Title: Best Islamorada Villas with a Pool in 2026 - Expedia.ca # Book villas with a pool in Islamorada ### Experience a Dream Getaway with Private Pool Villas in Islamorada Villas with a private pool in Islamorada offer the perfect blend of luxury and comfort for families seeking a memorable vacation. Nestled in the stunning Florida Keys, these villas provide an idyllic setting for relaxation and adventure. With lush landscapes and the calming sounds of the ocean, you can unwind by your own pool after a day of exploring the beautiful beaches and local attractions. Each villa is designed to create lasting family memories, making it an ideal choice for your next getaway. ## Our top choices for a great stay ![Beautiful Venetian Shores, Cozy home, Heated pool, Tiki, Boat Lift, Fish & Dive.](https://images.trvl-media.com/lodging/35000000/34090000/34089800/34089730/1e5a755c_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Beautiful Venetian Shores, Cozy home, Heated pool, Tiki, Boat Lift, Fish & Dive. Stay at this villa in Islamorada. Enjoy private pools, laundry facilities, and patios. Popular attractions Windley Key Fossil Reef Geological State Park and Rain Barrel Village are located nearby. 10/10 Exceptional! (6 reviews) [Get rates](https://expedia.ca/Islamorada-Hotels-Beautiful-Venetian-Shores.h34089730.Hotel-Information) [](https://expedia.ca/Islamorada-Hotels-Beautiful-Venetian-Shores.h34089730.Hotel-Information) ![Bayberry Key: Waterfront Htd Pool, FREE Boat Dockage Sep-Oct Only!](https://images.trvl-media.com/lodging/105000000/104970000/104966900/104966897/w6949h4631x4y4-14f74ba9_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Bayberry Key: Waterfront Htd Pool, FREE Boat Dockage Sep-Oct Only! Stay at this villa in Islamorada. Enjoy free WiFi, private pools, and a garden. Popular attractions Islamorada Brewery & Distillery and Keys History & Discovery Center are located nearby. 9.8/10 Exceptional! (6 reviews) [Get rates](https://expedia.ca/Islamorada-Hotels-Bayberry-Key-Waterfront-Boutique-Resort.h104966897.Hotel-Information) [](https://expedia.ca/Islamorada-Hotels-Bayberry-Key-Waterfront-Boutique-Resort.h104966897.Hotel-Information) ![Exclusive Private ViLLA , Beach, Boat Ramp, Dock, Pool](https://images.trvl-media.com/lodging/89000000/88910000/88902000/88901943/ed49d7cc_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Exclusive Private ViLLA , Beach, Boat Ramp, Dock, Pool Stay at this villa in Islamorada. Enjoy private pools, laundry facilities, and air conditioning. Popular attractions Rain Barrel Village and Islamorada County Park are located nearby. [Get rates](https://expedia.ca/Islamorada-Hotels-Exclusive-Private-ViLLA.h88901943.Hotel-Information) [](https://expedia.ca/Islamorada-Hotels-Exclusive-Private-ViLLA.h88901943.Hotel-Information) ![Islamorada house with best location. Lic # 24-0055](https://images.trvl-media.com/lodging/78000000/77980000/77977700/77977669/896ce6d1_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Islamorada house with best location. Lic # 24-0055 Book a stay at this family-friendly villa in Islamorada. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Windley Key Fossil Reef Geological State Park and Rain Barrel Village are located nearby. 10/10 Exceptional! (18 reviews) [Get rates](https://expedia.ca/Islamorada-Hotels-Anglers-Reef-Key-West-Style-Villa-Sleeps-6.h77977669.Hotel-Information) [](https://expedia.ca/Islamorada-Hotels-Anglers-Reef-Key-West-Style-Villa-Sleeps-6.h77977669.Hotel-Information) ![Isla Guava: Boutique Resort, FREE Boat Dockage Sept-Oct Only!](https://images.trvl-media.com/lodging/105000000/104520000/104514700/104514629/3fab3be8_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Isla Guava: Boutique Resort, FREE Boat Dockage Sept-Oct Only! Stay at this villa in Islamorada. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Islamorada Brewery & Distillery and Keys History & Discovery Center are located nearby. 9.6/10 Exceptional! (4 reviews) [Get rates](https://expedia.ca/Islamorada-Hotels-Isla-Key-Guava-Waterfront-Boutique-Resort.h104514629.Hotel-Information) [](https://expedia.ca/Islamorada-Hotels-Isla-Key-Guava-Waterfront-Boutique-Resort.h104514629.Hotel-Information) ![Isla Lychee: Boutique Resort, FREE Boat Dockage Sep-Oct Only!](https://images.trvl-media.com/lodging/105000000/104510000/104504900/104504831/3699137a_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Isla Lychee: Boutique Resort, FREE Boat Dockage Sep-Oct Only! Stay at this villa in Islamorada. Enjoy free WiFi, laundry facilities, and balconies. Popular attractions Islamorada Brewery & Distillery and Keys History & Discovery Center are located nearby. 10/10 Exceptional! (6 reviews) [Get rates](https://expedia.ca/Islamorada-Hotels-Isla-Lychee-Little-Basin-Villas.h104504831.Hotel-Information) [](https://expedia.ca/Islamorada-Hotels-Isla-Lychee-Little-Basin-Villas.h104504831.Hotel-Information) ![Island pool home awaits in Islamorada's Port Antigua](https://images.trvl-media.com/lodging/70000000/69960000/69951800/69951736/8524b947_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Island pool home awaits in Islamorada's Port Antigua Book a stay at this family-friendly vacation home in Islamorada. Enjoy free WiFi, private pools, and a water park. Popular attractions Sunset Drive Beach and Anne's Beach are located nearby. 10/10 Exceptional! (6 reviews) [Get rates](https://expedia.ca/Islamorada-Hotels-Island-Pool-Home-Awaits-In-Islamoradas-Port-Antigua.h69951736.Hotel-Information) [](https://expedia.ca/Islamorada-Hotels-Island-Pool-Home-Awaits-In-Islamoradas-Port-Antigua.h69951736.Hotel-Information) ![Isla Mirabelle: Boutique Resort, FREE Boat Dockage Sep-Oct Only!](https://images.trvl-media.com/lodging/105000000/104970000/104966900/104966895/c75a0e50_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Isla Mirabelle: Boutique Resort, FREE Boat Dockage Sep-Oct Only! Stay at this villa in Islamorada. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Islamorada Brewery & Distillery and Keys History & Discovery Center are located nearby. 10/10 Exceptional! (6 reviews) [Get rates](https://expedia.ca/Islamorada-Hotels-Isla-Mirabelle-Waterfront-Boutique-Resort.h104966895.Hotel-Information) [](https://expedia.ca/Islamorada-Hotels-Isla-Mirabelle-Waterfront-Boutique-Resort.h104966895.Hotel-Information) ![Villa with private plunge pool, boat dock, & amazing sunsets in Islamorada Fl](https://images.trvl-media.com/lodging/113000000/112180000/112179700/112179681/fa8b844d_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Villa with private plunge pool, boat dock, & amazing sunsets in Islamorada Fl Stay at this villa in Islamorada. Enjoy free WiFi, private pools, and laundry facilities. Popular attractions Keys History & Discovery Center and Florida Keys Brewing Co. are located nearby. 10/10 Exceptional! (2 reviews) [Get rates](https://expedia.ca/Islamorada-Hotels-Villa-With-Private-Plunge-Pool.h112179681.Hotel-Information) [](https://expedia.ca/Islamorada-Hotels-Villa-With-Private-Plunge-Pool.h112179681.Hotel-Information) ![Turtle Nest Estate in Islamorada](https://images.trvl-media.com/lodging/114000000/113390000/113386900/113386825/4084e624_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Turtle Nest Estate in Islamorada Stay at this villa in Islamorada. Enjoy a full-service spa. Popular attractions Robbie’s of Islamorada and Sunset Drive Beach are located nearby. [Get rates](https://expedia.ca/Islamorada-Hotels-Turtle-Nest-Estate-In-Islamorada.h113386825.Hotel-Information) [](https://expedia.ca/Islamorada-Hotels-Turtle-Nest-Estate-In-Islamorada.h113386825.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 a villa with a pool in Islamorada? Opting for a luxury pool vacation villa for rent in Islamorada instead of a hotel offers a unique experience tailored to your needs. These private villas with swimming pools provide ample space for families and couples to relax and reconnect, free from the constraints of hotel schedules and shared amenities. You can enjoy private poolside fun at your leisure, whether it's a morning swim or an evening barbecue under the stars. The villas often feature outdoor spaces perfect for family gatherings or intimate evenings, allowing you to create lasting memories in a tranquil setting. While hotels may offer convenience, villas provide a personalized touch, making it easy to blend relaxation with adventure. With nearby beaches and activities, your villa serves as a peaceful home base after a day of exploration, offering the best of both worlds—comfort and adventure—all in one beautiful destination. ### Top Destinations > - [Villas with a Pool in Cancun ](https://www.expedia.ca/lp/b/tgp/lodging/theme/villas-with-pool/179995/cancun) > - [Villas with a Pool in Las Vegas ](https://www.expedia.ca/lp/b/tgp/lodging/theme/villas-with-pool/178276/las-vegas) > - [Villas with a Pool in Miami ](https://www.expedia.ca/lp/b/tgp/lodging/theme/villas-with-pool/178286/miami) > - [Villas with a Pool in Kissimmee ](https://www.expedia.ca/lp/b/tgp/lodging/theme/villas-with-pool/7927/kissimmee) > - [Villas with a Pool in Punta Cana ](https://www.expedia.ca/lp/b/tgp/lodging/theme/villas-with-pool/601906/punta-cana) > - [Villas with a Pool in Ubud ](https://www.expedia.ca/lp/b/tgp/lodging/theme/villas-with-pool/12094/ubud) > - [Villas with a Pool in Puerto Plata ](https://www.expedia.ca/lp/b/tgp/lodging/theme/villas-with-pool/6048790/puerto-plata) > - [Villas with a Pool in Ocho Rios ](https://www.expedia.ca/lp/b/tgp/lodging/theme/villas-with-pool/553248635209673480/ocho-rios) > - [Villas with a Pool in Jarabacoa ](https://www.expedia.ca/lp/b/tgp/lodging/theme/villas-with-pool/6084371/jarabacoa) ### Explore more places to book > - [Positano Villas with Pools ](https://www.expedia.ca/lp/b/tgp/lodging/theme/villas-with-pool/4330/positano) > - [Tulum Villas with Pools ](https://www.expedia.ca/lp/b/tgp/lodging/theme/villas-with-pool/182189/tulum) > - [Port Aransas Villas with Pools ](https://www.expedia.ca/lp/b/tgp/lodging/theme/villas-with-pool/55180/port-aransas) > - [Cape Coral Villas with Pools ](https://www.expedia.ca/lp/b/tgp/lodging/theme/villas-with-pool/6521/cape-coral) > - [Vail Villas with Pools ](https://www.expedia.ca/lp/b/tgp/lodging/theme/villas-with-pool/7053/vail) > - [Cartagena Villas with Pools ](https://www.expedia.ca/lp/b/tgp/lodging/theme/villas-with-pool/926/cartagena) > - [Sorrento Villas with Pools ](https://www.expedia.ca/lp/b/tgp/lodging/theme/villas-with-pool/9716/sorrento) > - [La Fortuna Villas with Pools ](https://www.expedia.ca/lp/b/tgp/lodging/theme/villas-with-pool/6047145/la-fortuna) > - [Mykonos Villas with Pools ](https://www.expedia.ca/lp/b/tgp/lodging/theme/villas-with-pool/1707/mykonos) ![](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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