Holiday homes by the sea in Osprey
Choose the right place for you
FACILITIES
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Wi-Fi
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Non Smoking Only
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Pets Allowed
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
Holiday 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
Siesta Key Beach Front condo, Sunsets and sand 1st floor
- 6 Guests 2Bedrooms
9.8 Exceptional (198)This apartment is located in Siesta Key. While the natural beauty of Siesta Key Beach and Turtle Beach can be enjoyed by anyone, those looking for an activity can check out Marina Jack.
Coconuts Family ...Check Availability -
Osprey - United States
Unit 101a - walkout beachfront corner unit has the best Location on Siesta Key
- 6 Guests 2Bedrooms
10 Exceptional (45)This condo is located on the beach and in a walkable area with good shopping. Point of Rocks and Siesta Key Marina are worth checking out if an activity is on the agenda, while those looking for area attractions ...Check Availability -
Osprey - United States
Welcome To Our 2B/2B Beach Getaway That Is A Home Away From Home! B109
- 6 Guests 2Bedrooms
9.7 Exceptional (186)Located in Siesta Key, this condo is on the beach. Shoppers can check out St. Armands Circle, while everyone can enjoy the natural beauty of Siesta Key Beach and Lido Beach. Looking to enjoy an event or ...Check Availability -
Osprey - United States
Step Out Of Our 2nd Floor Condo And Step Right Onto The Beach B208
- 6 Guests 2Bedrooms
9.8 Exceptional (147)Located in Siesta Key, this condo is on the beach. Shoppers can check out St. Armands Circle, while everyone can enjoy the natural beauty of Siesta Key Beach and Lido Beach. Looking to enjoy an event or ...Check Availability -
Osprey - United States
Siesta Key Beach Front condo on Turtle Beach, 2nd floor
- 6 Guests 2Bedrooms
9.6 Exceptional (195)This apartment is located in Siesta Key. While the natural beauty of Siesta Key Beach and Turtle Beach can be enjoyed by anyone, those looking for an activity can check out Marina Jack.
Looking to ...Check Availability -
Osprey - United States
SEASONAL SPECIAL!! Gorgeous Gulf and Pool View No Streets between you & the Gulf
- 3 Guests 0Bedroom
10 Exceptional (22)This condo is located in Siesta Key. While the natural beauty of Siesta Key Beach and Turtle Beach can be enjoyed by anyone, those looking for an activity can check out Marina Jack.
Coconuts Family ...Check Availability -
Osprey - United States
Siesta Key Bungalow - Hibiscus - Queen unit at a Waterfront with Pool, on Siesta
- 3 Guests 1Bedroom
9.8 Exceptional (22)Located in Siesta Key, this apartment is near the beach. Shoppers can check out St. Armands Circle, while everyone can enjoy the natural beauty of Siesta Key Beach and Lido Beach. Consider Venice Train ...Check Availability -
Osprey - United States
Hickory on the Golf Course
- Hotel
With a stay at this condo in Sarasota (Palmer Ranch), you'll be within a 15-minute drive of Siesta Key Beach and Stoneybrook Golf & Country Club. This golf condo is 6.4 mi (10.3 km) from Nokomis Beach ...Check Availability -
Osprey - United States
Yellow Pine Villa
- 3 Guests 0Bedroom
When you stay at this condo in Sarasota, you'll be on the beach, within a 15-minute drive of Siesta Key Beach and Turtle Beach. This condo is 12.1 mi (19.4 km) from Lido Beach and 5.8 mi (9.3 km) from ...Check Availability -
Osprey - United States
Yellow Pine Duplex Close to Pool & Tennis
- 3 Guests 0Bedroom
When you stay at this condo in Sarasota, you'll be on the beach, within a 15-minute drive of Siesta Key Beach and Turtle Beach. This condo is 12 mi (19.3 km) from Lido Beach and 5.7 mi (9.2 km) from Nokomis ...Check Availability -
Osprey - United States
2/2 condo on siesta keys turtle beach with boat dock. sat to sat rentals
- 6 Guests 2Bedrooms
10 Exceptional (11)Located in Siesta Key, this condo is in the city center and on the beach. Shoppers can check out St. Armands Circle, while everyone can enjoy the natural beauty of Siesta Key Beach and Lido Beach. Jim ...Check Availability -
Osprey - United States
WINTER SPECIAL NOW!!! Fully furnished, Pool and Jacuzzi, FreeWiFi, BookNow!!!!!
- 4 Guests 1Bedroom
10 Exceptional (5)This condo is located in Palmer Ranch, a neighborhood in Sarasota. Shoppers can check out St. Armands Circle, while everyone can enjoy the natural beauty of Siesta Key Beach and Crescent Beach. Consider ...Check Availability -
Osprey - United States
Beautiful Stoneybrook Golf Course Condo! Veranda Greens - Overlooks 16th green
- 5 Guests 2Bedrooms
10 Exceptional (2)This condo is located in Palmer Ranch, a neighborhood in Sarasota. While the natural beauty of Siesta Key Beach and Nokomis Beach can be enjoyed by anyone, those looking for an activity can check out Marina ...Check Availability -
Osprey - United States
Siesta Key Charming Condo that Offers So Much and is So Affordable
- 4 Guests 1Bedroom
10 Exceptional (2)Located in Siesta Key, this condo is on the waterfront. While the natural beauty of Siesta Key Beach and Turtle Beach can be enjoyed by anyone, those looking for an activity can check out Marina Jack. ...Check Availability -
Osprey - United States
Siesta Key Condo, 2 Pools, Pvt. Beach, Boat Dock
- 3 Guests 0Bedroom
10 Exceptional (2)Located in Siesta Key, this condo is near the beach. While the natural beauty of Siesta Key Beach and Turtle Beach can be enjoyed by anyone, those looking for an activity can check out Marina Jack.
Traveling ...Check Availability -
Osprey - United States
Bayfront resort Condo, walk to Turtle Beach
- 4 Guests 1Bedroom
10 Exceptional (2)Located in Siesta Key, this condo is near theme parks and on the waterfront. Shoppers can check out St. Armands Circle, while everyone can enjoy the natural beauty of Siesta Key Beach and Lido Beach. Traveling ...Check Availability -
Osprey - United States
Siesta Key Beach Sunsets Awaits You
- 6 Guests 2Bedrooms
10 Exceptional (7)This condo is located in Palmer Ranch, a neighborhood in Sarasota, and is next to a golf course and near the beach. Shoppers can check out St. Armands Circle, while everyone can enjoy the natural beauty ...Check Availability -
Osprey - United States
Sarasota Condo on the Bay with 2 month MINIMUM rentals
- 6 Guests 2Bedrooms
10 Exceptional (1)Located on the waterfront, this condo is in Vamo, a neighborhood in Sarasota. Shoppers can check out St. Armands Circle, while everyone can enjoy the natural beauty of Siesta Key Beach and Venice Beach. ...Check Availability -
Osprey - United States
Gulf Front Millionarie's Retreat with Boat Dock & WiFi
- 6 Guests 2Bedrooms
9.8 Exceptional (16)Located in Siesta Key, this condo is on the beach. While the natural beauty of Siesta Key Beach and Turtle Beach can be enjoyed by anyone, those looking for an activity can check out Marina Jack.
Coconuts ...Check Availability -
Osprey - United States
Stoneybrook Golf & Country Club - Wonderful Golf & Lake Views in the Terraces!
- 6 Guests 2Bedrooms
9.8 Exceptional (9)This condo is located in Palmer Ranch, a neighborhood in Sarasota, and is next to a golf course. While the natural beauty of Siesta Key Beach and Nokomis Beach can be enjoyed by anyone, those looking for ...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 4 Bed & Breakfasts in Osprey
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Osprey - United States
Sarasota Villa w/ Pool Access ~ 4 Mi to Beach!
- 3 Guests 1Bedroom
10 Exceptional (17)With a stay at this villa in Sarasota, you'll be within a 10-minute drive of Siesta Key Beach and Sarasota Square. This villa is 12.3 mi (19.7 km) from Lido Beach and 6 mi (9.6 km) from Nokomis Beach. ...Check Availability -
Osprey - United States
Private guesthouse near the beach
- 4 Guests 2Bedrooms
9.2 Exceptional (12)Located near the beach, this guesthouse is in Vamo, a neighborhood in Sarasota with good shopping. Shoppers can check out St. Armands Circle, while everyone can enjoy the natural beauty of Siesta Key Beach ...Check Availability -
Osprey - United States
Guest House Next to Marina, Private Beach Access, Onsite Kayaks, Golf Cart
- 4 Guests 1Bedroom
7.2 Very Good (35)Located in Nokomis, this guesthouse is on the waterfront. Venice Theater and Nontando are cultural highlights, and some of the area's attractions include Jim Neville Marine Preserve and Nancy's Consignments. ...Check Availability -
Osprey - United States
Remodeled Waterfront Cottage
- 6 Guests 2Bedrooms
Remodeled Waterfront Cottage is located in Osprey. Shoppers can check out St. Armands Circle, while everyone can enjoy the natural beauty of Siesta Key Beach and Venice Beach. Nancy's Consignments and ...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 -
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Hotels in Osprey
Hotels in Osprey, our top selection just for you
Are you looking for hotels in Osprey? Here is a selection of the best hotels in Osprey
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Osprey - United States
Turtle Beach Resort and Inn
- Hotel
8.4 Fabulous (477)Located in Siesta Key, Turtle Beach Resort and Inn is by the ocean, a 1-minute drive from Turtle Beach and 6 minutes from Siesta Key Marina. This hotel is 3.7 mi (5.9 km) from Siesta Key Beach and 9 mi ...Check Availability -
Osprey - United States
Siesta Key Bungalows
- Hotel
8.6 Fabulous (245)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 ... -
Osprey - United States
Turtle Beach Resort
- Hotel
8.5 Fabulous (80)The 4-star Turtle Beach Resort offers comfort and convenience whether you're on business or holiday in Siesta Key (FL). The property features a wide range of facilities to make your stay a pleasant experience. ...Check Availability -
Osprey - United States
Casey Key Resorts - Mainland
- Hotel
5 Pleasant (3050)Situated in Osprey, 27 km from The John and Mable Ringling Museum of Art, Casey Key Resorts - Mainland features accommodation with an outdoor swimming pool, free private parking, a restaurant and a bar. ... -
Osprey - United States
Timberwoods Retreat
- Hotel
Timberwoods Retreat is situated in Sarasota, within 15 km of Marina Jack Restaurant and Marina and 16 km of Sarasota County Visitor Information Center and History Museum. ...Check Availability -
Osprey - United States
Island Reef A101
- Hotel
Located within 500 metres of Turtle Beach and 21 km of John and Mable Ringling Museum of Art, Island Reef A101 features rooms in Sarasota. ...Check Availability -
Osprey - United States
Turtle Bay Beauty
- Hotel
Located in Sarasota, 1.1 km from Turtle Beach, Turtle Bay Beauty features views of the pool. The property is situated 22 km from The John and Mable Ringling Museum of Art, 16 km from Sarasota Opera and ...Check Availability -
Osprey - United States
Siesta Key Bungalow - 3BR Pool-Side
- Hotel
10 Exceptional (1)Situated in Sarasota, within 2.3 km of Crescent Beach and 20 km of John and Mable Ringling Museum of Art, Siesta Key Bungalow - 3BR Pool-Side features accommodation with a restaurant and a garden, and ...Check Availability -
Osprey - United States
Siesta Key Bungalow - Inn
- Hotel
Located in Sarasota, within 2.3 km of Crescent Beach and 20 km of John and Mable Ringling Museum of Art, Siesta Key Bungalow - Inn provides accommodation with a restaurant and a garden, and free WiFi throughout ...Check Availability -
Osprey - United States
Siesta Key Bungalow - 3BR Lagoon-Front
- Hotel
Located in Sarasota, within 2.3 km of Crescent Beach and 20 km of John and Mable Ringling Museum of Art, Siesta Key Bungalow - 3BR Lagoon-Front provides accommodation with a restaurant and a garden, and ...Check Availability -
Osprey - United States
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Osprey - United States
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Osprey - United States
The best hotels with swimming pool in Osprey
Book your relaxing holiday, by choosing the best deals at hotels with swimming pools in Osprey
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Osprey - United States
Turtle Beach Resort and Inn
- Hotel
8.4 Fabulous (477)Located in Siesta Key, Turtle Beach Resort and Inn is by the ocean, a 1-minute drive from Turtle Beach and 6 minutes from Siesta Key Marina. This hotel is 3.7 mi (5.9 km) from Siesta Key Beach and 9 mi ...Check Availability -
Osprey - United States
Siesta Key Bungalows
- Hotel
8.6 Fabulous (245)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 ... -
Osprey - United States
Turtle Beach Resort
- Hotel
8.5 Fabulous (80)The 4-star Turtle Beach Resort offers comfort and convenience whether you're on business or holiday in Siesta Key (FL). The property features a wide range of facilities to make your stay a pleasant experience. ...Check Availability -
Osprey - United States
Casey Key Resorts - Mainland
- Hotel
5 Pleasant (3050)Situated in Osprey, 27 km from The John and Mable Ringling Museum of Art, Casey Key Resorts - Mainland features accommodation with an outdoor swimming pool, free private parking, a restaurant and a bar. ... -
Osprey - United States
Timberwoods Retreat
- Hotel
Timberwoods Retreat is situated in Sarasota, within 15 km of Marina Jack Restaurant and Marina and 16 km of Sarasota County Visitor Information Center and History Museum. ...Check Availability -
Osprey - United States
Island Reef A101
- Hotel
Located within 500 metres of Turtle Beach and 21 km of John and Mable Ringling Museum of Art, Island Reef A101 features rooms in Sarasota. ...Check Availability -
Osprey - United States
Turtle Bay Beauty
- Hotel
Located in Sarasota, 1.1 km from Turtle Beach, Turtle Bay Beauty features views of the pool. The property is situated 22 km from The John and Mable Ringling Museum of Art, 16 km from Sarasota Opera and ...Check Availability -
Osprey - United States
Siesta Key Bungalow - 3BR Pool-Side
- Hotel
10 Exceptional (1)Situated in Sarasota, within 2.3 km of Crescent Beach and 20 km of John and Mable Ringling Museum of Art, Siesta Key Bungalow - 3BR Pool-Side features accommodation with a restaurant and a garden, and ...Check Availability -
Osprey - United States
Siesta Key Bungalow - Inn
- Hotel
Located in Sarasota, within 2.3 km of Crescent Beach and 20 km of John and Mable Ringling Museum of Art, Siesta Key Bungalow - Inn provides accommodation with a restaurant and a garden, and free WiFi throughout ...Check Availability -
Osprey - United States
Siesta Key Bungalow - 3BR Lagoon-Front
- Hotel
Located in Sarasota, within 2.3 km of Crescent Beach and 20 km of John and Mable Ringling Museum of Art, Siesta Key Bungalow - 3BR Lagoon-Front provides accommodation with a restaurant and a garden, and ...Check Availability -
Osprey - United States
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Osprey - United States
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Osprey - United States
Verified owners in Osprey
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Osprey - United States
Private Beach Access - Siesta Key 2 BD/2Bath Condo
- 3 Guests 2Bedrooms
Warm natural light fills this home making it the vacation oasis you have always dreamed about! With 2 bedrooms and 2 bathrooms, everyone has plenty of space to call their own on your tropical vacation. ...
