Title: Osprey Vacation Rentals from CA $176: Short-Term Rentals for 2025 | Expedia.ca [Hotels in Osprey](https://expedia.ca/Osprey-Hotels.d55888.Travel-Guide-Hotels)[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) # Osprey Vacation Rentals ![](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 prices for these dates Tonight [Oct 28 - Oct 29](https://www.expedia.ca/Hotel-Search?regionId=55888&startDate=2025-10-28&endDate=2025-10-29&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [Oct 29 - Oct 30](https://www.expedia.ca/Hotel-Search?regionId=55888&startDate=2025-10-29&endDate=2025-10-30&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [Oct 31 - Nov 2](https://www.expedia.ca/Hotel-Search?regionId=55888&startDate=2025-10-31&endDate=2025-11-02&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [Nov 7 - Nov 9](https://www.expedia.ca/Hotel-Search?regionId=55888&startDate=2025-11-07&endDate=2025-11-09&adults=2&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Vacation Rentals in Osprey ![Outdoor pool, a heated pool, open 8 AM to 10 PM, pool umbrellas](https://images.trvl-media.com/lodging/2000000/1250000/1241000/1240909/606a9b3c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Courtyard](https://images.trvl-media.com/lodging/2000000/1250000/1241000/1240909/ab658cfb.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) ![View from property](https://images.trvl-media.com/lodging/2000000/1250000/1241000/1240909/7dc05471.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Tropical Beach Resorts South Village 9.4/10 Exceptional (5063) "Clean room, great A/C, close to beach, very quiet, easy parking, close to restaurants, clean beach, very nice staff. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Marta CA $177 CA $232 total includes taxes & fees Oct 29 - Oct 30 [](https://www.expedia.ca/Sarasota-Hotels-Tropical-Beach-Resorts.h1240909.Hotel-Information) ![Front of property - evening/night](https://images.trvl-media.com/lodging/2000000/1170000/1163600/1163507/3fe58375.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/2000000/1170000/1163600/1163507/3d46ab53.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/2000000/1170000/1163600/1163507/4d68eb6d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![The Luxury Single | Private kitchenette](https://images.trvl-media.com/lodging/2000000/1170000/1163600/1163507/13f03971.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Captiva Beach Resort South Village 9.0/10 Wonderful (1148) "Very good stay, clean, safe, and steps from the beach" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Brandon CA $197 CA $247 total includes taxes & fees Oct 29 - Oct 30 [](https://www.expedia.ca/Sarasota-Hotels-Captiva-Beach-Resort.h1163507.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/91000000/90030000/90021900/90021825/78c2df61.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/91000000/90030000/90021900/90021825/f58c5935.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Double Room, 2 Double Beds](https://images.trvl-media.com/lodging/91000000/90030000/90021900/90021825/c0cd244a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/91000000/90030000/90021900/90021825/58abfff3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Kon Tiki Inn Venice Island 10/10 Exceptional (239) "Charming, clean, and comfortable. Will definitely stay again when I'm the area. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Carla CA $169 CA $192 total includes taxes & fees Oct 29 - Oct 30 [](https://www.expedia.ca/Venice-Hotels-Kon-Tiki-Inn.h90021825.Hotel-Information) ![Cabin (Tiny House - The Siesta) | Living area](https://images.trvl-media.com/lodging/22000000/21440000/21431000/21430911/69212d51.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Cabin, 2 Bedrooms (Tiny House - Aqua Oasis)](https://images.trvl-media.com/lodging/22000000/21440000/21431000/21430911/8f76b808.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Cabin (Tiny House - Yellow Lifeguard Stand) | Living area](https://images.trvl-media.com/lodging/22000000/21440000/21431000/21430911/a6eb001c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/22000000/21440000/21431000/21430911/d76cc0aa.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Tiny House Siesta Sarasota 8.4/10 Very good (335) "We had a great time at Tiny House, location can not be better and everything was as described." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Elvia CA $138 CA $326 total includes taxes & fees Oct 30 - Oct 31 [](https://www.expedia.ca/Sarasota-Hotels-Tiny-House-Siesta.h21430911.Hotel-Information) ![Outdoor pool, a heated pool, open 7:00 AM to 8:00 PM, sun loungers](https://images.trvl-media.com/lodging/2000000/1220000/1213000/1212924/6ff58e07.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Full-size fridge, microwave, stovetop, coffee/tea maker](https://images.trvl-media.com/lodging/2000000/1220000/1213000/1212924/e6cbbbd1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/2000000/1220000/1213000/1212924/f710e6e0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Suite, 1 King Bed](https://images.trvl-media.com/lodging/2000000/1220000/1213000/1212924/9e206b23.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Hibiscus Suites - Gateway to Siesta Key Sarasota 8.6/10 Excellent (2187) "Excellent location! Friendly staff, clean and updated rooms." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Elba CA $155 CA $176 total includes taxes & fees Oct 29 - Oct 30 [](https://www.expedia.ca/Sarasota-Hotels-Hibiscus-Suites-Gateway-To-Siesta-Key.h1212924.Hotel-Information) ![Property amenity](https://images.trvl-media.com/lodging/4000000/3820000/3819700/3819631/a5a3d5ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Full-size fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/4000000/3820000/3819700/3819631/6330f667.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![55-inch TV with cable channels, MP3 dock](https://images.trvl-media.com/lodging/4000000/3820000/3819700/3819631/2e2e6989.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, pillowtop beds, in-room safe, free WiFi](https://images.trvl-media.com/lodging/4000000/3820000/3819700/3819631/w5097h3107x0y0-f4bbaa75.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Residences at Siesta Key Beach by Hyatt Vacation Club South Village 9.6/10 Exceptional (293) "Loved our stay! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Michelle CA $603 CA $752 total includes taxes & fees Nov 18 - Nov 19 [](https://www.expedia.ca/Siesta-Key-Hotels-The-Residences-At-Siesta-Key-Beach-By-Hyatt-Vacation-Club.h3819631.Hotel-Information) ![Property grounds](https://images.trvl-media.com/lodging/113000000/112390000/112387400/112387358/08b5bced.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/113000000/112390000/112387400/112387358/105c6d3d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Luxury Condo, 3 Bedrooms, Kitchen, Ocean View | Private kitchen](https://images.trvl-media.com/lodging/113000000/112390000/112387400/112387358/aa27a0eb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Luxury Condo, 3 Bedrooms, Kitchen, Ocean View | Microwave](https://images.trvl-media.com/lodging/113000000/112390000/112387400/112387358/3375a4fc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Chadwick Cove Resort & Marina Manasota Key 10/10 Exceptional (14) "Great place and location " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Cathy CA $116 CA $759 total includes taxes & fees Nov 3 - Nov 4 [](https://www.expedia.ca/Englewood-Hotels-Chadwick-Cove-Resort-Marina.h112387358.Hotel-Information) ![322 Calle Miramar, Siesta Key, FL W/pool | Private kitchen](https://images.trvl-media.com/lodging/90000000/89720000/89714300/89714291/aa15caa1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room amenity](https://images.trvl-media.com/lodging/90000000/89720000/89714300/89714291/08963d61.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![153 Beach Rd, Siesta Key, FL W/jacuzzi | Living area](https://images.trvl-media.com/lodging/90000000/89720000/89714300/89714291/fa023698.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Room amenity](https://images.trvl-media.com/lodging/90000000/89720000/89714300/89714291/9ff42f58.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Siesta Key Island Rentals Siesta Key 9.6/10 Exceptional (48) "This place was incredible. We have traveled a lot with family and this was the best. Very comfortable and accommodating! I really cannot say enough good about this house. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Julianna CA $129 CA $350 total includes taxes & fees Oct 29 - Oct 30 [](https://www.expedia.ca/Siesta-Key-Hotels-Siesta-Key-Island-Rentals.h89714291.Hotel-Information) ![Deluxe Studio, Bay View | View from room](https://images.trvl-media.com/lodging/16000000/15450000/15448000/15447995/849d8adc.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beachside Studio | Living area](https://images.trvl-media.com/lodging/16000000/15450000/15448000/15447995/fb0d40be.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor wedding area](https://images.trvl-media.com/lodging/16000000/15450000/15448000/15447995/3b04b83b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Modern Waterfront Studio | Water view](https://images.trvl-media.com/lodging/16000000/15450000/15448000/15447995/0c22198e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Casey Key Resort - Gulf Shores Casey Key 8.4/10 Very good (262) "Amazing place" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Ricardo CA $240 CA $285 total includes taxes & fees Oct 29 - Oct 30 [](https://www.expedia.ca/Sarasota-Hotels-Casey-Key-Resort-Gulf-Shores.h15447995.Hotel-Information) ![Condo, Pool View | Private kitchen](https://images.trvl-media.com/lodging/60000000/59670000/59661500/59661429/0ea98630.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/60000000/59670000/59661500/59661429/93c41295.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House, Lake View | Private kitchen](https://images.trvl-media.com/lodging/60000000/59670000/59661500/59661429/74e8ca6f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![39-inch flat-screen TV with digital channels, TV, streaming services](https://images.trvl-media.com/lodging/60000000/59670000/59661500/59661429/044717f5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Siesta Heron Suites & Villas Siesta Key 8.4/10 Very good (37) "It was perfect for my family of 4 for our beach vacation!!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jesse CA $120 CA $417 total includes taxes & fees Oct 29 - Oct 30 [](https://www.expedia.ca/Sarasota-Hotels-Siesta-Heron-Suites-Villas.h59661429.Hotel-Information) ![Deluxe Suite, 2 Bedrooms | Living area](https://images.trvl-media.com/lodging/115000000/114190000/114189500/114189452/62be52d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Signature Room](https://images.trvl-media.com/lodging/115000000/114190000/114189500/114189452/1e7203ea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Superior Studio Suite](https://images.trvl-media.com/lodging/115000000/114190000/114189500/114189452/c5bfb01f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Signature Room](https://images.trvl-media.com/lodging/115000000/114190000/114189500/114189452/9d53ae34.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### SeaSpray Resort Siesta Key 9.4/10 Exceptional (54) "Clean room, incredibly helpful staff. Will be staying here again" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Caleb CA $306 CA $346 total includes taxes & fees Oct 29 - Oct 30 [](https://www.expedia.ca/Siesta-Key-Hotels-SeaSpray-Resort.h114189452.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/67000000/66890000/66882900/66882864/f2353686.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Condo (Siesta Sands Beach Resort 4th Floor w) | Exterior](https://images.trvl-media.com/lodging/67000000/66890000/66882900/66882864/f172ba47.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Condo (Siesta Sands Beach Resort 4th Floor w) | Exterior](https://images.trvl-media.com/lodging/67000000/66890000/66882900/66882864/79a8e613.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Condo (Siesta Sands Beach Resort 4th Floor w) | Exterior](https://images.trvl-media.com/lodging/67000000/66890000/66882900/66882864/73d791e1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Siesta Sands Beach Resort 4th Floor With Elevator South Village CA $292 CA $862 total includes taxes & fees Nov 14 - Nov 15 [](https://www.expedia.ca/Sarasota-Hotels-Siesta-Sands-Beach-Resort-4th-Floor-With-Elevator.h66882864.Hotel-Information) ![Deluxe Villa | Living area](https://images.trvl-media.com/lodging/116000000/115140000/115131000/115130957/w1270h862x20y1-2157a508.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Deluxe Villa | Private kitchen](https://images.trvl-media.com/lodging/116000000/115140000/115131000/115130957/w1286h860x4y2-e6289e11.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/116000000/115140000/115131000/115130957/w1286h858x4y3-7d39bd0b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Dining](https://images.trvl-media.com/lodging/116000000/115140000/115131000/115130957/w1286h850x4y0-d4db1721.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Bradenton Breeze West Samoset 6.0/10 (2) "It was good! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Shayna [](https://www.expedia.ca/Bradenton-Hotels-Bradenton-Breeze.h115130957.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/120000000/119140000/119136800/119136706/43f3d109.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/120000000/119140000/119136800/119136706/42e87310.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/120000000/119140000/119136800/119136706/1a4fd88d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Interior](https://images.trvl-media.com/lodging/120000000/119140000/119136800/119136706/bf74e9db.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### 4BR Spacious Paradise Siesta Key Village CA $674 CA $1,182 total includes taxes & fees Oct 29 - Oct 30 [](https://www.expedia.ca/Siesta-Key-Hotels-4BR-Spacious-Paradise.h119136706.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/114000000/113010000/113003100/113003026/a05328c1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Luxury Condo, Beach View | Microwave](https://images.trvl-media.com/lodging/114000000/113010000/113003100/113003026/12d35053.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Luxury Condo, Beach View | Room amenity](https://images.trvl-media.com/lodging/114000000/113010000/113003100/113003026/a2a79e2f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Luxury Condo, Beach View | Living area](https://images.trvl-media.com/lodging/114000000/113010000/113003100/113003026/98167131.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Gulf View Condominiums Manasota Key CA $566 CA $1,403 total includes taxes & fees Oct 29 - Oct 30 [](https://www.expedia.ca/Englewood-Hotels-Gulf-View-Condominiums.h113003026.Hotel-Information) ![Condo (LuLu's Key House Leatherback 2/2 Down) | Exterior](https://images.trvl-media.com/lodging/68000000/67220000/67211600/67211563/0f940b0c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Condo (LuLu's Key House Leatherback 2/2 Down) | Exterior](https://images.trvl-media.com/lodging/68000000/67220000/67211600/67211563/0a9cdfa2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/68000000/67220000/67211600/67211563/bfcc1e29.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Condo (LuLu's Key House Leatherback 2/2 Down) | Exterior](https://images.trvl-media.com/lodging/68000000/67220000/67211600/67211563/27c86f41.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Lulu's Key House Leatherback 2/2 Downstairs Siesta Key Village [](https://www.expedia.ca/Sarasota-Hotels-Lulus-Key-House-Leatherback-22-Downstairs.h67211563.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=2025-11-11&endDate=2025-11-12®ionId=55888&adults=2&sort=RECOMMENDED&openPlayBack=true) ![](https://a.travel-assets.com/pricing-claim/sparkle_dark.svg) Save an average of 15% on thousands of hotels when you're signed in [Sign in](https://expedia.ca/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FOsprey-Vacation-Rentals.d55888.Travel-Guide-VacationRentals)[Sign up, it's free](https://expedia.ca/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FOsprey-Vacation-Rentals.d55888.Travel-Guide-VacationRentals) ## Top Osprey Hotel Reviews ![Golden Host Resort - Sarasota](//images.trvl-media.com/lodging/1000000/30000/21400/21331/125fc79b_y.jpg) ### Golden Host Resort - Sarasota 10/10 Excellent "Reception staff was very friendly." [](https://expedia.ca/Sarasota-Hotels-Golden-Host-Resort-Sarasota.h21331.Hotel-Information) ![Carlisle Inn](//images.trvl-media.com/lodging/20000000/19770000/19761100/19761082/9a1b0e30_y.jpg) ### Carlisle Inn 10/10 Excellent "Beautiful property, very clean, very well kept " [](https://expedia.ca/Sarasota-Hotels-Carlisle-Inn.h19761082.Hotel-Information) ![Kompose Boutique Hotel](//images.trvl-media.com/lodging/39000000/38220000/38215400/38215316/e948f2e5_y.jpg) ### Kompose Boutique Hotel 10/10 Excellent "This hotel was one for the books for my boyfriend and I. first saty here and we're already looking forward to our next stay. Location, staff, comfortability, safety, cleanliness and everything in-between was amazing!!" [](https://expedia.ca/Sarasota-Hotels-Kompose-Hotel-Sarasota.h38215316.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 "Cute place near the beach. A great place for a gateway with the wife." [](https://expedia.ca/Sarasota-Hotels-Siesta-Key-Palms-Resort.h15191010.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 "Staff were very friendly & accommodating, rooms are clean. " [](https://expedia.ca/Sarasota-Hotels-Casey-Key-Resorts-Mainland.h6619300.Hotel-Information) ![Tropical Breeze Resort](//images.trvl-media.com/lodging/1000000/880000/879700/879629/9de12888_y.jpg) ### Tropical Breeze Resort 10/10 Excellent "Excellent staff and always a great place to stay when in Siesta Key!!!" [](https://expedia.ca/Sarasota-Hotels-Tropical-Breeze-Resort.h879629.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 "The hotel was good and staff was great" [](https://expedia.ca/Sarasota-Hotels-Comfort-Suites-Sarasota-Siesta-Key.h5637457.Hotel-Information) ![Spark by Hilton Sarasota Siesta Key Gateway](//images.trvl-media.com/lodging/1000000/30000/26400/26397/18d283d6_y.jpg) ### Spark by Hilton Sarasota Siesta Key Gateway 10/10 Excellent "I love the bartender girl from the pool bar… so sweet" [](https://expedia.ca/Sarasota-Hotels-Best-Western-Plus-Siesta-Key-Gateway.h26397.Hotel-Information) ![Art Ovation Hotel, Autograph Collection](//images.trvl-media.com/lodging/20000000/19910000/19901000/19900973/w4000h2662x0y0-652c5c90_y.jpg) ### Art Ovation Hotel, Autograph Collection 10/10 Excellent "Great" [](https://expedia.ca/Sarasota-Hotels-Art-Ovation-Hotel.h19900973.Hotel-Information) ## Find out more about Osprey **Everything you need to know about** **Osprey** **vacation rentals** Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Osprey vacation rental for you. At Expedia, you can take your pick from [private vacation homes](https://www.expedia.ca/aa/PrivateVacationHomes), [apartments](https://www.expedia.ca/aa/Apartments), cottages, [cabins](https://www.expedia.ca/aa/Cabins), villas... The list goes on, and on… and on! There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Osprey vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.  **Osprey vacation rentals: An excellent choice for every season** Whenever you want to travel, a warm welcome awaits you in Osprey. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in .  Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Osprey vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Osprey vacation rentals we have selected for you start as low as CA $176 per night. Entering your travel dates in the search wizard you might find even better deals! **How to find incredible deals on Osprey rentals** At Expedia, we put the best Osprey vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.  To find some top Osprey rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Osprey vacation. If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Osprey. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.  ## Explore a world of travel with Expedia - Trending destinations on Expedia.ca - All accommodation types in Osprey ### Trending destinations on Expedia.ca - [Canmore Vacation Rentals](https://www.expedia.ca/Canmore-Vacation-Rentals.d10131.Travel-Guide-VacationRentals) - [Maui Vacation Rentals](https://www.expedia.ca/Maui-Vacation-Rentals.d180073.Travel-Guide-VacationRentals) - [Kelowna Vacation Rentals](https://www.expedia.ca/Kelowna-Vacation-Rentals.d3997.Travel-Guide-VacationRentals) - [Whistler Vacation Rentals](https://www.expedia.ca/Whistler-Vacation-Rentals.d4115.Travel-Guide-VacationRentals) - [Florida Vacation Rentals](https://www.expedia.ca/Destinations-In-Florida.d211.Vacation-Rental-Destinations) - [Victoria Vacation Rentals](https://www.expedia.ca/Victoria-Vacation-Rentals.d4138.Travel-Guide-VacationRentals) - [Vancouver Vacation Rentals](https://www.expedia.ca/Vancouver-Vacation-Rentals.d178315.Travel-Guide-VacationRentals) - [Palm Springs Vacation Rentals](https://www.expedia.ca/Palm-Springs-Vacation-Rentals.d180676.Travel-Guide-VacationRentals) - [Tofino Vacation Rentals](https://www.expedia.ca/Tofino-Vacation-Rentals.d6094955.Travel-Guide-VacationRentals) - [Calgary Vacation Rentals](https://www.expedia.ca/Calgary-Vacation-Rentals.d178245.Travel-Guide-VacationRentals) - [Costa Rica Vacation Rentals](https://www.expedia.ca/Destinations-In-Costa-Rica.d42.Vacation-Rental-Destinations) - [Vancouver Island Vacation Rentals](https://www.expedia.ca/Vancouver-Island-Vacation-Rentals.d6058387.Travel-Guide-VacationRentals) - [Puerto Vallarta Vacation Rentals](https://www.expedia.ca/Puerto-Vallarta-Vacation-Rentals.d180016.Travel-Guide-VacationRentals) - [Hawaii Vacation Rentals](https://www.expedia.ca/Destinations-In-Hawaii.d213.Vacation-Rental-Destinations) - [Toronto Vacation Rentals](https://www.expedia.ca/Toronto-Vacation-Rentals.d178314.Travel-Guide-VacationRentals) - [Banff Vacation Rentals](https://www.expedia.ca/Banff-Vacation-Rentals.d10550.Travel-Guide-VacationRentals) - [Penticton Vacation Rentals](https://www.expedia.ca/Penticton-Vacation-Rentals.d4135.Travel-Guide-VacationRentals) - [Osoyoos Vacation Rentals](https://www.expedia.ca/Osoyoos-Vacation-Rentals.d181782.Travel-Guide-VacationRentals) - [Mont Tremblant Vacation Rentals](https://www.expedia.ca/Mont-Tremblant-Vacation-Rentals.d55374.Travel-Guide-VacationRentals) - [Big White Ski Resort Vacation Rentals](https://www.expedia.ca/Big-White-Ski-Resort-Vacation-Rentals.d6058319.Travel-Guide-VacationRentals) - [Ontario Vacation Rentals](https://www.expedia.ca/Destinations-In-Ontario.d11178.Vacation-Rental-Destinations) - [British Columbia Vacation Rentals](https://www.expedia.ca/Destinations-In-British-Columbia.d11117.Vacation-Rental-Destinations) - [Prince Edward Island Vacation Rentals](https://www.expedia.ca/Destinations-In-Prince-Edward-Island.d6058122.Vacation-Rental-Destinations) - [Québec Vacation Rentals](https://www.expedia.ca/Quebec-Vacation-Rentals.d180017.Travel-Guide-VacationRentals) - [Vacation Homes in Osprey](https://expedia.ca/Osprey-Private-Vacation-Homes.d55888-aaPrivateVacationHomes.Travel-Guide-Accommodation) - [Condo Rentals in Osprey](https://expedia.ca/Osprey-Condos.d55888-aaCondos.Travel-Guide-Accommodation) - [Apartments in Osprey](https://expedia.ca/Osprey-Apartments.d55888-aaApartments.Travel-Guide-Accommodation) - [Villas in Osprey](https://expedia.ca/Osprey-Villas.d55888-aaVillas.Travel-Guide-Accommodation) - [Cottages in Osprey](https://expedia.ca/Osprey-Cottages.d55888-aaCottages.Travel-Guide-Accommodation) - [Aparthotels in Osprey](https://expedia.ca/Osprey-Apart-Hotels.d55888-aaApartHotels.Travel-Guide-Accommodation) - [Resorts in Osprey](https://expedia.ca/Osprey-Resort-Hotels.d55888-aaResortHotels.Travel-Guide-Accommodation) - [Guest Houses in Osprey](https://expedia.ca/Osprey-Guest-Houses.d55888-aaGuestHouses.Travel-Guide-Accommodation) - [Motels in Osprey](https://expedia.ca/Osprey-Motels.d55888-aaMotels.Travel-Guide-Accommodation) - [Chalets in Osprey](https://expedia.ca/Osprey-Chalets.d55888-aaChalets.Travel-Guide-Accommodation) - [Houseboats in Osprey](https://expedia.ca/Osprey-Houseboats.d55888-aaHouseboats.Travel-Guide-Accommodation) - [B&B in Osprey](https://expedia.ca/Osprey-Bed-And-Breakfast.d55888-aaBedAndBreakfast.Travel-Guide-Accommodation) - [Farmstay in Osprey](https://expedia.ca/Osprey-Agritourism.d55888-aaAgritourism.Travel-Guide-Accommodation) - [Cabin Rentals in Osprey](https://expedia.ca/Osprey-Cabins.d55888-aaCabins.Travel-Guide-Accommodation) - [RV Parks in Osprey](https://expedia.ca/Osprey-RV-Parks.d55888-aaRVParks.Travel-Guide-Accommodation) - [Lodges in Osprey](https://expedia.ca/Osprey-Lodges.d55888-aaLodges.Travel-Guide-Accommodation) ## Frequently asked questions ### Can I find vacation rentals in Osprey? > Yes, we have vacation rentals in Osprey near Jim Neville Marine Preserve, or you can go with a more secluded option if you're looking for extra privacy while you relax. Visitors to Osprey speak positively about the popular beaches and top-notch restaurants in this destination. While you're in the area, you can also enjoy the lively bars and shops. ### What are some of the best vacation rentals in Osprey? > [Charming Florida Beach Home w King Bed Patio](https://www.expedia.ca/Osprey-Hotels-Charming-Florida-Beach-Home-W-King-Bed-Patio.h99225713.Hotel-Information): Visitors give good reviews to this Osprey vacation home rental, which offers a garden and free WiFi to help you feel comfortable in your new surroundings. This vacation rental also comes with free parking to give you added peace of mind. ### How many vacation rentals are there in Osprey? > With 33 Expedia vacation rentals, you're sure to find just the right place for your Osprey stay. ### What’s there to see and do in Osprey? > Family-friendly attractions include Jim Neville Marine Preserve and Nancy's Consignments, whereas Turtle Beach and Nokomis Beach are a couple of great spots to enjoy the outdoors. While in the area, you can also visit popular places like Siesta Key Beach and Lido Beach. ### What’s a vacation rental in Osprey like? > Vacation rentals are private properties you can stay in for a long or short time in Osprey. Vacation rentals provide amenities such as WiFi and washers and dryers so you'll have all the comforts of home. If you're concerned about a sanitized environment, a vacation rental can offer a sense of security away from shared hotel elevators and lobbies packed with people while still allowing you the enjoyment of travel. You'll also have more space in a vacation rental than in a hotel, which makes a vacation rental an attractive option for families. ### Expedia's Latest Trends Hotels - [Hotels in Panama City Beach](https://expedia.ca/Panama-City-Beach-Hotels.d8021.Travel-Guide-Hotels) - [Hotels in St. Augustine](https://expedia.ca/St-Augustine-Hotels.d6047864.Travel-Guide-Hotels) - [Hotels in Key West](https://expedia.ca/Key-West-Hotels.d1187.Travel-Guide-Hotels) - [Oceanfront Hotels in Cocoa Beach](https://expedia.ca/Cocoa-Beach-Hotels-Oceanfront-Hotels.0-0-d6549-tOceanfrontHotels.Travel-Guide-Filter-Hotels) - [Beach Hotel in Siesta Key](https://expedia.ca/Siesta-Key-Hotels-Beach-Hotel.0-0-d6881-tBeachHotel.Travel-Guide-Filter-Hotels) - [Hotels in Key Largo](https://expedia.ca/Key-Largo-Hotels.d8369.Travel-Guide-Hotels) - [Hotels in Fort Myers Beach](https://expedia.ca/Fort-Myers-Beach-Hotels.d7194.Travel-Guide-Hotels) - [All Inclusive Resorts and Hotels in Key West](https://expedia.ca/Key-West-Hotels-All-Inclusive-Hotel.0-0-d1187-tAllInclusiveHotel.Travel-Guide-Filter-Hotels) - [Hotels in Naples](https://expedia.ca/Naples-Hotels.d602724.Travel-Guide-Hotels) - [Hotels in Daytona Beach](https://expedia.ca/Daytona-Beach-Hotels.d6023995.Travel-Guide-Hotels) - [Hotels in Marco Island](https://expedia.ca/Marco-Island-Hotels.d8812.Travel-Guide-Hotels) - [Hotels in West Palm Beach](https://expedia.ca/West-Palm-Beach-Hotels.d2742.Travel-Guide-Hotels) - [Hotels in Fort Myers](https://expedia.ca/Fort-Myers-Hotels.d602729.Travel-Guide-Hotels) - [Hotels in Sarasota](https://expedia.ca/Sarasota-Hotels.d602719.Travel-Guide-Hotels) Flights - [Flights to Sarasota](https://expedia.ca/Cheap-Flights-To-Sarasota.d602719.Travel-Guide-Flights) - [Flights to Naples](https://expedia.ca/Cheap-Flights-To-Naples.d602724.Travel-Guide-Flights) - [Flights to Fort Myers](https://expedia.ca/Cheap-Flights-To-Fort-Myers.d602729.Travel-Guide-Flights) - [Flights to Daytona Beach](https://expedia.ca/Cheap-Flights-To-Daytona-Beach.d6023995.Travel-Guide-Flights) - [Flights to Punta Gorda](https://expedia.ca/Cheap-Flights-To-Punta-Gorda.d9394.Travel-Guide-Flights) - [Flights to Cape Canaveral](https://expedia.ca/Cheap-Flights-To-Cape-Canaveral.d6484.Travel-Guide-Flights) - [Flights to Key West](https://expedia.ca/Cheap-Flights-To-Key-West.d1187.Travel-Guide-Flights) Cars - [Car rentals in Fort Myers](https://expedia.ca/Car-Rentals-In-Fort-Myers.d602729.Car-Rental-Guide) Activities - [Things to do in Sarasota](https://expedia.ca/Things-To-Do-In-Sarasota.d602719.Travel-Guide-Activities) - [Things to do in New Smyrna Beach](https://expedia.ca/Things-To-Do-In-New-Smyrna-Beach.d8943.Travel-Guide-Activities) - [Things to do in Daytona Beach](https://expedia.ca/Things-To-Do-In-Daytona-Beach.d6023995.Travel-Guide-Activities) - [Things to do in Key West](https://expedia.ca/Things-To-Do-In-Key-West.d1187.Travel-Guide-Activities) - [Things to do in Cape Coral](https://expedia.ca/Things-To-Do-In-Cape-Coral.d6521.Travel-Guide-Activities) - [Things to do in St. Augustine](https://expedia.ca/Things-To-Do-In-St-Augustine.d6047864.Travel-Guide-Activities) Packages - [Key West Vacations](https://expedia.ca/Key-West.d1187.Destination-Travel-Guides) General - [Visit Cocoa Beach](https://expedia.ca/Cocoa-Beach.dx6549) ![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg) ## Go further with the Expedia app Save on select hotels and earn double points when you book on the app. Our app deals help you to save on trips so you can travel more and manage it all on the go. Scan the QR code with your device camera and download our app ![QR code to download the app](data:image/png;base64,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)