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 26 - Oct 27](https://www.expedia.ca/Hotel-Search?regionId=55888&startDate=2025-10-26&endDate=2025-10-27&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 27 - Oct 28](https://www.expedia.ca/Hotel-Search?regionId=55888&startDate=2025-10-27&endDate=2025-10-28&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) In two weeks [Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=55888&startDate=2025-11-07&endDate=2025-11-09&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) ![Lobby](https://images.trvl-media.com/lodging/7000000/6620000/6619300/6619300/68922696.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 (1060) "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, 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 Island 7.6/10 Good (1004) "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, 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) ![Interior entrance](https://images.trvl-media.com/lodging/39000000/38220000/38215400/38215316/9cc80f05.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 (4526) "Great hotel for the price … staff is helpful and friendly. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Leslie 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) ![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) ![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) ### Sun Coast Inn Englewood South 7.8/10 Good (851) "For a last minute get-away, this worked for our purposes perfectly!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) John CA $111 CA $130 total includes taxes & fees Oct 27 - Oct 28 [](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) ![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/ead20e24.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 (1006) "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 $96 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](https://images.trvl-media.com/lodging/1000000/800000/790400/790359/d5755605.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, blackout drapes, iron/ironing board](https://images.trvl-media.com/lodging/1000000/800000/790400/790359/1cb9b06c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property amenity](https://images.trvl-media.com/lodging/1000000/800000/790400/790359/46286dd8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/800000/790400/790359/89a93c7d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### EVEN Hotel Sarasota-Lakewood Ranch by IHG Sarasota 8.4/10 Very good (1020) "Good location and plenty of parking." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Oswaldo CA $140 CA $159 total includes taxes & fees Oct 31 - Nov 1 [](https://www.expedia.ca/Sarasota-Hotels-EVEN-Hotel-Sarasota-Lakewood-Ranch.h790359.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) ![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) ![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) ![Front of property - evening/night](https://images.trvl-media.com/lodging/1000000/920000/911800/911761/4d4e5779.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Inn at the Beach Venice Island 9.8/10 Exceptional (1029) "Enjoyed the stay " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Michael CA $180 CA $240 total includes taxes & fees Oct 29 - Oct 30 [](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) ![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/e9208c79.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 Gateway 8.4/10 Very good (320) "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 Nov 2 - Nov 3 [](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) ![Exterior](https://images.trvl-media.com/lodging/93000000/92410000/92408200/92408147/a528ee56.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) ![Exterior](https://images.trvl-media.com/lodging/93000000/92410000/92408200/92408147/c8c50457.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 $147 CA $166 total includes taxes & fees Oct 28 - Oct 29 [](https://www.expedia.ca/Nokomis-Hotels-Holiday-Inn-Express-Suites-Nokomis-Sarasota-South.h92408147.Hotel-Information) ![BBQ/picnic area](https://images.trvl-media.com/lodging/1000000/430000/425300/425274/7143bca1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![1 bedroom, premium bedding, desk, laptop workspace](https://images.trvl-media.com/lodging/1000000/430000/425300/425274/fd94a741.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Lobby](https://images.trvl-media.com/lodging/1000000/430000/425300/425274/c61bdadc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/1000000/430000/425300/425274/1d47d82f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Comfort Inn & Suites Sarasota I75 Fruitville 8.6/10 Excellent (1004) "Love everything about the place " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Helen CA $152 CA $171 total includes taxes & fees Oct 27 - Oct 28 [](https://www.expedia.ca/Sarasota-Hotels-La-Quinta-Inn-Suites-By-Wyndham-Sarasota-I75.h425274.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=2025-11-09&endDate=2025-11-10®ionId=55888&adults=2&amenities=POOL&sort=RECOMMENDED&openPlayBack=true) ## Top Osprey Hotel Reviews ![Siesta Key Palms Resort](//images.trvl-media.com/lodging/16000000/15200000/15191100/15191010/86bd1cda_y.jpg) ### Siesta Key Palms Resort 10/10 Excellent "This resort goes beyond our expectation. We absolutely loved it. It is not luxurious hotel, but everything is just as good as you can think of. the entire outdoor place is beautiful and full of character. The staff are friendly. The microwave, stove, and fridge in the room are huge and new. They make our stay extremely enjoyble and relaxing. We just felt like home." [](https://expedia.ca/Sarasota-Hotels-Siesta-Key-Palms-Resort.h15191010.Hotel-Information) ![Captiva Beach Resort](//images.trvl-media.com/lodging/2000000/1170000/1163600/1163507/3fe58375_y.jpg) ### Captiva Beach Resort 10/10 Excellent "Nice quick walk to the beach. Close to restaurants. Would love to go back!" [](https://expedia.ca/Sarasota-Hotels-Captiva-Beach-Resort.h1163507.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 "Clean room, nice sitting area, the only issue was with the bathroom door. It’s a cramped toilet/shower space making it a challenge to get out of the bathroom after your shower." [](https://expedia.ca/Sarasota-Hotels-Hyatt-Place-SarasotaBradenton-Airport.h2277489.Hotel-Information) ![Lantern Inn & Suites](//images.trvl-media.com/lodging/1000000/450000/448500/448416/4f77412a_y.jpg) ### Lantern Inn & Suites 10/10 Excellent "I am Walking Across America for Mental Health Awareness & Recovery, over 9,100 miles! I have been in the Manatee County, Florida area for a little while, as I’ve been covered some extra distance and meeting people. This hotel has been freshly renovated, and they have amazing grades as they are trying to let people know where to go around here, especially if you want a really nice room and save a few bucks compared to everything else in the area! The people have been very friendly, And the rooms are definitely nice. Pretty good size TV as well. Definitely enjoyed it!" [](https://expedia.ca/Sarasota-Hotels-Lantern-Inn-Suites.h448416.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 "Good value for the price " [](https://expedia.ca/Sarasota-Hotels-Golden-Host-Resort-Sarasota.h21331.Hotel-Information) ![Comfort Suites Sarasota - Siesta Key](//images.trvl-media.com/lodging/6000000/5640000/5637500/5637457/a4f997ef_y.jpg) ### Comfort Suites Sarasota - Siesta Key 10/10 Excellent "Great room for the price. My bed was comfortable, the room was clean and orderly, and the great view of the pond was nice! I would definitely stay here again. " [](https://expedia.ca/Sarasota-Hotels-Comfort-Suites-Sarasota-Siesta-Key.h5637457.Hotel-Information) ![Casey Key Resorts - Mainland](//images.trvl-media.com/lodging/7000000/6620000/6619300/6619300/164f19b9_y.jpg) ### Casey Key Resorts - Mainland 10/10 Excellent "Stay was great room was very clean, bed was comfortable and the heated pool was nice." [](https://expedia.ca/Sarasota-Hotels-Casey-Key-Resorts-Mainland.h6619300.Hotel-Information) ![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 Breeze Resort](//images.trvl-media.com/lodging/1000000/880000/879700/879629/9de12888_y.jpg) ### Tropical Breeze Resort 10/10 Excellent "I arrived a day early and extended for a full week. The staff was so helpful and the variety of amenities made this a wonderful trip and experience. Perfect for solo to family events. I’ll be back" [](https://expedia.ca/Sarasota-Hotels-Tropical-Breeze-Resort.h879629.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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