The 10 best holiday homes in Osprey, USA | Booking.com
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Holiday Homes in Osprey

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The best holiday homes in Osprey

Check out our pick of great holiday homes in Osprey

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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

Tiny House Siesta

Sarasota (Near Osprey)

Tiny House Siesta offers self-catering tiny houses in Sarasota, Florida. Features include a kitchenette, TV, and free WiFi. Siesta Key is less than 1 km away and Siesta Key Beach is 1.6 km away.

R
REGINA
From
United States
I loved the location, the size of "The Starfish" was amazing! The house was very clean. Plenty of hot water :)
Scored out of 10, guest rating 8.3
Very good - What previous guests thought, 634 reviews
Price from
US$101
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
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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.

M
Marilyn
From
Portugal
It was quiet and felt very safe. Great location for me. I loved having a washer and dryer in the unit.
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 8.8
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.

L
Leigh
From
United Kingdom
The location was amazing, walking distance from the beach and bars/restaurants. They also catered for everything you need to enjoy a day at the beach like the beach wagon, cool bag which they would fill with ice and waters if needed. The staff were very friendly and helpful. Our apartment was quite small but catered for our needs.
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
All holiday homes in Osprey

Looking for a holiday home?

Great for families or large parties, holiday homes are privately owned accommodation, available for long or short-term rental. These homes are furnished and equipped with kitchen facilities for self-catering, although breakfast may be offered as an add-on. These properties have their own independent front door, which makes them different to apartments.

Most booked holiday homes in Osprey and surroundings in the past month

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Save money on holiday homes in Osprey and nearby – budget options available

  • 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$248.43 per night

  • Tiny House Siesta

    Sarasota
    Budget options available
    Scored out of 10, guest rating 8.3
    Very good - What previous guests thought, 634 reviews

    Tiny House Siesta offers self-catering tiny houses in Sarasota, Florida. Features include a kitchenette, TV, and free WiFi. Siesta Key is less than 1 km away and Siesta Key Beach is 1.6 km away.

    From US$167.24 per night
  • 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.

  • Sarasota - Dunmore 8730

    Sarasota
    Budget options available
    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.

Enjoy breakfast in Osprey and nearby

  • 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 in Sarasota and only 19 km from John And Mable Ringling Museum Of Art, Relaxing 2 bed Siesta Key bungalow minutes from the beach features accommodation with garden views, free WiFi and free...

  • Scored out of 10, guest rating 9.5
    Exceptional - What previous guests thought, 4 reviews

    Sarasota Villa with Pool Access about 4 Mi to Beach! is set in Sarasota, 21 km from The John And Mable Ringling Museum Of Art, 15 km from Sarasota Opera, as well as 15 km from Marina Jack Restaurant...

  • Set in Nokomis, Huge Pool, Close to Beaches, Restaurants & Shops offers accommodation with private pool, free WiFi and free private parking for guests who drive.

  • Scored out of 10, guest rating 10.0
    Exceptional - What previous guests thought, 3 reviews

    Lanai and Community Pool Access Sarasota Oasis! is set in Sarasota, 20 km from The John And Mable Ringling Museum Of Art, 15 km from Sarasota Opera, as well as 15 km from Marina Jack Restaurant And...

  • Scored out of 10, guest rating 8.0
    Very good - What previous guests thought, 1 review

    Boasting garden views, Heated Pool, Dock, on Lagoon, Turtle Beach 1 mile and Crescent Beach 2 miles, 1bdr offers accommodation with water sports facilities and a patio, around 20 km from The John And...

  • Featuring pool views, Heron Lagoon, dock, pool, the Tortuga at Siesta Key Bungalows offers accommodation with water sports facilities and a patio, around 20 km from John And Mable Ringling Museum Of...

  • Boasting air-conditioned accommodation with a private pool, Heron Lagoon, dock, pool, the Dolphin at Siesta Key Bungalows is situated in Siesta Key.

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