Compare Osprey Villas

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Featured Villas in Osprey

Private Beach Retreat on Siesta Key! Bright Villa

Private Beach Retreat on Siesta Key! Bright Villa

Sarasota FL
At this villa, guests have access to features like an arcade/game room. This beach villa also has barbecue grills.
Pool
Kitchen
Waterfront Villa Seaglass

Waterfront Villa Seaglass

Englewood FL
Guests staying at this villa have access to laundry facilities, a garden, and barbecue grills.
Pool
Kitchen
19 Premium Plus - Coastal Comfort

19 Premium Plus - Coastal Comfort

Sarasota FL
At this villa, guests have access to barbecue grills.
Pool
Kitchen
Direct Beachfront Gulf with Amazing Views

Direct Beachfront Gulf with Amazing Views

Longboat Key FL
Guests staying at this villa enjoy an outdoor pool, laundry facilities, and local meal delivery service. Other amenities at this beach villa include barbecue grills and a garden.
Pool
Kitchen
Tranquil villa with private beach, 2br/2ba 3 pools, complex on beach!! Renovated

Tranquil villa with private beach, 2br/2ba 3 pools, complex on beach!! Renovated

Sarasota FL
At this villa, guests have access to features like laundry facilities.
Pool
Kitchen
NEW 3BR Home with Pool, Hot Tub, Cafe, Minutes to Venice and Englewood Beaches

NEW 3BR Home with Pool, Hot Tub, Cafe, Minutes to Venice and Englewood Beaches

Englewood FL
Guests staying at this villa enjoy a hot tub, laundry facilities, and barbecue grills.
Pool
Hot Tub
Modern Villa steps away from the white sandy beach on upscale Lido Key, Sarasota

Modern Villa steps away from the white sandy beach on upscale Lido Key, Sarasota

Sarasota FL
Features of this villa include an outdoor pool and a gym.
Pool
Kitchen
Top Rated Villa For Rent! Short Walk To Beach. Swimming Pool. Family-Friendly

Top Rated Villa For Rent! Short Walk To Beach. Swimming Pool. Family-Friendly

Englewood FL
Guests of this villa enjoy features like an outdoor pool, a hot tub, and laundry facilities. Additional amenities include barbecue grills and a garden.
Pool
Hot Tub
Waterfront Paradise Bay

Waterfront Paradise Bay

Englewood FL
This villa features free WiFi in public areas and a garden. This smoke-free villa also has barbecue grills.
Pool
Kitchen
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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.

Hotel Options in Osprey

    Casey Key Resorts - Mainland

    Casey Key Resorts - Mainland

    1650 South Tamiami Trail Osprey FL
    $210 nightly
    The price is $237 total per night from Mar 8 to Mar 9
    $237 total
    Mar 8 - Mar 9
    Total with taxes and fees
    8.8/10 Excellent! (1,148 reviews)
    Kompose Boutique Hotel

    Kompose Boutique Hotel

    965 University Pkwy Sarasota FL
    $144 nightly
    The price is $163 total per night from Mar 22 to Mar 23
    $163 total
    Mar 22 - Mar 23
    Total with taxes and fees
    9.2/10 Wonderful! (5,105 reviews)
    Golden Host Resort - Sarasota

    Golden Host Resort - Sarasota

    4675 N Tamiami Trl Sarasota FL
    $98 nightly
    The price is $110 total per night from Apr 6 to Apr 7
    $110 total
    Apr 6 - Apr 7
    Total with taxes and fees
    8.4/10 Very Good! (2,338 reviews)

Luxury Villas

Book luxury villas in Osprey
There are plenty of ways to up your vacation game, but one of the best is by staying in a luxury villa in Osprey. Villas, with their thoughtful layout and elegant décor, let you travel in style. They come in a variety of sizes and offer a great experience, whether you’re traveling on your own or with a group of friends. Orbitz has fantastic deals on villas in Osprey, so book one now. You’ll feel like a million bucks before you even check in.

Spacious luxury villas in Osprey
You won’t have a problem finding your own space in Osprey. If you’re traveling in a group, go for a three-bedroom or larger villa; separate bedrooms can make it that much easier to keep the peace, especially when you’re all staying in one house. You can also explore Osprey on your own and use a one-bedroom villa as your home base.

A top-end villa experience in Osprey rivals that of a luxury resort. Float in a swimming pool with an elaborate mosaic bottom, work out in your own gym, and let the daily housekeeping staff clean up after you while a private chef whips up one delicious meal after another. This is the life!

Osprey Villas essential information

Accommodation
413 Villas
Lowest Price
$110
Highest Price
$237
Popular accommodation
Private Beach Retreat on Siesta Key! Bright Villa, Waterfront Villa Seaglass, 19 Premium Plus - Coastal Comfort, Direct Beachfront Gulf with Amazing Views , Tranquil villa with private beach, 2br/2ba 3 pools, complex on beach!! Renovated, NEW 3BR Home with Pool, Hot Tub, Cafe, Minutes to Venice and Englewood Beaches, Modern Villa steps away from the white sandy beach on upscale Lido Key, Sarasota, Top Rated Villa For Rent! Short Walk To Beach. Swimming Pool. Family-Friendly, Waterfront Paradise Bay

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