Title: Book the Best Hotels with POOL in Osprey in 2025 | Expedia.ca [Hotels in Osprey](https://expedia.ca/Osprey-Hotels.d55888.Travel-Guide-Hotels)[Vacation Rentals in Osprey](https://expedia.ca/Osprey-Vacation-Rentals.d55888.Travel-Guide-VacationRentals)[Flights to Osprey](https://expedia.ca/Cheap-Flights-To-Osprey.d55888.Travel-Guide-Flights)[Osprey Car Rentals](https://expedia.ca/Car-Rentals-In-Osprey.d55888.Car-Rental-Guide)[Osprey Vacation Packages](https://expedia.ca/Osprey.d55888.Destination-Travel-Guides) ![](https://a.travel-assets.com/findyours-php/viewfinder/images/res70/495000/495790-osprey.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Hotels with a Pool in Osprey, 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 Osprey Hotels with a Pool Tonight [Oct 24 - Oct 25](https://www.expedia.ca/Hotel-Search?regionId=55888&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=55888&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=55888&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=55888&startDate=2025-10-31&endDate=2025-11-02&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Osprey Hotels with a Pool ![Outdoor dining](https://images.trvl-media.com/lodging/7000000/6620000/6619300/6619300/164f19b9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/7000000/6620000/6619300/6619300/93021f2f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe King Suite](https://images.trvl-media.com/lodging/7000000/6620000/6619300/6619300/c4f21556.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe King Room](https://images.trvl-media.com/lodging/7000000/6620000/6619300/6619300/b68095b2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Casey Key Resorts - Mainland Osprey 8.6/10 Excellent (1057) "Nice place to stay" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Kareen CA $167 CA $189 total includes taxes & fees Nov 10 - Nov 11 [](https://www.expedia.ca/Sarasota-Hotels-Casey-Key-Resorts-Mainland.h6619300.Hotel-Information) ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/39000000/38220000/38215400/38215316/c2a1ef6e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Wine bar](https://images.trvl-media.com/lodging/39000000/38220000/38215400/38215316/746f55c4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Design Studio, 1 King Bed, Non Smoking](https://images.trvl-media.com/lodging/39000000/38220000/38215400/38215316/23c6a2fc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby sitting area](https://images.trvl-media.com/lodging/39000000/38220000/38215400/38215316/e948f2e5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Kompose Boutique Hotel Sarasota 9.2/10 Wonderful (4516) "Beautiful hotel especially for the price." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jonathan CA $70 CA $96 total includes taxes & fees Oct 27 - Oct 28 [](https://www.expedia.ca/Sarasota-Hotels-Kompose-Hotel-Sarasota.h38215316.Hotel-Information) ![Outdoor pool](https://images.trvl-media.com/lodging/17000000/16030000/16022600/16022589/7c471d0a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Suite, 1 King Bed with Sofa bed](https://images.trvl-media.com/lodging/17000000/16030000/16022600/16022589/51f34991.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/17000000/16030000/16022600/16022589/4ec007b0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/17000000/16030000/16022600/16022589/bab9ae46.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sun Coast Inn Englewood South 7.8/10 Good (849) "If you are traveling with a pet(s) and going through Englewood Florida, this is the place to spend the night. We had a double queen bed room and it was more spacious than a lot of mini-suite rooms, and updated as well as clean. With two nice restaurants within 50 yards and a Dunkin down the road for an early coffee, this is once again truly the place to spend the night. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) John CA $111 CA $130 total includes taxes & fees Oct 25 - Oct 26 [](https://www.expedia.ca/Port-Charlotte-Charlotte-Harbor-Hotels-Sun-Coast-Inn.h16022589.Hotel-Information) ![2 outdoor pools, a heated pool](https://images.trvl-media.com/lodging/16000000/15200000/15191100/15191010/86bd1cda.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Courtyard Studio Suite (1 Queen Bed and 1 Sofabed)](https://images.trvl-media.com/lodging/16000000/15200000/15191100/15191010/caf0a3e3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Siesta Suite (1 Queen Bed and 1 Sofabed) | Private kitchen](https://images.trvl-media.com/lodging/16000000/15200000/15191100/15191010/ae6a5d94.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/16000000/15200000/15191100/15191010/5717bd96.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Siesta Key Palms Resort Sarasota 9.2/10 Wonderful (1001) "Everything was good, siesta key palm resort is a wonderful place " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Claudia CA $95 CA $179 total includes taxes & fees Nov 18 - Nov 19 [](https://www.expedia.ca/Sarasota-Hotels-Siesta-Key-Palms-Resort.h15191010.Hotel-Information) ![Outdoor pool, open 9:00 AM to 6:00 PM, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/3000000/2750000/2745600/2745513/2742babb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/3000000/2750000/2745600/2745513/d5664f90.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Studio, 1 King Bed, Kitchen | Private kitchen](https://images.trvl-media.com/lodging/3000000/2750000/2745600/2745513/a144f545.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Room, 1 King Bed, Kitchenette | View from room](https://images.trvl-media.com/lodging/3000000/2750000/2745600/2745513/5e155451.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Island Sun Inn & Suites - Venice, Florida Historic Downtown & Beach Getaway Venice 7.6/10 Good (1002) "Beautiful rooms clean, friendly staff. Great place to stay all around. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Stephanie CA $77 CA $91 total includes taxes & fees Oct 27 - Oct 28 [](https://www.expedia.ca/Sarasota-Hotels-Island-Sun-Inn-Suites-Venice.h2745513.Hotel-Information) ![Outdoor pool, pool umbrellas, sun loungers](https://images.trvl-media.com/lodging/1000000/120000/117100/117009/01ed8c5d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/120000/117100/117009/bbaa2af7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Desk, laptop workspace, blackout drapes, iron/ironing board](https://images.trvl-media.com/lodging/1000000/120000/117100/117009/29dbe003.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/120000/117100/117009/d81d6192.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Best Western Plus Ambassador Suites Venice Venice 9.0/10 Wonderful (1004) "The stay, place, ambient & staff were spectacular. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Abdul CA $137 CA $155 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Sarasota-Hotels-Best-Western-Plus-Ambassador-Suites-Venice.h117009.Hotel-Information) ![Seasonal outdoor pool](https://images.trvl-media.com/lodging/59000000/59000000/58998500/58998474/d6dcbcc8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Minibar](https://images.trvl-media.com/lodging/59000000/59000000/58998500/58998474/693fd300.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Minibar](https://images.trvl-media.com/lodging/59000000/59000000/58998500/58998474/1b8e958f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/59000000/59000000/58998500/58998474/9744f034.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn & Suites North Port North Port 9.4/10 Exceptional (569) "Great place great staff" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) RICHARD CA $169 CA $191 total includes taxes & fees Nov 24 - Nov 25 [](https://www.expedia.ca/Port-Charlotte-Charlotte-Harbor-Hotels-Hampton-Inn-Suites-North-Port.h58998474.Hotel-Information) ![Outdoor pool, a heated pool, sun loungers](https://images.trvl-media.com/lodging/1000000/920000/911800/911761/8ebcc1b1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![View from property](https://images.trvl-media.com/lodging/1000000/920000/911800/911761/d8baa37c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![King Studio | Terrace/patio](https://images.trvl-media.com/lodging/1000000/920000/911800/911761/f085aee7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Standard Room, 2 Double Beds | View from room](https://images.trvl-media.com/lodging/1000000/920000/911800/911761/764de11d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Inn at the Beach Venice 9.8/10 Exceptional (1027) "Great place to stay. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Brandon CA $180 CA $240 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Sarasota-Hotels-Inn-At-The-Beach.h911761.Hotel-Information) ![Outdoor pool](https://images.trvl-media.com/lodging/2000000/1010000/1000800/1000717/031d6bbe.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/2000000/1010000/1000800/1000717/e9208c79.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![BBQ/picnic area](https://images.trvl-media.com/lodging/2000000/1010000/1000800/1000717/8742e093.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/2000000/1010000/1000800/1000717/8ed35aed.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Motel 6 Venice, FL Venice 8.4/10 Very good (319) "Excellent service, friendly staff and confortable stay. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Fred CA $76 CA $88 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Sarasota-Hotels-Motel-6-Venice.h1000717.Hotel-Information) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/93000000/92410000/92408200/92408147/07040c4b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![In-room safe, desk, blackout drapes, iron/ironing board](https://images.trvl-media.com/lodging/93000000/92410000/92408200/92408147/5ed39958.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/93000000/92410000/92408200/92408147/c8c50457.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/93000000/92410000/92408200/92408147/c49363b1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Express & Suites Nokomis Sarasota South by IHG Nokomis 9.6/10 Exceptional (330) "I love this hotel close to the beaches great stay for great price" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Anthony CA $141 CA $160 total includes taxes & fees Oct 26 - Oct 27 [](https://www.expedia.ca/Nokomis-Hotels-Holiday-Inn-Express-Suites-Nokomis-Sarasota-South.h92408147.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=55888&adults=2&amenities=POOL&sort=RECOMMENDED&openPlayBack=true) ## Top Osprey Hotel Reviews ![DoubleTree by Hilton Sarasota Bradenton Airport](//images.trvl-media.com/lodging/3000000/2410000/2403800/2403753/eda954e7_y.jpg) ### DoubleTree by Hilton Sarasota Bradenton Airport 10/10 Excellent "Breakfast was NOT free - it was posted as being $20 a person and online did not indicate this" [](https://expedia.ca/Sarasota-Hotels-Holiday-Inn-Sarasota-Airport.h2403753.Hotel-Information) ![Tropical Beach Resorts](//images.trvl-media.com/lodging/2000000/1250000/1241000/1240909/606a9b3c_y.jpg) ### Tropical Beach Resorts 10/10 Excellent "Wonderful little getaway. Private and fun for the whole family. Or peaceful for yourself." [](https://expedia.ca/Sarasota-Hotels-Tropical-Beach-Resorts.h1240909.Hotel-Information) ![Lido Beach Resort](//images.trvl-media.com/lodging/1000000/40000/34600/34597/d9fc7fce_y.jpg) ### Lido Beach Resort 10/10 Excellent "Great beach view!" [](https://expedia.ca/Sarasota-Hotels-Lido-Beach-Resort.h34597.Hotel-Information) ![Golden Host Resort - Sarasota](//images.trvl-media.com/lodging/1000000/30000/21400/21331/125fc79b_y.jpg) ### Golden Host Resort - Sarasota 10/10 Excellent "All good" [](https://expedia.ca/Sarasota-Hotels-Golden-Host-Resort-Sarasota.h21331.Hotel-Information) ![Lantern Inn & Suites](//images.trvl-media.com/lodging/1000000/450000/448500/448416/4f77412a_y.jpg) ### Lantern Inn & Suites 10/10 Excellent "The room was very clean, and the ac worked very well. The staff was very friendly. I would highly recommend this hotel " [](https://expedia.ca/Sarasota-Hotels-Lantern-Inn-Suites.h448416.Hotel-Information) ![Hyatt Place Sarasota/Bradenton Airport](//images.trvl-media.com/lodging/3000000/2280000/2277500/2277489/6e9ac4ec_y.jpg) ### Hyatt Place Sarasota/Bradenton Airport 10/10 Excellent "Good" [](https://expedia.ca/Sarasota-Hotels-Hyatt-Place-SarasotaBradenton-Airport.h2277489.Hotel-Information) ![Tropical Breeze Resort](//images.trvl-media.com/lodging/1000000/880000/879700/879629/9de12888_y.jpg) ### Tropical Breeze Resort 10/10 Excellent "Beautiful rooms and comfortable right on the beach shore " [](https://expedia.ca/Sarasota-Hotels-Tropical-Breeze-Resort.h879629.Hotel-Information) ![Siesta Key Palms Resort](//images.trvl-media.com/lodging/16000000/15200000/15191100/15191010/86bd1cda_y.jpg) ### Siesta Key Palms Resort 10/10 Excellent "Everything was great" [](https://expedia.ca/Sarasota-Hotels-Siesta-Key-Palms-Resort.h15191010.Hotel-Information) ![The Westin Sarasota](//images.trvl-media.com/lodging/17000000/16820000/16819000/16818933/7ee146c3_y.jpg) ### The Westin Sarasota 10/10 Excellent "The hotel was beautiful and the service was excellent! The only complaint is tge mandatory $50 a day to park the car , also the taxes were crazy. But if that doesn't concern you I highly recommend. " [](https://expedia.ca/Sarasota-Hotels-The-Westin-Sarasota.h16818933.Hotel-Information) ## Frequently asked questions ### What are some hotels with pools in Osprey? > [Casey Key Resorts - Mainland](https://www.expedia.ca/Sarasota-Hotels-Casey-Key-Resorts-Mainland.h6619300.Hotel-Information): Features a snack bar/deli, an outdoor pool, and free self parking. [Kompose Boutique Hotel](https://www.expedia.ca/Sarasota-Hotels-Kompose-Hotel-Sarasota.h38215316.Hotel-Information): Offers a snack bar/deli, a pool, and complimentary wireless internet access. [Tropical Beach Resorts](https://www.expedia.ca/Sarasota-Hotels-Tropical-Beach-Resorts.h1240909.Hotel-Information): Aparthotel, 9-minute walk from Crescent Beach. Provides free self parking, an outdoor pool, and complimentary wireless internet access. [Spark by Hilton Sarasota Siesta Key Gateway](https://www.expedia.ca/Sarasota-Hotels-Best-Western-Plus-Siesta-Key-Gateway.h26397.Hotel-Information): Hotel located near Siesta Key Beach. Features daily, an outdoor pool, and free self parking. [The Westin Sarasota](https://www.expedia.ca/Sarasota-Hotels-The-Westin-Sarasota.h16818933.Hotel-Information): Hotel located near Lido Beach. Offers 2 restaurants, an outdoor pool, and a full-service spa. ### What is there to see and do in Osprey? > Explore places like Siesta Key Beach and Lido Beach while you're in the area. Make a point to visit attractions like Turtle Beach and Nokomis Beach. Osprey appeals to visitors with its beautiful beaches, bar scene, and array of dining options. ### When is the best time to book a hotel with a pool in Osprey? > Taking into account the local weather in Osprey can help you maximize your time at the pool during your trip. The hottest months are usually August and July with an average temp of 82°F, while the coldest months are January and February with an average of 66°F. 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