4 Stars Hotels in Osprey, Florida from CA $233

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Check availability on Osprey 4 Star Hotels

Top Osprey 4 Star Hotels

Casey Key Resorts - Mainland
Outdoor dining

Casey Key Resorts - Mainland

3.0 star property
8.6 out of 10, Excellent, (1051)
"1-day business stay Site helped in many ways - super close to my work site; filled a gap late in the day; great find that I have passed but didn't realize what the site offered. Will return - positive experience."
The price is CA $288
CA $364 total
includes taxes & fees
Mar 18 - Mar 19
Casey Key Resorts - Mainland
Bentley's Boutique Hotel, BW Premier Collection
Outdoor pool, free cabanas, pool umbrellas

Bentley's Boutique Hotel, BW Premier Collection

2.5 star property
8.6 out of 10, Excellent, (1000)
"The rooms can use new AC units as the rooms smelled due to water leaking I’m from the unties onto the floor. One of our rooms smelled bad. The showers have been updated but do not keep the water in the shower and leak onto the bathroom flooding which can cause a slip and fall."
Bentley's Boutique Hotel, BW Premier Collection
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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 St. Regis Longboat Key Resort

The St. Regis Longboat Key Resort

1601 Gulf Of Mexico Drive, Longboat Key, FL
The price is CA $2,114 per night from Apr. 7 to Apr. 8
CA $2,114
CA $2,479 total
includes taxes & fees
Apr 7 - Apr 8
10/10 Exceptional! (14 reviews)
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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.

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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 CA $1,033

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.
Does Osprey have any 4-star all-inclusive resorts?
Use our “All inclusive” filter to find your next dream escape in Osprey where just about everything is taken care of, from your accommodations to your food, entertainment and activities. We can also help you find standard 4-star stays in and around this leading destination.
Are there any 4-star casino hotels in Osprey?
To find your perfect getaway in Osprey, simply use our convenient filter tools to refine your search. With resort-style amenities and a superb level of service, staying in a 4-star casino hotel is a sure bet for a good time.
What are the top 4-star apartments in Osprey?
Book a stay at Harbor Towers, one of our top 4-star Osprey properties. With well-appointed kitchens and lounges, making and sharing meals with your group couldn’t be easier in our apartments.