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Featured Villas in Osprey

Paradise Cove at Lemon Bay
3.5 star property
8.0 out of 10, Very Good, (72)
"Older property but well-kept. Nice little get-away spot. "
Paradise Cove at Lemon Bay
Sol y Mar by Beachside Management
4.0 star property
8.6 out of 10, Excellent, (4)
"It was close to the beach, had a nice hot tub around back, was clean, and had all the tv channels. I didn’t like how small it was, they didn’t provide any shampoo/conditioner, and the pillows were very uncomfortable. "
Sol y Mar by Beachside Management
Sunny Gulf Coast Villa: Direct Beach & Pool Access
3.0 star property
8.0 out of 10, Very Good, (2)
"Great place to stay for a couple. Direct beach access with umbrella/beach chairs/towels provided. Very nice and clean. Shower head leaks and mattresses are older so not that comfortable. Otherwise this place is great and highly recommend!"
Sunny Gulf Coast Villa: Direct Beach & Pool Access
Lanai + Community Pool Access: Sarasota Oasis!
3.0 star property
Lanai + Community Pool Access: Sarasota Oasis!
Sarasota Villa w/ Pool Access ~ 4 Mi to Beach!
3.0 star property
Sarasota Villa w/ Pool Access ~ 4 Mi to Beach!
1200 Tree Bay
4.0 star property
1200 Tree Bay
Great Shape After Idalia
2.0 star property
Great Shape After Idalia
Great Shape After Idalia
2.0 star property
Great Shape After Idalia
Great Shape After Idalia
2.0 star property
Great Shape After Idalia
Bianco Sands - 1118A by Beachside Management
2.0 star property
Bianco Sands - 1118A by Beachside Management
Bianco Sands - 1118B by Beachside Management
2.0 star property
Bianco Sands - 1118B by Beachside Management
Great Shape After Idalia
2.0 star property
Great Shape After Idalia
Island House Beach Resort V18 by RedAwning
3.5 star property
Island House Beach Resort V18 by RedAwning
Canopy Cottage on Siesta Key
4.0 star property
Canopy Cottage on Siesta Key
Luxury Private Condo on The Anchorage, Siesta Key Condo 1024
4.5 star property
Luxury Private Condo on The Anchorage, Siesta Key Condo 1024
Siesta Town House
3.0 star property
Siesta Town House
Crescent Street 1138 B, 1 Bedrooms, Pool, pet Friendly, Walk to the Beach
3.5 star property
Crescent Street 1138 B, 1 Bedrooms, Pool, pet Friendly, Walk to the Beach
Diamond By The Sea in Siesta Key
2.0 star property
Diamond By The Sea in Siesta Key
Siesta Key Pool Home and Dock
2.0 star property
Siesta Key Pool Home and Dock
Beautiful Apartment on The Anchorage, Siesta Key Apartment 1019
4.0 star property
Beautiful Apartment on The Anchorage, Siesta Key Apartment 1019
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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Other property types in Osprey

Hibiscus Suites - Gateway to Siesta Key
2.5 star property
8.6 out of 10, Excellent, (2074)
"Our suite was very clean and the hospitality was wonderful. Would definitely recommend to anyone. If we ever visit the area again we would definitely stay there."
The price is P10,323
P11,665 total
includes taxes & fees
Nov 24 - Nov 25
Hibiscus Suites - Gateway to Siesta Key
The Residences at Siesta Key Beach by Hyatt Vacation Club
3.5 star property
9.8 out of 10, Exceptional, (211)
"This property is off the charts wonderful. Beautiful grounds, kind staff and incredible rooms. Loved every minute of our four night stay!"
The price is P21,826
P27,660 total
includes taxes & fees
Dec 3 - Dec 4
The Residences at Siesta Key Beach by Hyatt Vacation Club
Tropical Beach Resorts
3.5 star property
9.4 out of 10, Exceptional, (4537)
"The stay at the hotel was good. Issue was if you didn’t purchase their chair and umbrella then you were forced to sit at the end where the beach area is not kept nice. You’re spending the same money as everyone else to stay at resort. Should have the same right to sit where you want on the beach. "
Tropical Beach Resorts
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.

Frequently asked questions

How much do villas in Osprey cost?
Prices for villas in Osprey range between and per night. No matter your budget, you’ll find someplace that suits your needs on Expedia. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
What are the best villas in Osprey?
There are multiple villas in Osprey with a total average guest review rating of 8.2. Island House Beach Resort V39 is a hit with travelers. This 3-star stay offers a barbecue grill and a swimming pool. Island House Beach Resort V1 on the beautiful Crescent Beach in Siesta Key is another great option. It has a 2.5-star rating and conveniences such as a swimming pool and a barbecue grill.
How many villas are there in Osprey?
Osprey has 37 villas to choose from. Find your perfect stay quickly and easily by selecting the “Villa” checkbox under the “Property type” tab in our handy filter tool.
Are there any family-friendly villas in Osprey?
Settle in at Island House Beach Resort V39, a 3-star option just a quick drive from downtown. Conveniences here include a barbecue grill and clothes washing facilities. Another family-friendly getaway is Island House Beach Resort V1 on the beautiful Crescent Beach in Siesta Key. Clothes washing facilities and a barbecue grill help make this 2.5-star retreat a top pick among guests. Osprey has lots of family-friendly attractions to check out when you need to keep the kids busy. Historic Spanish Point and Oscar Scherer State Park deliver fun for visitors of all ages.
Why book your villa in Osprey with Expedia?
With Expedia, it’s a cinch to find your dream villa in Osprey. Getting away with the family? Make the most of our filters to look for stays with amenities like free WiFi. If you have a set budget, choose how much you want to spend and the star rating of the property. We’ll help you find the right place that matches your taste and style.
How can I find cheap villas in Osprey?
The simplest way to track down cheap villas in Osprey is with Expedia’s convenient filter tool. Refine your search results by amenities, star rating and budget to grab unbeatable bargains in only a few keystrokes.
What is there to do near my villa in Osprey?
After you’ve unpacked your suitcases, venture out and explore the incredible things Osprey has to offer. Oscar Scherer State Park is a top attraction to add to your must-do list.