marathon
5 out of 5 average rating, 3 reviews

Grand Blue Arenas/ 120'Dock/Mini golf/GameRoom

GinaRating, 5 stars1 week ago
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!
Guest favourite
Home in Marathon
4.97 out of 5 average rating, 115 reviews

Anglers Terrace, Condé Nast Traveler's Best Airbnb

SusanneRating, 5 stars1 day ago
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!
Guest favourite
Home in Key Colony Beach
4.95 out of 5 average rating, 20 reviews

Private Pool! Luxury Paradise Pointe, Pet Friendly

KimberlyRating, 5 stars4 weeks ago
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

Guest favourite
Condo in Tavernier
4.9 out of 5 average rating, 134 reviews

1BR - Key Largo Sun & Sand Hideaway

JosephRating, 5 stars2 months ago
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.
Superhost
Condo in Tavernier
4.88 out of 5 average rating, 155 reviews

Reel Large END Unit in Ocean Point Suites

JenniferRating, 5 stars6 days ago
Something for the whole family to do right at location. Pool was great.
Guest favourite
Condo in Key Largo
4.94 out of 5 average rating, 111 reviews

Gorgeous lagoon-front 2BR Townhouse with 2 pools

MarissaRating, 5 stars2 weeks ago
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!
Top Guest favourite
Condo in Tavernier
4.98 out of 5 average rating, 196 reviews

Ocean Views at Ocean Pointe

PattyRating, 5 stars1 month ago
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!
Top Guest favourite
Condo in Marathon
4.96 out of 5 average rating, 103 reviews

Slip, Ramp, Pool, Trailer Parking, Bait Freezer

AlexRating, 5 stars3 weeks ago
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.
Superhost
Condo in Islamorada
4.77 out of 5 average rating, 96 reviews

Studio with Balcony, Kitchen, Open Living Space

BenjaminRating, 5 stars2 weeks ago
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!
Guest favourite
Condo in Tavernier
4.94 out of 5 average rating, 111 reviews

Modern and Coastal 3212 is Across from Pool

Amanda Rating, 5 stars4 weeks ago
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!
Guest favourite
Condo in Key Colony Beach
4.81 out of 5 average rating, 138 reviews

Beachside Unit 28 - Private Beach, Pool & Paradise

RandyRating, 5 stars1 week ago
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

Destinations to explore

  1. Airbnb
  2. United States
  3. Florida
  4. Monroe County
  5. Islamorada
  6. Rentals with pools