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Check prices for these dates

In two weeks
26 Dec - 28 Dec
In two months
6 Feb - 8 Feb
In three months
6 Mar - 8 Mar
In four months
3 Apr - 5 Apr

Our top choices for Osprey holiday rentals

Cabin (Tiny House - The Siesta) | Living area | Flat-screen TV, Netflix, streaming services
Tiny House Siesta

Mobile Home in Sarasota

Tiny House Siesta
2.0 star property
8.4 out of 10, Very good, (346)
"Enjoyable stay. "
United States
Lori
The price is ₹9,348
₹21,484 total
includes taxes & fees
11 Dec - 12 Dec
Tiny House Siesta
Outdoor pool, a heated pool, open 8 AM to 10 PM, pool umbrellas
Tropical Beach Resorts

Aparthotel in South Village

Tropical Beach Resorts
3.5 star property
9.4 out of 10, Exceptional, (5141)
"Wonderful trip! Great location! Great staff!"
United States
Kevin
The price is ₹11,384
₹14,895 total
includes taxes & fees
11 Dec - 12 Dec
Tropical Beach Resorts
Front of property
The Ringling Beach House

Apartment in Siesta Key

The Ringling Beach House
3.5 star property
9.0 out of 10, Wonderful, (344)
"great location, very clean, quiet"
United States
Joaquin
The Ringling Beach House
Outdoor pool, a heated pool, open 8:00 AM to 8:00 PM, pool umbrellas
The Inn On Siesta Key

Cottage in Siesta Key

The Inn On Siesta Key
3.5 star property
10.0 out of 10, Exceptional, (191)
"Great place to stay! "
United States
Carlos
The price is ₹42,207
₹53,280 total
includes taxes & fees
28 Dec - 29 Dec
The Inn On Siesta Key
Front of property – evening/night
Captiva Beach Resort

Condo in South Village

Captiva Beach Resort
3.0 star property
9.0 out of 10, Wonderful, (1171)
"Clean room, snd friendly staff. Great location "
United States
Stephanie
Captiva Beach Resort
Exterior
Kon Tiki Inn

Aparthotel in Venice Island

Kon Tiki Inn
2.5 star property
10.0 out of 10, Exceptional, (246)
"Staff was great, room was clean and comfortable. It was a short stay but we enjoyed our time there. We will be back!"
United States
Joan
The price is ₹14,612
₹16,512 total
includes taxes & fees
15 Dec - 16 Dec
Kon Tiki Inn
Condo, Pool View | Private kitchen | Full-sized fridge, microwave, oven, stovetop
Siesta Heron Suites & Villas

Holiday Home in Siesta Key

Siesta Heron Suites & Villas
3.5 star property
8.6 out of 10, Excellent, (38)
"It was perfect for my family of 4 for our beach vacation!!"
United States
Jesse
The price is ₹12,018
₹31,659 total
includes taxes & fees
13 Dec - 14 Dec
Siesta Heron Suites & Villas
Outdoor pool, a heated pool, open 7:00 AM to 8:00 PM, pool loungers
Hibiscus Suites - Gateway to Siesta Key

Aparthotel in Sarasota

Hibiscus Suites - Gateway to Siesta Key
2.5 star property
8.6 out of 10, Excellent, (2209)
"Excellent location! Friendly staff, clean and updated rooms."
United States
Elba
Hibiscus Suites - Gateway to Siesta Key
Exterior
Siesta Key Island Rentals

Holiday Home in Siesta Key

Siesta Key Island Rentals
3.0 star property
9.6 out of 10, Exceptional, (53)
"Wonderful stay,Great owners,Fun times"
United States
Cornelia
The price is ₹11,227
₹26,016 total
includes taxes & fees
18 Dec - 19 Dec
Siesta Key Island Rentals
Deluxe Suite, 2 Bedrooms | Living area | TV
SeaSpray Resort

Aparthotel in Siesta Key

SeaSpray Resort
4.0 star property
9.4 out of 10, Exceptional, (75)
"Clean room, incredibly helpful staff. Will be staying here again"
United States
Caleb
The price is ₹22,430
₹25,346 total
includes taxes & fees
14 Dec - 15 Dec
SeaSpray Resort
Property amenity
The Residences at Siesta Key Beach by Hyatt Vacation Club

Aparthotel in South Village

The Residences at Siesta Key Beach by Hyatt Vacation Club
3.5 star property
9.6 out of 10, Exceptional, (299)
"Great spacious room with updated amenities as well as a great white beach and amazing staff! "
United States
Rebecca
The price is ₹32,995
₹41,854 total
includes taxes & fees
17 Dec - 18 Dec
The Residences at Siesta Key Beach by Hyatt Vacation Club
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.
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Top Osprey Hotel Reviews

Hibiscus Suites - Gateway to Siesta Key

Hibiscus Suites - Gateway to Siesta Key

10/10 Excellent
"Was wonderful stay and I will back. Large rooms well updated "
Charles 2-night trip
Posted 1 day ago
Hibiscus Suites - Gateway to Siesta Key

Find out more about Osprey

Holiday Rentals in Osprey

Search for holiday rentals in Osprey on Expedia.co.uk! You can easily find your home rentals, villas, holiday apartments in Osprey using one of the methods below:

  • View our selection of featured holiday rentals in Osprey
  • Use the map to find apartments and other holiday homes in the Osprey neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Osprey while they last

Look no further and take a look at our great range of rental properties in Osprey!

Frequently asked questions

Can I find holiday rentals in Osprey?

Yes, there are holiday rentals in Osprey close to Jim Neville Marine Preserve, or you can select a more secluded option if you're looking for a relaxing stay. Visitors to Osprey speak positively about the popular beaches and top-notch restaurants in this destination. While you're in the area, you can also enjoy the lively bars and shops.

What are some of the best holiday rentals that Osprey has to offer?

Charming Florida Beach Home w King Bed Patio: This highly rated holiday home rental in Osprey offers a garden and free WiFi to help you feel comfortable in your new surroundings. This holiday rental also comes with free parking to give you added peace of mind.

How many holiday rentals are there in Osprey?

With 20 Expedia holiday rentals, you're guaranteed to find just the right place for your Osprey stay.

What’s there to see and do in Osprey?

Family-friendly attractions include Jim Neville Marine Preserve and Nancy's Consignments, whereas Turtle Beach and Nokomis Beach are a couple of great spots to enjoy the outdoors. While in the area, you can also visit popular places such as Siesta Key Beach and Lido Beach.

What’s a holiday rental in Osprey like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Osprey. Holiday rentals feature extras such as kitchens and laundry facilities so you'll feel just like you're staying in your own home. If you're concerned about cleanliness, holiday rentals can provide a sense of security away from shared hotel lifts and lobbies bustling with people while still allowing you the experience of travel. You'll also have more space in a holiday rental than in a standard hotel, which makes a holiday rental a popular choice for families.