Title: Holiday Rentals Osprey from £107: Find Short-Term Rentals & Holiday Accommodations | Expedia.co.uk [Osprey Travel Guide](https://expedia.co.uk/Osprey.dx55888)[Hotels in Osprey](https://expedia.co.uk/Osprey-Hotels.d55888.Travel-Guide-Hotels)[Things to do in Osprey](https://expedia.co.uk/Things-To-Do-In-Osprey.d55888.Travel-Guide-Activities)[Osprey Car Hire](https://expedia.co.uk/Compare-Cheap-Car-Hire-In-Osprey.d55888.Car-Hire-Guide)[Osprey Holidays](https://expedia.co.uk/Osprey.d55888.Holidays-City-Breaks) ![Great Heron](https://images.trvl-media.com/place/55888/92c919ca-2448-4c40-b1eb-f9207c3d50df.jpg?impolicy=fcrop&w=1200&h=500&q=medium) # Search Holiday Rentals in Osprey - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__price_find.svg) ### Change your mind Book hotels with free cancellation - ![](https://a.travel-assets.com/travel-assets-manager/pictogram-bex/light__deals.svg) ### Treat yourself Save instantly and earn perks with One Key [Learn about One Key](https://www.expedia.co.uk/welcome-one-key) - ![](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 [25 Nov - 26 Nov](https://www.expedia.co.uk/Hotel-Search?regionId=55888&startDate=2025-11-25&endDate=2025-11-26&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Tomorrow [26 Nov - 27 Nov](https://www.expedia.co.uk/Hotel-Search?regionId=55888&startDate=2025-11-26&endDate=2025-11-27&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) This weekend [28 Nov - 30 Nov](https://www.expedia.co.uk/Hotel-Search?regionId=55888&startDate=2025-11-28&endDate=2025-11-30&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) Next weekend [5 Dec - 7 Dec](https://www.expedia.co.uk/Hotel-Search?regionId=55888&startDate=2025-12-05&endDate=2025-12-07&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true) ## Top Holiday Rentals in Osprey ![House | 2 bedrooms, Internet](https://images.trvl-media.com/lodging/100000000/99230000/99225800/99225713/91ed60d9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House | 2 bedrooms, Internet](https://images.trvl-media.com/lodging/100000000/99230000/99225800/99225713/769f8563.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House | 2 bedrooms, Internet](https://images.trvl-media.com/lodging/100000000/99230000/99225800/99225713/83080812.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![House | 2 bedrooms, Internet](https://images.trvl-media.com/lodging/100000000/99230000/99225800/99225713/d838df32.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Charming Florida Beach Home w King Bed Patio Bay Acres 10/10 Exceptional (2) "The best place to stay! Super clean home and friendly service. I would stay here again. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Alyssa [](https://www.expedia.co.uk/Osprey-Hotels-Charming-Florida-Beach-Home-W-King-Bed-Patio.h99225713.Hotel-Information) ![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 (5115) "The room was clean and the staff was very nice." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jill £107 includes taxes & fees 30 Nov - 1 Dec [](https://www.expedia.co.uk/Sarasota-Hotels-Tropical-Beach-Resorts.h1240909.Hotel-Information) ![Outdoor pool, a heated pool, open 7:00 AM to 8:00 PM, pool loungers](https://images.trvl-media.com/lodging/2000000/1220000/1213000/1212924/6ff58e07.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![42-inch flat-screen TV with satellite channels, TV](https://images.trvl-media.com/lodging/2000000/1220000/1213000/1212924/4b30e45d.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 | Premium bedding, pillow-top beds, in-room safe, desk](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 (2199) "Excellent location! Friendly staff, clean and updated rooms." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Elba £108 includes taxes & fees 27 Nov - 28 Nov [](https://www.expedia.co.uk/Sarasota-Hotels-Hibiscus-Suites-Gateway-To-Siesta-Key.h1212924.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) ![Florida Family Single | Private kitchen | Fridge, microwave, coffee/tea maker, toaster](https://images.trvl-media.com/lodging/2000000/1170000/1163600/1163507/06d7bc78.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) ### Captiva Beach Resort South Village 9.0/10 Wonderful (1163) "Very good stay, clean, safe, and steps from the beach" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Brandon [](https://www.expedia.co.uk/Sarasota-Hotels-Captiva-Beach-Resort.h1163507.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) ![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) ![Outdoor pool, free pool cabanas](https://images.trvl-media.com/lodging/4000000/3820000/3819700/3819631/876c7c10.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Premium bedding, pillow-top 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 (297) "Loved our stay! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Michelle £331 includes taxes & fees 17 Dec - 18 Dec [](https://www.expedia.co.uk/Siesta-Key-Hotels-The-Residences-At-Siesta-Key-Beach-By-Hyatt-Vacation-Club.h3819631.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) ![Deluxe Room | Terrace/patio](https://images.trvl-media.com/lodging/115000000/114190000/114189500/114189452/be5906a9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Superior Studio Suite | 2 bedrooms, in-room safe, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/115000000/114190000/114189500/114189452/c5bfb01f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Signature Room | 2 bedrooms, in-room safe, iron/ironing board, free WiFi](https://images.trvl-media.com/lodging/115000000/114190000/114189500/114189452/1e7203ea.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### SeaSpray Resort Siesta Key 9.4/10 Exceptional (70) "Clean room, incredibly helpful staff. Will be staying here again" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Caleb £215 includes taxes & fees 2 Dec - 3 Dec [](https://www.expedia.co.uk/Siesta-Key-Hotels-SeaSpray-Resort.h114189452.Hotel-Information) ![Front of property](https://images.trvl-media.com/lodging/6000000/5460000/5453000/5452904/e9de80f2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, a heated pool, open 7:00 AM to 9:00 PM, pool umbrellas](https://images.trvl-media.com/lodging/6000000/5460000/5453000/5452904/e9c999e3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Front of property](https://images.trvl-media.com/lodging/6000000/5460000/5453000/5452904/278a5fae.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Full-sized fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/6000000/5460000/5453000/5452904/2c6b16f6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Ringling Beach House Siesta Key 9.0/10 Wonderful (337) "Clean, friendly and beach!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Mary £372 includes taxes & fees 24 Dec - 25 Dec [](https://www.expedia.co.uk/Sarasota-Hotels-The-Ringling-Beach-House.h5452904.Hotel-Information) ![Cabin (Tiny House - The Siesta) | Living area | Flat-screen TV, Netflix, streaming services](https://images.trvl-media.com/lodging/22000000/21440000/21431000/21430911/69212d51.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Cabin (Tiny House Blue Lifeguard Stand) | 1 bedroom, individually decorated, individually furnished, soundproofing](https://images.trvl-media.com/lodging/22000000/21440000/21431000/21430911/aa6fce22.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) ![Cabin, 2 Bedrooms (Tiny House - Aqua Oasis) | 1 bedroom, individually decorated, individually furnished, soundproofing](https://images.trvl-media.com/lodging/22000000/21440000/21431000/21430911/8f76b808.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Tiny House Siesta Sarasota 8.4/10 Very good (343) "Enjoyable stay. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lori £185 includes taxes & fees 26 Nov - 27 Nov [](https://www.expedia.co.uk/Sarasota-Hotels-Tiny-House-Siesta.h21430911.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) ![Terrace/patio](https://images.trvl-media.com/lodging/91000000/90030000/90021900/90021825/58abfff3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Double Room, 2 Double Beds | Iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/91000000/90030000/90021900/90021825/c0cd244a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Full-sized fridge, microwave, stovetop, cookware/dishes/utensils](https://images.trvl-media.com/lodging/91000000/90030000/90021900/90021825/04923579.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Kon Tiki Inn Venice Island 10/10 Exceptional (244) "Staff was great, room was clean and comfortable. It was a short stay but we enjoyed our time there. We will be back!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Joan £140 includes taxes & fees 2 Dec - 3 Dec [](https://www.expedia.co.uk/Venice-Hotels-Kon-Tiki-Inn.h90021825.Hotel-Information) ![On the beach, white sand](https://images.trvl-media.com/lodging/2000000/1540000/1533200/1533163/d13a0271.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beachside One Bedroom Suite | Private kitchen | Fridge, microwave, stovetop, coffee/tea maker](https://images.trvl-media.com/lodging/2000000/1540000/1533200/1533163/55fa2e0f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Bayview 3 Bedroom | Living room | TV](https://images.trvl-media.com/lodging/2000000/1540000/1533200/1533163/5c776782.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beachside Efficiency | Bathroom | Shower, free toiletries, hair dryer, towels](https://images.trvl-media.com/lodging/2000000/1540000/1533200/1533163/8ce15104.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### A Beach Retreat Casey Key 9.2/10 Wonderful (574) "Location, very clean and comfortable. Nice efficiency." ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Chuck [](https://www.expedia.co.uk/Sarasota-Hotels-A-Beach-Retreat.h1533163.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/90000000/89720000/89714300/89714291/45ae6432.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) ![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) ### Siesta Key Island Rentals Siesta Key 9.6/10 Exceptional (50) "Very nice place, we loved it. Great location. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Derrick £215 includes taxes & fees 3 Dec - 4 Dec [](https://www.expedia.co.uk/Siesta-Key-Hotels-Siesta-Key-Island-Rentals.h89714291.Hotel-Information) ![On the beach, white sand](https://images.trvl-media.com/lodging/9000000/8110000/8109300/8109251/8623a3bb.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Reception](https://images.trvl-media.com/lodging/9000000/8110000/8109300/8109251/81bf853e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Studio with Balcony | View from room](https://images.trvl-media.com/lodging/9000000/8110000/8109300/8109251/7c582a96.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Villa, 2 Bedrooms, Partial Ocean View, Courtyard Area | View from room](https://images.trvl-media.com/lodging/9000000/8110000/8109300/8109251/38876c4d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Sea Club I Beach Resort Longboat Key 9.2/10 Wonderful (333) "Very nice beach themed bungalow. Loved the quiet and the views. " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Jennifer [](https://www.expedia.co.uk/Sarasota-Hotels-Sea-Club-I-Beach-Resort.h8109251.Hotel-Information) ![Outdoor pool, a heated pool, open 8:00 AM to 8:00 PM, pool umbrellas](https://images.trvl-media.com/lodging/10000000/9770000/9769000/9768901/1bfe228b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![The Cottage, 3 Bedroom 2 Bath (2 Kings, 1 Queen, 2 Twins) | Living area | 65-inch Smart TV with cable channels, TV, DVD player](https://images.trvl-media.com/lodging/10000000/9770000/9769000/9768901/66da17bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach nearby, white sand, beach umbrellas, beach towels](https://images.trvl-media.com/lodging/10000000/9770000/9769000/9768901/e9ce27d7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Full-sized fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/10000000/9770000/9769000/9768901/83aeeea9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### The Inn On Siesta Key Siesta Key 10/10 Exceptional (189) "Great place to stay! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Carlos [](https://www.expedia.co.uk/Sarasota-Hotels-The-Inn-On-Siesta-Key.h9768901.Hotel-Information) ![Beach nearby, beach umbrellas, beach towels](https://images.trvl-media.com/lodging/38000000/37880000/37877900/37877891/2173fe57.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Garden](https://images.trvl-media.com/lodging/38000000/37880000/37877900/37877891/b9fb6ae9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/38000000/37880000/37877900/37877891/5a507f37.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/38000000/37880000/37877900/37877891/ade5882a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Tropical Villas of Venice Beach Venice Island 9.6/10 Exceptional (240) "Great Location !!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Orleys [](https://www.expedia.co.uk/Sarasota-Hotels-Tropical-Villas-Of-Venice-Beach.h37877891.Hotel-Information) ![Garden](https://images.trvl-media.com/lodging/12000000/11900000/11897700/11897601/90d49a4a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Beach nearby, white sand, sun-loungers, beach umbrellas](https://images.trvl-media.com/lodging/12000000/11900000/11897700/11897601/ae35116d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Condo, 2 Bedrooms (225 Sea Escape) | Private kitchen | Full-sized fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/12000000/11900000/11897700/11897601/c5e64875.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Condo, 1 Bedroom (123 Sea Spray) | In-room dining](https://images.trvl-media.com/lodging/12000000/11900000/11897700/11897601/d400f106.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Siesta Palms By the Beach South Village 9.4/10 Exceptional (136) "Comfy and clean, nice and close to the beach. Pool was very clean. Quiet, safe area. Would highly recommend!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Lynn [](https://www.expedia.co.uk/Sarasota-Hotels-Siesta-Palms-By-The-Beach.h11897601.Hotel-Information) ![Exterior](https://images.trvl-media.com/lodging/109000000/108760000/108753100/108753056/w2398h1348x2y6-214d5e5a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Apartment, 1 Bedroom | Private kitchen | Full-sized fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/109000000/108760000/108753100/108753056/f8635480.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Apartment, 2 Bedrooms | Terrace/patio](https://images.trvl-media.com/lodging/109000000/108760000/108753100/108753056/8e37360c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Apartment, 1 Bedroom | 2 bedrooms, individually decorated, individually furnished](https://images.trvl-media.com/lodging/109000000/108760000/108753100/108753056/ca54386b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Bradenton Apartments by Landing Bradenton 7.6/10 Good (54) "Perfect place " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) chavelys [](https://www.expedia.co.uk/Bradenton-Hotels-Barsala-At-Champions-Walk.h108753056.Hotel-Information) ![Condo, Pool View | Private kitchen | Full-sized fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/60000000/59670000/59661500/59661429/0ea98630.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) ![House, Lake View | Private kitchen | Full-sized fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/60000000/59670000/59661500/59661429/74e8ca6f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/60000000/59670000/59661500/59661429/d3b33d16.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 £265 includes taxes & fees 10 Dec - 11 Dec [](https://www.expedia.co.uk/Sarasota-Hotels-Siesta-Heron-Suites-Villas.h59661429.Hotel-Information) ![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/74000000/73780000/73778600/73778592/ed74b914.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/74000000/73780000/73778600/73778592/446945d2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Terrace/patio](https://images.trvl-media.com/lodging/74000000/73780000/73778600/73778592/0c4a9d23.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/74000000/73780000/73778600/73778592/3a232745.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### Stunning Home, Resort Pool Area w/ Waterslide and Spa, Gulf Views Siesta Key Village 10/10 Exceptional (40) "This was the perfect place to stay for a large family with kids. The location to the beach and restaurants couldn't have been more convenient. Amazing vacation!" ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Frances E. [](https://www.expedia.co.uk/Siesta-Key-Hotels-Heated-PoolSpa-And-Waterslide.h73778592.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) ![Luxury Condo, 3 Bedrooms, Kitchen, Ocean View | Private kitchen | Full-sized fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/113000000/112390000/112387400/112387358/aa27a0eb.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 | 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 £419 includes taxes & fees 30 Nov - 1 Dec [](https://www.expedia.co.uk/Englewood-Hotels-Chadwick-Cove-Resort-Marina.h112387358.Hotel-Information) ![On the beach, sun-loungers, beach towels](https://images.trvl-media.com/lodging/36000000/35550000/35541700/35541645/9273c908.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Outdoor dining](https://images.trvl-media.com/lodging/36000000/35550000/35541700/35541645/f6af5460.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Desk, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/36000000/35550000/35541700/35541645/8e8db79f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ![Exterior](https://images.trvl-media.com/lodging/36000000/35550000/35541700/35541645/73815609.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium) ### THE BEACH CONDO #107 BEACHFRONT FULL VIEW Longboat Key 9.8/10 Exceptional (80) "Had a wonderful time at this condo. It was a great location and was kept very clean. The owner was very nice and helpful. Will definitely be back! " ![United States](https://a.travel-assets.com/egds/marks/flags/us.svg) Karen £303 includes taxes & fees 26 Nov - 27 Nov [](https://www.expedia.co.uk/Longboat-Key-Hotels-THE-BEACH.h35541645.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.co.uk/Hotel-Search?startDate=2025-12-09&endDate=2025-12-10®ionId=55888&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true) ![](https://forever.travel-assets.com/flex/flexmanager/images/2025/11/05/BEX-BF-25_FR-DE-MX-UK_1_Desktop.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh) ## Black Friday Sale Save up to 40% on select hotels. [Book now](https://expedia.co.uk/cheap-deals?rfrr=VR_BF_PROMO_55888) ## Find holiday rentals that suit your style Aparthotels [](https://www.expedia.co.uk/Hotel-Search?destination=Osprey%2C+Florida%2C+United+States+of+America®ionId=55888&latLong=27.196163%2C-82.490372&adults=2&startDate=2026-02-23&d1=2026-02-23&endDate=2026-02-26&d2=2026-02-26&lodging=APART_HOTEL) Apartments [](https://www.expedia.co.uk/Hotel-Search?destination=Osprey%2C+Florida%2C+United+States+of+America®ionId=55888&latLong=27.196163%2C-82.490372&adults=2&startDate=2026-02-23&d1=2026-02-23&endDate=2026-02-26&d2=2026-02-26&lodging=APARTMENT) Condos [](https://www.expedia.co.uk/Hotel-Search?destination=Osprey%2C+Florida%2C+United+States+of+America®ionId=55888&latLong=27.196163%2C-82.490372&adults=2&startDate=2026-02-23&d1=2026-02-23&endDate=2026-02-26&d2=2026-02-26&lodging=CONDO) Private holiday homes [](https://www.expedia.co.uk/Hotel-Search?destination=Osprey%2C+Florida%2C+United+States+of+America®ionId=55888&latLong=27.196163%2C-82.490372&adults=2&startDate=2026-02-23&d1=2026-02-23&endDate=2026-02-26&d2=2026-02-26&lodging=VACATION_HOME) Cottages [](https://www.expedia.co.uk/Hotel-Search?destination=Osprey%2C+Florida%2C+United+States+of+America®ionId=55888&latLong=27.196163%2C-82.490372&adults=2&startDate=2026-02-23&d1=2026-02-23&endDate=2026-02-26&d2=2026-02-26&lodging=COTTAGE) Villas [](https://www.expedia.co.uk/Hotel-Search?destination=Osprey%2C+Florida%2C+United+States+of+America®ionId=55888&latLong=27.196163%2C-82.490372&adults=2&startDate=2026-02-23&d1=2026-02-23&endDate=2026-02-26&d2=2026-02-26&lodging=VILLA) ![](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.co.uk/user/signin?ckoflag=0&uurl=e3id%3Dredr%26rurl%3D%2FOsprey-Holiday-Rentals.d55888.Travel-Guide-HolidayRentals)[Sign up, it's free](https://expedia.co.uk/signup?enable_registration=true&+=&uurl=e3id%3Dredr%26rurl%3D%2FOsprey-Holiday-Rentals.d55888.Travel-Guide-HolidayRentals) ## Top Osprey Hotel Reviews ![Hibiscus Suites - Gateway to Siesta Key](https://images.trvl-media.com/lodging/2000000/1220000/1213000/1212924/6ff58e07_y.jpg) ### Hibiscus Suites - Gateway to Siesta Key 10/10 Excellent "All very nice " [](https://expedia.co.uk/Sarasota-Hotels-Hibiscus-Suites-Gateway-To-Siesta-Key.h1212924.Hotel-Information) ![Kompose Boutique Hotel](https://images.trvl-media.com/lodging/39000000/38220000/38215400/38215316/e948f2e5_y.jpg) ### Kompose Boutique Hotel 10/10 Excellent "Staff was extremely hospitable, the hotel was gorgeous and so hip, the rooms each space was taken up perfectly with the most amazing amenities. The attention to detail in this hotel was incredible " [](https://expedia.co.uk/Sarasota-Hotels-Kompose-Hotel-Sarasota.h38215316.Hotel-Information) ![Lido Beach Resort](https://images.trvl-media.com/lodging/1000000/40000/34600/34597/d9fc7fce_y.jpg) ### Lido Beach Resort 10/10 Excellent "Ocean view and beach view. I'd do it again." [](https://expedia.co.uk/Sarasota-Hotels-Lido-Beach-Resort.h34597.Hotel-Information) ![Tropical Beach Resorts](https://images.trvl-media.com/lodging/2000000/1250000/1241000/1240909/606a9b3c_y.jpg) ### Tropical Beach Resorts 10/10 Excellent "People were nice, place was clean, 1 minute walk to the Gulf." [](https://expedia.co.uk/Sarasota-Hotels-Tropical-Beach-Resorts.h1240909.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 "Everything was great." [](https://expedia.co.uk/Sarasota-Hotels-Best-Western-Plus-Siesta-Key-Gateway.h26397.Hotel-Information) ![Tropical Breeze Resort](https://images.trvl-media.com/lodging/1000000/880000/879700/879629/9de12888_y.jpg) ### Tropical Breeze Resort 10/10 Excellent "Pretty impressed, actually. I’m and OCD clean freak and this property is spot on! Kudos to Tropical Breeze Resort!!!" [](https://expedia.co.uk/Sarasota-Hotels-Tropical-Breeze-Resort.h879629.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 "Great stay!" [](https://expedia.co.uk/Sarasota-Hotels-Holiday-Inn-Sarasota-Airport.h2403753.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 "Super clean room. Whole place was really clean. Staff was super friendly and professional. Highly recommend and will stay there again in the future." [](https://expedia.co.uk/Sarasota-Hotels-Casey-Key-Resorts-Mainland.h6619300.Hotel-Information) ![Carlisle Inn](https://images.trvl-media.com/lodging/20000000/19770000/19761100/19761082/9a1b0e30_y.jpg) ### Carlisle Inn 10/10 Excellent "Beautiful, clean and smelled amazing! Also free cookies in the evening! " [](https://expedia.co.uk/Sarasota-Hotels-Carlisle-Inn.h19761082.Hotel-Information) ## Find out more about Osprey **Everything you need to know about** **Osprey** **holiday rentals** Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Osprey holiday rental for you. At Expedia, you can take your pick from private holiday homes, [apartments](https://www.expedia.co.uk/aa/Apartments), cottages, [apart-hotels](https://www.expedia.co.uk/aa/ApartHotels), cabins, [villas](https://www.expedia.co.uk/aa/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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.  **Osprey holiday 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 holiday 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 holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Osprey holiday rentals we have selected for you start as low as £107 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 holiday 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 holiday. 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.co.uk - All accommodation types in Osprey ### Trending destinations on Expedia.co.uk - [Holiday Rentals in the Cotswold](https://www.expedia.co.uk/lp/b/vr/cotswold) - [Holiday Rentals in Lake District](https://www.expedia.co.uk/lp/b/vr/lake-district) - [Devon Holiday Rentals](https://www.expedia.co.uk/Destinations-In-Devon.d6046196.Holiday-Rental-Destinations) - [Norfolk Holiday Rentals](https://www.expedia.co.uk/Destinations-In-Norfolk.d6046223.Holiday-Rental-Destinations) - [Bedfordshire Holiday Rentals](https://www.expedia.co.uk/Destinations-In-Bedfordshire.d6046189.Holiday-Rental-Destinations) - [Dorset Holiday Rentals](https://www.expedia.co.uk/Destinations-In-Dorset.d6046198.Holiday-Rental-Destinations) - [Northumberland Holiday Rentals](https://www.expedia.com/Destinations-In-Northumberland.d6046225.Vacation-Rental-Destinations) - [Herefordshire Holiday Rentals](https://www.expedia.co.uk/Destinations-In-Herefordshire.d6046203.Holiday-Rental-Destinations) - [Essex Holiday Rentals](https://www.expedia.co.uk/Destinations-In-Essex.d6046201.Holiday-Rental-Destinations) - [Cumbria Holiday Rentals](https://www.expedia.co.uk/Destinations-In-Cumbria.d6046194.Holiday-Rental-Destinations) - [Yorkshire Holiday Rentals](https://www.expedia.co.uk/Yorkshire-Holiday-Rentals.d6342462.Travel-Guide-HolidayRentals) - [South Wales Holiday Rentals](https://www.expedia.co.uk/South-Wales-Holiday-Rentals.d6054274.Travel-Guide-HolidayRentals) - [North Wales Holiday Rentals](https://www.expedia.co.uk/North-Wales-Holiday-Rentals.d6054276.Travel-Guide-HolidayRentals) - [London Holiday Rentals](https://www.expedia.co.uk/London-Holiday-Rentals.d178279.Travel-Guide-HolidayRentals) - [York Holiday Rentals](https://www.expedia.co.uk/York-Holiday-Rentals.d5489.Travel-Guide-HolidayRentals) - [Blackpool Holiday Rentals](https://www.expedia.co.uk/Blackpool-Holiday-Rentals.d619.Travel-Guide-HolidayRentals) - [Isle of Wight Holiday Rentals](https://www.expedia.com/Destinations-In-Isle-Of-Wight.d6046218.Vacation-Rental-Destinations) - [Scarborough Holiday Rentals](https://www.expedia.co.uk/Scarborough-Holiday-Rentals.d5680.Travel-Guide-HolidayRentals) - [Edinburgh Holiday Rentals](https://www.expedia.co.uk/Edinburgh-Holiday-Rentals.d6069845.Travel-Guide-HolidayRentals) - [Bath Holiday Rentals](https://www.expedia.co.uk/Bath-Holiday-Rentals.d6084496.Travel-Guide-HolidayRentals) - [Bournemouth Holiday Rentals](https://www.expedia.co.uk/Bournemouth-Holiday-Rentals.d654.Travel-Guide-HolidayRentals) - [England Holiday Rentals](https://www.expedia.co.uk/Destinations-In-England.d11218.Holiday-Rental-Destinations) - [Scotland Holiday Rentals](https://www.expedia.co.uk/Destinations-In-Scotland.d11219.Holiday-Rental-Destinations) - [Cornwall Holiday Rentals](https://www.expedia.co.uk/Destinations-In-Cornwall.d6046193.Holiday-Rental-Destinations) - [Wales Holiday Rentals](https://www.expedia.co.uk/Destinations-In-Wales.d11220.Holiday-Rental-Destinations) - [Northern Ireland Holiday Rentals](https://www.expedia.co.uk/Destinations-In-Northern-Ireland.d11221.Holiday-Rental-Destinations) - [B&B in Osprey](https://expedia.co.uk/Osprey-Bed-And-Breakfasts.d55888-aaBedAndBreakfasts.Travel-Guide-Accommodation) ## Frequently asked questions ### Can I find holiday rentals in Osprey? > Yes, there are holiday rentals in Osprey close to Jim Neville Marine Preserve, or you can select a more secluded option if you're looking for a relaxing stay. 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 holiday rentals that Osprey has to offer? > [Charming Florida Beach Home w King Bed Patio](https://www.expedia.co.uk/Osprey-Hotels-Charming-Florida-Beach-Home-W-King-Bed-Patio.h99225713.Hotel-Information): This highly rated holiday home rental in Osprey offers a garden and free WiFi to help you feel comfortable in your new surroundings. This holiday rental also comes with free parking to give you added peace of mind. ### How many holiday rentals are there in Osprey? > With 34 Expedia holiday rentals, you're guaranteed 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 such as Siesta Key Beach and Lido Beach. ### What’s a holiday rental in Osprey like? > Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Osprey. Holiday rentals feature extras such as kitchens and laundry facilities so you'll feel just like you're staying in your own home. If you're concerned about cleanliness, holiday rentals can provide a sense of security away from shared hotel lifts and lobbies bustling with people while still allowing you the experience of travel. You'll also have more space in a holiday rental than in a standard hotel, which makes a holiday rental a popular choice for families. ![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg) ## Go further with the Expedia app Save on select hotels when you book in 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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)