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.

The Best 4 Star Hotels in Osprey, FL from $96

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

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Our top choices for Osprey 4-star hotels

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

1. The Westin Sarasota

Central Sarasota

Mariuxi

$231 nightly

Nov 22 - Nov 23

Total with taxes and fees

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

2. DoubleTree by Hilton Sarasota Bradenton Airport

Sarasota

Jose Luis

$118 nightly

Nov 1 - Nov 2

Total with taxes and fees

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

3. Art Ovation Hotel, Autograph Collection

Central Sarasota

Arta

$195 nightly

Nov 22 - Nov 23

Total with taxes and fees

A pool area with lounge chairs and umbrellas, a palm tree, and a view of the ocean.

4. Lido Beach Resort

Lido Key

Debra

$393 nightly

Nov 1 - Nov 2

Total with taxes and fees

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

5. Legacy Hotel at IMG Academy

Bradenton

Chad

$187 nightly

Nov 3 - Nov 4

Total with taxes and fees

A spacious restaurant with wooden ceilings and large windows offering a view of the ocean. Tables are set with white chairs and dining ware.

6. Zota Beach Resort

Longboat Key

Thomas

$259 nightly

Oct 28 - Oct 29

Total with taxes and fees

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

7. Casey Key Resorts - Mainland

Osprey

Vito

$85 nightly

Oct 28 - Oct 29

Total with taxes and fees

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

8. Cirque St. Armands Beachside

Lido Key

Christopher

$284 nightly

Oct 28 - Oct 29

Total with taxes and fees

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

9. The Sarasota Modern, a Tribute Portfolio Hotel

Central Sarasota

Heather

$204 nightly

Nov 22 - Nov 23

Total with taxes and fees

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.

10. SeaSpray Resort

Siesta Key

Geraldine

$204 nightly

Nov 2 - Nov 3

Total with taxes and fees

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

11. The Resort at Longboat Key Club

Longboat Key

Carlos

$499 nightly

Oct 28 - Oct 29

Total with taxes and fees

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

12. Chadwick Cove Resort & Marina

Manasota Key

Niovys

$573 nightly

Oct 30 - Oct 31

Total with taxes and fees

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

13. Bradenton Apartments by Landing

Bradenton

Brett

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

14. Casa Mar By Beachside Management

Siesta Key

Dianne

A hotel room with two beds, a balcony with a view, and a TV on a cabinet.

15. Anchorage Resort

South Village

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

16. Beach Club at Siesta Key Poolside D

South Village

Jeff

17. Coastal Surfside by Beachside Management

Siesta Key Village

"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...

Lorie

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

18. Ocean Vue By Beachside Management

Siesta Key

Malisa

19. Private Beach Retreat on Siesta Key! Bright Villa

Siesta Key

"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...

Rod

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

Siesta Key Village

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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

1111 Ritz Carlton Dr Sarasota FL

$687 nightly

$776 total

Oct 28 - Oct 29

Total with taxes and fees

9.2/10 Wonderful! (1,019 reviews)

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Pool Spa Hot tub Breakfast included Waterpark

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.

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A nest on a wooden platform by a lake at sunset with birds flying around.

Top Osprey Hotel Reviews

Lido Beach Resort

10/10 Excellent

"Awesome place to stay and beach is fabulous"

Casey Key Resorts - Mainland

10/10 Excellent

"I received excellent customer service at Casey Key Resorts. They truly care about their guests. When I checked in, I was greeted by Nan. She was very accommodating to my room request. The next day, I had another request and spoke with Nicole at the front desk. She provided me with exceptional customer service to ensure that I had a very comfortable and peaceful staycation. Thank you!😊💜"

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 $776

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.

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Things to do in Siesta Key

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Check availability on Osprey 4 Star Hotels

Our top choices for Osprey 4-star hotels

1. The Westin Sarasota

2. DoubleTree by Hilton Sarasota Bradenton Airport

3. Art Ovation Hotel, Autograph Collection

4. Lido Beach Resort

5. Legacy Hotel at IMG Academy

6. Zota Beach Resort

7. Casey Key Resorts - Mainland

8. Cirque St. Armands Beachside

9. The Sarasota Modern, a Tribute Portfolio Hotel

10. SeaSpray Resort

11. The Resort at Longboat Key Club

12. Chadwick Cove Resort & Marina

13. Bradenton Apartments by Landing

14. Casa Mar By Beachside Management

15. Anchorage Resort

16. Beach Club at Siesta Key Poolside D

17. Coastal Surfside by Beachside Management

18. Ocean Vue By Beachside Management

19. Private Beach Retreat on Siesta Key! Bright Villa

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

Explore similar 5-star hotels

The Ritz-Carlton, Sarasota

The St. Regis Longboat Key Resort

Learn more about Osprey

Top Osprey Hotel Reviews

Lido Beach Resort

Casey Key Resorts - Mainland

DoubleTree by Hilton Sarasota Bradenton Airport

Cirque St. Armands Beachside

The Westin Sarasota

Find out more about Osprey

Osprey Four Star Hotel Information

Frequently asked questions

Explore a world of travel with Expedia

Find 4 Star Hotels in Osprey, FL from $96

Upfront pricing

Treat yourself

Be picky

Check availability on Osprey 4 Star Hotels

Our top choices for Osprey 4-star hotels

1. The Westin Sarasota

2. DoubleTree by Hilton Sarasota Bradenton Airport

3. Art Ovation Hotel, Autograph Collection

4. Lido Beach Resort

5. Legacy Hotel at IMG Academy

6. Zota Beach Resort

7. Casey Key Resorts - Mainland

8. Cirque St. Armands Beachside

9. The Sarasota Modern, a Tribute Portfolio Hotel

10. SeaSpray Resort

11. The Resort at Longboat Key Club

12. Chadwick Cove Resort & Marina

13. Bradenton Apartments by Landing

14. Casa Mar By Beachside Management

15. Anchorage Resort

16. Beach Club at Siesta Key Poolside D

17. Coastal Surfside by Beachside Management

18. Ocean Vue By Beachside Management

19. Private Beach Retreat on Siesta Key! Bright Villa

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

Explore similar 5-star hotels

The Ritz-Carlton, Sarasota

Learn more about Osprey

Top Osprey Hotel Reviews

Lido Beach Resort

Find out more about Osprey

Osprey Four Star Hotel Information

Frequently asked questions

Explore a world of travel with Expedia