The 10 best villas in Osprey, USA | Booking.com
Skip to main content

Villas in Osprey

Find the villas that appeal to you the most

Villas for every style

Find the right villa for you in Osprey

The best villas in Osprey

Check out our pick of great villas in Osprey

Show hotels on map

Filter by:

Review score

Poolside Paradise Near Siesta Key Beach

Sarasota (Near Osprey)

Poolside Paradise Near Siesta Key Beach is located in Sarasota, 13 km from Marina Jack Restaurant And Marina, 13 km from Sarasota Opera, as well as 15 km from Sarasota County Visitor Information...

Scored out of 10, guest rating 9.4
Superb - What previous guests thought, 5 reviews
Price from
US$392.32
1 night, 2 adults
Check availability

2bed/2bath Condo next to Siesta Key ~A Hidden Gem

Sarasota (Near Osprey)

Situated in Sarasota, 2bed/2bath Condo next to Siesta Key ~A Hidden Gem offers accommodation with a private pool. This property offers access to a balcony, free private parking and free WiFi.

C
Carrera
From
Netherlands
Beautiful villa! Great atmosphere, clean, great facilities and a great location
Scored out of 10, guest rating 9.3
Superb - What previous guests thought, 27 reviews
Price from
US$148.50
1 night, 2 adults
Check availability

5min from the beach 8 min from Siesta Key

Sarasota (Near Osprey)

Located in Sarasota in the Florida region, 5min from the beach 8 min from Siesta Key features a patio.

h
huanhua
From
China
i dont know, i was asked if i can cancel, she told, can not cancel. and i have no time to go there in the end, so i did not check in and live in here at all
Scored out of 10, guest rating 9.0
Superb - What previous guests thought, 20 reviews
Price from
US$198
1 night, 2 adults
Check availability

Pool Home on Gulf Gate 5min away from Siesta Key

Sarasota (Near Osprey)

Featuring air-conditioned accommodation with a private pool, pool view and a patio, Pool Home on Gulf Gate 5min away from Siesta Key is located in Sarasota.

H
Helen
From
United Kingdom
We all thoroughly enjoyed our stay here. I have been many times to Sarasota and this was the best house that we have stayed in. It is close to the beach and all the shops.
Scored out of 10, guest rating 9.4
Superb - What previous guests thought, 6 reviews
Price from
US$3,000
1 night, 2 adults
Check availability

Sunny Oasis Getaway -Heated Pool-Mini Golf-Near Beach

Nokomis (Near Osprey)

Featuring a garden, private pool and garden views, Sunny Oasis Getaway -Heated Pool-Mini Golf-Near Beach is set in Nokomis.

Z
Zuzana
From
Slovakia
Beautifull house with everything needed for the family stay. Can inly reccomend, very good communication with the owner. Thanks for all
Scored out of 10, guest rating 8.9
Fabulous - What previous guests thought, 20 reviews
Price from
US$264.34
1 night, 2 adults
Check availability

Sarasota Updated pool home, Near Siesta Key

Sarasota (Near Osprey)

Featuring air-conditioned accommodation with a private pool, garden view and a balcony, Sarasota Updated pool home, Near Siesta Key is located in Sarasota.

R
Rulo
From
United States
Location was good, home was nicely updated inside and overall comfortable.
Scored out of 10, guest rating 8.9
Fabulous - What previous guests thought, 10 reviews
Price from
US$546.70
1 night, 2 adults
Check availability

Beautiful property on Siesta Key

Siesta Key (Near Osprey)

Featuring air-conditioned accommodation with a private pool, garden view and a patio, Beautiful property on Siesta Key is located in Siesta Key.

P
Pauline
From
United Kingdom
I spent a month in this fabulous property. It was so comfortable it felt like I had lived there forever. Kitchen had everything I needed. Pool was great but it was just minutes from the beach and dock. Do yourselves a favour and book this property you will not be disappointed
Scored out of 10, guest rating 8.2
Very good - What previous guests thought, 53 reviews
Price from
US$200
1 night, 2 adults
Check availability

Siesta Key Beachside Villas

Sarasota (Near Osprey)

Siesta Key Beachside Villas is located in the heart of Siesta Key. It features an outdoor pool and free WiFi. Beach access is a 2 minutes' walk from the property.

S
Sybil
From
United States
Loved the room. So pretty and updated. Beautiful shower. Location was perfect. Very short stroll to beach. And steps away from all the good restaurants.
Scored out of 10, guest rating 8.7
Fabulous - What previous guests thought, 394 reviews
Price from
US$228.33
1 night, 2 adults
Check availability

Siesta Key Beach Resort and Suites

Sarasota (Near Osprey)

Located just 1 minutes’ walk from the beach, this Siesta Key resort features a swimming pool. Guests can also enjoy access to free WiFi in common areas.

R
Ramiro Fabian
From
Argentina
location excellent parking and well equipped
Scored out of 10, guest rating 8.3
Very good - What previous guests thought, 687 reviews
Price from
US$286.25
1 night, 2 adults
Check availability

Flamingo by the Sea Cozy Spacious Modern 5 min to Beach Video Tour Sleep up to 10

Venice (Near Osprey)

Flamingo by the Sea Cozy Spacious Modern 5 min to Beach Video Tour Sleep up to 10 is situated in Venice, 43 km from Fishermen's Village, 8.4 km from Venice Theatre, and 17 km from Warm Mineral...

Scored out of 10, guest rating 8.6
Fabulous - What previous guests thought, 10 reviews
Price from
US$270
1 night, 2 adults
Check availability
All villas in Osprey

Looking for a villa?

Perfect for families, groups or couples who enjoy luxury and independence while travelling. Enjoy the space and privacy of these fully-furnished, self-standing mansions — travellers can cook, lounge and explore at their leisure. Note that in Bali, a resort will also be called a villa.

Most booked villas in Osprey and surroundings in the past month

See all

Enjoy breakfast in Osprey and nearby

  • Scored out of 10, guest rating 10.0
    Exceptional - What previous guests thought, 1 review

    Located in Sarasota in the Florida region, 5 Mi to Beach Family Retreat in Sarasota! has a patio. Free WiFi is offered throughout the property and private parking is available on site.

  • Scored out of 10, guest rating 10.0
    Exceptional - What previous guests thought, 1 review

    Featuring air-conditioned accommodation with a private pool, Sarasota - Dunmore 8730 is located in Sarasota. The 4-star holiday home is 21 km from The John And Mable Ringling Museum Of Art.

  • Scored out of 10, guest rating 10.0
    Exceptional - What previous guests thought, 2 reviews

    Featuring air-conditioned accommodation with a patio, Bayside Escape-Condo w Dock Pool and Near Beach is set in Sarasota.

  • Situated in Sarasota, 21 km from John And Mable Ringling Museum Of Art and 21 km from The John And Mable Ringling Museum Of Art, Tropical Shores Retreat-10 Min to Siesta Key Beach offers air...

  • Boasting a spa bath, Pinestone Condo On Palmer Ranch is situated in Sarasota.

  • Scored out of 10, guest rating 1.0
    Bad - What previous guests thought, 1 review

    Boasting air-conditioned accommodation with a private pool, Siesta Key Marvel Pool SPA Deeded Beach Access is situated in Sarasota. This holiday home features accommodation with a patio.

  • Scored out of 10, guest rating 10.0
    Exceptional - What previous guests thought, 1 review

    Boasting air-conditioned accommodation with a private pool, garden view and a patio, Villa Pine Tree Pool close to the beaches Siesta Key is set in Sarasota.

  • Situated 19 km from The John And Mable Ringling Museum Of Art and 21 km from Sarasota International Convention Center in Sarasota, Cozy 2 bed Siesta Key bungalow 5 min from beach offers accommodation...

Travelling by car? These villas in Osprey and nearby offer free parking

  • Scored out of 10, guest rating 10.0
    Exceptional - What previous guests thought, 1 review

    Set 21 km from John And Mable Ringling Museum Of Art, Cute 3/2 Siesta home steps from Siesta waters offers accommodation with free WiFi and free private parking.

    From US$517.54 per night
  • Scored out of 10, guest rating 7.8
    Good - What previous guests thought, 45 reviews

    Situated in Vamo, LUX VILLAs on beautiful Palmer Ranch offers a balcony with lake and pool views, as well as a year-round outdoor pool, hot tub and fitness centre.

    From US$427.84 per night
  • Scored out of 10, guest rating 10.0
    Exceptional - What previous guests thought, 1 review

    Set in Sarasota, 19 km from John And Mable Ringling Museum Of Art and 19 km from The John And Mable Ringling Museum Of Art, Sarasota 15 min from Siesta offers a garden and air conditioning.

    From US$415.06 per night

  • Situated in Nokomis in the Florida region, Peaceful Nokomis Escape 5 Mins to Beach 55 features accommodation with free WiFi and free private parking.

    From US$250.72 per night
  • Scored out of 10, guest rating 9.4
    Superb - What previous guests thought, 6 reviews

    Featuring air-conditioned accommodation with a private pool, pool view and a patio, Pool Home on Gulf Gate 5min away from Siesta Key is located in Sarasota.

    From US$3,640 per night
  • Scored out of 10, guest rating 8.6
    Fabulous - What previous guests thought, 29 reviews

    Set in Sarasota, Bernice 3bd2bth With Heated Pool Near Siesta Key! offers accommodation with private pool, free WiFi and free private parking for guests who drive.

    From US$487.24 per night
  • Scored out of 10, guest rating 9.1
    Superb - What previous guests thought, 8 reviews

    House by Siesta Key, a property with a garden, is set in Sarasota, 11 km from Marina Jack Restaurant And Marina, 13 km from Sarasota County Visitor Information Center And History Museum, as well as 15...

    From US$321.17 per night
  • Scored out of 10, guest rating 9.0
    Superb - What previous guests thought, 20 reviews

    Located in Sarasota in the Florida region, 5min from the beach 8 min from Siesta Key features a patio.

    From US$352.09 per night

Research, refine and make plans for your whole trip

Hotels near Tampa International Airport

Got a stopover, late arrival or early departure? Find hotels conveniently close to the airport.

Hotels near Sarasota Bradenton International Airport

Perfect for a late arrival or early departure.

Hotels with Parking in Osprey

More great accommodation options for your trip.

Hotels with Pools in Osprey

More great accommodation options for your trip.

Cottages in Osprey

More great accommodation options for your trip.

Holiday Homes in Osprey

More great accommodation options for your trip.

Apartments in Osprey

Explore more great accommodation options in Osprey, starting with apartments.

Villas in New York

Discover another destination in the United States.

Villas in Las Vegas

Discover another destination in the United States.