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 [Jan 27 - Jan 28](https://www.expedia.ca/Hotel-Search?regionId=10768&startDate=2026-01-27&endDate=2026-01-28&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Jan 28 - Jan 29](https://www.expedia.ca/Hotel-Search?regionId=10768&startDate=2026-01-28&endDate=2026-01-29&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Jan 30 - Feb 1](https://www.expedia.ca/Hotel-Search?regionId=10768&startDate=2026-01-30&endDate=2026-02-01&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Feb 6 - Feb 8](https://www.expedia.ca/Hotel-Search?regionId=10768&startDate=2026-02-06&endDate=2026-02-08&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Islamorada hotels with a pool ![Outdoor pool](https://images.trvl-media.com/lodging/92000000/91750000/91743100/91743042/1641bbd2.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/92000000/91750000/91743100/91743042/92a650b5.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 (127 reviews) "Very peaceful and comfortable stay! Dallas and Hannah were amazing hosts! Thank you so much !" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Nick CA $182 CA $398 total includes taxes & fees Jan 30 - Jan 31 [](https://www.expedia.ca/Islamorada-Hotels-Treasure-Harbor.h91743042.Hotel-Information) ![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) ![Room](https://images.trvl-media.com/lodging/1000000/890000/882300/882254/9e920762.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 (1,148 reviews) "Excellent location, beautiful property, friendly staff. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Michael CA $227 CA $317 total includes taxes & fees Jan 29 - Jan 30 [](https://www.expedia.ca/Long-Key-Hotels-Lime-Tree-Bay-Resort.h882254.Hotel-Information) ![Aerial view](https://images.trvl-media.com/lodging/2000000/1190000/1186200/1186162/0f5b3686.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/2000000/1190000/1186200/1186162/aed267ad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![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) ### 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 (1,007 reviews) "Nice place. Excellent location. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Carmen CA $259 CA $335 total includes taxes & fees Feb 1 - Feb 2 [](https://www.expedia.ca/Key-Largo-Hotels-Dove-Creek-Resort-Marina.h1186162.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) ![Dock](https://images.trvl-media.com/lodging/58000000/57190000/57185500/57185414/4deb6af1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premier Cabin, 1 King Bed, Bay View](https://images.trvl-media.com/lodging/58000000/57190000/57185500/57185414/00031550.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) ### Rock Reef Resort [](https://www.expedia.ca/Key-Largo-Hotels-Rock-Reef-Resort.h57185414.Hotel-Information) Rock Harbor 9.2/10 Wonderful (1,083 reviews) "Nice place to spend some time in the Keys conveniently located,clean rooms and helpful staff with excellent views of Bay." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Harry CA $248 CA $279 total includes taxes & fees Feb 1 - Feb 2 [](https://www.expedia.ca/Key-Largo-Hotels-Rock-Reef-Resort.h57185414.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) ![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) ![Deluxe Ocean View Two Queen Suite | Balcony](https://images.trvl-media.com/lodging/1000000/10000/4200/4170/1d1a1984.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 (1,663 reviews) "Wonderful breakfast with omelettes cooked to order, great pancakes, fresh fruit, etc. very pleasant staff and beautiful beach area." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kurt CA $298 CA $413 total includes taxes & fees Jan 28 - Jan 29 [](https://www.expedia.ca/Islamorada-Hotels-Chesapeake-Beach-Resort.h4170.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) ![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) ![Kayaking](https://images.trvl-media.com/lodging/5000000/4290000/4287400/4287368/81979d64.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 (1,008 reviews) "Great" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kelly CA $215 CA $290 total includes taxes & fees Jan 29 - Jan 30 [](https://www.expedia.ca/Islamorada-Hotels-Drop-Anchor.h4287368.Hotel-Information) ![Outdoor pool, sun loungers](https://images.trvl-media.com/lodging/17000000/16580000/16574700/16574668/ac9bc991.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Apartment, 1 Bedroom, Bay View (Upstairs Sleeps 6)](https://images.trvl-media.com/lodging/17000000/16580000/16574700/16574668/65014355.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private beach, fishing](https://images.trvl-media.com/lodging/17000000/16580000/16574700/16574668/74e26d92.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Apartment, 1 Bedroom, Bay View (Upstairs Sleeps 6) | Living area](https://images.trvl-media.com/lodging/17000000/16580000/16574700/16574668/736a4da5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### La Jolla Resort [](https://www.expedia.ca/Islamorada-Hotels-La-Jolla-Resort.h16574668.Hotel-Information) Matecumbe 9.2/10 Wonderful (1,005 reviews) "This place is amazing " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) cindy [](https://www.expedia.ca/Islamorada-Hotels-La-Jolla-Resort.h16574668.Hotel-Information) ![Fishing](https://images.trvl-media.com/lodging/2000000/1580000/1576800/1576773/371bf8f6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Sundeck](https://images.trvl-media.com/lodging/2000000/1580000/1576800/1576773/d461c69c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/2000000/1580000/1576800/1576773/f135208c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/2000000/1580000/1576800/1576773/4743fa46.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Creekside Inn [](https://www.expedia.ca/Tavernier-Hotels-Creekside-Inn-Islamorada.h1576773.Hotel-Information) Tavernier 7.8/10 Good (1,003 reviews) "It is an awesome experience with wonderful views, the location is a big advantage for this hotel" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Vamsi kalyan CA $232 CA $260 total includes taxes & fees Jan 28 - Jan 29 [](https://www.expedia.ca/Tavernier-Hotels-Creekside-Inn-Islamorada.h1576773.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/30000/22700/22657/ad31d180.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/30000/22700/22657/78ecf44f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premier One Bedroom Waterfront Suite Bayview with Sofabed](https://images.trvl-media.com/lodging/1000000/30000/22700/22657/8552ad16.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/1000000/30000/22700/22657/97f26711.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Bayside Inn Key Largo [](https://www.expedia.ca/Key-Largo-Hotels-Bayside-Inn-Key-Largo.h22657.Hotel-Information) Key Largo 8.6/10 Excellent (1,664 reviews) "Spotless rooms, staff is so friendly and helpful! Amazing place to stay." ![Canada](https://a.travel-assets.com/egds/marks/flags/ca.svg) Jeannie CA $192 CA $250 total includes taxes & fees Jan 28 - Jan 29 [](https://www.expedia.ca/Key-Largo-Hotels-Bayside-Inn-Key-Largo.h22657.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 9.2/10 Wonderful (665 reviews) "Friendly, hospitable staff and beautifully landscaped grounds. Complimentary coffee and Peg's scones for breakfast. Peg offers a different variety of scones each day. The scones are the best you'll ever eat! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Cindy CA $281 CA $316 total includes taxes & fees Jan 28 - Jan 29 [](https://www.expedia.ca/Key-Largo-Hotels-Bay-Harbor-Lodge.h10985658.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=2026-02-10&endDate=2026-02-11®ionId=10768&adults=2&amenities=POOL&sort=RECOMMENDED&openPlayBack=true) ## Choose what matters most at hotels with a pool in Islamorada Ocean view Breakfast included 4 stars Beach Hot tub ## Hotels with pools and ocean views 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) ![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) ![Deluxe Ocean View Two Queen Suite | Balcony](https://images.trvl-media.com/lodging/1000000/10000/4200/4170/1d1a1984.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 (1663) CA $298 CA $413 total includes taxes & fees Jan 28 - Jan 29 [](https://www.expedia.ca/Islamorada-Hotels-Chesapeake-Beach-Resort.h4170.Hotel-Information) ![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) ![Room](https://images.trvl-media.com/lodging/1000000/890000/882300/882254/9e920762.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 (1148) CA $227 CA $317 total includes taxes & fees Jan 29 - Jan 30 [](https://www.expedia.ca/Long-Key-Hotels-Lime-Tree-Bay-Resort.h882254.Hotel-Information) ![Sundeck](https://images.trvl-media.com/lodging/58000000/57190000/57185500/57185414/6ddda999.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 Cabin, 1 King Bed, Bay View](https://images.trvl-media.com/lodging/58000000/57190000/57185500/57185414/00031550.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) ### Rock Reef Resort [](https://www.expedia.ca/Key-Largo-Hotels-Rock-Reef-Resort.h57185414.Hotel-Information) Rock Harbor 9.2/10 Wonderful (1083) CA $248 CA $279 total includes taxes & fees Feb 1 - Feb 2 [](https://www.expedia.ca/Key-Largo-Hotels-Rock-Reef-Resort.h57185414.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) ![Restaurant](https://images.trvl-media.com/lodging/2000000/1190000/1186200/1186162/aed267ad.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) ![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) ### 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 $259 CA $335 total includes taxes & fees Feb 1 - Feb 2 [](https://www.expedia.ca/Key-Largo-Hotels-Dove-Creek-Resort-Marina.h1186162.Hotel-Information) ![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) ![Alligator Reef Oceanfront Room King | Beach/ocean view](https://images.trvl-media.com/lodging/1000000/70000/62000/61976/43c465e8.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 (1276) CA $284 CA $420 total includes taxes & fees Jan 29 - Jan 30 [](https://www.expedia.ca/Islamorada-Hotels-Amara-Cay-Resort.h61976.Hotel-Information) ![Balcony](https://images.trvl-media.com/lodging/1000000/10000/5800/5780/4608d7e2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/1000000/10000/5800/5780/981feca1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Daily full breakfast for a fee](https://images.trvl-media.com/lodging/1000000/10000/5800/5780/b210c979.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Poolside bar](https://images.trvl-media.com/lodging/1000000/10000/5800/5780/387633fc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cheeca Lodge & Spa [](https://www.expedia.ca/Islamorada-Hotels-Cheeca-Lodge-Spa.h5780.Hotel-Information) Matecumbe 9.2/10 Wonderful (1303) CA $451 CA $608 total includes taxes & fees Jan 29 - Jan 30 [](https://www.expedia.ca/Islamorada-Hotels-Cheeca-Lodge-Spa.h5780.Hotel-Information) ![Outdoor pool, open 8:00 AM to 11:00 PM, sun loungers](https://images.trvl-media.com/lodging/1000000/10000/5600/5502/7f240362.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/1000000/10000/5600/5502/084177d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from room](https://images.trvl-media.com/lodging/1000000/10000/5600/5502/f0191d8a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Sundeck](https://images.trvl-media.com/lodging/1000000/10000/5600/5502/dfb81707.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Ocean Pointe Suites at Key Largo [](https://www.expedia.ca/Tavernier-Hotels-Ocean-Pointe-Suites-At-Key-Largo.h5502.Hotel-Information) Tavernier 8.4/10 Very good (1021) CA $266 CA $324 total includes taxes & fees Jan 28 - Jan 29 [](https://www.expedia.ca/Tavernier-Hotels-Ocean-Pointe-Suites-At-Key-Largo.h5502.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) ![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) ![Reception](https://images.trvl-media.com/lodging/1000000/20000/14100/14042/3b0a2582.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 (1004) CA $483 CA $619 total includes taxes & fees Feb 4 - Feb 5 [](https://www.expedia.ca/Key-Largo-Hotels-Bakers-Cay-Resort-Key-Largo.h14042.Hotel-Information) ![Oceanfront King Suite w/ Kitchen & Private Balcony | Beach/ocean view](https://images.trvl-media.com/lodging/5000000/4290000/4287400/4287368/7fd0f78d.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) ![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) ### Drop Anchor [](https://www.expedia.ca/Islamorada-Hotels-Drop-Anchor.h4287368.Hotel-Information) Islamorada 8.8/10 Excellent (1008) CA $215 CA $290 total includes taxes & fees Jan 29 - Jan 30 [](https://www.expedia.ca/Islamorada-Hotels-Drop-Anchor.h4287368.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) ![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) ![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/5000000/4190000/4182600/4182524/11b76aad.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 (173) CA $337 CA $380 total includes taxes & fees Feb 5 - Feb 6 [](https://www.expedia.ca/Islamorada-Hotels-Coconut-Cove-Resort-And-Marina.h4182524.Hotel-Information) [View all properties](https://expedia.ca/Hotel-Search?startDate=2026-02-10&endDate=2026-02-11®ionId=10768&adults=2&amenities=POOL&sort=RECOMMENDED&amenities=OCEAN_VIEW&openPlayBack=true) ## 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) ![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) ![Deluxe Ocean View Two Queen Suite | Balcony](https://images.trvl-media.com/lodging/1000000/10000/4200/4170/1d1a1984.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 (1663) CA $298 CA $413 total includes taxes & fees Jan 28 - Jan 29 [](https://www.expedia.ca/Islamorada-Hotels-Chesapeake-Beach-Resort.h4170.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) ![Restaurant](https://images.trvl-media.com/lodging/2000000/1190000/1186200/1186162/aed267ad.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) ![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) ### 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 $259 CA $335 total includes taxes & fees Feb 1 - Feb 2 [](https://www.expedia.ca/Key-Largo-Hotels-Dove-Creek-Resort-Marina.h1186162.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) ![Serves lunch and dinner](https://images.trvl-media.com/lodging/12000000/11920000/11919100/11919055/bb9d7ce2.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 (1000) CA $690 CA $852 total includes taxes & fees Feb 9 - Feb 10 [](https://www.expedia.ca/Key-Largo-Hotels-Playa-Largo-Resort-Spa.h11919055.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) ![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) ![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/5000000/4190000/4182600/4182524/11b76aad.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 (173) CA $337 CA $380 total includes taxes & fees Feb 5 - Feb 6 [](https://www.expedia.ca/Islamorada-Hotels-Coconut-Cove-Resort-And-Marina.h4182524.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) ![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) ![Reception](https://images.trvl-media.com/lodging/1000000/20000/14100/14042/3b0a2582.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 (1004) CA $483 CA $619 total includes taxes & fees Feb 4 - Feb 5 [](https://www.expedia.ca/Key-Largo-Hotels-Bakers-Cay-Resort-Key-Largo.h14042.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/31000000/30220000/30216000/30215914/89ca05e3.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) ![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 (1010) CA $231 CA $260 total includes taxes & fees Feb 5 - Feb 6 [](https://www.expedia.ca/Key-Largo-Hotels-Key-Largo-Inn.h30215914.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) ![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) ![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) ### Fisher Inn Resort & Marina [](https://www.expedia.ca/Islamorada-Hotels-Fisher-Inn-Resort-Marina.h3274374.Hotel-Information) Islamorada 8.2/10 Very good (1009) CA $326 CA $411 total includes taxes & fees Feb 3 - Feb 4 [](https://www.expedia.ca/Islamorada-Hotels-Fisher-Inn-Resort-Marina.h3274374.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) ![Exterior](https://images.trvl-media.com/lodging/1000000/20000/11900/11864/w4000h2663x0y0-d63f21e0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 2 Double Beds, Balcony, Oceanfront | Living area](https://images.trvl-media.com/lodging/1000000/20000/11900/11864/ab6da82f.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) ### 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 (136) CA $464 CA $613 total includes taxes & fees Jan 28 - Jan 29 [](https://www.expedia.ca/Islamorada-Hotels-Three-Waters-Resort-And-Marina.h11864.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 9.2/10 Wonderful (665) CA $281 CA $316 total includes taxes & fees Jan 28 - Jan 29 [](https://www.expedia.ca/Key-Largo-Hotels-Bay-Harbor-Lodge.h10985658.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/4000000/3490000/3489100/3489061/f05102d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/4000000/3490000/3489100/3489061/d35570a3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/4000000/3490000/3489100/3489061/92345daf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium Suite, 1 Bedroom, Patio, Bay View](https://images.trvl-media.com/lodging/4000000/3490000/3489100/3489061/bbfdbeb0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Coconut Palm Inn [](https://www.expedia.ca/Tavernier-Hotels-Coconut-Palm-Inn.h3489061.Hotel-Information) Tavernier 9.4/10 Exceptional (533) CA $396 CA $493 total includes taxes & fees Jan 28 - Jan 29 [](https://www.expedia.ca/Tavernier-Hotels-Coconut-Palm-Inn.h3489061.Hotel-Information) [View all properties](https://expedia.ca/Hotel-Search?startDate=2026-02-10&endDate=2026-02-11®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) ![Alligator Reef Oceanfront Room King | Beach/ocean view](https://images.trvl-media.com/lodging/1000000/70000/62000/61976/43c465e8.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 (1276) CA $284 CA $420 total includes taxes & fees Jan 29 - Jan 30 [](https://www.expedia.ca/Islamorada-Hotels-Amara-Cay-Resort.h61976.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) ![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) ![Reception](https://images.trvl-media.com/lodging/1000000/20000/14100/14042/3b0a2582.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 (1004) CA $483 CA $619 total includes taxes & fees Feb 4 - Feb 5 [](https://www.expedia.ca/Key-Largo-Hotels-Bakers-Cay-Resort-Key-Largo.h14042.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) ![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) ![Exterior](https://images.trvl-media.com/lodging/3000000/2480000/2477600/2477508/c134a889.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 (1003) CA $269 CA $403 total includes taxes & fees Jan 29 - Jan 30 [](https://www.expedia.ca/Islamorada-Hotels-La-Siesta-Resort-Marina.h2477508.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) ![Exterior](https://images.trvl-media.com/lodging/1000000/20000/11900/11864/w4000h2663x0y0-d63f21e0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 2 Double Beds, Balcony, Oceanfront | Living area](https://images.trvl-media.com/lodging/1000000/20000/11900/11864/ab6da82f.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) ### 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 (136) CA $464 CA $613 total includes taxes & fees Jan 28 - Jan 29 [](https://www.expedia.ca/Islamorada-Hotels-Three-Waters-Resort-And-Marina.h11864.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) ![View from room](https://images.trvl-media.com/lodging/1000000/480000/475500/475438/7f55fd9c.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 (1013) CA $373 CA $512 total includes taxes & fees Jan 28 - Jan 29 [](https://www.expedia.ca/Islamorada-Hotels-Islander-Resort.h475438.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) ![Serves lunch and dinner](https://images.trvl-media.com/lodging/12000000/11920000/11919100/11919055/bb9d7ce2.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 (1000) CA $690 CA $852 total includes taxes & fees Feb 9 - Feb 10 [](https://www.expedia.ca/Key-Largo-Hotels-Playa-Largo-Resort-Spa.h11919055.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) ![Premium bedding, pillowtop beds, in-room safe, individually decorated](https://images.trvl-media.com/lodging/55000000/54780000/54774300/54774228/a064415d.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) ![Balcony view](https://images.trvl-media.com/lodging/55000000/54780000/54774300/54774228/95dbc957.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 (70) CA $834 CA $1,014 total includes taxes & fees Jan 28 - Jan 29 [](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=2026-02-10&endDate=2026-02-11®ionId=10768&adults=2&amenities=POOL&sort=RECOMMENDED&star=40&openPlayBack=true) ## Top Islamorada Hotel Reviews ![La Jolla Resort](https://images.trvl-media.com/lodging/17000000/16580000/16574700/16574668/74e26d92_y.jpg) ### La Jolla Resort 10/10 Excellent "Great location. Friendly staff. Cold AC! " [](https://expedia.ca/Islamorada-Hotels-La-Jolla-Resort.h16574668.Hotel-Information) ![Chesapeake Beach Resort](https://images.trvl-media.com/lodging/1000000/10000/4200/4170/689f4306_y.jpg) ### Chesapeake Beach Resort 10/10 Excellent "Staff was very nice. Nice to use the complimentary clear bottom kayaks. Breakfast was good, Didi made a great omelette!" [](https://expedia.ca/Islamorada-Hotels-Chesapeake-Beach-Resort.h4170.Hotel-Information) ![La Siesta Resort & Villas](https://images.trvl-media.com/lodging/3000000/2480000/2477600/2477508/eda54a36_y.jpg) ### La Siesta Resort & Villas 10/10 Excellent "We stayed in one of the bungalows and absolutely loved it! It was awesome to walk right out of your room onto the beach. We really enjoyed the kayaking. " [](https://expedia.ca/Islamorada-Hotels-La-Siesta-Resort-Marina.h2477508.Hotel-Information) ![Cheeca Lodge & Spa](https://images.trvl-media.com/lodging/1000000/10000/5800/5780/617c0723_y.jpg) ### Cheeca Lodge & Spa 10/10 Excellent "This palce is awesome. Clean rooms. 2 large pools with a view. Covered garage spot. " [](https://expedia.ca/Islamorada-Hotels-Cheeca-Lodge-Spa.h5780.Hotel-Information) ![Pines & Palms Resort](https://images.trvl-media.com/lodging/1000000/1000000/990500/990422/6ac4045c_y.jpg) ### Pines & Palms Resort 10/10 Excellent "Yes" [](https://expedia.ca/Islamorada-Hotels-Pines-Palms-Resort.h990422.Hotel-Information) ![Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort](https://images.trvl-media.com/lodging/1000000/20000/11900/11864/d10a018b_y.jpg) ### Three Waters Resort and Marina, Islamorada, a Tribute Portfolio Resort 10/10 Excellent "Great place" [](https://expedia.ca/Islamorada-Hotels-Three-Waters-Resort-And-Marina.h11864.Hotel-Information) ![Islander Resort](https://images.trvl-media.com/lodging/1000000/480000/475500/475438/5adae4af_y.jpg) ### Islander Resort 10/10 Excellent "This place is great. A must stay. Everyone is so friendly. Place is spotless clean" [](https://expedia.ca/Islamorada-Hotels-Islander-Resort.h475438.Hotel-Information) ![Drop Anchor](https://images.trvl-media.com/lodging/5000000/4290000/4287400/4287368/7fd0f78d_y.jpg) ### Drop Anchor 10/10 Excellent "Great stay, better than I even expected from the pictures. Quiet, quaint little place right on the water. The edge is actually a dock, but it looks like it’s right on its own, private, wide beach! The internet was good - I had a half day of doing Zoom work calls and had no problems. It’s quiet, the bed and pillows were comfortable, and the coffee in the room was strong and good. Close to a couple restaurants within walking distance, one of which was dockside with outdoor seating that was so relaxing (Island Grill). Definitely would stay again. " [](https://expedia.ca/Islamorada-Hotels-Drop-Anchor.h4287368.Hotel-Information) ![Hadley Resort and Marina](https://images.trvl-media.com/lodging/1000000/20000/12200/12200/9afce9bd_y.jpg) ### Hadley Resort and Marina 10/10 Excellent "Really liked overall. Outdoor porch was awesome. Really close to Robbies, though a little treck to Bahia Honda, if you're looking for nice beaches. One or two odd things. First there was no light in the living room. So I had to keep the light on in the kitchen. Also there was only 1 lamp next to the bed & no bedroom light besides this. It would have also been nice if there was a stove & pots/pans/silverware, etc. Finally there really is no beach. Boat dock, but not really a beach. But otherwise really great & would definitely stay there again. " [](https://expedia.ca/Islamorada-Hotels-Hadley-House-Islamorada.h12200.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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