Holiday homes by the sea in Osprey
Choose the right place for you
REVIEWS
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9+ Exceptional
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8+ Fabulous
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7+ Very Good
DISTANCE FROM CENTRE
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Less than 1 km
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Less than 3 km
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Less than 5 km
Vacation rental deals in Osprey
We have selected the best holiday accommodation by the sea in Osprey. Bluepillow allows you to save money, by finding the best rates on the main vacation rental websites in Osprey
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Osprey - United States
Private 2-b ,1 b Apt. 5min to Beach! Access I-75.
- 3 Guests 2Bedrooms
10 Exceptional (60)Private 2 bed/1 bath efficiency unit with 1/2 acre private large fenced backyard.. Pool & Private patio! ***I take extreme effort in cleanliness, check my reviews. Remember these are short term rentals ...Check Availability -
Osprey - United States
Cozy Cottage by the Bay
- 2 Guests 1Bedroom
10 Exceptional (103)Enjoy this modern yet rustic looking guest cottage in historic Osprey, one of Sarasota County's first settlements. Walk to the bayfront, restaurants, shopping, library, and parks. A short drive takes ...Check Availability -
Osprey - United States
Our American Dream - A Paradise Destination
- 7 Guests 2Bedrooms
10 Exceptional (75)Our "American Dream" is centrally located close to restaurants, beaches (Siesta Key Beach), activities, national parks, down town Sarasota and shopping malls. You will love our accommodation as it is newly ...Check Availability -
Osprey - United States
Siesta Key - 2bdrm on the beach - amazing views!!
- 5 Guests 2Bedrooms
10 Exceptional (34)The condo benefits from its own private pool. The living room, master bedroom, and lanai (balcony) all have stunning ocean views. The lanai, with over $10,000 of new doors and windows, is furnished ...Check Availability -
Osprey - United States
Private Mother In-Law Suit Siesta Key
- 2 Guests 0Bedroom
10 Exceptional (45)Located south Siesta Key with no busy streets to cross, it’s a leisurely stroll to the Gulf of Mexico and to Point of Rocks, the best snorkeling beach on the Key. There are many restaurants, lots of shopping, ...Check Availability -
Osprey - United States
Charming 1 bedroom apartment for 2 with pool.
- 2 Guests 1Bedroom
10 Exceptional (20)Large comfortable apartment, attached to private home. Located in quiet residential neighborhood, less than 10 minutes drive to Nokomis beach and 20 minutes to Siesta Key Beach. Beautiful view of pool, ...Check Availability
Bed and breakfast offers in Osprey by the sea
Are you looking for an accommodation in Osprey and do you want to save money? Choose from 19 Bed & Breakfasts in Osprey
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Osprey - United States
Bentley's Boutique Hotel, BW Premier Collection
- Hotel
8 Fabulous (1056)Situated in the historical district, this resort is 0.3 mi (0.5 km) from Oscar Scherer State Park, and within 3 mi (5 km) of Turtle Beach and Nokomis Beach. Venice Beach and Siesta Key Public Beach are ...Check Availability -
Osprey - United States
Siesta Key Bungalows
- Hotel
8.8 Fabulous (519)One of our top picks in Siesta Key.Located in Sarasota, Florida, this resort features a heated outdoor swimming pool and direct access to Heron Lagoon. Free bicycle and kayak use is offered. A fully ...Check Availability -
Osprey - United States
The Catamaran Waterview One-Bedroom.
- Hotel
9 Exceptional (4)The Catamaran bungalow has a sitting area off the front of the bungalow that includes two wicker chairs. This bungalow includes a full kitchen including a microwave, coffee pot, toaster, oven, and fridge. ...Check Availability -
Osprey - United States
Turtle Beach Resort and Inn
- Hotel
8 Fabulous (459)Situated on the waterfront, this romantic resort is within 3 miles (5 km) of Turtle Beach, Siesta Key Public Beach and Siesta Key Marina. Crescent Beach and Point of Rocks are also within 3 miles (5 km). ...Check Availability -
Osprey - United States
Turtle Beach Resort
- Hotel
8.5 Fabulous (80)Located on the coast of Little Sarasota Bay, this secluded Turtle Beach Resort features an outdoor pool and kayaks. Guests will be 2 minutes’ walk from Turtle Beach on the Gulf Coast. A private furnished ...Check Availability -
Osprey - United States
Remodeled Waterfront Home
- Hotel
Newly renovated and furnished guest house just steps from the intracoastal waterway, boat ramp, and fishing pier. Layout features kitchen/dining area, living room, office, master bedroom, guest bedroom, ...Check Availability
Farmhouse or Hotel? Choose from the best offers
Choose the accommodation tailor-made for you for your next vacation: sleep in a farmhouse or sleep in a hotel?
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![Farmstays in Osprey]()
Farmstays in Osprey -
![Hotels in Osprey]()
Hotels in Osprey
The best places to stay in Osprey
Book an apartment in Osprey and choose the right accommodation for your needs
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Osprey - United States
Cozy and Private Duplex Near Beach and Trails
- 2 Guests 1Bedroom
10 Exceptional (6)This cozy, quiet, and well equipped apartment has a private outside entrance, separate bedroom, living room/kitchenette, private bath, private lanai and yard. (A second bedroom and bath are available upon ...Check Availability -
Osprey - United States
Quiet private bedroom/bath for female guest
- 1 Guest 1Bedroom
10 Exceptional (3)Private clean quiet light filled bedroom with full bed and private bathroom. Shared living spaces of kitchen/laundry/dinning room in upscale clean newer home. Shared living space with female, therefore ...Check Availability -
Osprey - United States
Storybook Cottage With Pool Near the Bay & Beach
- 2 Guests 1Bedroom
10 Exceptional (9)Storybook one-bedroom cottage on historic street of 1920's homes, less than 15 minutes from Siesta Key and just steps from Old Sarasota Bay. Ideal, quiet location close to parks, shopping, restaurants ...Check Availability -
Osprey - United States
Sarasota Siesta Key
- 6 Guests 2Bedrooms
10 Exceptional (20)Amazing two bedroom two bath home, Great location close to West Field Mall and beaches Siesta Key # 1 USA. *TROPICAL SHORES Water Access: Yes-Intracoastal Waterway. HAS A PRIVATE #BAYFRONT PARK WITH #BOAT ...Check Availability -
Osprey - United States
COMFY QUEEN BEDS, NEAR TO SIESTA, FAMOUS BEACHES
- 4 Guests 0Bedroom
10 Exceptional (20)Cozy cute private studio, small fridge, microwave, coffee maker with basic necessities. 15 minutes to SIESTA BEACH and 10 minutes to NOKOMIS BEACH. Grocery stores within a mile. (Website hidden by Airbnb) ...Check Availability -
Osprey - United States
Country Club Gem on ground floor
- 6 Guests 2Bedrooms
10 Exceptional (6)We are restricted to 1 guest a month so please scroll down and send us a message. Enjoy a good night's sleep on new luxury mattresses while overlooking the rich green fairway. This ground floor unit in ...Check Availability
