4 Stars Hotels in Osprey, Florida from CA $197

  • 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

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, (1,189 reviews)
"Clean friendly staff, great location. "
United States
Debra
The price is CA $331
CA $408 total
includes taxes & fees
May 3 - May 4
The Westin Sarasota
Breakfast, lunch, dinner served; American cuisine

DoubleTree by Hilton Sarasota Bradenton Airport

DoubleTree by Hilton Sarasota Bradenton Airport
4.0 star property
Sarasota
8.8 out of 10, Excellent, (1,590 reviews)
"We love the hotel super clean and comfortable "
United States
Juan
The price is CA $174
CA $197 total
includes taxes & fees
Apr 26 - Apr 27
DoubleTree by Hilton Sarasota Bradenton Airport
2 outdoor pools, sun loungers

Lido Beach Resort

Lido Beach Resort
4.0 star property
Lido Key
8.8 out of 10, Excellent, (1,006 reviews)
"Beautiful resort and sunsets!"
United States
Christina
The price is CA $455
CA $577 total
includes taxes & fees
Apr 26 - Apr 27
Lido Beach Resort
Outdoor pool, sun loungers

Legacy Hotel at IMG Academy

Legacy Hotel at IMG Academy
4.0 star property
Bradenton
9.0 out of 10, Wonderful, (982 reviews)
"Very nice hotel!"
United States
Bernard
The price is CA $183
CA $246 total
includes taxes & fees
May 13 - May 14
Legacy Hotel at IMG Academy
Breakfast, lunch and dinner served

Zota Beach Resort

Zota Beach Resort
4.0 star property
Longboat Key
9.0 out of 10, Wonderful, (1,002 reviews)
"Beautiful property. "
United States
Richard
The price is CA $331
CA $436 total
includes taxes & fees
May 10 - May 11
Zota Beach Resort
Exterior

Casey Key Resorts - Mainland

Casey Key Resorts - Mainland
4.0 star property
Osprey
8.8 out of 10, Excellent, (1,135 reviews)
"Clean room, great staff, quiet!"
United States
Jerel
The price is CA $158
CA $200 total
includes taxes & fees
Apr 13 - Apr 14
Casey Key Resorts - Mainland
Room, 1 King Bed, Ocean View

Cirque St. Armands Beachside

Cirque St. Armands Beachside
4.0 star property
Lido Key
8.6 out of 10, Excellent, (1,003 reviews)
"Staff were lovely Hotel was amazing Restaurant food was stunning "
United States
Sarah
The price is CA $386
CA $491 total
includes taxes & fees
May 10 - May 11
Cirque St. Armands Beachside
Outdoor pool, open 7:00 AM to 7:00 PM, cabanas (surcharge)

Art Ovation Hotel, Autograph Collection

Art Ovation Hotel, Autograph Collection
4.0 star property
Central Sarasota
9.4 out of 10, Exceptional, (1,002 reviews)
"Very nice hotel and staff"
United States
Raymond
The price is CA $253
CA $330 total
includes taxes & fees
May 3 - May 4
Art Ovation Hotel, Autograph Collection
Breakfast, lunch, dinner served; local and international cuisine

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, (539 reviews)
"Great stay!"
United States
Sara
The price is CA $211
CA $277 total
includes taxes & fees
May 10 - May 11
The Sarasota Modern, a Tribute Portfolio Hotel
Deluxe Suite, 2 Bedrooms

SeaSpray Resort

SeaSpray Resort
4.0 star property
Siesta Key
9.6 out of 10, Exceptional, (106 reviews)
"Perfect location, nice amenities for the beach, pet friendly, would stay here again! Super convenient and clean "
United States
Jayline
The price is CA $428
CA $483 total
includes taxes & fees
May 4 - May 5
SeaSpray Resort
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, (701 reviews)
"The staff is all so friendly and accommodating. We also enjoyed our suite on the beach very much. They were even so kind as to upgrade us to a better view since it was our anniversary. We will be coming back. "
United States
Barbara
The price is CA $691
CA $859 total
includes taxes & fees
May 3 - May 4
The Resort at Longboat Key Club
Exterior

Chadwick Cove Resort & Marina

Chadwick Cove Resort & Marina
4.0 star property
Manasota Key
10.0 out of 10, Exceptional, (17 reviews)
"Great place and location "
United States
Cathy
The price is CA $187
CA $555 total
includes taxes & fees
May 10 - May 11
Chadwick Cove Resort & Marina
Exterior

Bradenton Apartments by Landing

Bradenton Apartments by Landing
4.5 star property
Bradenton
7.4 out of 10, Good, (58 reviews)
"Perfect place "
United States
chavelys
Bradenton Apartments by Landing
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
House, Multiple Beds (Vue B) | Beach

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
Aerial view

Anchorage Resort

Anchorage Resort
4.0 star property
South Village
Anchorage Resort
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
Beach Club at Siesta Key Poolside D
Smart TV

Coastal Paradise Condo

Coastal Paradise Condo
4.0 star property
South Village
8.6 out of 10, Excellent, (4 reviews)
"The condo was great. Clean, neighborhood was clean and safe. Was walking distance to the beach. Less than 10 min walk from the condo to the water. Kitchen well equipped. Property has a washer and dryer in common area. But you need quarters. There were 5 of us. It was big enough for all of us to be comfortable. Near walking distance to restaurants and some shopping. Short drive to anything else you need. I would stay here again. "
United States
Sergio
Coastal Paradise Condo
On the beach, white sand, sun loungers, beach umbrellas

Casa Del Mar Longboat Key

Casa Del Mar Longboat Key
4.0 star property
Longboat Key
9.4 out of 10, Exceptional, (159 reviews)
"Great value, with easy access to beautiful beach. "
United States
Timothy
Casa Del Mar Longboat Key
Premier Condo | Private kitchen

Siesta Key

Siesta Key
4.0 star property
Siesta Key
10.0 out of 10, Exceptional, (6 reviews)
"The property was well taken care of, well stocked, and just overall lovely. We enjoyed it very much!"
United States
John
Siesta Key
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 CA $1,397 per night from Apr 26 to Apr 27
CA $1,397
CA $1,680 total
Apr 26 - Apr 27
includes taxes & fees
9.8/10 Exceptional! (69 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
Great Heron

Top Osprey Hotel Reviews

The Westin Sarasota

The Westin Sarasota

10/10 Excellent
"Everything from check in to check out was great. Food was excellent at all places. Would definitely go back."
Patricia 3-night trip
Posted 13 hours ago
The Westin Sarasota

Find out more about Osprey

If you’re looking for a spot with great rates, just-for-you amenities, and a world of luxurious little perks, the best 4 Stars hotels in Osprey are calling your name. Known for providing first-rate service in amazing locations, each of the Osprey 4 Stars hotels lets discerning travelers bask in an unforgettable experience.

Kick back in your spacious room. Relax in the lobby’s sumptuous surroundings. Start the day with delicious room service, and then use the complimentary body care items to freshen up before you head out for the day.

It’s all waiting for you at the top four star hotels in Osprey. Plus, when you book with Expedia.ca, you might find a cheap deal on a 4 Stars hotel in Osprey, Florida, neighbourhoods near the most popular attractions, so you can see the sights and bask in the discounts all in one trip. Whether you’re planning a romantic retreat or simply want to experience everything the area has to offer, the top Osprey hotels with 4 Stars provide everything you need to unwind in style.

Frequently asked questions

What are the best 4-star hotels in Osprey?
Kick back in comfortable luxury at Siesta Key Palms Resort. According to reviews by travellers, this is one of Osprey's popular 4-star hotels.
How much does it cost to stay in a 4-star hotel in Osprey?
To book a 4-star hotel in Osprey that's within your budget, make use of Expedia's filter tool. Check out what's available during your preferred dates and use our pricing filter to set your maximum rate. You can also list your results by the most economical stay first.

  • Search for the lowest price from CA $1,058

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 upmarket surroundings, these properties are typically packed with amenities such as complimentary bathrobes, large beds and plenty more. A 5-star hotel will go above and beyond to make your stay an even more lavish and unforgettable one. 24-hour front desk, luxurious spas and gourmet dining are only the start of the exclusive conveniences and services you'll likely get access to.

Explore a world of travel with Expedia