Title: Book the Best Hotels with POOL in Islamorada in 2025 | 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 showing a sandy beach](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/191000/191197-Islamorada.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Hotels with a Pool in Islamorada, FL from CA $120 ![](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 [Oct 24 - Oct 25](https://www.expedia.ca/Hotel-Search?regionId=10768&startDate=2025-10-24&endDate=2025-10-25&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 25 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=10768&startDate=2025-10-25&endDate=2025-10-26&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 24 - Oct 26](https://www.expedia.ca/Hotel-Search?regionId=10768&startDate=2025-10-24&endDate=2025-10-26&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=10768&startDate=2025-10-31&endDate=2025-11-02&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Islamorada Hotels with a Pool ![Exterior detail](https://images.trvl-media.com/lodging/58000000/57190000/57185500/57185414/9bcc8c75.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Panoramic Suite](https://images.trvl-media.com/lodging/58000000/57190000/57185500/57185414/w1485h1001x15y0-19c35a33.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Sundeck](https://images.trvl-media.com/lodging/58000000/57190000/57185500/57185414/6ddda999.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private beach, beach towels, kayaking](https://images.trvl-media.com/lodging/58000000/57190000/57185500/57185414/528adcf7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Rock Reef Resort Key Largo 9.2/10 Wonderful (1049) "Had a wonderful stay. The staff was great!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Angel CA $106 CA $120 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Key-Largo-Hotels-Rock-Reef-Resort.h57185414.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/1000000/890000/882300/882254/6f2246e8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/1000000/890000/882300/882254/4b49fc53.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Waterfront Standard King Bed](https://images.trvl-media.com/lodging/1000000/890000/882300/882254/e7a0378c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/1000000/890000/882300/882254/393ff3a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Lime Tree Bay Resort Long Key 9.2/10 Wonderful (1086) "Friendly staff clean and updated room " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ryan CA $124 CA $203 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Long-Key-Hotels-Lime-Tree-Bay-Resort.h882254.Hotel-Information) ![Aerial view](https://images.trvl-media.com/lodging/2000000/1190000/1186200/1186162/4ac8a422.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) ![Sun loungers, beach umbrellas, beach towels, kayaking](https://images.trvl-media.com/lodging/2000000/1190000/1186200/1186162/ac9979c6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily continental breakfast](https://images.trvl-media.com/lodging/2000000/1190000/1186200/1186162/eec761cd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Dove Creek Resort & Marina, Trademark Collection by Wyndham Key Largo 7.6/10 Good (1002) "Clean room, nice bed, quiet" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Carmen CA $130 CA $190 total includes taxes & fees Oct 30 - Oct 31 [](https://www.expedia.ca/Key-Largo-Hotels-Dove-Creek-Resort-Marina.h1186162.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 | Terrace/patio](https://images.trvl-media.com/lodging/5000000/4290000/4287400/4287368/42d378ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/5000000/4290000/4287400/4287368/f44c6b22.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/5000000/4290000/4287400/4287368/29680b52.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Drop Anchor Islamorada 8.8/10 Excellent (1000) "Beautiful property and the staff was amazing." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) John CA $169 CA $239 total includes taxes & fees Oct 28 - Oct 29 [](https://www.expedia.ca/Islamorada-Hotels-Drop-Anchor.h4287368.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/92000000/91750000/91743100/91743042/12c235b3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/92000000/91750000/91743100/91743042/ee0752b0.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) ### Treasure Harbor Islamorada 8.8/10 Excellent (108) "If you are looking for a laid back vibe with no hassle here is the place. Friendly staff. Aqualodge was cute and comfortable. Easily rented a boat for the day...found great snorkeling and beautiful views. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) JoAnn CA $138 CA $352 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Islamorada-Hotels-Treasure-Harbor.h91743042.Hotel-Information) ![3 bars/lounges, poolside bar](https://images.trvl-media.com/lodging/1000000/70000/62000/61976/28233e0b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Alligator Reef Oceanfront Accessible Room King Bed | View from room](https://images.trvl-media.com/lodging/1000000/70000/62000/61976/1b5ced17.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![3 bars/lounges, poolside bar](https://images.trvl-media.com/lodging/1000000/70000/62000/61976/60b7c04d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/70000/62000/61976/84b50729.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Amara Cay Resort Matecumbe 8.8/10 Excellent (1264) "Great hotel with a perfect location and friendly staff." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Amir CA $186 CA $303 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Islamorada-Hotels-Amara-Cay-Resort.h61976.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/75000000/74510000/74501700/74501641/396da292.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/75000000/74510000/74501700/74501641/3c8fb00e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/75000000/74510000/74501700/74501641/fcd75612.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite | Living area](https://images.trvl-media.com/lodging/75000000/74510000/74501700/74501641/4ae3e8fd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Kona Kai Resort and Gallery - Adults Only Key Largo 9.8/10 Exceptional (270) "Property was very clean including beach, pool, and grounds." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Drew CA $162 CA $222 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Key-Largo-Hotels-Kona-Kai-Resort-And-Gallery.h74501641.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/1000000/10000/5800/5780/981feca1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Balcony](https://images.trvl-media.com/lodging/1000000/10000/5800/5780/79d31a44.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/10000/5800/5780/e32d7e53.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private beach, sun loungers, beach umbrellas, beach towels](https://images.trvl-media.com/lodging/1000000/10000/5800/5780/617c0723.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Cheeca Lodge & Spa Matecumbe 9.2/10 Wonderful (1251) "This resort was amazing!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Paul CA $194 CA $313 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Islamorada-Hotels-Cheeca-Lodge-Spa.h5780.Hotel-Information) ![Terrace/patio](https://images.trvl-media.com/lodging/1000000/30000/22700/22657/419b7787.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/30000/22700/22657/8e763282.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool](https://images.trvl-media.com/lodging/1000000/30000/22700/22657/46aade65.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/dd3dbaaa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Bayside Inn Key Largo Key Largo 8.6/10 Excellent (1588) "Wonderful resort ! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Amir CA $154 CA $209 total includes taxes & fees Nov 19 - Nov 20 [](https://www.expedia.ca/Key-Largo-Hotels-Bayside-Inn-Key-Largo.h22657.Hotel-Information) ![Superior Bungalow, Multiple Beds, Beachfront (Ground Level Sleeps 6) | View from room](https://images.trvl-media.com/lodging/17000000/16580000/16574700/16574668/f30bc378.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Superior Suite, 2 Queen Beds, Kitchenette, Bay View](https://images.trvl-media.com/lodging/17000000/16580000/16574700/16574668/c0d44f4e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/17000000/16580000/16574700/16574668/31d6a642.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Private beach, fishing](https://images.trvl-media.com/lodging/17000000/16580000/16574700/16574668/d330cb53.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### La Jolla Resort Matecumbe 9.0/10 Wonderful (1002) "The location is great..nice beach and dock area..room was very nice.. will definitely plan to return for a longer stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ronnie CA $111 CA $165 total includes taxes & fees Oct 27 - Oct 28 [](https://www.expedia.ca/Islamorada-Hotels-La-Jolla-Resort.h16574668.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=2025-11-07&endDate=2025-11-08®ionId=10768&adults=2&amenities=POOL&sort=RECOMMENDED&openPlayBack=true) ## Top Islamorada Hotel Reviews ![La Siesta Resort & Villas](//images.trvl-media.com/lodging/3000000/2480000/2477600/2477508/eda54a36_y.jpg) ### La Siesta Resort & Villas 10/10 Excellent "Very friendly staff. Clean and very comfortable rooms. Pool drained after first day we were there. I liked how the pool, beach and amenities were so convenient . Still enjoyed boat to Three Waters and their pool. Boat and shuttle between resorts very convenient and nice. Went kayaking.Love the feel of old Florida at La Siesta! Plan to return" [](https://expedia.ca/Islamorada-Hotels-La-Siesta-Resort-Marina.h2477508.Hotel-Information) ![La Jolla Resort](//images.trvl-media.com/lodging/17000000/16580000/16574700/16574668/74e26d92_y.jpg) ### La Jolla Resort 10/10 Excellent "This was a very nice and quaint place and the people were so friendly! Have beach access was awesome! We will definitely be back!" [](https://expedia.ca/Islamorada-Hotels-La-Jolla-Resort.h16574668.Hotel-Information) ![Cheeca Lodge & Spa](//images.trvl-media.com/lodging/1000000/10000/5800/5780/617c0723_y.jpg) ### Cheeca Lodge & Spa 10/10 Excellent "Nice room with everything you need." [](https://expedia.ca/Islamorada-Hotels-Cheeca-Lodge-Spa.h5780.Hotel-Information) ![Pines & Palms Resort](//images.trvl-media.com/lodging/1000000/1000000/990500/990422/6ac4045c_y.jpg) ### Pines & Palms Resort 10/10 Excellent "Our experience was amazing, the staff is really sweet and kind. " [](https://expedia.ca/Islamorada-Hotels-Pines-Palms-Resort.h990422.Hotel-Information) ![Breezy Palms Resort](//images.trvl-media.com/lodging/12000000/11950000/11945900/11945889/96b58c48_y.jpg) ### Breezy Palms Resort 10/10 Excellent "Beautiful room with great set up, enjoyed eating breakfast on screened porch each morning while enjoying the view and no bugs!" [](https://expedia.ca/Islamorada-Hotels-Breezy-Palms-Resort.h11945889.Hotel-Information) ![Chesapeake Beach Resort](//images.trvl-media.com/lodging/1000000/10000/4200/4170/689f4306_y.jpg) ### Chesapeake Beach Resort 10/10 Excellent "Resort offered alot considering it was somewhat smaller. Excellent staff and rooms/amenities..will definitely go back. " [](https://expedia.ca/Islamorada-Hotels-Chesapeake-Beach-Resort.h4170.Hotel-Information) ![Islander Resort](//images.trvl-media.com/lodging/1000000/480000/475500/475438/5adae4af_y.jpg) ### Islander Resort 10/10 Excellent "Beautiful place. Would go back again." [](https://expedia.ca/Islamorada-Hotels-Islander-Resort.h475438.Hotel-Information) ![Coconut Cove Resort and Marina](//images.trvl-media.com/lodging/5000000/4190000/4182600/4182524/667446d9_y.jpg) ### Coconut Cove Resort and Marina 10/10 Excellent "Really great facility, very relaxing " [](https://expedia.ca/Islamorada-Hotels-Coconut-Cove-Resort-And-Marina.h4182524.Hotel-Information) ![Amara Cay Resort](//images.trvl-media.com/lodging/1000000/70000/62000/61976/84b50729_y.jpg) ### Amara Cay Resort 10/10 Excellent "This was our second stay there and will definitely go back. The location is great and there is plenty of well-maintained beach area to enjoy. The room was large, clean and updated. However, the view from the room left a lot to be desired. We booked a standard room so we didn't have expectations one way or the other, but the window was located chest-up (bottom half was wall) and overlooked the roof of the restaurant. We did have a partial view of the ocean, but only if you looked out the corner. The Rum Runner (water taxi) and free shuttle were great amenities to have!" [](https://expedia.ca/Islamorada-Hotels-Amara-Cay-Resort.h61976.Hotel-Information) ## Frequently asked questions ### What's it like visiting Islamorada? > If taking it easy by the pool is your idea of the perfect getaway, you might want to think about relaxing Islamorada, which offers 111 places to stay with pools. During your trip, you can explore sights such as Bud n' Mary's Dive Center and Islamorada County Park, and then relax and unwind poolside at one of the accommodations in Islamorada that guests like for their pools. ### What are some accommodations with pools in Islamorada? > [Chesapeake Beach Resort](https://www.expedia.ca/Islamorada-Hotels-Chesapeake-Beach-Resort.h4170.Hotel-Information): Features a private beach, 2 outdoor pools, and daily. [Fisher Inn Resort & Marina](https://www.expedia.ca/Islamorada-Hotels-Fisher-Inn-Resort-Marina.h3274374.Hotel-Information): Offers a private beach, a pool, and daily. [Bayside Villas by Islander Resort](https://www.expedia.ca/Islamorada-Hotels-Islander-Bayside-Villas-And-Boatslips.h3861342.Hotel-Information): Provides 3 restaurants, an outdoor pool, and free self parking. [Drop Anchor](https://www.expedia.ca/Islamorada-Hotels-Drop-Anchor.h4287368.Hotel-Information): Features free self parking, an outdoor pool, and complimentary bicycles. [Sands of Islamorada](https://www.expedia.ca/Islamorada-Hotels-Sands-Of-Islamorada.h12653483.Hotel-Information): Offers free self parking, a pool, and complimentary wireless internet access. ### How many pool hotels should I expect to find in Islamorada? > Expedia's 111 hotels in Islamorada give you a great choice for your poolside getaway. ### What is there to see and do in Islamorada? > Spend some time experiencing the great outdoors at Islamorada County Park and Anne's Beach. Discover sights such as Bud n' Mary's Dive Center, Fiesta Key, and Everglades National Park during your stay. Islamorada appeals to visitors with its beautiful ocean views and top seafood restaurants. ### When is the best time to book a hotel with a pool in Islamorada? > Taking into account the local weather in Islamorada is an important factor for planning your visit, especially if you plan to spend your trip poolside. The hottest months are usually August and July with an average temp of 83°F, while the coldest months are January and February with an average of 72°F. Average annual precipitation for Islamorada is 44 inches. ## 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) - [Casino Hotels in Brickell](https://www.expedia.ca/Brickell-Miami-Hotels-Casino-Hotel.0-n6240961-0-tCasinoHotel.Travel-Guide-Filter-Hotels) - [Hotels & Resorts for Couples in Brickell](https://www.expedia.ca/Brickell-Miami-Hotels-Couples-Resorts-Hotels.0-n6240961-0-tCouplesResortsHotels.Travel-Guide-Filter-Hotels) - [Hotels with Early Check-in in Brickell](https://www.expedia.ca/Brickell-Miami-Hotels-Hotel-With-Early-Check-In.0-n6240961-0-thotelwithearlycheckin.Travel-Guide-Filter-Hotels) - 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