Title: Book the Best Hotels with POOL in Osprey in 2026 | 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) ![Default HTG hotel image](https://a.travel-assets.com/travel-assets-manager/fallback-images-brand/bex_lodging_v2.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Find Hotels with a Pool in Osprey, FL from CA $93 - ![](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 [Dec 23 - Dec 24](https://www.expedia.ca/Hotel-Search?regionId=55888&startDate=2025-12-23&endDate=2025-12-24&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Dec 24 - Dec 25](https://www.expedia.ca/Hotel-Search?regionId=55888&startDate=2025-12-24&endDate=2025-12-25&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=55888&startDate=2025-12-26&endDate=2025-12-28&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Jan 2 - Jan 4](https://www.expedia.ca/Hotel-Search?regionId=55888&startDate=2026-01-02&endDate=2026-01-04&adults=2&amenities=POOL&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Our top choices for Osprey hotels with a pool ![Premium Pool View King Suite | View from room](https://images.trvl-media.com/lodging/7000000/6620000/6619300/6619300/e1a96b97.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Daily full breakfast for a fee](https://images.trvl-media.com/lodging/7000000/6620000/6619300/6619300/04230bd1.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 Room](https://images.trvl-media.com/lodging/7000000/6620000/6619300/6619300/21b61591.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Casey Key Resorts - Mainland [](https://www.expedia.ca/Sarasota-Hotels-Casey-Key-Resorts-Mainland.h6619300.Hotel-Information) Osprey 8.8/10 Excellent (1119) "Great place for our family to stay! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jordan CA $164 CA $185 total includes taxes & fees Dec 25 - Dec 26 [](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/3000000/2750000/2745600/2745513/1e44f415.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Restaurant](https://images.trvl-media.com/lodging/3000000/2750000/2745600/2745513/35ef17f5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/3000000/2750000/2745600/2745513/6c740597.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Courtyard](https://images.trvl-media.com/lodging/3000000/2750000/2745600/2745513/4967eafa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Island Sun Inn & Suites - Venice, Florida Historic Downtown & Beach Getaway [](https://www.expedia.ca/Sarasota-Hotels-Island-Sun-Inn-Suites-Venice.h2745513.Hotel-Information) Venice Island 7.6/10 Good (1004) "Price, clean and friendly!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Karen CA $95 CA $112 total includes taxes & fees Dec 24 - Dec 25 [](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) ![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/39000000/38220000/38215400/38215316/3006ffef.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Design Studio, 1 King Bed, Non Smoking](https://images.trvl-media.com/lodging/39000000/38220000/38215400/38215316/60adc343.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Kompose Boutique Hotel [](https://www.expedia.ca/Sarasota-Hotels-Kompose-Hotel-Sarasota.h38215316.Hotel-Information) Sarasota 9.2/10 Wonderful (4802) "Would happily stay here again!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) STYLIANOS CA $117 CA $149 total includes taxes & fees Dec 25 - Dec 26 [](https://www.expedia.ca/Sarasota-Hotels-Kompose-Hotel-Sarasota.h38215316.Hotel-Information) ![Outdoor pool](https://images.trvl-media.com/lodging/2000000/1010000/1000800/1000717/2fa7c591.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free WiFi, bed sheets](https://images.trvl-media.com/lodging/2000000/1010000/1000800/1000717/337b4953.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) ![Interior](https://images.trvl-media.com/lodging/2000000/1010000/1000800/1000717/e9208c79.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Motel 6 Venice, FL [](https://www.expedia.ca/Sarasota-Hotels-Motel-6-Venice.h1000717.Hotel-Information) Gateway 8.2/10 Very good (361) "Great Staff, Good Room" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Joseph CA $80 CA $93 total includes taxes & fees Dec 25 - Dec 26 [](https://www.expedia.ca/Sarasota-Hotels-Motel-6-Venice.h1000717.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) ![Exterior](https://images.trvl-media.com/lodging/1000000/120000/117100/117009/8db4d91b.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) ![Reception](https://images.trvl-media.com/lodging/1000000/120000/117100/117009/bbaa2af7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Best Western Plus Ambassador Suites Venice [](https://www.expedia.ca/Sarasota-Hotels-Best-Western-Plus-Ambassador-Suites-Venice.h117009.Hotel-Information) Venice 9.0/10 Wonderful (1000) "The room was spotless and the staff were terrific." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lorraine CA $154 CA $174 total includes taxes & fees Dec 30 - Dec 31 [](https://www.expedia.ca/Sarasota-Hotels-Best-Western-Plus-Ambassador-Suites-Venice.h117009.Hotel-Information) ![Sundeck](https://images.trvl-media.com/lodging/16000000/15200000/15191100/15191010/0ef16925.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) ![Siesta Suite (1 Queen Bed and 1 Sofabed)](https://images.trvl-media.com/lodging/16000000/15200000/15191100/15191010/c31401f6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/16000000/15200000/15191100/15191010/0e0af5c8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Siesta Key Palms Resort [](https://www.expedia.ca/Sarasota-Hotels-Siesta-Key-Palms-Resort.h15191010.Hotel-Information) Sarasota 9.2/10 Wonderful (1000) "Tiki bar was a definite plus" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) thomas CA $106 CA $190 total includes taxes & fees Jan 5 - Jan 6, 2026 [](https://www.expedia.ca/Sarasota-Hotels-Siesta-Key-Palms-Resort.h15191010.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) ![Exterior](https://images.trvl-media.com/lodging/17000000/16030000/16022600/16022589/0e1f7e4f.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) ![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 [](https://www.expedia.ca/Port-Charlotte-Charlotte-Harbor-Hotels-Sun-Coast-Inn.h16022589.Hotel-Information) Englewood South 7.8/10 Good (863) "Room was was good. Location was good." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Brian CA $125 CA $146 total includes taxes & fees Dec 26 - Dec 27 [](https://www.expedia.ca/Port-Charlotte-Charlotte-Harbor-Hotels-Sun-Coast-Inn.h16022589.Hotel-Information) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/93000000/92410000/92408200/92408147/edcab928.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) ![Meeting facility](https://images.trvl-media.com/lodging/93000000/92410000/92408200/92408147/2262ed13.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room amenity](https://images.trvl-media.com/lodging/93000000/92410000/92408200/92408147/b40a3405.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Holiday Inn Express & Suites Nokomis Sarasota South by IHG [](https://www.expedia.ca/Nokomis-Hotels-Holiday-Inn-Express-Suites-Nokomis-Sarasota-South.h92408147.Hotel-Information) Nokomis 9.6/10 Exceptional (360) "Very clean hotel. Great service and very clean and comfortable room" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Iris CA $162 CA $183 total includes taxes & fees Dec 25 - Dec 26 [](https://www.expedia.ca/Nokomis-Hotels-Holiday-Inn-Express-Suites-Nokomis-Sarasota-South.h92408147.Hotel-Information) ![Outdoor pool, sun loungers](https://images.trvl-media.com/lodging/1000000/50000/41500/41455/db3f2b79.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/1000000/50000/41500/41455/09de26d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Free daily buffet breakfast](https://images.trvl-media.com/lodging/1000000/50000/41500/41455/11a97df5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, pillowtop beds, iron/ironing board](https://images.trvl-media.com/lodging/1000000/50000/41500/41455/e81d5e74.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hampton Inn Sarasota - I-75 Bee Ridge [](https://www.expedia.ca/Sarasota-Hotels-Hampton-Inn-Sarasota-I-75-Bee-Ridge.h41455.Hotel-Information) Sarasota 8.6/10 Excellent (347) "Everything was great!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Juan CA $139 CA $157 total includes taxes & fees Dec 29 - Dec 30 [](https://www.expedia.ca/Sarasota-Hotels-Hampton-Inn-Sarasota-I-75-Bee-Ridge.h41455.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/2000000/1250000/1241000/1240909/f85b62a5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Point of interest](https://images.trvl-media.com/lodging/2000000/1250000/1241000/1240909/28955014.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Property grounds](https://images.trvl-media.com/lodging/2000000/1250000/1241000/1240909/cfa0f723.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1250000/1241000/1240909/0e0257b4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Tropical Beach Resorts [](https://www.expedia.ca/Sarasota-Hotels-Tropical-Beach-Resorts.h1240909.Hotel-Information) South Village 9.4/10 Exceptional (5168) "Great place, easy beach access and property was beautiful. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Maria CA $198 CA $254 total includes taxes & fees Dec 24 - Dec 25 [](https://www.expedia.ca/Sarasota-Hotels-Tropical-Beach-Resorts.h1240909.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=2026-01-06&endDate=2026-01-07®ionId=55888&adults=2&amenities=POOL&sort=RECOMMENDED&openPlayBack=true) ## Top Osprey Hotel Reviews ![Lido Beach Resort](https://images.trvl-media.com/lodging/1000000/40000/34600/34597/d9fc7fce_y.jpg) ### Lido Beach Resort 10/10 Excellent "Room was clean and tidy. However, a ceiling fan ran constantly and there was no way/switch to turn it off. Management said they would call engineering, but nobody showed. Room was too cold and uncomfortable.!" [](https://expedia.ca/Sarasota-Hotels-Lido-Beach-Resort.h34597.Hotel-Information) ![Siesta Key Palms Resort](https://images.trvl-media.com/lodging/16000000/15200000/15191100/15191010/86bd1cda_y.jpg) ### Siesta Key Palms Resort 10/10 Excellent "Fun tiki bar " [](https://expedia.ca/Sarasota-Hotels-Siesta-Key-Palms-Resort.h15191010.Hotel-Information) ![DoubleTree by Hilton Sarasota Bradenton Airport](https://images.trvl-media.com/lodging/3000000/2410000/2403800/2403753/eda954e7_y.jpg) ### DoubleTree by Hilton Sarasota Bradenton Airport 10/10 Excellent "Was so close to airport and on site restaurant was very good." [](https://expedia.ca/Sarasota-Hotels-Holiday-Inn-Sarasota-Airport.h2403753.Hotel-Information) ![Spark by Hilton Sarasota Siesta Key Gateway](https://images.trvl-media.com/lodging/1000000/30000/26400/26397/18d283d6_y.jpg) ### Spark by Hilton Sarasota Siesta Key Gateway 10/10 Excellent "Beautiful clean room with large shower and toiletries. Coffee and water refreshments all day. Very friendly, helpful staff. " [](https://expedia.ca/Sarasota-Hotels-Best-Western-Plus-Siesta-Key-Gateway.h26397.Hotel-Information) ![Tropical Beach Resorts](https://images.trvl-media.com/lodging/2000000/1250000/1241000/1240909/606a9b3c_y.jpg) ### Tropical Beach Resorts 10/10 Excellent "Nice to come back to a clean room everyday. Location is perfect, walking distance to everything." [](https://expedia.ca/Sarasota-Hotels-Tropical-Beach-Resorts.h1240909.Hotel-Information) ![Comfort Suites Sarasota - Siesta Key](https://images.trvl-media.com/lodging/6000000/5640000/5637500/5637457/a4f997ef_y.jpg) ### Comfort Suites Sarasota - Siesta Key 10/10 Excellent "Yes everything was fine." [](https://expedia.ca/Sarasota-Hotels-Comfort-Suites-Sarasota-Siesta-Key.h5637457.Hotel-Information) ![The Westin Sarasota](https://images.trvl-media.com/lodging/17000000/16820000/16819000/16818933/7ee146c3_y.jpg) ### The Westin Sarasota 10/10 Excellent "Very clean and nice staff. Loved the location. The rooftop bar and pool area was a great view. True prices were really good and the Cuban was very large and delicious!" [](https://expedia.ca/Sarasota-Hotels-The-Westin-Sarasota.h16818933.Hotel-Information) ![Golden Host Resort - Sarasota](https://images.trvl-media.com/lodging/1000000/30000/21400/21331/125fc79b_y.jpg) ### Golden Host Resort - Sarasota 10/10 Excellent "Really nice hotel for the money. Very clean and the staff is great! Stayed 3 more nights not booked thru expedia. Beatriz and Cat at the front desk were wonderful as well as the housekeeping staff. Paul who bartends at the Tiki bar and does maint. was very nice also. This will be my go to hotel when in Sarasota! Very easy/short drive to beaches. Love the big TV in room too! Was really impressed with the amount of staff and their effort to keep it clean and nice! A big thank you to all the great staff there! " [](https://expedia.ca/Sarasota-Hotels-Golden-Host-Resort-Sarasota.h21331.Hotel-Information) ![Casey Key Resorts - Mainland](https://images.trvl-media.com/lodging/7000000/6620000/6619300/6619300/164f19b9_y.jpg) ### Casey Key Resorts - Mainland 10/10 Excellent "No complaints about anything. Very satisfied." [](https://expedia.ca/Sarasota-Hotels-Casey-Key-Resorts-Mainland.h6619300.Hotel-Information) ## Frequently asked questions ### What are the best hotels in Osprey with outdoor pools? > With a traveller rating of 8.6, Casey Key Resorts is not just about the pool; the spacious and clean rooms provide a comfortable retreat after a day of adventures. The hotel's location is praised for its accessibility to nearby attractions, making it a convenient base for exploring the beautiful Gulf Coast. Plus, the excellent dining options make it easy to enjoy delicious meals without venturing far from your cozy accommodations. ### How much does a hotel with outdoor pool in Osprey cost? ### Are there hotels in Osprey with outdoor pool cabanas or loungers? > Guests rave about the friendly and accommodating staff, who go above and beyond to ensure a pleasant stay. The clean, spacious rooms provide a comfortable retreat after a day of adventure, and the on-site poolside bar offers refreshing drinks to enjoy while lounging by the water. With a review rating of 8.6, travellers appreciate the excellent food options and the hotel's prime location, which enhances the overall experience. ### Which Osprey hotels offer poolside service for food and drinks? > Families will appreciate the spacious rooms, which are not only clean but also designed for comfort, making it an ideal retreat after a day of adventure. The friendly and attentive staff further enhances the experience, ensuring that your stay is both enjoyable and relaxing. ### Are there hotels with outdoor pools that are close to Nokomis Beach? > What truly sets this resort apart is its inviting outdoor pool area, complete with poolside cabanas and sun loungers, superb for relaxing after a fun day at the beach. Guests rave about the cleanliness and spaciousness of the rooms, along with the excellent food offerings available on-site, making it a convenient choice for families looking to balance adventure and comfort. > > > In addition to its appealing amenities, Casey Key Resorts - Mainland boasts a prime location that allows for easy access to the beautiful shores of Nokomis Beach, making it an ideal base for both relaxation and outdoor activities. ### Are there hotels in Osprey with outdoor pool activities or events? > Gilmore Resorts, which includes both Driftwood Lodge and Osprey on the Gulf, stands out with its heated pools adjacent to the stunning Gulf of Mexico. Here, families can enjoy barbecue stations, beachfront volleyball, and a splash pad that delights children. The planned events foster a vibrant, family-friendly atmosphere, ensuring everyone has a memorable time. > > > For those travelling with families, Casey Key Resorts is another excellent choice. This hotel boasts an outdoor heated pool and a poolside bar, creating a laid-back environment where parents can unwind while kids splash about. With amenities like banquet rooms for hosting events, families can easily plan gatherings or celebrations during their stay. > > > Moreover, you'll discover other hotels in Osprey that advertise outdoor pools, some heated, complete with poolside bars and outdoor dining options. This variety promises an array of opportunities for leisurely afternoons spent by the water, mingling with fellow guests, and enjoying the beautiful Florida sunshine. ### Is it cheaper to book flights and a hotel in Osprey as a package? ### How can I save on a hotel in Osprey with Expedia? ### Can I cancel my hotel reservation on Expedia? ## Explore a world of travel with Expedia - Lodging - More ways to book - [Beach Hotel Hotels in Bay Acres ](https://www.expedia.ca/Bay-Acres-Osprey-Hotels-Beach-Hotel.0-n553248635976472153-0-tBeachHotel.Travel-Guide-Filter-Hotels) - [Beach Hotel Hotels in Casey Key ](https://www.expedia.ca/Casey-Key-Hotels-Beach-Hotel.0-0-d6167273-tBeachHotel.Travel-Guide-Filter-Hotels) - [Boutique Hotels in Casey Key ](https://www.expedia.ca/Casey-Key-Hotels-Boutique-Hotel.0-0-d6167273-tBoutiqueHotel.Travel-Guide-Filter-Hotels) - [Casino Hotels in Casey Key ](https://www.expedia.ca/Casey-Key-Hotels-Casino-Hotel.0-0-d6167273-tCasinoHotel.Travel-Guide-Filter-Hotels) - 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