Search Villas in Osprey

    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

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

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
Jul 18 - Jul 20
In two weeks
Jul 25 - Jul 27
In one month
Aug 8 - Aug 10
In two months
Sep 5 - Sep 7

Featured Villas in Osprey

Paradise Cove at Lemon Bay
Exterior

Paradise Cove at Lemon Bay

3.5 star property
8.2 out of 10, Very Good, (77)
"The property was outstanding. The owners were marvelous would definitely go back."
Paradise Cove at Lemon Bay
Bianco Sands - 1118A by Beachside Management
Beach

Bianco Sands - 1118A by Beachside Management

2.0 star property
Bianco Sands - 1118A by Beachside Management
1200 Tree Bay
Exterior

1200 Tree Bay

4.0 star property
1200 Tree Bay
Sunny Gulf Coast Villa: Direct Beach & Pool Access
Interior

Sunny Gulf Coast Villa: Direct Beach & Pool Access

3.0 star property
8.0 out of 10, Very Good, (4)
"Excellent property with amenities. Ease of check in and out was helpful "
Sunny Gulf Coast Villa: Direct Beach & Pool Access
Bianco Sands 1114 by Beachside Management
Beach

Bianco Sands 1114 by Beachside Management

2.0 star property
Bianco Sands 1114 by Beachside Management
Bianco Sands - 1118B by Beachside Management
Beach

Bianco Sands - 1118B by Beachside Management

2.0 star property
Bianco Sands - 1118B by Beachside Management
Lanai + Community Pool Access: Sarasota Oasis!
Outdoor pool

Lanai + Community Pool Access: Sarasota Oasis!

3.5 star property
Lanai + Community Pool Access: Sarasota Oasis!
Sarasota Villa w/ Pool Access ~ 4 Mi to Beach!
Interior

Sarasota Villa w/ Pool Access ~ 4 Mi to Beach!

3.0 star property
Sarasota Villa w/ Pool Access ~ 4 Mi to Beach!
Sarasota Resort-like Living Near Siesta Key For 10
Internet

Sarasota Resort-like Living Near Siesta Key For 10

2.0 star property
Sarasota Resort-like Living Near Siesta Key For 10
Bianco Sands - 1110 by Beachside Management
Beach

Bianco Sands - 1110 by Beachside Management

2.0 star property
Bianco Sands - 1110 by Beachside Management
Bianco Sands - 1108 by Beachside Management
Beach

Bianco Sands - 1108 by Beachside Management

2.0 star property
Bianco Sands - 1108 by Beachside Management
Bianco Sands - 1112 by Beachside Management
Beach

Bianco Sands - 1112 by Beachside Management

2.0 star property
Bianco Sands - 1112 by Beachside Management
Crescent Beach Villas - West by Beachside Management
Pool

Crescent Beach Villas - West by Beachside Management

2.0 star property
Crescent Beach Villas - West by Beachside Management
Canopy Cottage on Siesta Key
Exterior

Canopy Cottage on Siesta Key

4.0 star property
Canopy Cottage on Siesta Key
Bianco Sands 1126 by Beachside Management
Beach

Bianco Sands 1126 by Beachside Management

2.0 star property
Bianco Sands 1126 by Beachside Management
Bianco Sands - 1116 by Beachside Management
Beach

Bianco Sands - 1116 by Beachside Management

2.0 star property
Bianco Sands - 1116 by Beachside Management
Siesta Town House
Private kitchen

Siesta Town House

3.0 star property
Siesta Town House
Coastal Venice Villa w/ Patio & Resort Amenities!
Private kitchen

Coastal Venice Villa w/ Patio & Resort Amenities!

3.0 star property
Coastal Venice Villa w/ Patio & Resort Amenities!
Luxury Private Condo on The Anchorage, Siesta Key Condo 1024
Beach

Luxury Private Condo on The Anchorage, Siesta Key Condo 1024

4.5 star property
Luxury Private Condo on The Anchorage, Siesta Key Condo 1024
Crescent Street 1138 B, 1 Bedrooms, Pool, pet Friendly, Walk to the Beach
Outdoor pool

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
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Frequently asked questions

How much do villas in Osprey cost?
Villas in Osprey cost between and per night. These getaways provide the privacy to enjoy your own space at a price that won't stretch the budget. 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?
Osprey has multiple villas with a total average guest review rating of 8.0. Island House Beach Resort V39 is a popular choice with Expedia guests. Visitors staying at this 3-star retreat will enjoy access to a swimming pool and a barbecue grill. Island House Beach Resort V1 On The Beautiful Crescent Beach In Siesta Key is another sought-after stay. This 2.5-star villa offers a barbecue grill and a swimming pool, among other conveniences.
How many villas are there in Osprey?
Take your pick of 26 villas in Osprey. No matter if you're vacationing with the family or getting away with some friends, Expedia will help you find the best space for your whole crew.