Title: Book the Best Hotels with POOL in Islamorada in 2026 | Expedia.ca [Islamorada Travel Guide](https://expedia.ca/Islamorada.dx10768)[Hotels in Islamorada](https://expedia.ca/Islamorada-Hotels.d10768.Travel-Guide-Hotels)[Vacation Rentals in Islamorada](https://expedia.ca/Islamorada-Vacation-Rentals.d10768.Travel-Guide-VacationRentals)[Flights to Islamorada](https://expedia.ca/Cheap-Flights-To-Islamorada.d10768.Travel-Guide-Flights)[Things to do in Islamorada](https://expedia.ca/Things-To-Do-In-Islamorada.d10768.Travel-Guide-Activities)[Islamorada Car Rentals](https://expedia.ca/Car-Rentals-In-Islamorada.d10768.Car-Rental-Guide)[Islamorada Vacation Packages](https://expedia.ca/Islamorada.d10768.Destination-Travel-Guides) ![Islamorada featuring a sunset and general coastal views](https://images.trvl-media.com/place/10768/7014979e-dcd6-42fa-a69b-b138a0a93305.jpg?impolicy=fcrop&w=1200&h=500&q=medium) ![](https://images.trvl-media.com/place/10768/7014979e-dcd6-42fa-a69b-b138a0a93305.jpg?impolicy=fcrop&w=1200&h=500&q=medium) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__calendar_shield.svg) ### Change your mind Book hotels with free cancellation - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Sign in to save 10% or more on thousands of hotels [Sign in](https://www.expedia.ca/login) - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__bed.svg) ### Be picky Search almost a million properties worldwide ## Check availability on Islamorada Hotels with a Pool Tonight [Mar 13 - Mar 14](https://www.expedia.ca/Hotel-Search?regionId=10768&startDate=2026-03-13&endDate=2026-03-14&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Mar 14 - Mar 15](https://www.expedia.ca/Hotel-Search?regionId=10768&startDate=2026-03-14&endDate=2026-03-15&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Mar 13 - Mar 15](https://www.expedia.ca/Hotel-Search?regionId=10768&startDate=2026-03-13&endDate=2026-03-15&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Mar 20 - Mar 22](https://www.expedia.ca/Hotel-Search?regionId=10768&startDate=2026-03-20&endDate=2026-03-22&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Islamorada hotels with a pool ![Hibiscus Waterfront 2-Bedroom, Two Bath Master Suite (Brand New) | Terrace/patio](https://images.trvl-media.com/lodging/1000000/890000/882300/882254/55bf0b8b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room | Private kitchen](https://images.trvl-media.com/lodging/1000000/890000/882300/882254/4077334d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 outdoor pools, open 7:30 AM to 6:00 PM, sun loungers](https://images.trvl-media.com/lodging/1000000/890000/882300/882254/ca18911f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hibiscus Waterfront 2-Bedroom, Two Bath Master Suite (Brand New) | Terrace/patio](https://images.trvl-media.com/lodging/1000000/890000/882300/882254/2d5dd8eb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Lime Tree Bay Resort [](https://www.expedia.ca/Long-Key-Hotels-Lime-Tree-Bay-Resort.h882254.Hotel-Information) Long Key 9.2/10 Wonderful (1,202 reviews) - A sun-drenched retreat with three tropical pools and private beach access awaits at this waterfront Florida Keys resort. CA $284 CA $381 total includes taxes & fees Apr 12 - Apr 13 [](https://www.expedia.ca/Long-Key-Hotels-Lime-Tree-Bay-Resort.h882254.Hotel-Information) ![Outdoor pool](https://images.trvl-media.com/lodging/92000000/91750000/91743100/91743042/1641bbd2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![25-inch flat-screen TV with digital channels, TV](https://images.trvl-media.com/lodging/92000000/91750000/91743100/91743042/92a650b5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/92000000/91750000/91743100/91743042/17a61bb5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![25-inch flat-screen TV with digital channels, TV](https://images.trvl-media.com/lodging/92000000/91750000/91743100/91743042/12c235b3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Treasure Harbor [](https://www.expedia.ca/Islamorada-Hotels-Treasure-Harbor.h91743042.Hotel-Information) Islamorada 9.0/10 Wonderful (143 reviews) CA $213 CA $432 total includes taxes & fees Mar 22 - Mar 23 [](https://www.expedia.ca/Islamorada-Hotels-Treasure-Harbor.h91743042.Hotel-Information) ![Exterior detail](https://images.trvl-media.com/lodging/58000000/57190000/57185500/57185414/9bcc8c75.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private beach, beach towels, kayaking](https://images.trvl-media.com/lodging/58000000/57190000/57185500/57185414/ec70fa51.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dock](https://images.trvl-media.com/lodging/58000000/57190000/57185500/57185414/4deb6af1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premier Cottage, Bay View | Terrace/patio](https://images.trvl-media.com/lodging/58000000/57190000/57185500/57185414/0c81ecd6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Rock Reef Resort [](https://www.expedia.ca/Key-Largo-Hotels-Rock-Reef-Resort.h57185414.Hotel-Information) Rock Harbor 9.2/10 Wonderful (1,101 reviews) - Dive into a sun-soaked Florida Keys getaway with a heated pool, private beach, and lounger paradise with stunning sunset views. CA $289 CA $326 total includes taxes & fees Apr 12 - Apr 13 [](https://www.expedia.ca/Key-Largo-Hotels-Rock-Reef-Resort.h57185414.Hotel-Information) ![Private beach, white sand, sun loungers, beach towels](https://images.trvl-media.com/lodging/11000000/10990000/10985700/10985658/5b866117.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/11000000/10990000/10985700/10985658/d813ee44.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/11000000/10990000/10985700/10985658/657544f0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Cottage, 1 Queen Bed with Sofa bed, Kitchen (#06 Poolside with Tiki Hut) | Living area](https://images.trvl-media.com/lodging/11000000/10990000/10985700/10985658/c16e9bea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Bay Harbor Lodge [](https://www.expedia.ca/Key-Largo-Hotels-Bay-Harbor-Lodge.h10985658.Hotel-Information) Rock Harbor 9.4/10 Exceptional (673 reviews) - Soak in serenity at this pristine waterfront lodge with a quiet pool and private beach access. CA $375 CA $422 total includes taxes & fees Mar 17 - Mar 18 [](https://www.expedia.ca/Key-Largo-Hotels-Bay-Harbor-Lodge.h10985658.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/54000000/53830000/53826700/53826692/43f0ebf9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Balcony](https://images.trvl-media.com/lodging/54000000/53830000/53826700/53826692/6adbeb09.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![BBQ/picnic area](https://images.trvl-media.com/lodging/54000000/53830000/53826700/53826692/0412cdfa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Grand Room | Water view](https://images.trvl-media.com/lodging/54000000/53830000/53826700/53826692/a4ce58d8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Bahia Bay Resort [](https://www.expedia.ca/Key-Largo-Hotels-Bahia-Bay-Resort.h53826692.Hotel-Information) Rock Harbor 9.0/10 Wonderful (155 reviews) - Splash into sun-soaked days at the outdoor pool, with loungers for ultimate relaxation at this bay retreat. CA $300 CA $338 total includes taxes & fees Mar 15 - Mar 16 [](https://www.expedia.ca/Key-Largo-Hotels-Bahia-Bay-Resort.h53826692.Hotel-Information) ![Outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/1000000/70000/62000/61976/af6ef0d3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Alligator Reef Oceanfront Room King Lanai with Queen Sofabed](https://images.trvl-media.com/lodging/1000000/70000/62000/61976/2728b985.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![One Bedroom Oceanfront Suite Two Queens Lanai](https://images.trvl-media.com/lodging/1000000/70000/62000/61976/a737b04b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Alligator Reef Oceanfront Room King Lanai with Queen Sofabed | View from room](https://images.trvl-media.com/lodging/1000000/70000/62000/61976/4186365f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Amara Cay Resort [](https://www.expedia.ca/Islamorada-Hotels-Amara-Cay-Resort.h61976.Hotel-Information) Matecumbe 8.8/10 Excellent (1,251 reviews) - Splash into serenity at this resort's private beach and outdoor pool with lounge chairs and umbrellas. CA $315 CA $455 total includes taxes & fees Mar 26 - Mar 27 [](https://www.expedia.ca/Islamorada-Hotels-Amara-Cay-Resort.h61976.Hotel-Information) ![Beach/ocean view](https://images.trvl-media.com/lodging/1000000/10000/4200/4170/3197fca4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Water view](https://images.trvl-media.com/lodging/1000000/10000/4200/4170/8979e9b1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hypo-allergenic bedding, pillowtop beds, laptop workspace](https://images.trvl-media.com/lodging/1000000/10000/4200/4170/c2caabe9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![43-inch flat-screen TV with cable channels, TV](https://images.trvl-media.com/lodging/1000000/10000/4200/4170/77344fea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Chesapeake Beach Resort [](https://www.expedia.ca/Islamorada-Hotels-Chesapeake-Beach-Resort.h4170.Hotel-Information) Matecumbe 9.2/10 Wonderful (1,665 reviews) - Splash into paradise with two stunning outdoor pools overlooking a private white sand beach. CA $322 CA $440 total includes taxes & fees Apr 12 - Apr 13 [](https://www.expedia.ca/Islamorada-Hotels-Chesapeake-Beach-Resort.h4170.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/12000000/11950000/11945900/11945889/8d8082f0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/12000000/11950000/11945900/11945889/98989626.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/12000000/11950000/11945900/11945889/19240ce2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![On the beach, beach towels](https://images.trvl-media.com/lodging/12000000/11950000/11945900/11945889/4550dbd5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Breezy Palms Resort [](https://www.expedia.ca/Islamorada-Hotels-Breezy-Palms-Resort.h11945889.Hotel-Information) Matecumbe 8.8/10 Excellent (635 reviews) - Serene outdoor pool with comfy loungers provides a sunny retreat just steps from the private beach and marina access. CA $240 CA $340 total includes taxes & fees Apr 8 - Apr 9 [](https://www.expedia.ca/Islamorada-Hotels-Breezy-Palms-Resort.h11945889.Hotel-Information) ![Oceanfront King Suite w/ Kitchen & Private Balcony | Water view](https://images.trvl-media.com/lodging/5000000/4290000/4287400/4287368/3997e962.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Oceanfront King Suite w/ Kitchen & Private Balcony](https://images.trvl-media.com/lodging/5000000/4290000/4287400/4287368/d0b4fd2b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/5000000/4290000/4287400/4287368/f42604af.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Water view](https://images.trvl-media.com/lodging/5000000/4290000/4287400/4287368/36b1fb04.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Drop Anchor [](https://www.expedia.ca/Islamorada-Hotels-Drop-Anchor.h4287368.Hotel-Information) Islamorada 8.8/10 Excellent (1,002 reviews) - Sun-drenched serenity awaits at this Art Deco hotel's outdoor pool with loungers. CA $431 CA $532 total includes taxes & fees Mar 26 - Mar 27 [](https://www.expedia.ca/Islamorada-Hotels-Drop-Anchor.h4287368.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/57000000/56960000/56952700/56952622/da1d792f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Apartment](https://images.trvl-media.com/lodging/57000000/56960000/56952700/56952622/8beb804e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/57000000/56960000/56952700/56952622/323dbfbe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/57000000/56960000/56952700/56952622/77268f5e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Ragged Edge Resort & Marina [](https://www.expedia.ca/Islamorada-Hotels-Ragged-Edge-Resort-Marina.h56952622.Hotel-Information) Islamorada 9.6/10 Exceptional (231 reviews) - Dive into poolside paradise with comfy loungers at Ragged Edge Resort, a cyclist-friendly escape. CA $325 CA $366 total includes taxes & fees Apr 12 - Apr 13 [](https://www.expedia.ca/Islamorada-Hotels-Ragged-Edge-Resort-Marina.h56952622.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. [View all properties](https://expedia.ca/Hotel-Search?startDate=2026-03-27&endDate=2026-03-28®ionId=10768&adults=2&amenities=POOL&sort=RECOMMENDED&openPlayBack=true) ## Choose what matters most at hotels with a pool in Islamorada Breakfast included 4 stars 5 stars Beach Hot tub ![](https://forever.travel-assets.com/flex/flexmanager/images/2026/02/06/expedia-sale-2026-desktop-us-ca.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## The Annual Vacation Sale Members save up to 40% on hotels and homes. Plan this year’s big trip and save. [Book now](https://expedia.ca/deals?rfrr=AFFINITY_SPRING_PROMO_10768) ## Hotels with pools and free breakfast in Islamorada ![Private beach, white sand, sun loungers, beach towels](https://images.trvl-media.com/lodging/1000000/10000/4200/4170/689f4306.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Water view](https://images.trvl-media.com/lodging/1000000/10000/4200/4170/8979e9b1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Hypo-allergenic bedding, pillowtop beds, laptop workspace](https://images.trvl-media.com/lodging/1000000/10000/4200/4170/c2caabe9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![43-inch flat-screen TV with cable channels, TV](https://images.trvl-media.com/lodging/1000000/10000/4200/4170/77344fea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Chesapeake Beach Resort [](https://www.expedia.ca/Islamorada-Hotels-Chesapeake-Beach-Resort.h4170.Hotel-Information) Matecumbe 9.2/10 Wonderful (1665) CA $322 CA $440 total includes taxes & fees Apr 12 - Apr 13 [](https://www.expedia.ca/Islamorada-Hotels-Chesapeake-Beach-Resort.h4170.Hotel-Information) ![Beach/ocean view](https://images.trvl-media.com/lodging/11000000/10990000/10985700/10985658/59d87217.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/11000000/10990000/10985700/10985658/d813ee44.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/11000000/10990000/10985700/10985658/657544f0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Cottage, 1 Queen Bed with Sofa bed, Kitchen (#06 Poolside with Tiki Hut) | Living area](https://images.trvl-media.com/lodging/11000000/10990000/10985700/10985658/c16e9bea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Bay Harbor Lodge [](https://www.expedia.ca/Key-Largo-Hotels-Bay-Harbor-Lodge.h10985658.Hotel-Information) Rock Harbor 9.4/10 Exceptional (673) CA $375 CA $422 total includes taxes & fees Mar 17 - Mar 18 [](https://www.expedia.ca/Key-Largo-Hotels-Bay-Harbor-Lodge.h10985658.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/31000000/30220000/30216000/30215914/aba51715.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/31000000/30220000/30216000/30215914/328193c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/31000000/30220000/30216000/30215914/8f845907.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![King, Non Smoking](https://images.trvl-media.com/lodging/31000000/30220000/30216000/30215914/037b040a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Key Largo Inn [](https://www.expedia.ca/Key-Largo-Hotels-Key-Largo-Inn.h30215914.Hotel-Information) Key Largo 6.6/10 (1003) CA $222 CA $250 total includes taxes & fees Mar 19 - Mar 20 [](https://www.expedia.ca/Key-Largo-Hotels-Key-Largo-Inn.h30215914.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/12000000/11920000/11919100/11919055/8c74658c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![On the beach, beach cabanas, sun loungers, beach umbrellas](https://images.trvl-media.com/lodging/12000000/11920000/11919100/11919055/d9cc2f68.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, cabanas (surcharge), pool umbrellas](https://images.trvl-media.com/lodging/12000000/11920000/11919100/11919055/ba58782b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 restaurants, breakfast, lunch, dinner served; American cuisine](https://images.trvl-media.com/lodging/12000000/11920000/11919100/11919055/92d23e9a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Playa Largo Resort & Spa, Autograph Collection [](https://www.expedia.ca/Key-Largo-Hotels-Playa-Largo-Resort-Spa.h11919055.Hotel-Information) Rock Harbor 8.8/10 Excellent (1003) CA $543 CA $685 total includes taxes & fees Apr 12 - Apr 13 [](https://www.expedia.ca/Key-Largo-Hotels-Playa-Largo-Resort-Spa.h11919055.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/2000000/1190000/1186200/1186162/42d47c50.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach/ocean view](https://images.trvl-media.com/lodging/2000000/1190000/1186200/1186162/2d6f6a20.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Aerial view](https://images.trvl-media.com/lodging/2000000/1190000/1186200/1186162/0f5b3686.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Coffee/tea maker](https://images.trvl-media.com/lodging/2000000/1190000/1186200/1186162/340e7f1c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Dove Creek Resort & Marina, Trademark Collection by Wyndham [](https://www.expedia.ca/Key-Largo-Hotels-Dove-Creek-Resort-Marina.h1186162.Hotel-Information) Key Largo 7.6/10 Good (1007) CA $288 CA $367 total includes taxes & fees Apr 12 - Apr 13 [](https://www.expedia.ca/Key-Largo-Hotels-Dove-Creek-Resort-Marina.h1186162.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/4000000/3280000/3274400/3274374/9ae0ece9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Oceanview Seaside Villa](https://images.trvl-media.com/lodging/4000000/3280000/3274400/3274374/481f59bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, individually decorated, individually furnished](https://images.trvl-media.com/lodging/4000000/3280000/3274400/3274374/711bb33e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach/ocean view](https://images.trvl-media.com/lodging/4000000/3280000/3274400/3274374/d3f7ab96.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Fisher Inn Resort & Marina [](https://www.expedia.ca/Islamorada-Hotels-Fisher-Inn-Resort-Marina.h3274374.Hotel-Information) Islamorada 8.4/10 Very good (1000) CA $360 CA $449 total includes taxes & fees Apr 12 - Apr 13 [](https://www.expedia.ca/Islamorada-Hotels-Fisher-Inn-Resort-Marina.h3274374.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/5000000/4190000/4182600/4182524/667446d9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/5000000/4190000/4182600/4182524/8147c88b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/5000000/4190000/4182600/4182524/be3c8b08.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/5000000/4190000/4182600/4182524/63ef26aa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Coconut Cove Resort and Marina [](https://www.expedia.ca/Islamorada-Hotels-Coconut-Cove-Resort-And-Marina.h4182524.Hotel-Information) Islamorada 9.0/10 Wonderful (216) CA $529 CA $595 total includes taxes & fees Mar 15 - Mar 16 [](https://www.expedia.ca/Islamorada-Hotels-Coconut-Cove-Resort-And-Marina.h4182524.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/11000000/10540000/10531800/10531753/29952335.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Villa, 1 Bedroom, Kitchen (25)](https://images.trvl-media.com/lodging/11000000/10540000/10531800/10531753/10f479ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Waterview King (26)](https://images.trvl-media.com/lodging/11000000/10540000/10531800/10531753/fd4b899f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Villa, 1 Bedroom, Kitchen (25) | Terrace/patio](https://images.trvl-media.com/lodging/11000000/10540000/10531800/10531753/0c8ddcdb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Coconut Bay Resort Key Largo [](https://www.expedia.ca/Key-Largo-Hotels-Coconut-Bay-Resort-Key-Largo.h10531753.Hotel-Information) Rock Harbor 9.6/10 Exceptional (199) CA $401 CA $451 total includes taxes & fees Mar 16 - Mar 17 [](https://www.expedia.ca/Key-Largo-Hotels-Coconut-Bay-Resort-Key-Largo.h10531753.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/910000/900500/900424/180cb0c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/910000/900500/900424/2237ce7b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Shangri-La Suite | Terrace/patio](https://images.trvl-media.com/lodging/1000000/910000/900500/900424/58abb15a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/910000/900500/900424/b7eb418d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Casa Morada [](https://www.expedia.ca/Islamorada-Hotels-Casa-Morada.h900424.Hotel-Information) Matecumbe 9.4/10 Exceptional (428) CA $570 CA $738 total includes taxes & fees Mar 29 - Mar 30 [](https://www.expedia.ca/Islamorada-Hotels-Casa-Morada.h900424.Hotel-Information) ![In-room safe, individually decorated, individually furnished](https://images.trvl-media.com/lodging/1000000/20000/11900/11864/4671ebc2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 outdoor pools, a heated pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/1000000/20000/11900/11864/e438dbb2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/20000/11900/11864/w4000h2663x0y0-d63f21e0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Banquet hall](https://images.trvl-media.com/lodging/1000000/20000/11900/11864/cb9f9f1a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort [](https://www.expedia.ca/Islamorada-Hotels-Three-Waters-Resort-And-Marina.h11864.Hotel-Information) Islamorada 9.0/10 Wonderful (169) CA $484 CA $635 total includes taxes & fees Mar 23 - Mar 24 [](https://www.expedia.ca/Islamorada-Hotels-Three-Waters-Resort-And-Marina.h11864.Hotel-Information) [View all properties](https://expedia.ca/Hotel-Search?startDate=2026-03-27&endDate=2026-03-28®ionId=10768&adults=2&amenities=POOL&sort=RECOMMENDED&mealPlan=FREE_BREAKFAST&openPlayBack=true) ## 4-star hotels with pools in Islamorada ![Alligator Reef Oceanfront Room King Lanai with Queen Sofabed | View from room](https://images.trvl-media.com/lodging/1000000/70000/62000/61976/4186365f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Alligator Reef Oceanfront Room King Lanai with Queen Sofabed](https://images.trvl-media.com/lodging/1000000/70000/62000/61976/2728b985.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![One Bedroom Oceanfront Suite Two Queens Lanai](https://images.trvl-media.com/lodging/1000000/70000/62000/61976/a737b04b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/1000000/70000/62000/61976/af6ef0d3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Amara Cay Resort [](https://www.expedia.ca/Islamorada-Hotels-Amara-Cay-Resort.h61976.Hotel-Information) Matecumbe 8.8/10 Excellent (1251) CA $315 CA $455 total includes taxes & fees Mar 26 - Mar 27 [](https://www.expedia.ca/Islamorada-Hotels-Amara-Cay-Resort.h61976.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/480000/475500/475438/f8d2863e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 restaurants, breakfast served](https://images.trvl-media.com/lodging/1000000/480000/475500/475438/d49c45e7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 restaurants, breakfast served](https://images.trvl-media.com/lodging/1000000/480000/475500/475438/2bff44ae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/480000/475500/475438/5d218fa9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Islander Resort [](https://www.expedia.ca/Islamorada-Hotels-Islander-Resort.h475438.Hotel-Information) Matecumbe 9.2/10 Wonderful (1002) CA $444 CA $592 total includes taxes & fees Apr 12 - Apr 13 [](https://www.expedia.ca/Islamorada-Hotels-Islander-Resort.h475438.Hotel-Information) ![Suite, 1 King Bed with Sofa bed, Ocean View](https://images.trvl-media.com/lodging/3000000/2480000/2477600/2477508/18023e21.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/3000000/2480000/2477600/2477508/c134a889.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, sun loungers](https://images.trvl-media.com/lodging/3000000/2480000/2477600/2477508/eed3d949.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 King Bed with Sofa bed, Ocean View | Exterior](https://images.trvl-media.com/lodging/3000000/2480000/2477600/2477508/b304e7ea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### La Siesta Resort & Villas [](https://www.expedia.ca/Islamorada-Hotels-La-Siesta-Resort-Marina.h2477508.Hotel-Information) Matecumbe 8.8/10 Excellent (1000) CA $299 CA $437 total includes taxes & fees Mar 22 - Mar 23 [](https://www.expedia.ca/Islamorada-Hotels-La-Siesta-Resort-Marina.h2477508.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/12000000/11920000/11919100/11919055/8c74658c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![On the beach, beach cabanas, sun loungers, beach umbrellas](https://images.trvl-media.com/lodging/12000000/11920000/11919100/11919055/d9cc2f68.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, cabanas (surcharge), pool umbrellas](https://images.trvl-media.com/lodging/12000000/11920000/11919100/11919055/ba58782b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 restaurants, breakfast, lunch, dinner served; American cuisine](https://images.trvl-media.com/lodging/12000000/11920000/11919100/11919055/92d23e9a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Playa Largo Resort & Spa, Autograph Collection [](https://www.expedia.ca/Key-Largo-Hotels-Playa-Largo-Resort-Spa.h11919055.Hotel-Information) Rock Harbor 8.8/10 Excellent (1003) CA $543 CA $685 total includes taxes & fees Apr 12 - Apr 13 [](https://www.expedia.ca/Key-Largo-Hotels-Playa-Largo-Resort-Spa.h11919055.Hotel-Information) ![In-room safe, individually decorated, individually furnished](https://images.trvl-media.com/lodging/1000000/20000/11900/11864/4671ebc2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 outdoor pools, a heated pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/1000000/20000/11900/11864/e438dbb2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/20000/11900/11864/w4000h2663x0y0-d63f21e0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Banquet hall](https://images.trvl-media.com/lodging/1000000/20000/11900/11864/cb9f9f1a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort [](https://www.expedia.ca/Islamorada-Hotels-Three-Waters-Resort-And-Marina.h11864.Hotel-Information) Islamorada 9.0/10 Wonderful (169) CA $484 CA $635 total includes taxes & fees Mar 23 - Mar 24 [](https://www.expedia.ca/Islamorada-Hotels-Three-Waters-Resort-And-Marina.h11864.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/1000000/20000/14100/14042/7c755dc1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 restaurants, breakfast served](https://images.trvl-media.com/lodging/1000000/20000/14100/14042/4de34d26.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![32-inch LCD TV with satellite channels, TV, iPod dock](https://images.trvl-media.com/lodging/1000000/20000/14100/14042/bbdba544.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![2 outdoor pools, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/1000000/20000/14100/14042/0df3bfb3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Baker's Cay Resort Key Largo, Curio Collection by Hilton [](https://www.expedia.ca/Key-Largo-Hotels-Bakers-Cay-Resort-Key-Largo.h14042.Hotel-Information) Key Largo 8.6/10 Excellent (1001) CA $584 CA $732 total includes taxes & fees Apr 13 - Apr 14 [](https://www.expedia.ca/Key-Largo-Hotels-Bakers-Cay-Resort-Key-Largo.h14042.Hotel-Information) ![On the beach, sun loungers, beach umbrellas, beach towels](https://images.trvl-media.com/lodging/55000000/54780000/54774300/54774228/dd7d4fab.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Smart TV, Netflix, Hulu, streaming services](https://images.trvl-media.com/lodging/55000000/54780000/54774300/54774228/fcc01350.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Balcony view](https://images.trvl-media.com/lodging/55000000/54780000/54774300/54774228/95dbc957.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Balcony view](https://images.trvl-media.com/lodging/55000000/54780000/54774300/54774228/55a08207.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Islands of Islamorada [](https://www.expedia.ca/Islamorada-Hotels-The-Islands-Of-Islamorada.h54774228.Hotel-Information) Matecumbe 9.8/10 Exceptional (72) CA $953 CA $1,147 total includes taxes & fees Apr 13 - Apr 14 [](https://www.expedia.ca/Islamorada-Hotels-The-Islands-Of-Islamorada.h54774228.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. [View all properties](https://expedia.ca/Hotel-Search?startDate=2026-03-27&endDate=2026-03-28®ionId=10768&adults=2&amenities=POOL&sort=RECOMMENDED&star=40&openPlayBack=true) ## Top Islamorada Hotel Reviews ![Chesapeake Beach Resort](https://images.trvl-media.com/lodging/1000000/10000/4200/4170/689f4306_y.jpg) ### Chesapeake Beach Resort 2/10 Terrible "This place has a literal COCKROACH INFESTATION. WORST STAY EVER. THEY DID NOT COMPENSATE PROPER OR TAKE CARE OF THE BUG PROBLEM. DO NOT STAY HERE UNTIL THEY CAN PROVE THE BUGS HAVE BEEN TAKEN CARE OF." [](https://expedia.ca/Islamorada-Hotels-Chesapeake-Beach-Resort.h4170.Hotel-Information) ![Coconut Cove Resort and Marina](https://images.trvl-media.com/lodging/5000000/4190000/4182600/4182524/667446d9_y.jpg) ### Coconut Cove Resort and Marina 2/10 Terrible "This property is not at all as it appears on Expedia. While the Front Office Manager was lovely, the property is very dated and tired looking. When we walked into our room we were overwhelmed by the smell of mildew such that we could not stay. We left the key on the counter and searched for another property. When we told the Front Office Manager we did not stay she did offer to move us to another room but given the property was not at all what we expected we declined. While the staff must have done their best to clean, because of the age of the property there is only so much that can be done. If you are looking for an authentic, tired, 1950s style Key West property...this is the one. Triple check what you see on Expedia as it isn't always what you get. Disappointing.... " [](https://expedia.ca/Islamorada-Hotels-Coconut-Cove-Resort-And-Marina.h4182524.Hotel-Information) ![Amara Cay Resort](https://images.trvl-media.com/lodging/1000000/70000/62000/61976/4186365f_y.jpg) ### Amara Cay Resort 4/10 Poor "We had a partial view of ocean from our room. We did not use the pool but it was a decent looking. The staff was kind and professional. The room we had smelled of mold strongly. " [](https://expedia.ca/Islamorada-Hotels-Amara-Cay-Resort.h61976.Hotel-Information) ![Drop Anchor](https://images.trvl-media.com/lodging/5000000/4290000/4287400/4287368/f42604af_y.jpg) ### Drop Anchor 10/10 Excellent "We could see the ocean from the bed so we'd wake up, open the curtains and watch the sunrise from the bed! Amazing!" [](https://expedia.ca/Islamorada-Hotels-Drop-Anchor.h4287368.Hotel-Information) ![Cheeca Lodge & Spa](https://images.trvl-media.com/lodging/1000000/10000/5800/5780/4608d7e2_y.jpg) ### Cheeca Lodge & Spa 6/10 Okay "We did not use the spa services, we may have been able to barely see a small portion of the ocean out a window" [](https://expedia.ca/Islamorada-Hotels-Cheeca-Lodge-Spa.h5780.Hotel-Information) ![La Jolla Resort](https://images.trvl-media.com/lodging/17000000/16580000/16574700/16574668/40f72f1c_y.jpg) ### La Jolla Resort 10/10 Excellent "The property was clean and inviting. We stayed in the room above the office. It was very quiet, clean and smelled fresh. The staff was excellent; he answered our questions and was very helpful when approached. Would happily stay here again! " [](https://expedia.ca/Islamorada-Hotels-La-Jolla-Resort.h16574668.Hotel-Information) ![Breezy Palms Resort](https://images.trvl-media.com/lodging/12000000/11950000/11945900/11945889/19240ce2_y.jpg) ### Breezy Palms Resort 10/10 Excellent "Beautiful . Paradise." [](https://expedia.ca/Islamorada-Hotels-Breezy-Palms-Resort.h11945889.Hotel-Information) ![Islander Resort](https://images.trvl-media.com/lodging/1000000/480000/475500/475438/f8d2863e_y.jpg) ### Islander Resort 10/10 Excellent "Absolutely loved this place. A little gem we found as we were driving. Decided to come in and take a look and booked straight away for a few days. Will be returning next year" [](https://expedia.ca/Islamorada-Hotels-Islander-Resort.h475438.Hotel-Information) ![Fisher Inn Resort & Marina](https://images.trvl-media.com/lodging/4000000/3280000/3274400/3274374/9ae0ece9_y.jpg) ### Fisher Inn Resort & Marina 8/10 Good "The room is smaller than in the photos and rooms are more run down. WiFi never worked during our stay and we did not receive the complimentary cocktail and snack upon arrival as promised. Staff wasn't great but they did fix the broken shower head the day before we left. It was fine but not as great as we hoped for. Would've been 2 stars if they didn't fix the shower head. " [](https://expedia.ca/Islamorada-Hotels-Fisher-Inn-Resort-Marina.h3274374.Hotel-Information) ## Frequently asked questions ### What are the best hotels in Islamorada with outdoor pools? > Another fantastic option is the [Sunset Inn](https://www.expedia.ca/Islamorada-Hotels-Sunset-Inn.h30568049.Hotel-Information), a cozy 3-star hotel known for its warm outdoor pool and spacious rooms. Travellers appreciate the friendly and helpful staff, as well as the central location that makes exploring Islamorada a breeze. With free bicycle rentals and self-parking, it's an excellent value for families wanting to make the most of their adventure. > > > For a more upscale experience, consider [Casa Morada](https://www.expedia.ca/Islamorada-Hotels-Casa-Morada.h900424.Hotel-Information), also a 3.5-star hotel, which features an inviting outdoor pool alongside a poolside bar. Guests enjoy complimentary breakfast and praise the excellent reception and helpful staff. The comfortable rooms and good facilities make it a popular choice among travellers who value quality. > > > [Chesapeake Beach Resort](https://www.expedia.ca/Islamorada-Hotels-Chesapeake-Beach-Resort.h4170.Hotel-Information), another 3.5-star gem, offers a clean and well-maintained outdoor pool, along with friendly service and a beautiful location. Guests love the complimentary breakfast and the comfortable, clean rooms that enhance their stay in this picturesque destination. > > > Lastly, for those looking for a luxurious escape, [Cheeca Lodge & Spa](https://www.expedia.ca/Islamorada-Hotels-Cheeca-Lodge-Spa.h5780.Hotel-Information) stands out with its stunning outdoor pool and resort-style amenities. This 5-star hotel features a poolside bar, cabanas, and even private beach access, ensuring a lavish experience. Guests frequently highlight the exceptional service, beautiful accommodations, and delicious food, making it a top choice for those wishing to indulge during their family getaway. ### How much does a hotel with outdoor pool in Islamorada cost? ### Are there hotels in Islamorada that have private outdoor pools? > This resort is highly rated, boasting a traveller review score of 9.2, and it's no surprise why. Guests rave about the friendly and amazing staff, the beautiful and clean rooms, and the overall excellent service. The amenities are designed for relaxation and indulgence, featuring options like a private hot tub, deep-soaking bathtubs, and even massages on the beach for those looking to unwind. > > > In addition to the luxurious pools, Cheeca Lodge & Spa provides a range of activities, including onsite tennis and golf, ensuring that families and couples alike can find something to enjoy. The beachfront restaurant offers delicious dining options, superb for a sunset meal after a day filled with adventure. ### What are some of the best Islamorada hotels with outdoor pools and scenic views? > For those looking for a mix of comfort and great service, the [Chesapeake Beach Resort](https://www.expedia.ca/Islamorada-Hotels-Chesapeake-Beach-Resort.h4170.Hotel-Information), also rated at 3.5 stars, is another excellent choice. Its outdoor pool is well-maintained, and the complimentary continental breakfast is a hit among travellers, who describe the staff as friendly and the location as beautifully scenic. The resort boasts lovely beach views, creating an inclusive setting for families wanting to soak up the sun. > > > If luxury is on your agenda, [Cheeca Lodge & Spa](https://www.expedia.ca/Islamorada-Hotels-Cheeca-Lodge-Spa.h5780.Hotel-Information) stands out as a 5-star gem. It features a stunning outdoor pool surrounded by cabanas, a poolside bar, and a private beach area, making it great for those who enjoy upscale relaxation. Guests rave about the friendly and amazing staff, coupled with the beautifully clean rooms and excellent dining options, ensuring a memorable experience for everyone. > > > For a more laid-back vibe, the [Islander Resort](https://www.expedia.ca/Islamorada-Hotels-Islander-Resort.h475438.Hotel-Information), rated 4 stars, provides an inviting outdoor pool, poolside bar, and stunning beach views. Families will appreciate the spacious rooms and the attentive service, which travellers have highlighted as both friendly and accommodating. > > > Lastly, the [Pines & Palms Resort](https://www.expedia.ca/Islamorada-Hotels-Pines-Palms-Resort.h990422.Hotel-Information) offers a cozy atmosphere with its outdoor pool and beautiful ocean views, great for families looking to enjoy a peaceful retreat. With clean rooms and a welcoming location, it's an ideal spot to unwind after a day of adventure in the scenic surroundings of Islamorada. ### Are there hotels in Islamorada with outdoor pool cabanas or loungers? > Another excellent option is the [Islander Resort](https://www.expedia.ca/Islamorada-Hotels-Islander-Resort.h475438.Hotel-Information), rated 9.2 by travellers. This 4-star hotel features spacious outdoor pool cabanas and sun loungers, great for families looking to unwind after a day of exploring. The pool area is described as beautiful and expansive, providing a serene atmosphere for both adults and children. > > > For those seeking a charming stay, the [Sunset Inn](https://www.expedia.ca/Islamorada-Hotels-Sunset-Inn.h30568049.Hotel-Information) offers a cozy 3-star experience. With free pool cabanas and a warm, welcoming pool environment, this hotel boasts a stellar review rating of 9.4, where guests appreciate the cleanliness and helpful staff. > > > Lastly, [Casa Morada](https://www.expedia.ca/Islamorada-Hotels-Casa-Morada.h900424.Hotel-Information), a 3.5-star hotel, offers resort-inclusive amenities including outdoor pool sun loungers and a poolside bar, ensuring a delightful day in the sun. With a rating of 9.4, guests praise the comfort of the rooms and the excellent reception service. ### Which Islamorada hotels offer poolside service for food and drinks? > Another top choice is the luxurious [Cheeca Lodge & Spa](https://www.expedia.ca/Islamorada-Hotels-Cheeca-Lodge-Spa.h5780.Hotel-Information), a 5-star gem that features an expansive outdoor pool, complete with poolside cabanas and a bar serving refreshing drinks. Guests rave about the beautiful and clean rooms, as well as the amazing service provided by the friendly staff. With a stellar review score of 9.2, this hotel not only caters to your relaxation needs but also offers a range of amenities, including a beachfront restaurant and spa services. > > > For a well-rounded stay, the [Islander Resort](https://www.expedia.ca/Islamorada-Hotels-Islander-Resort.h475438.Hotel-Information) stands out with its outdoor pool and poolside bar, superb for cooling off and enjoying a drink in the sun. Rated at 9.2, guests love the beautiful and spacious pool area, along with the friendly staff that enhance the overall experience. > > > If you're looking for a more intimate setting, consider the [Pines & Palms Resort](https://www.expedia.ca/Islamorada-Hotels-Pines-Palms-Resort.h990422.Hotel-Information), a 3-star option that also provides an inviting outdoor pool with a poolside bar. With a review score of 9.2, it's noted for its beautiful location and clean rooms, making it a cozy retreat for families and couples alike. > > > Lastly, [Amara Cay Resort](https://www.expedia.ca/Islamorada-Hotels-Amara-Cay-Resort.h61976.Hotel-Information), a 4-star hotel, features a lovely outdoor pool with poolside service for food and drinks. Guests have appreciated the beautiful location and comfortable accommodations, giving it a rating of 8.8\. The friendly staff and the beachside restaurant add to the hotel's appeal, ensuring a delightful experience during your stay in Islamorada. ### Are there hotels with outdoor pools that are close to MoradaWay Arts & Cultural District? > Just a short distance from the MoradaWay Arts & Cultural District, the [Sunset Inn](https://www.expedia.ca/Islamorada-Hotels-Sunset-Inn.h30568049.Hotel-Information) is another fantastic option. This 3-star hotel boasts a warm outdoor pool and spacious, clean rooms. Rated at 9.4, travellers appreciate the friendly service and excellent central location, along with free bicycle rentals that make exploring the area even easier. > > > For a more upscale experience, [Casa Morada](https://www.expedia.ca/Islamorada-Hotels-Casa-Morada.h900424.Hotel-Information), also rated 9.4, provides a resort-style outdoor pool complemented by a poolside bar and free breakfast options. Guests love the comfortable accommodations and attentive staff, making it a great spot for families looking to unwind after a day of adventure. > > > Finally, if you're in search of a luxurious retreat, [Cheeca Lodge & Spa](https://www.expedia.ca/Islamorada-Hotels-Cheeca-Lodge-Spa.h5780.Hotel-Information) stands out with its expansive outdoor pool, poolside cabanas, and a host of amenities including a beachfront restaurant and a wellness spa. With a rating of 9.2, it's renowned for its exceptional service and beautiful surroundings, creating a memorable getaway for those who wish to indulge. ### Are there hotels in Islamorada with outdoor pool activities or events? > For families looking for a fun-filled getaway, the [Cheeca Lodge & Spa](https://www.expedia.ca/Islamorada-Hotels-Cheeca-Lodge-Spa.h5780.Hotel-Information) stands out with its luxurious family pool area, complemented by a full-service watersports facility nearby. This allows for a mix of poolside relaxation and thrilling aquatic adventures, ensuring there's something for everyone. The option to reserve private cabanas by the spa pool or infinity pool adds an extra touch of luxury, superb for parents wanting a serene escape while kids enjoy the water. > > > Couples seeking a romantic retreat will love the [Chesapeake Beach Resort](https://www.expedia.ca/Islamorada-Hotels-Chesapeake-Beach-Resort.h4170.Hotel-Information), which features two outdoor pools with breathtaking ocean views. The resort's oceanfront event venue creates opportunities for intimate gatherings or sunset celebrations, providing a picturesque backdrop for unforgettable moments together. > > > For those who appreciate a more laid-back atmosphere, the [Fisher Inn Resort & Marina](https://www.expedia.ca/Islamorada-Hotels-Fisher-Inn-Resort-Marina.h3274374.Hotel-Information) offers an outdoor heated pool surrounded by sun loungers and outdoor furniture. This setting is ideal for leisurely days spent soaking up the sun, with easy access to the beach for a refreshing dip in the ocean. > > > With a variety of hotels that blend outdoor pool activities with great experiences, Islamorada promises a delightful stay for all types of travellers. ### Is it cheaper to book flights and a hotel in Islamorada as a package? ### How can I save on a hotel in Islamorada with Expedia? ### Can I cancel my hotel reservation on Expedia? ## Explore a world of travel with Expedia - Lodging - More ways to book - [Cheap Hotels in Bahia Honda Key ](https://www.expedia.ca/Bahia-Honda-Key-Hotels-Cheap-Hotels.0-0-d553248635083902001-tCheapHotels.Travel-Guide-Filter-Hotels) - [Luxury Hotels in Bahia Honda Key ](https://www.expedia.ca/Bahia-Honda-Key-Hotels-Luxury-Hotel.0-0-d553248635083902001-tLuxuryHotel.Travel-Guide-Filter-Hotels) - [Adults Only Resorts & in Brickell ](https://www.expedia.ca/Brickell-Miami-Hotels-Adults-Only-Resorts.0-n6240961-0-tAdultsOnlyResorts.Travel-Guide-Filter-Hotels) - 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