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Find 4 Star Hotels in Osprey, FL from $103

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Check prices for these dates, December 14 – 15, 2026

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Our top choices for Osprey 4-star hotels

1. The Westin Sarasota

A rooftop terrace with a fire feature, seating area, and a view of the city skyline.

Location: Central Sarasota
Guest rating: 9.2/10 (Wonderful, 1207 reviews)
Price: $231 nightly, $261 total, Nov 22 - Nov 23, Total with taxes and fees, for Our top choices for Osprey 4-star hotels
Review: Great place, by Mariuxi

2. DoubleTree by Hilton Sarasota Bradenton Airport

A circular fire pit surrounded by a covered seating area with a view of palm trees.

Location: Sarasota
Guest rating: 8.8/10 (Excellent, 1833 reviews)
Price: $118 nightly, $134 total, Nov 29 - Nov 30, Total with taxes and fees, for Our top choices for Osprey 4-star hotels
Review: Wonderful place to stay, by Beatriz

3. Art Ovation Hotel, Autograph Collection

A rooftop bar with outdoor seating, a pool, and a view of the sea.

Location: Central Sarasota
Guest rating: 9.4/10 (Exceptional, 1002 reviews)
Price: $179 nightly, $202 total, Nov 29 - Nov 30, Total with taxes and fees, for Our top choices for Osprey 4-star hotels
Review: Top notch hotel, by Robert

4. Lido Beach Resort

A resort with a pool, beach, and ocean view.

Location: Lido Key
Guest rating: 9.2/10 (Wonderful, 1001 reviews)
Price: $369 nightly, $417 total, Nov 30 - Dec 1, Total with taxes and fees, for Our top choices for Osprey 4-star hotels
Review: Awesome place to stay and beach is fabulous, by Bryan

5. Legacy Hotel at IMG Academy

A modern hotel with a swimming pool, sun loungers, and palm trees.

Location: Bradenton
Guest rating: 9/10 (Wonderful, 1000 reviews)
Price: $189 nightly, $214 total, Nov 16 - Nov 17, Total with taxes and fees, for Our top choices for Osprey 4-star hotels
Review: Great place to stay great staff, by Chad

6. Zota Beach Resort

A pool area with lounge chairs and umbrellas, surrounded by palm trees and a building with balconies.

Location: Longboat Key
Guest rating: 9.2/10 (Wonderful, 1002 reviews)
Price: $249 nightly, $281 total, Nov 15 - Nov 16, Total with taxes and fees, for Our top choices for Osprey 4-star hotels
Review: Loved the beach, by Sven

7. Casey Key Resorts - Mainland

A pathway flanked by palm trees and a building with a covered patio area.

Location: Osprey
Guest rating: 8.6/10 (Excellent, 1255 reviews)
Price: $92 nightly, $104 total, Dec 14 - Dec 15, Total with taxes and fees, for Our top choices for Osprey 4-star hotels
Review: loved out stay in that hotel, by Ivy

8. Cirque St. Armands Beachside

A modern hotel room with a large bed, a desk, and a view of the ocean.

Location: Lido Key
Guest rating: 9/10 (Wonderful, 1004 reviews)
Price: $284 nightly, $321 total, Nov 15 - Nov 16, Total with taxes and fees, for Our top choices for Osprey 4-star hotels
Review: Great stay, by Christopher

9. The Sarasota Modern, a Tribute Portfolio Hotel

An outdoor patio area with multiple seating arrangements, including sofas and chairs, and ceiling fans.

Location: Central Sarasota
Guest rating: 8.2/10 (Very good, 590 reviews)
Price: $184 nightly, $208 total, Nov 22 - Nov 23, Total with taxes and fees, for Our top choices for Osprey 4-star hotels
Review: It was a fun place to be without having to venture from the property, by Heather

10. SeaSpray Resort

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.

Location: Siesta Key
Guest rating: 9.6/10 (Exceptional, 209 reviews)
Price: $292 nightly, $330 total, Nov 16 - Nov 17, Total with taxes and fees, for Our top choices for Osprey 4-star hotels
Review: The room was clean and had all of the necessities. The place was adorable and the location is great!, by Dolores

11. The Resort at Longboat Key Club

A coastal resort with beachfront properties, a sandy beach, and a marina.

Location: Longboat Key
Guest rating: 9/10 (Wonderful, 777 reviews)
Price: $529 nightly, $598 total, Nov 17 - Nov 18, Total with taxes and fees, for Our top choices for Osprey 4-star hotels
Review: Great hotel, by Carlos

12. Chadwick Cove Resort & Marina

An aerial view of a coastal town with beachfront properties, a marina, and clear blue waters.

Location: Manasota Key
Guest rating: 8.8/10 (Excellent, 31 reviews)
Price: $579 nightly, $624 total, Nov 17 - Nov 18, Total with taxes and fees, for Our top choices for Osprey 4-star hotels
Review: Without a doubt, the best place—very spacious and in an excellent location. You have the beach right out front, and Gasparilla Beach—which is very beautiful—is just 25 minutes away. Communication with the owner was excellent, the sunsets were fantastic, and the terrace overlooking the bay—with the breeze blowing—was a delight. We will definitely be back!, by Niovys

13. Bradenton Apartments by Landing

An aerial view of a residential area with a large body of water, a swimming pool, and several buildings with sloped roofs.

Location: Bradenton
Guest rating: 7.4/10 (Good, 64 reviews)
Review: Gym/pool nice, by Brett

14. Casa Mar By Beachside Management

A beach with clear skies, palm trees, and a pathway leading to beach umbrellas.

Location: Siesta Key
Guest rating: 9.8/10 (Exceptional, 8 reviews)
Review: This was a great location. Easy to get everywhere you need to , by Dianne

15. Anchorage Resort

An aerial view of a coastal area with a curved white sandy beach, a dense cluster of buildings, and a clear blue sea.

Location: South Village
Guest rating: 4/10 (1 review)

16. Beach Club at Siesta Key Poolside D

An aerial view of a coastal city with a long sandy beach, numerous hotels, and clear blue waters.

Location: South Village
Guest rating: 9.6/10 (Exceptional, 4 reviews)
Review: Nice getaway. , by Jeff

17. Coastal Surfside by Beachside Management

Location: Siesta Key Village
Guest rating: 8/10 (Very good, 1 review)
Review: "It was a great place to stay. I would have liked a little more communication about how to do things, I.e beach access, parking. Ect. Booking was kinda of misleading with all the units mixed. I thought I booked in the house next to us, but was not. There were TVs in those unit bedrooms but not ours. Just Something our kids thought we had. I was offered a partial refund, before we checked in, due to an issue with the room and it took atleast 5 attempts to get that part rolling. Haven’t..., by Lorie

18. Ocean Vue By Beachside Management

A two-story house with a garage, a balcony, and a driveway.

Location: Siesta Key
Guest rating: 10/10 (Exceptional, 3 reviews)
Review: It was a beautiful home and clean and very close to the beach!, by Malisa

19. Private Beach Retreat on Siesta Key! Bright Villa

Location: Siesta Key
Guest rating: 10/10 (Exceptional, 1 review)
Review: "Wonderful stay indeed! We chose to stay here because of the close proximity to the beach & it was very well appointed! Our family enjoyed the quiet, clean, comfortable and beautifully decorated condo. Plenty of room for our family of three to stretch out and relax. After days full of enjoying the many fun outdoor activities Siesta Key has to offer, this was the perfect temperature-controlled haven to rest up and rejuvenate for the next day. The beds were comfy and the showers were hot, just like..., by Rod

20. Lulu's Key House Leatherback 2/2 Downstairs

Location: Siesta Key Village

Top Osprey Hotel Reviews

Casey Key Resorts - Mainland

Address: 1650 South Tamiami Trail, Osprey, FL, 34229, US
Location: Osprey
Star rating: 4/5
Guest rating: 8.6/10 (1255 reviews)
Review: We like Casey Key because it has a restaurant which serves all meals, which are quite good. The location is excellent for our needs. You can sit by the pool or better yet on their private beach which you can drive to(if parking is available) or ride a shuttle bus. The price was very reasonable. The staff including wait staff are pleasant and friendly. I highly recommend Casey Key., by Marilyn, February 1, 2025, rated 10/10 Excellent

Art Ovation Hotel, Autograph Collection

Address: 1255 North Palm Avenue, Sarasota, FL, 34234, US
Location: Central Sarasota
Star rating: 4/5
Guest rating: 9.4/10 (1002 reviews)
Review: Wonderful stay for so many reasons. The comfortable spacious rooms, delicious breakfast, rooftop pool and bar combined with the helpful staff all makes this the best value in Sarasota!, by David, September 29, 2023, rated 10/10 Excellent

The Westin Sarasota

Address: 100 Marina View Drive, Sarasota, FL, 34236, US
Location: Central Sarasota
Star rating: 4/5
Guest rating: 9.2/10 (1207 reviews)
Review: Great hotel, by Estefanny, June 12, 2025, rated 10/10 Excellent

SeaSpray Resort

Address: 574 Canal Rd, Siesta Key, FL, 34242, US
Location: Siesta Key
Star rating: 4/5
Guest rating: 9.6/10 (209 reviews)
Review: We spent three nights here. Everything is excellent, safe, quiet, and very close to the beach. Will be back next time, by Tram Anh, July 31, 2025, rated 10/10 Excellent

Cirque St. Armands Beachside

Address: 233 Ben Franklin Dr, Sarasota, FL, 34236, US
Location: Lido Key
Star rating: 4/5
Guest rating: 9/10 (1004 reviews)
Review: Perfect location, right across from the beach and walkable to Armond circle with restaurants and boutiques. The hotel has everything you need, by Irina, June 1, 2023, rated 10/10 Excellent

Zota Beach Resort

Address: 4711 Gulf of Mexico Dr, Longboat Key, FL, 34228, US
Location: Longboat Key
Star rating: 4/5
Guest rating: 9.2/10 (1002 reviews)
Review: What a beautiful beach resort!! We completely enjoyed our stay at Zota Beach Resort. The entire staff delivers great service. Our room was wonderful and the bed and pillows very comfortable. The pool is heated and we could swim no matter the temperature outside. Pool and beach service-available for drinks and food. The food was so delicious!! The staff work so hard so you can enjoy your vacation. And there are fun extras like Cornhole, a ping pong table outside, a large chess game, Connect Four..., by Donna, February 26, 2024, rated 10/10 Excellent

Legacy Hotel at IMG Academy

Address: 5450 Bollettieri Blvd., Bradenton, FL, 34210, US
Location: Bradenton
Star rating: 4/5
Guest rating: 9/10 (1000 reviews)
Review: 5 night stay for IMG camp, by Yingxu, June 12, 2024, rated 10/10 Excellent

DoubleTree by Hilton Sarasota Bradenton Airport

Address: 8009 15th Street E, Sarasota, FL, 34243, US
Location: Sarasota
Star rating: 4/5
Guest rating: 8.8/10 (1833 reviews)
Review: Everything was great and convenient, by Gladys, May 4, 2025, rated 10/10 Excellent

The Sarasota Modern, a Tribute Portfolio Hotel

Address: 1290 Boulevard of the Arts, Sarasota, FL, 34236, US
Location: Central Sarasota
Star rating: 4/5
Guest rating: 8.2/10 (590 reviews)
Review: pools are beautiful. Rooms are huge and new. We were upgraded to a suite., by Anonymous traveler, April 13, 2019, rated 10/10 Excellent

Chadwick Cove Resort & Marina

Address: 1825 Gulf Blvd, Englewood, FL, 34223, US
Location: Manasota Key
Star rating: 4/5
Guest rating: 8.8/10 (31 reviews)
Review: Without a doubt, the best place—very spacious and in an excellent location. You have the beach right out front, and Gasparilla Beach—which is very beautiful—is just 25 minutes away. Communication with the owner was excellent, the sunsets were fantastic, and the terrace overlooking the bay—with the breeze blowing—was a delight. We will definitely be back!, by Niovys, September 14, 2026, rated 10/10 Excellent

4 Mi to Siesta Key Beach: Condo w/ Pool Access

A kitchen with wooden cabinets, stainless steel appliances, a granite countertop, and a ceiling fan.

Location: Sarasota
Review: The property was clean and decorated so cute. It was easy to find and simple check in. We had a problem with the ac and they fixed it right away. The host was great and communicated very well. Highly recommended!, by Lori, July 6, 2026, rated 10/10 Excellent

Find out more about Osprey

Osprey Four Star Hotel Information

When you need to book a room with luxurious amazing amenities and the best rates, the 4 star hotels in Osprey, Florida are incredible options. Known for their extra perks, first-rate service, and fantastic locations, each of the Osprey 4 star hotels offers the ultimate experience for globe-trotting travelers. Relax in your expertly designed room. Kick back with around-the-clock room service.

Get a good night’s sleep with the ultra-plush bedding, and freshen up in the morning with designer-inspired body products. It’s all available when you stay at one of the top book a four star hotels in Osprey. What’s more, thanks to Expedia you might even score a cheap great deal on a 4 star hotel in Osprey, Florida, areas near the hottest attractions, so you can plan a sightseeing adventure and take advantage of unbeatable discounts in one fell swoop.

Whether you’re putting together a serene getaway or want to revel in the most vibrant entertainment district, 4 star Osprey hotels offer everything your heart desires.

Frequently Asked Questions

What are the best 4-star hotels in Osprey?

Unwind in refined comfort at Hyatt Siesta Key Beach. According to Expedia guest reviews, this is one of Osprey's leading 4-star hotels.

How much does it cost to stay in a 4-star hotel in Osprey?

Expedia can help you easily track down the ideal 4-star hotel for your trip to Osprey. Use our filter tool to tailor your search by things like price, amenities and hotel star rating and get access to unbeatable deals in a few clicks.

Search for the lowest price from $103

What's the difference between 5-star and 4-star hotels in Osprey?

Give yourself the luxury treatment during your Osprey vacation by staying at a 4-star hotel. As well as featuring upscale accommodations, these retreats are typically packed with amenities such as bathrobes, large beds and plenty more. A 5-star hotel will go the extra mile to make your stay an even more lavish and special one. Concierge assistance, on-site spas and gourmet dining are only the start of the superior conveniences and services you'll likely have access to.

Does Osprey have any 4-star all-inclusive resorts?

Enjoy a carefree vacation experience where everything is included in the one upfront rate by using our "All inclusive" filter. Budgeting is easy when your accommodations, food and many activities are already taken care of. After something different? Check out the offers on our standard 4-star options in and around Osprey.

Are there any 4-star casino hotels in Osprey?

To find what you're after in Osprey, simply use our convenient filter tools to narrow your search. Offering resort-style amenities and a superb level of service, our 4-star casino hotels are a safe bet for a good time.

What are the top 4-star apartments in Osprey?

Harbor Towers is a desirable 4-star choice in Osprey. With more space to relax compared to standard hotels and plenty of character, our apartments are a superb way to experience this destination like a local.