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, 636 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
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 8.1
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.

a
andrea
From
United Kingdom
Spotlessly clean and perfect for relaxing in comfort
Scored out of 10, guest rating 8.7
Fabulous - What previous guests thought, 397 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
Lauren
From
Canada
Great location, super friendly owner and staff. Extra touches like bikes, wagons, beach chairs, bug spray and bags of local made for a memorable and happy experience. Thank you!
Scored out of 10, guest rating 8.3
Very good - What previous guests thought, 683 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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Holiday Homes with swimming pools in Osprey and nearby

  • Scored out of 10, guest rating 8.5
    Very good - What previous guests thought, 202 reviews

    Situated within 20 km of The John And Mable Ringling Museum Of Art and 14 km of Sarasota Opera, Siesta Heron Suites & Villas features rooms with air conditioning and a private bathroom in Siesta Key.

    From US$408.09 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$356.50 per night
  • Scored out of 10, guest rating 9.2
    Superb - What previous guests thought, 23 reviews

    Crescent Beach 1011 #1, a property with an outdoor swimming pool, is located in Sarasota, 18 km from The John And Mable Ringling Museum Of Art, 20 km from Sarasota International Convention Center, as...

    From US$362.07 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, 30 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 8.9
    Fabulous - What previous guests thought, 10 reviews

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

    From US$578 per night
  • 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.

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

  • 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$357.81 per night
  • Scored out of 10, guest rating 9.0
    Superb - What previous guests thought, 1 review

    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$258.74 per night

  • Set in Siesta Key, 2 km from Crescent Beach and 16 km from John And Mable Ringling Museum Of Art, Tiny House Pirate Ship - Sleeps 2 near Siesta Key beach offers air conditioning.

    From US$161.98 per night

  • Tiny House Siesta

    Sarasota
    Budget options available
    Scored out of 10, guest rating 8.3
    Very good - What previous guests thought, 636 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.

  • 8730 Dunmore Dr

    Vamo
    Budget options available

    Set in Vamo, 21 km from John And Mable Ringling Museum Of Art and 21 km from The John And Mable Ringling Museum Of Art, 8730 Dunmore Dr offers spacious air-conditioned accommodation with a patio and...

  • 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.

Enjoy breakfast in Osprey and nearby

  • 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.

  • Lakefront Escape

    Vamo
    Breakfast options

    Set in Vamo in the Florida region, Lakefront Escape has a patio. The property is around 22 km from The John And Mable Ringling Museum Of Art, 23 km from Sarasota International Convention Center and 16...

  • Waterview Dream

    Vamo
    Breakfast options

    Situated in Vamo, 21 km from John And Mable Ringling Museum Of Art and 22 km from The John And Mable Ringling Museum Of Art, Waterview Dream offers air conditioning.

  • Playing Hooky

    Siesta Key
    Breakfast options

    Located in Siesta Key, Playing Hooky features accommodation with an outdoor pool, massage services and a garden.

  • Featuring air-conditioned accommodation with a private pool, Nokomis Home with Screened Pool, 3 Mi to Beaches! is located in Nokomis. This holiday home provides 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 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...

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