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Holiday Homes in Osprey

Find the holiday homes that appeal to you the most

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

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.

K
Kevin
From
United Kingdom
Short drive to centre so good location. Quiet neighbourhood. Problem locking front door resolved by owners relation living close by who kindly came to assist. Booking. Com had given us wrong access code so no reflection on property!
Scored out of 10, guest rating 9.4
Superb - What previous guests thought, 28 reviews
Price from
US$148.50
1 night, 2 adults

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

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.

D
David
From
Venezuela
Great location, comfortable, great price. I’ll back here.
Scored out of 10, guest rating 8.3
Very good - What previous guests thought, 636 reviews
Price from
US$120
1 night, 2 adults

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

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, 54 reviews
Price from
US$200
1 night, 2 adults

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

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 8.4
Very good - What previous guests thought, 681 reviews
Price from
US$286.25
1 night, 2 adults

New Gem! Charming vacation home - Casa Y&V

Venice (Near Osprey)

New Gem! Charming vacation home - Casa Y&V is a recently renovated holiday home in Venice, where guests can take a dip in its outdoor swimming pool and make the most of its free WiFi, private beach...

K
Kristine
From
United States
I enjoyed the location. The pool was great! The home was very cozy and comfortable.
Scored out of 10, guest rating 8.6
Fabulous - What previous guests thought, 15 reviews
Price from
US$175.50
1 night, 2 adults

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 8.5
Very good - What previous guests thought, 12 reviews
Price from
US$270
1 night, 2 adults
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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Popular with guests booking holiday homes in Osprey

Popular with guests booking holiday homes in Osprey

Popular with guests booking holiday homes in Osprey

Popular with guests booking holiday homes in Osprey

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

Popular with guests booking holiday homes in Osprey

Popular with guests booking holiday homes in Osprey

Popular with guests booking holiday homes in Sarasota

Scored out of 10, guest rating 8.3
Very good - What previous guests thought, 636 reviews

Popular with guests booking holiday homes in Siesta Key

Scored out of 10, guest rating 9.4
Superb - What previous guests thought, 23 reviews

Popular with guests booking holiday homes in Nokomis

Scored out of 10, guest rating 9.3
Superb - What previous guests thought, 4 reviews

Popular with guests booking holiday homes in Siesta Key

Scored out of 10, guest rating 8.7
Fabulous - What previous guests thought, 109 reviews

Holiday Homes with swimming pools in Osprey and nearby

Scored out of 10, guest rating 7.7
Good - What previous guests thought, 44 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 8.8
Fabulous - What previous guests thought, 22 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$391.84 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 10
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
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.

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.

Situated in Siesta Key, 80 metres from Turtle Beach and 21 km from John And Mable Ringling Museum Of Art, 2 Bedroom Condo with beach access and heated pool offers a garden and air conditioning.

Scored out of 10, guest rating 10
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.

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

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$246.14 per night
Scored out of 10, guest rating 10
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.

Lakefront Escape

Vamo
Budget options available

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
Budget options available

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.

Situated in Sarasota, 19 km from John And Mable Ringling Museum Of Art and 19 km from The John And Mable Ringling Museum Of Art, Relaxing 2 bed Siesta Key bungalow minutes from the beach features...

Enjoy breakfast in Osprey and nearby

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 8.6
Fabulous - What previous guests thought, 197 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$429.41 per night

Situated 20 km from The John And Mable Ringling Museum Of Art and 22 km from Sarasota International Convention Center in White Beach, Siesta Heron 5 Key Lime offers accommodation with a kitchen.

Siesta Heron 1

White Beach
Breakfast options

Situated in White Beach, Siesta Heron 1 offers accommodation with a private pool and lake views.

Siesta Heron 7

White Beach
Breakfast options

Located in White Beach, Siesta Heron 7 features accommodation with a private pool and lake views.

Siesta Heron 2

White Beach
Breakfast options

Boasting accommodation with a private pool, lake view and a patio, Siesta Heron 2 is situated in White Beach.

From US$485.07 per night

Siesta Heron 4

White Beach
Breakfast options

Situated in White Beach, Siesta Heron 4 features accommodation with a private pool and lake views.

From US$520.69 per night