Compare and book 4 Star hotels in Osprey, Florida

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Osprey 4 Star Hotels

This weekend
29 May - 31 May
Next weekend
5 Jun - 7 Jun

Our top choices for Osprey 4-star hotels

Property amenity

The Westin Sarasota

The Westin Sarasota
4.0 star property
Central Sarasota
9.0 out of 10, Wonderful, (1,182 reviews)
"Loved the location and the roof top pool and bar!!"
United States
Bonnie Sue
The price is 5.506.105 ₫
6.876.836 ₫ total
includes taxes & fees
14 Jun - 15 Jun
The Westin Sarasota
Indoor pool

DoubleTree by Hilton Sarasota Bradenton Airport

DoubleTree by Hilton Sarasota Bradenton Airport
4.0 star property
Sarasota
8.8 out of 10, Excellent, (1,642 reviews)
"Excellent place"
United States
Ely
The price is 3.003.067 ₫
3.393.466 ₫ total
includes taxes & fees
1 Jun - 2 Jun
DoubleTree by Hilton Sarasota Bradenton Airport
2 outdoor pools, pool loungers

Lido Beach Resort

Lido Beach Resort
4.0 star property
Lido Key
8.8 out of 10, Excellent, (1,009 reviews)
"Nice, clean, great beach and pool and bar"
United States
Shailin
The price is 8.140.605 ₫
10.389.678 ₫ total
includes taxes & fees
3 Jun - 4 Jun
Lido Beach Resort
Outdoor pool, pool loungers

Legacy Hotel at IMG Academy

Legacy Hotel at IMG Academy
4.0 star property
Bradenton
9.0 out of 10, Wonderful, (1,000 reviews)
"Great hotel to stay while visiting img"
United States
Tammie
The price is 4.406.723 ₫
5.723.996 ₫ total
includes taxes & fees
31 May - 1 Jun
Legacy Hotel at IMG Academy
Room, 1 King Bed, Ocean View | Premium bedding, in-room safe, desk, laptop workspace

Cirque St. Armands Beachside

Cirque St. Armands Beachside
4.0 star property
Lido Key
8.6 out of 10, Excellent, (1,000 reviews)
"Attentive staff, good outdoor pool, clean rooms."
United States
A Gilchrist
The price is 7.086.805 ₫
9.040.814 ₫ total
includes taxes & fees
28 May - 29 May
Cirque St. Armands Beachside
Breakfast, lunch and dinner served

Zota Beach Resort

Zota Beach Resort
4.0 star property
Longboat Key
9.2 out of 10, Wonderful, (1,000 reviews)
"Nice place for a long weekend!!"
United States
Alejandro
The price is 6.559.905 ₫
8.603.487 ₫ total
includes taxes & fees
3 Jun - 4 Jun
Zota Beach Resort
Outdoor pool, open 7:00 AM to 7:00 PM, pool cabanas (surcharge)

Art Ovation Hotel, Autograph Collection

Art Ovation Hotel, Autograph Collection
4.0 star property
Central Sarasota
9.4 out of 10, Exceptional, (1,001 reviews)
"Great hotel, great location easy to walk to everything"
United States
Nick
The price is 4.188.855 ₫
5.566.963 ₫ total
includes taxes & fees
22 Jun - 23 Jun
Art Ovation Hotel, Autograph Collection
Exterior

Casey Key Resorts - Mainland

Casey Key Resorts - Mainland
4.0 star property
Osprey
8.8 out of 10, Excellent, (1,177 reviews)
"Great stay"
United States
Pamela
The price is 3.004.594 ₫
3.802.615 ₫ total
includes taxes & fees
28 May - 29 May
Casey Key Resorts - Mainland
Breakfast, lunch and dinner served

The Sarasota Modern, a Tribute Portfolio Hotel

The Sarasota Modern, a Tribute Portfolio Hotel
4.0 star property
Central Sarasota
8.2 out of 10, Very good, (552 reviews)
"Breakfast was amazing – everything was fresh and delicious. The restaurant was modern and stylish, and the overall atmosphere was very relaxing. I’ll definitely visit again."
United States
Osiris
The price is 3.336.594 ₫
4.508.011 ₫ total
includes taxes & fees
15 Jun - 16 Jun
The Sarasota Modern, a Tribute Portfolio Hotel
Exterior

The Resort at Longboat Key Club

The Resort at Longboat Key Club
4.0 star property
Longboat Key
9.0 out of 10, Wonderful, (710 reviews)
"It was the best place we have ever stayed. The views were the best."
United States
Gary
The price is 12.355.805 ₫
15.450.553 ₫ total
includes taxes & fees
28 May - 29 May
The Resort at Longboat Key Club
Deluxe Suite, 2 Bedrooms | In-room safe, iron/ironing board, free WiFi

SeaSpray Resort

SeaSpray Resort
4.0 star property
Siesta Key
9.6 out of 10, Exceptional, (131 reviews)
"Very nice room and easy access to an amazing beach."
United States
Michael
The price is 7.877.155 ₫
8.901.185 ₫ total
includes taxes & fees
1 Jun - 2 Jun
SeaSpray Resort
Exterior

Chadwick Cove Resort & Marina

Chadwick Cove Resort & Marina
4.0 star property
Manasota Key
9.6 out of 10, Exceptional, (19 reviews)
"Great place and location "
United States
Cathy
The price is 2.093.209 ₫
14.199.644 ₫ total
includes taxes & fees
28 May - 29 May
Chadwick Cove Resort & Marina
Exterior

Bradenton Apartments by Landing

Bradenton Apartments by Landing
4.5 star property
Bradenton
7.4 out of 10, Good, (59 reviews)
"Perfect place "
United States
chavelys
Bradenton Apartments by Landing
House, Multiple Beds (Vue B) | Beach | Beach nearby, white sand

Ocean Vue By Beachside Management

Ocean Vue By Beachside Management
4.0 star property
Siesta Key
10.0 out of 10, Exceptional, (3 reviews)
"It was a beautiful home and clean and very close to the beach!"
United States
Malisa
Ocean Vue By Beachside Management
Exterior

Hidden Paradise by Beachside Management

Hidden Paradise by Beachside Management
4.0 star property
South Village
10.0 out of 10, Exceptional, (4 reviews)
"Close to the beach and clean "
United States
Mike Allen
Hidden Paradise by Beachside Management
Exterior

Happy Gecko

Happy Gecko
4.0 star property
Sarasota
Happy Gecko
Condo, Multiple Beds, Lake View (C103) | Beach | Beach nearby, white sand

Our House Lake House by Beachside Mgt

Our House Lake House by Beachside Mgt
4.0 star property
Siesta Key
10.0 out of 10, Exceptional, (1 review)
Our House Lake House by Beachside Mgt
Aerial view

Anchorage Resort

Anchorage Resort
4.0 star property
South Village
Anchorage Resort
Condo, 1 King Bed with Sofa bed, Pool View (Gulf Holiday - Unit 10) | Beach | Beach nearby

Gulf Holiday by Beachside Management

Gulf Holiday by Beachside Management
4.0 star property
Siesta Key Village
7.8 out of 10, Good, (57 reviews)
"Amazing access to the beach and walkable to the village."
United States
Amy A
Gulf Holiday by Beachside Management
Beach nearby, white sand, beach umbrellas, beach towels

Beach Club at Siesta Key Poolside D

Beach Club at Siesta Key Poolside D
4.0 star property
South Village
9.4 out of 10, Exceptional, (3 reviews)
"Nice getaway. "
United States
Jeff
The price is 9.062.511 ₫
17.695.156 ₫ total
includes taxes & fees
11 Jun - 12 Jun
Beach Club at Siesta Key Poolside D
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

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 St. Regis Longboat Key Resort

The St. Regis Longboat Key Resort

1601 Gulf Of Mexico Drive Longboat Key FL
The price is 26.055.205 ₫ per night from 14 Jun to 15 Jun
26.055.205 ₫
31.377.422 ₫ total
14 Jun - 15 Jun
includes taxes & fees
9.8/10 Exceptional! (74 reviews)
Still don't see what you're looking for?
See all properties in Osprey.
You can also use these popular filters to refine your search.
PoolSpaHot tubBreakfast includedWaterpark
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
Osprey tending their nest

Top Osprey Hotel Reviews

Casey Key Resorts - Mainland

Casey Key Resorts - Mainland

10/10 Excellent
"Recently renovated room. Clean but could use some final touches."
lisa 2-night trip
Posted 10 hours ago
Casey Key Resorts - Mainland

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 19.544.565 ₫

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.