Title: Best Islamorada Resorts with Pools in 2026 - Expedia.ca # Book resorts with pools in Islamorada ### Experience the Ultimate Family Getaway at Resorts with Pools in Islamorada Resorts with pools in Islamorada provide the perfect backdrop for a memorable family vacation. Nestled in the picturesque Florida Keys, these resorts offer a blend of relaxation and adventure, making them an ideal choice for families looking to escape the hustle and bustle of everyday life. With the soothing sounds of the ocean and lush tropical landscapes, your family can enjoy quality time together while splashing in the pool or lounging by the water. These properties often feature a variety of amenities designed to entertain and engage guests of all ages, ensuring a fantastic experience for everyone. ## Our top choices for a great stay ![Cheeca Lodge & Spa](https://images.trvl-media.com/lodging/1000000/10000/5800/5780/4608d7e2_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Cheeca Lodge & Spa CA $528 CA $694 total Mar 6 - Mar 7 includes taxes & fees Book a stay at this luxury resort in Islamorada. Enjoy free parking, 3 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Florida Keys Brewing Co. and MoradaWay Arts & Cultural District are located nearby. 9.2/10 Wonderful! (1,299 reviews) [](https://expedia.ca/Islamorada-Hotels-Cheeca-Lodge-Spa.h5780.Hotel-Information) ![Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort](https://images.trvl-media.com/lodging/1000000/20000/11900/11864/4671ebc2_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort CA $556 CA $716 total Mar 23 - Mar 24 includes taxes & fees Book a stay at this beach resort in Islamorada. Enjoy free WiFi, 3 outdoor pools, and 4 restaurants. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Windley Key Fossil Reef Geological State Park and History of Diving Museum are located nearby. 9/10 Wonderful! (163 reviews) [](https://expedia.ca/Islamorada-Hotels-Three-Waters-Resort-And-Marina.h11864.Hotel-Information) ![Amara Cay Resort](https://images.trvl-media.com/lodging/1000000/70000/62000/61976/4186365f_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Amara Cay Resort CA $351 CA $495 total Mar 25 - Mar 26 includes taxes & fees Book a stay at this beach resort in Islamorada. Enjoy 2 restaurants, a private beach, and 3 bars/lounges. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Bud n' Mary's Dive Center and Hurricane Monument are located nearby. 8.8/10 Excellent! (1,262 reviews) [](https://expedia.ca/Islamorada-Hotels-Amara-Cay-Resort.h61976.Hotel-Information) ![La Siesta Resort & Villas](https://images.trvl-media.com/lodging/3000000/2480000/2477600/2477508/18023e21_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### La Siesta Resort & Villas CA $387 CA $536 total Mar 8 - Mar 9 includes taxes & fees Book a stay at this beach resort in Islamorada. Enjoy a private beach, a marina, and breakfast (surcharge). Our guests praise the helpful staff and the spacious rooms in our reviews. Popular attractions Bud n' Mary's Dive Center and Hurricane Monument are located nearby. 8.8/10 Excellent! (1,003 reviews) [](https://expedia.ca/Islamorada-Hotels-La-Siesta-Resort-Marina.h2477508.Hotel-Information) ![Matecumbe Resort](https://images.trvl-media.com/lodging/113000000/112180000/112177000/112176968/ad734a43_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Matecumbe Resort CA $457 CA $515 total Mar 6 - Mar 7 includes taxes & fees Book a stay at this beach resort in Islamorada. Enjoy free WiFi, free parking, and a private beach. Popular attractions Robbie’s of Islamorada and Indian Key Historic State Park are located nearby. 8.8/10 Excellent! (97 reviews) [](https://expedia.ca/Islamorada-Hotels-Matecumbe-Resort.h112176968.Hotel-Information) ![Keys Villa](https://images.trvl-media.com/lodging/75000000/74230000/74229000/74228939/30bff6fb_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Keys Villa Stay at this resort in Islamorada. Enjoy free WiFi, laundry facilities, and balconies. Popular attractions Sunset Drive Beach and Anne's Beach are located nearby. 10/10 Exceptional! (7 reviews) [Get rates](https://expedia.ca/Islamorada-Hotels-Keys-Villa.h74228939.Hotel-Information) [](https://expedia.ca/Islamorada-Hotels-Keys-Villa.h74228939.Hotel-Information) ![Beautiful oceanfront resort located at mile marker 73.8](https://images.trvl-media.com/lodging/79000000/78080000/78072500/78072441/e0ad2c05_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Beautiful oceanfront resort located at mile marker 73.8 Stay at this resort in Islamorada. Enjoy patios, cable/satellite TV service, and an in-room coffeemaker. Popular attractions Anne's Beach and Sunset Drive Beach are located nearby. [Get rates](https://expedia.ca/Islamorada-Hotels-Beautiful-Oceanfront-Resort-Located-At-Mile-Marker-738.h78072441.Hotel-Information) [](https://expedia.ca/Islamorada-Hotels-Beautiful-Oceanfront-Resort-Located-At-Mile-Marker-738.h78072441.Hotel-Information) ![JULY 4th Islamorada BEACH paradise - 2 Bedrooms Boat Slip Ramp Pier Pool Hot Tub](https://images.trvl-media.com/lodging/40000000/39150000/39147300/39147207/w973h1235x0y0-221a49ea_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### JULY 4th Islamorada BEACH paradise - 2 Bedrooms Boat Slip Ramp Pier Pool Hot Tub Stay at this resort in Islamorada. Enjoy free WiFi, laundry facilities, and balconies. Popular attractions Sunset Drive Beach and Anne's Beach are located nearby. [Get rates](https://expedia.ca/Islamorada-Hotels-Sleeps-6-WATER-BEACH-2-Bedrooms-2-Bath-Boat-Slip.h39147207.Hotel-Information) [](https://expedia.ca/Islamorada-Hotels-Sleeps-6-WATER-BEACH-2-Bedrooms-2-Bath-Boat-Slip.h39147207.Hotel-Information) ![On the water in Islamorada elevated detached unit!!!](https://images.trvl-media.com/lodging/88000000/87380000/87370400/87370340/w1280h718x0y0-7bf5f357_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### On the water in Islamorada elevated detached unit!!! Stay at this resort in Islamorada. Enjoy patios, cable/satellite TV service, and air conditioning. Popular attractions Sunset Drive Beach and Anne's Beach are located nearby. [Get rates](https://expedia.ca/Islamorada-Hotels-On-The-Water-In-Islamorada-Elevated-Detached-Unit.h87370340.Hotel-Information) [](https://expedia.ca/Islamorada-Hotels-On-The-Water-In-Islamorada-Elevated-Detached-Unit.h87370340.Hotel-Information) ![2 BD/2BA VILLA WITH BOAT SLIP IN ISLAMORADA,FL](https://images.trvl-media.com/lodging/110000000/109910000/109905800/109905778/w2560h1201x0y0-015402f5_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### 2 BD/2BA VILLA WITH BOAT SLIP IN ISLAMORADA,FL Stay at this resort in Islamorada. Enjoy a fitness center, laundry facilities, and patios. Popular attractions Sunset Drive Beach and Anne's Beach are located nearby. 9.4/10 Exceptional! (3 reviews) [Get rates](https://expedia.ca/Islamorada-Hotels-2-BD2BA-VILLA-WITH-BOAT-SLIP-IN-ISLAMORADA.h109905778.Hotel-Information) [](https://expedia.ca/Islamorada-Hotels-2-BD2BA-VILLA-WITH-BOAT-SLIP-IN-ISLAMORADA.h109905778.Hotel-Information) Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply. ### Why choose family resorts with pools in Islamorada over hotels? Opting for family resorts with pools in Islamorada can elevate your vacation experience beyond what traditional hotels offer. While hotels may provide basic accommodations, these resorts feature expansive outdoor spaces and exciting water features designed for family enjoyment. Picture your family bonding over poolside adventures, where kids can play freely, and parents can unwind in a serene atmosphere. The added amenities at these vacation resorts often include organized activities, family-friendly dining options, and direct beach access, all tailored to enhance your stay. With the opportunity to create lasting memories in a vibrant setting, choosing a resort with a pool is a fantastic way to enjoy both relaxation and exploration during your family retreat. ### Top Destinations > - [Resorts with Pools in Destin ](https://www.expedia.ca/lp/b/tgp/lodging/theme/resorts-with-pools/6906/destin) > - [Resorts with Pools in Puerto Peñasco ](https://www.expedia.ca/lp/b/tgp/lodging/theme/resorts-with-pools/9456/puerto-penasco) > - [Resorts with Pools in Phoenix ](https://www.expedia.ca/lp/b/tgp/lodging/theme/resorts-with-pools/178298/phoenix) > - [Resorts with Pools in Kissimmee ](https://www.expedia.ca/lp/b/tgp/lodging/theme/resorts-with-pools/7927/kissimmee) > - [Resorts with Pools in Wisconsin Dells ](https://www.expedia.ca/lp/b/tgp/lodging/theme/resorts-with-pools/6059846/wisconsin-dells) > - [Resorts with Pools in Palm Springs ](https://www.expedia.ca/lp/b/tgp/lodging/theme/resorts-with-pools/180676/palm-springs) > - [Resorts with Pools in Scottsdale ](https://www.expedia.ca/lp/b/tgp/lodging/theme/resorts-with-pools/9829/scottsdale) > - [Resorts with Pools in Myrtle Beach ](https://www.expedia.ca/lp/b/tgp/lodging/theme/resorts-with-pools/601685/myrtle-beach) > - [Resorts with Pools in Virginia Beach ](https://www.expedia.ca/lp/b/tgp/lodging/theme/resorts-with-pools/10271/virginia-beach) ### Explore more places to book > - [Tulum Resorts with a Pool ](https://www.expedia.ca/lp/b/tgp/lodging/theme/resorts-with-pools/182189/tulum) > - [Stowe Resorts with a Pool ](https://www.expedia.ca/lp/b/tgp/lodging/theme/resorts-with-pools/6057386/stowe) > - [Vail Resorts with a Pool ](https://www.expedia.ca/lp/b/tgp/lodging/theme/resorts-with-pools/7053/vail) > - [West Yellowstone Resorts with a Pool ](https://www.expedia.ca/lp/b/tgp/lodging/theme/resorts-with-pools/3846/west-yellowstone) > - [Mazatlán Resorts with a Pool ](https://www.expedia.ca/lp/b/tgp/lodging/theme/resorts-with-pools/180011/mazatlan) > - [Ogunquit Resorts with a Pool ](https://www.expedia.ca/lp/b/tgp/lodging/theme/resorts-with-pools/55878/ogunquit) > - [Lake Buena Vista Resorts with a Pool ](https://www.expedia.ca/lp/b/tgp/lodging/theme/resorts-with-pools/10870/lake-buena-vista) > - [Bora Bora Resorts with a Pool ](https://www.expedia.ca/lp/b/tgp/lodging/theme/resorts-with-pools/602861/bora-bora) > - [Pompano Beach Resorts with a Pool ](https://www.expedia.ca/lp/b/tgp/lodging/theme/resorts-with-pools/9459/pompano-beach) ![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg) ## Go further with the Expedia app Save on select hotels and earn double points when you book on the app. Our app deals help you to save on trips so you can travel more and manage it all on the go. 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