A marina with docked boats, a wooden bridge, and a building with a red roof.

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Check availability on Osprey 4 Star Hotels

Tonight
24 Sep - 25 Sep
Tomorrow
25 Sep - 26 Sep
This weekend
25 Sep - 27 Sep
Next weekend
2 Oct - 4 Oct

Our top choices for Osprey 4-star hotels

A rooftop terrace with a fire feature, seating area, and a view of the city skyline.
A modern lobby with a vertical garden, comfortable seating, and a geometric light fixture.
A modern lobby with a vertical garden, seating area, and a bar.
A modern restaurant with high ceilings, large windows, and a mix of seating arrangements including tables and booths.

1. The Westin Sarasota

The Westin Sarasota
Central Sarasota
United States
THANG
3.734.900 ₫
4.866.797 ₫ total
includes taxes & fees
27 Sept - 28 Sept
The Westin Sarasota
A circular fire pit surrounded by a wooden pergola with cushioned seating and colorful pillows.
A multi-level atrium with a central seating area, glass railings, and a large black door.
A multi-level atrium with glass railings and a central skylight.
A spacious lobby with multiple seating areas, a large window with colorful panels, and a modern interior design.

2. DoubleTree by Hilton Sarasota Bradenton Airport

DoubleTree by Hilton Sarasota Bradenton Airport
Sarasota
United States
Da thao
2.750.280 ₫
3.107.816 ₫ total
includes taxes & fees
27 Sept - 28 Sept
DoubleTree by Hilton Sarasota Bradenton Airport
A pool area with lounge chairs and umbrellas, a palm tree, and a view of the ocean.
A coastal hotel with multiple buildings, a beach with sun loungers, and clear blue waters.
A bar area with wooden furniture and hanging lights, overlooking a pool and beach area.
A modern restaurant with a long counter, multiple dining tables, and large windows offering a view of the sea.

3. Lido Beach Resort

Lido Beach Resort
Lido Key
United States
Faris
8.242.000 ₫
10.488.660 ₫ total
includes taxes & fees
12 Oct - 13 Oct
Lido Beach Resort
A rooftop bar with outdoor seating, a pool, and a view of the sea.
A modern lounge area with contemporary furniture, a large abstract painting, and a view of the kitchen and dining area.
A long dining table set with multiple candles, vases, and floral arrangements.
A hotel with a rooftop pool area, outdoor seating, and a view of the surrounding cityscape.

4. Art Ovation Hotel, Autograph Collection

Art Ovation Hotel, Autograph Collection
Central Sarasota
United States
Arta
4.344.505 ₫
5.732.406 ₫ total
includes taxes & fees
18 Oct - 19 Oct
Art Ovation Hotel, Autograph Collection
A spacious restaurant with wooden ceilings and large windows offering a view of the ocean. Tables are set with white chairs and dining ware.
A spacious lobby with a modern sofa set, a round coffee table, and a small seating area with stools.
A pool area with lounge chairs and umbrellas, surrounded by palm trees and a building with balconies.
A hotel room with a large bed, a desk with a TV, a balcony with a view of the ocean, and a seating area with a table and chairs.

5. Zota Beach Resort

Zota Beach Resort
Longboat Key
United States
Alejandra
5.434.000 ₫
7.315.620 ₫ total
includes taxes & fees
27 Sept - 28 Sept
Zota Beach Resort
A modern hotel with a swimming pool, sun loungers, and palm trees.
A hotel lobby with a reception desk, a staircase, and a glass railing.
A spacious lobby with a modern design, featuring a sofa, armchairs, and a coffee table. A staircase is visible in the background leading to an upper level.
A modern hotel with a glass facade, a prominent entrance, and a landscaped area with palm trees.

6. Legacy Hotel at IMG Academy

Legacy Hotel at IMG Academy
Bradenton
United States
Daniel
3.524.560 ₫
4.864.080 ₫ total
includes taxes & fees
29 Sept - 30 Sept
Legacy Hotel at IMG Academy
A modern hotel room with a large bed, a desk, and a view of the ocean.
A swimming pool with lounge chairs and umbrellas, surrounded by palm trees and a clear blue sky.
A restaurant with round tables and chairs, large windows, and a view of palm trees.
A hotel room with two beds, a large mirror, a TV, and a balcony with curtains.

7. Cirque St. Armands Beachside

Cirque St. Armands Beachside
Lido Key
United States
Hope
6.734.000 ₫
8.637.720 ₫ total
includes taxes & fees
27 Sept - 28 Sept
Cirque St. Armands Beachside
A pathway flanked by palm trees and a building with a covered patio area.
A modern bedroom with two beds, a desk, a chair, a TV, and a balcony with a view of greenery.
A modern reception area with a wooden reception desk, a flat-screen TV, and a sign for Casey Key Resorts Mainland.
A modern restaurant with multiple dining tables and chairs, a kitchen area, and large windows offering views of greenery.

8. Casey Key Resorts - Mainland

Casey Key Resorts - Mainland
Osprey
United States
Dylan James
2.208.960 ₫
2.795.659 ₫ total
includes taxes & fees
5 Oct - 6 Oct
Casey Key Resorts - Mainland
An outdoor patio area with multiple seating arrangements, including sofas and chairs, and ceiling fans.
A pool area with lounge chairs, a bar, and a building with a modern design.
A bar area with a circular bar, multiple seating options, and a modern ceiling design.
A modern lobby with a high ceiling, concrete pillars, and a mix of indoor and outdoor greenery.

9. The Sarasota Modern, a Tribute Portfolio Hotel

The Sarasota Modern, a Tribute Portfolio Hotel
Central Sarasota
United States
Darcy
3.734.900 ₫
4.948.437 ₫ total
includes taxes & fees
30 Sept - 1 Oct
The Sarasota Modern, a Tribute Portfolio Hotel
A modern living room with a flat-screen TV on a wooden cabinet, a grey sofa with patterned cushions, and a large window with sheer curtains.
A modern kitchen with white cabinetry, a black countertop, and a framed sign on the wall.
A narrow concrete pathway flanked by white walls, leading to a lush green area with palm trees and a small grassy patch.
A modern living room with a flat-screen TV, a round coffee table, and a sofa.

10. SeaSpray Resort

SeaSpray Resort
Siesta Key
United States
Michelle Suzanne
5.826.600 ₫
6.584.058 ₫ total
includes taxes & fees
27 Sept - 28 Sept
SeaSpray Resort
A coastal resort with beachfront properties, a sandy beach, and a marina.
A poolside area with lounge chairs and umbrellas, palm trees, and a view of the beach.
A modern outdoor bar area with a pool, lounge chairs, and a view of the ocean at sunset.
A dining area with tables set for service, large windows offering views of palm trees and the beach, and a ceiling with wooden beams and recessed lighting.

11. The Resort at Longboat Key Club

The Resort at Longboat Key Club
Longboat Key
United States
Sergio
11.414.000 ₫
14.366.820 ₫ total
includes taxes & fees
27 Sept - 28 Sept
The Resort at Longboat Key Club
An aerial view of a coastal town with beachfront properties, a marina, and clear blue waters.
A covered outdoor deck with a table and chairs, overlooking a body of water and palm trees.
A modern kitchen with white cabinetry, a built-in dishwasher, and a coffee maker.
A marina with multiple boats docked, surrounded by residential buildings and palm trees.

12. Chadwick Cove Resort & Marina

Chadwick Cove Resort & Marina
Manasota Key
United States
Niovys
4.179.240 ₫
16.380.750 ₫ total
includes taxes & fees
27 Sept - 28 Sept
Chadwick Cove Resort & Marina
An aerial view of a residential area with a large body of water, a swimming pool, and several buildings with sloped roofs.
A living room with a grey sofa, a glass coffee table, a lamp, and a painting on the wall.
A poolside area with lounge chairs and a pool.
An outdoor bar area with a grill, seating, and tropical plants.

13. Bradenton Apartments by Landing

Bradenton Apartments by Landing
Bradenton
United States
Brett
Bradenton Apartments by Landing
An aerial view of a coastal area with a curved white sandy beach, a dense cluster of buildings, and a clear blue sea.
A spacious living room with a large L-shaped sofa, a coffee table, and a dining area with a pool table in the background.
A modern kitchen with white cabinetry, a stainless steel refrigerator, and a black countertop.
A spacious living room with a large window, a sofa, a dining table with chairs, and a television.

14. Anchorage Resort

Anchorage Resort
South Village
Anchorage Resort
An aerial view of a beach with white sand, clear blue water, and a few buildings in the foreground.
A compact living space with a dining area, a sofa, a kitchen, and a bedroom.

15. Gulf Holiday by Beachside Management

Gulf Holiday by Beachside Management
Siesta Key Village
United States
Amy A
Gulf Holiday by Beachside Management
An aerial view of a coastal city with a long sandy beach, numerous hotels, and clear blue waters.
A waterfront hotel with a marina, palm trees, and high-rise buildings in the background.
A modern building with a flat roof, large windows, and a covered outdoor area with seating.
A pool area with lounge chairs, a staircase, and a building with balconies.

16. Beach Club at Siesta Key Poolside D

Beach Club at Siesta Key Poolside D
South Village
United States
Jeff
Beach Club at Siesta Key Poolside D

17. Coastal Surfside by Beachside Management

Coastal Surfside by Beachside Management
Siesta Key Village
United States
Lorie
Coastal Surfside by Beachside Management
A spacious bedroom with a large bed, a ceiling fan, and a view of the outside balcony.
A spacious living room with a large window, a sofa set, a coffee table, and a white cabinet.

18. Ocean Vue By Beachside Management

Ocean Vue By Beachside Management
Siesta Key
United States
Malisa
Ocean Vue By Beachside Management
An aerial view of a coastal city with a long sandy beach, numerous hotels, and clear blue waters.
A waterfront hotel with a marina, palm trees, and high-rise buildings in the background.
A modern living room with a sofa, chairs, a dining area with a table and chairs, a TV, and a ceiling fan.
A hotel with a tennis court, pool, and beach view.

19. House of The Sun Siesta Key Crescent Beach

House of The Sun Siesta Key Crescent Beach
South Village
United States
Margaret Theresa
House of The Sun Siesta Key Crescent Beach
A modern living room with a sofa, ottoman, and wooden chairs. There is a glass door leading to a balcony.

20. Private Beach Retreat on Siesta Key! Bright Villa

Private Beach Retreat on Siesta Key! Bright Villa
Siesta Key
United States
Rod
Private Beach Retreat on Siesta Key! Bright Villa
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Explore similar 5-star hotels

Many 5-star hotels have the same amenities as 4-star hotels. See all 5-star hotels in Osprey.
The Ritz-Carlton, Sarasota

The Ritz-Carlton, Sarasota

1111 Ritz Carlton Dr Sarasota FL
13.900.900 ₫
17.398.016 ₫ total
25 Oct - 26 Oct
includes taxes & fees
9.2/10 Wonderful! (1,023 reviews)
The Ritz-Carlton, Sarasota
The St. Regis Longboat Key Resort

The St. Regis Longboat Key Resort

1601 Gulf Of Mexico Drive Longboat Key FL
19.474.000 ₫
23.915.319 ₫ total
27 Sept - 28 Sept
includes taxes & fees
9.8/10 Exceptional! (96 reviews)
The St. Regis Longboat Key Resort
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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.

Learn more about Osprey

Paddle through Oscar Scherer State Park's serene waterways where you might spot eagles, turtles, and alligators along the way. Nearby Sarasota's white-sand beaches and Myakka River State Park offer perfect day trips from this peaceful Gulf Coast community.

See all hotels in Osprey
A nest on a wooden platform by a lake at sunset with birds flying around.

Top Osprey Hotel Reviews

Casey Key Resorts - Mainland

Casey Key Resorts - Mainland

8/10 Good
"Very nice hotel. Friendly and helpful staff. Pool area is nice."
Vincent 2-night trip
Posted 1 day ago
Casey Key Resorts - Mainland
DoubleTree by Hilton Sarasota Bradenton Airport

DoubleTree by Hilton Sarasota Bradenton Airport

10/10 Excellent
"Perfect location for our travel baseball team for the weekend. Close enough to the multiple locations we played at and near many different food options. The staff was nice and inviting. Breakfast was good and the hotel itself was well maintained."
Carrie 1-night trip
Posted 2 days ago
DoubleTree by Hilton Sarasota Bradenton Airport

Frequently asked questions

What are the best 4-star hotels in Osprey?
Kick back in upmarket comfort at Hyatt Siesta Key Beach. According to reviews by our guests, this is one of Osprey's best 4-star hotels.
How much does it cost to stay in a 4-star hotel in Osprey?
To find a 4-star hotel in Osprey that fits your budget, use Expedia's sort and search filters. Browse what's available during your travel dates and use our pricing filter to set your limit. You can also list your results by the most affordable stay first.
  • Search for the lowest price from 17.398.016 ₫
What's the difference between 5-star and 4-star hotels in Osprey?
Offering a friendly guest experience and upscale surroundings, 4-star hotels are a wonderful option for your Osprey trip. These types of stays generally come with loads of useful amenities that make it simple to kick back and relax — think 24-hour room service, gyms and restaurants. Or get a taste of the high life at a 5-star hotel designed to spoil you with luxury perks and amenities. Full-service health clubs, oversized bathrooms and fine dining are typically featured at these plush properties.

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