Title: Book the Best Hotels with POOL in Caribbean Isle in 2025 | Expedia.ca [Vacation Rentals in Navarre](https://expedia.ca/Navarre-Vacation-Rentals.d136973.Travel-Guide-VacationRentals)[Flights to Navarre](https://expedia.ca/Cheap-Flights-To-Navarre.d136973.Travel-Guide-Flights)[Caribbean Isle Car Rentals](https://expedia.ca/Car-Rentals-In-Caribbean-Isle.d553248635976473048.Car-Rental-Guide)[Caribbean Isle Vacations](https://expedia.ca/Caribbean-Isle.d553248635976473048.Destination-Travel-Guides) ![](https://mediaim.expedia.com/destination/9/9133541d7ad88700adf32bb96f3a6142.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Hotels with a Pool in Caribbean Isle, FL from CA $88 ![](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 Caribbean Isle Hotels with a Pool Tonight [Oct 30 - Oct 31](https://www.expedia.ca/Hotel-Search?regionId=553248635976473048&startDate=2025-10-30&endDate=2025-10-31&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 31 - Nov 1](https://www.expedia.ca/Hotel-Search?regionId=553248635976473048&startDate=2025-10-31&endDate=2025-11-01&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=553248635976473048&startDate=2025-10-31&endDate=2025-11-02&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=553248635976473048&startDate=2025-11-07&endDate=2025-11-09&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Caribbean Isle Hotels with a Pool ![Indoor pool, outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/18000000/17500000/17495200/17495112/a707b3d6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby lounge](https://images.trvl-media.com/lodging/18000000/17500000/17495200/17495112/b736a3cc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Poolside bar](https://images.trvl-media.com/lodging/18000000/17500000/17495200/17495112/822272c9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/18000000/17500000/17495200/17495112/b0ba83e5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hilton Garden Inn Ft. Walton Beach Okaloosa Island 8.8/10 Excellent (1006) "The view is stunning, hotel super clean and spacious. I can't wait to go back" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jessica CA $128 CA $149 total includes taxes & fees Nov 8 - Nov 9 [](https://www.expedia.ca/Pensacola-Hotels-Hilton-Garden-Inn-Fort-Walton-Beach.h17495112.Hotel-Information) ![One King Bed, Gulf View With Balcony, Non-Smoking | Living area](https://images.trvl-media.com/lodging/1000000/30000/24800/24770/6b25e26a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![One King Bed, Accessible, Gulf View With Balcony, Non-Smoking | Living area](https://images.trvl-media.com/lodging/1000000/30000/24800/24770/0561421b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 Bedroom Suite w/Kitchen, 2 Balconies, Gulf Front, Non-Smoking | Living area](https://images.trvl-media.com/lodging/1000000/30000/24800/24770/9c87c2c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/1000000/30000/24800/24770/9a74c97a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn Pensacola Beach Plaza Primera 8.4/10 Very good (2216) "Great location, perfect for families. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Mallory CA $133 CA $152 total includes taxes & fees Nov 18 - Nov 19 [](https://www.expedia.ca/Pensacola-Hotels-Hampton-Inn-Pensacola-Beach.h24770.Hotel-Information) ![Outdoor pool](https://images.trvl-media.com/lodging/13000000/12510000/12502100/12502012/18c7c804.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/13000000/12510000/12502100/12502012/298409fa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Suite, Non Smoking | Living area](https://images.trvl-media.com/lodging/13000000/12510000/12502100/12502012/894b171a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/13000000/12510000/12502100/12502012/531774d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Gulf Coast Inn Gulf Breeze 8.8/10 Excellent (1135) "A lovely stay in every way." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Leslie CA $78 CA $88 total includes taxes & fees Nov 2 - Nov 3 [](https://www.expedia.ca/Pensacola-Hotels-Gulf-Coast-Inn.h12502012.Hotel-Information) ![Outdoor pool](https://images.trvl-media.com/lodging/1000000/50000/40700/40611/b8fcdc6f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room safe, desk, laptop workspace, blackout drapes](https://images.trvl-media.com/lodging/1000000/50000/40700/40611/f656c6af.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, 1 King Bed, Balcony](https://images.trvl-media.com/lodging/1000000/50000/40700/40611/929ed2b0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room safe, desk, laptop workspace, blackout drapes](https://images.trvl-media.com/lodging/1000000/50000/40700/40611/5bc2f8f0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Express Pensacola Beach by IHG Villa Sabine 9.6/10 Exceptional (1099) "stay was enjoyable and staff was very helpful and polite" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) randy CA $183 CA $209 total includes taxes & fees Nov 16 - Nov 17 [](https://www.expedia.ca/Pensacola-Hotels-Holiday-Inn-Express-Pensacola-Beach.h40611.Hotel-Information) ![Outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/1000000/20000/16600/16596/3512c628.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Executive Room, 1 King Bed, Balcony (Gulf Front)](https://images.trvl-media.com/lodging/1000000/20000/16600/16596/9b32fa6a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Executive Room, 1 King Bed, Balcony (Bay Front)](https://images.trvl-media.com/lodging/1000000/20000/16600/16596/c2ca33b1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Executive Room, 1 King Bed, Balcony (Bay Front)](https://images.trvl-media.com/lodging/1000000/20000/16600/16596/447a0d37.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Pensacola Beach Resort Villa Sabine 9.4/10 Exceptional (2572) "Great staff, awesome resort restaurant and well maintained/beautiful beach" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Autumn CA $200 CA $232 total includes taxes & fees Nov 16 - Nov 17 [](https://www.expedia.ca/Pensacola-Hotels-Margaritaville-Beach-Hotel.h16596.Hotel-Information) ![Garden](https://images.trvl-media.com/lodging/1000000/20000/10100/10029/0e3a2504.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Suite, Multiple Beds (Penthouse)](https://images.trvl-media.com/lodging/1000000/20000/10100/10029/70af92c4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room, 2 Queen Beds (Gulf View)](https://images.trvl-media.com/lodging/1000000/20000/10100/10029/4d946bad.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Studio, 1 King Bed (Bahama, Partial View)](https://images.trvl-media.com/lodging/1000000/20000/10100/10029/9d521a49.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Wyndham Garden Fort Walton Beach Destin Okaloosa Island 8.0/10 Very good (2049) "Loved our stay will definitely be back " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Luzy CA $124 CA $140 total includes taxes & fees Nov 30 - Dec 1 [](https://www.expedia.ca/Pensacola-Hotels-Wyndham-Garden-Fort-Walton-Beach-Destin.h10029.Hotel-Information) ![Outdoor pool](https://images.trvl-media.com/lodging/9000000/8100000/8094900/8094830/138dd770.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room safe, desk, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/9000000/8100000/8094900/8094830/2b97c064.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/9000000/8100000/8094900/8094830/c64be1b8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/9000000/8100000/8094900/8094830/dabfce38.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Fairfield Inn & Suites Fort Walton Beach-West Destin Okaloosa Island 9.2/10 Wonderful (1015) "Good value hotel, clean rooms, beach access. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Steve CA $123 CA $139 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Pensacola-Hotels-Fairfield-Inn-Suites-Fort-Walton-Beach-West-Destin.h8094830.Hotel-Information) ![Aerial view](https://images.trvl-media.com/lodging/1000000/20000/14500/14499/faab91e9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Gift shop](https://images.trvl-media.com/lodging/1000000/20000/14500/14499/20c002a9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property entrance](https://images.trvl-media.com/lodging/1000000/20000/14500/14499/33a4547c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/1000000/20000/14500/14499/e32781d6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Surf & Sand Hotel Pensacola Beach 8.8/10 Excellent (2861) "Great views of Pensacola Beach and the inlet. Wonderful staff and very good breakfast." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Michael [](https://www.expedia.ca/Pensacola-Hotels-Surf-Sand-Hotel.h14499.Hotel-Information) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/104000000/103850000/103847700/103847688/42a51db7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/104000000/103850000/103847700/103847688/fd8a5b9d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Single Room, 1 King Bed, Non Smoking](https://images.trvl-media.com/lodging/104000000/103850000/103847700/103847688/16b4fcdf.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/104000000/103850000/103847700/103847688/3ef86fe6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sleep Inn & Suites Fort Walton Beach - Destin West Downtown Fort Walton Beach 8.8/10 Excellent (371) "Hotel was clean and staff and facilities were top notch" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Angela CA $100 CA $113 total includes taxes & fees Nov 16 - Nov 17 [](https://www.expedia.ca/Fort-Walton-Beach-Hotels-Sleep-Inn-Suites.h103847688.Hotel-Information) ![Outdoor pool](https://images.trvl-media.com/lodging/7000000/6870000/6861300/6861278/b718bbc1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/7000000/6870000/6861300/6861278/0304ae1f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/7000000/6870000/6861300/6861278/422ebed8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/7000000/6870000/6861300/6861278/2f91df75.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Seabreeze Inn Seabreeze 8.0/10 Very good (1011) "The hotel was as expected.loved the water view all stores and beach easily accessible " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) michael [](https://www.expedia.ca/Fort-Walton-Beach-Hotels-Seabreeze-Inn.h6861278.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=2025-11-13&endDate=2025-11-14®ionId=553248635976473048&adults=2&amenities=POOL&sort=RECOMMENDED&openPlayBack=true) ## Top Caribbean Isle Hotel Reviews ![Holiday Inn Resort Pensacola Beach by IHG](//images.trvl-media.com/lodging/1000000/540000/537800/537766/214fc1d2_y.jpg) ### Holiday Inn Resort Pensacola Beach by IHG 10/10 Excellent "The girl that checked me in was delightful. She was very efficient and very sweet. The room was nice and large and very clean.We did not have a balcony or beach view, but we did have a view of the Bay." [](https://expedia.ca/Pensacola-Hotels-Holiday-Inn-Resort-Pensacola-Beach.h537766.Hotel-Information) ![Wyndham Garden Fort Walton Beach Destin](//images.trvl-media.com/lodging/1000000/20000/10100/10029/46cb556a_y.jpg) ### Wyndham Garden Fort Walton Beach Destin 10/10 Excellent "Amazing view and loved to 2 pools and the hot tub. Along with being right on the water. " [](https://expedia.ca/Pensacola-Hotels-Wyndham-Garden-Fort-Walton-Beach-Destin.h10029.Hotel-Information) ![Surf & Sand Hotel](//images.trvl-media.com/lodging/1000000/20000/14500/14499/faab91e9_y.jpg) ### Surf & Sand Hotel 10/10 Excellent "Property was clean and quiet. Breakfast was decent. Bed was comfortable. Friendly staff " [](https://expedia.ca/Pensacola-Hotels-Surf-Sand-Hotel.h14499.Hotel-Information) ![Hampton Inn Pensacola Beach](//images.trvl-media.com/lodging/1000000/30000/24800/24770/e16914ac_y.jpg) ### Hampton Inn Pensacola Beach 10/10 Excellent "The beach was wonderful and so relaxing. A quick reminder if you didn't bring any chairs you can rent them as well as umbrellas for $15 and up. The staff was wonderful. I will definitely be back. " [](https://expedia.ca/Pensacola-Hotels-Hampton-Inn-Pensacola-Beach.h24770.Hotel-Information) ![ The Pensacola Beach Resort](//images.trvl-media.com/lodging/1000000/20000/16600/16596/3512c628_y.jpg) ### The Pensacola Beach Resort 10/10 Excellent "Our room was incredible. It was an executive suite which was very big & had balcony with gulf & bay view. The swimming pool was really nice overlooking gulf & bay. Can’t wait to return again in future. " [](https://expedia.ca/Pensacola-Hotels-Margaritaville-Beach-Hotel.h16596.Hotel-Information) ![Fairfield Inn & Suites by Marriott Pensacola Beach](//images.trvl-media.com/lodging/1000000/10000/3900/3814/06738b3d_y.jpg) ### Fairfield Inn & Suites by Marriott Pensacola Beach 10/10 Excellent "Loved staying here: super clean, great service, on the beach, lazy river pool as well as regular pool and hot tub, on site/beach front restaurant, great laundry services. Just all around great experience!" [](https://expedia.ca/Pensacola-Beach-Hotels-Fairfield-Inn-Suites-By-Marriott-Pensacola-Beach.h3814.Hotel-Information) ![Holiday Inn Resort Fort Walton Beach by IHG](//images.trvl-media.com/lodging/7000000/6530000/6528900/6528819/ec3cc1d0_y.jpg) ### Holiday Inn Resort Fort Walton Beach by IHG 10/10 Excellent "Nice amenities, everything was nice " [](https://expedia.ca/Pensacola-Hotels-Holiday-Inn-Resort-Fort-Walton-Beach.h6528819.Hotel-Information) ![Four Points by Sheraton Destin-Fort Walton Beach](//images.trvl-media.com/lodging/1000000/10000/1200/1146/w4000h2663x0y0-53a8829a_y.jpg) ### Four Points by Sheraton Destin-Fort Walton Beach 10/10 Excellent "This place was amazing.The beds were comfortable.The pillows were soft.The room was clean.The beach view was awesome and the staff was really great.We are definitely going back next year. We really enjoyed the food as well." [](https://expedia.ca/Pensacola-Hotels-Four-Points-By-Sheraton-Destin-Fort-Walton-Beach.h1146.Hotel-Information) ![Hilton Garden Inn Ft. Walton Beach](//images.trvl-media.com/lodging/18000000/17500000/17495200/17495112/a707b3d6_y.jpg) ### Hilton Garden Inn Ft. Walton Beach 10/10 Excellent "The view is stunning, hotel super clean and spacious. I can't wait to go back" [](https://expedia.ca/Pensacola-Hotels-Hilton-Garden-Inn-Fort-Walton-Beach.h17495112.Hotel-Information) ## Frequently asked questions ### What are some accommodations with pools in Caribbean Isle? > [Surf & Sand Hotel](https://www.expedia.ca/Pensacola-Hotels-Surf-Sand-Hotel.h14499.Hotel-Information): Hotel steps from Pensacola Beach Gulf Pier. Features daily, an outdoor pool, and complimentary bicycles. [Wyndham Garden Fort Walton Beach Destin](https://www.expedia.ca/Pensacola-Hotels-Wyndham-Garden-Fort-Walton-Beach-Destin.h10029.Hotel-Information): Hotel, 5-minute walk from Okaloosa Island Beach. Offers a snack bar/deli, 2 outdoor pools, and sun loungers. [Hampton Inn Pensacola Beach](https://www.expedia.ca/Pensacola-Hotels-Hampton-Inn-Pensacola-Beach.h24770.Hotel-Information): Hotel, 3-minute walk from Pensacola Beach Beaches. Provides a snack bar/deli, 2 outdoor pools, and buffet. [The Pensacola Beach Resort](https://www.expedia.ca/Pensacola-Hotels-Margaritaville-Beach-Hotel.h16596.Hotel-Information): Hotel, 3-minute walk from Pensacola Beach Beaches. Features a snack bar/deli, an outdoor pool, and complimentary wired internet access. [Holiday Inn Resort Pensacola Beach by IHG](https://www.expedia.ca/Pensacola-Hotels-Holiday-Inn-Resort-Pensacola-Beach.h537766.Hotel-Information): Hotel, 7-minute walk from Pensacola Beach Beaches. Offers a children's pool, an indoor pool, and a lazy river. ### What is there to see and do in Caribbean Isle? > Explore places like Navarre Beach while you're in the area. Spend some time experiencing the great outdoors at Santa Rosa Sound. ### When is the best time to book a hotel with a pool in Caribbean Isle? > You may want to think about an accommodation with an outdoor swimming pool if you plan to visit in the hottest months of August, July, or June when the average temperature is 82°F. Lodging offering an indoor pool may be what you want if you are visiting during the coldest months of January, February, or December when the average temp is 57°F. ## Explore a world of travel with Expedia - Lodging - Flights - Packages - Cars - Vacation Rental - More ways to book - [1 Star Hotels in Santa Rosa Island](https://www.expedia.ca/1Star-Santa-Rosa-Island-Hotels.s10-0-d6341180.Travel-Guide-Filter-Hotels) - [4 Star Hotels in Navarre](https://www.expedia.ca/4Star-Navarre-Hotels.s40-0-d136973.Travel-Guide-Filter-Hotels) - [Hotels & Resorts for Couples in Destin](https://www.expedia.ca/Destin-Hotels-Couples-Resorts-Hotels.0-0-d6906-tCouplesResortsHotels.Travel-Guide-Filter-Hotels) - [Hotels with Childcare in Destin](https://www.expedia.ca/Destin-Hotels-Hotels-With-Childcare.0-0-d6906-tHotelswithChildcare.Travel-Guide-Filter-Hotels) - [Hotels with Free Parking in Destin](https://www.expedia.ca/Destin-Hotels-Hotels-With-Free-Parking.0-0-d6906-tHotelswithFreeParking.Travel-Guide-Filter-Hotels) - 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