A marina with docked boats, a wooden bridge, and a building with a red roof.

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Check prices for these dates

In two weeks
14 Aug - 16 Aug
In two months
25 Sept - 27 Sept
In three months
23 Oct - 25 Oct
In four months
20 Nov - 22 Nov

Our top choices for Osprey holiday rentals

Outdoor pool, a heated pool, open 7:00 AM to 8:00 PM, pool loungers

1. Hibiscus Suites - Gateway to Siesta Key

Hibiscus Suites - Gateway to Siesta Key
2.5 star property
Sarasota
8.6 out of 10, Excellent, (2,389 reviews)
"Staff was helpful, and room were very clean"
United States
Doris Isabel
The price is ₹13,016
₹14,708 total
includes taxes & fees
11 Aug - 12 Aug
Hibiscus Suites - Gateway to Siesta Key
Property grounds

2. Tropical Beach Resorts

Tropical Beach Resorts
3.5 star property
South Village
9.4 out of 10, Exceptional, (5,705 reviews)
"Great location, very close to the beach, very nice and helpful front desk."
United States
Airida
The price is ₹14,558
₹18,937 total
includes taxes & fees
23 Aug - 24 Aug
Tropical Beach Resorts
Cabin (Tiny House - The Siesta) | Living area | Flat-screen TV, Netflix, streaming services

3. Tiny House Siesta

Tiny House Siesta
2.0 star property
Sarasota
8.4 out of 10, Very good, (382 reviews)
"Great place"
United States
Mario
The price is ₹7,228
₹14,630 total
includes taxes & fees
3 Aug - 4 Aug
Tiny House Siesta
Beachside One Bedroom Suite | Premium bedding, pillow-top beds, iron/ironing board (on request)

4. A Beach Retreat

A Beach Retreat
2.5 star property
Casey Key
9.2 out of 10, Wonderful, (657 reviews)
"The beach is right there, very clean and nice place."
United States
Maryna
The price is ₹17,625
₹19,916 total
includes taxes & fees
3 Aug - 4 Aug
A Beach Retreat
Front of property – evening/night

5. Captiva Beach Resort

Captiva Beach Resort
3.0 star property
South Village
9.0 out of 10, Wonderful, (1,294 reviews)
"Very helpful staff and excellent beach!"
United States
Vania
The price is ₹14,884
₹18,440 total
includes taxes & fees
10 Aug - 11 Aug
Captiva Beach Resort
Outdoor wedding area

6. Casey Key Resort - Gulf Shores

Casey Key Resort - Gulf Shores
3.0 star property
Casey Key
8.4 out of 10, Very good, (280 reviews)
"Is was a great place to stay, everything was perfect!"
United States
Tracie Costello
The price is ₹16,226
₹20,171 total
includes taxes & fees
18 Aug - 19 Aug
Casey Key Resort - Gulf Shores
House (2 Bedrooms) | Interior

7. Siesta Heron 6 / Sunset

Siesta Heron 6 / Sunset
3.0 star property
Siesta Key
The price is ₹45,336
₹76,466 total
includes taxes & fees
25 Aug - 26 Aug
Siesta Heron 6 / Sunset
Apartment (1 Bedroom) | Interior

8. Explore Sarasota: Condo w/ Pool Access, Near Dtwn

Explore Sarasota: Condo w/ Pool Access, Near Dtwn
3.5 star property
Sarasota
The price is ₹9,756
₹28,212 total
includes taxes & fees
3 Aug - 4 Aug
Explore Sarasota: Condo w/ Pool Access, Near Dtwn
House, Lakeside | Living area | 39-inch flat-screen TV with digital channels, TV, streaming services

9. Siesta Heron Suites & Villas

Siesta Heron Suites & Villas
3.5 star property
Siesta Key
8.6 out of 10, Excellent, (44 reviews)
"Clean rooms, convenient location, nice property and amenities. Simple check-in and check-out"
United States
Christopher Robert
The price is ₹12,369
₹33,215 total
includes taxes & fees
3 Aug - 4 Aug
Siesta Heron Suites & Villas
Superior Suite, 2 Bedrooms | In-room safe, iron/ironing board, free WiFi

10. SeaSpray Resort

SeaSpray Resort
4.0 star property
Siesta Key
9.6 out of 10, Exceptional, (156 reviews)
"We love the hotel the cleaners the facility was amazing"
United States
yisel
The price is ₹21,968
₹24,824 total
includes taxes & fees
31 Aug - 1 Sept
SeaSpray Resort
Condo (Beach Club Modern Condo C Building) | Exterior

11. Beach Club Modern Condo C Bldg

Beach Club Modern Condo C Bldg
3.0 star property
South Village
The price is ₹22,474
₹56,788 total
includes taxes & fees
19 Aug - 20 Aug
Beach Club Modern Condo C Bldg
5365 Calle Florida, Siesta Key, FL W/Pool | Private kitchen

12. Siesta Key Island Rentals

Siesta Key Island Rentals
3.0 star property
Siesta Key
9.6 out of 10, Exceptional, (74 reviews)
"Great location, very clean and spacious."
United States
Jason
The price is ₹14,824
₹37,043 total
includes taxes & fees
3 Aug - 4 Aug
Siesta Key Island Rentals
Beach nearby, white sand, beach umbrellas, beach towels

13. The Inn On Siesta Key

The Inn On Siesta Key
3.5 star property
Siesta Key
10.0 out of 10, Exceptional, (201 reviews)
"We had a wonderful stay at The Inn on Siesta Key. The Cabana was perfect for our family of 4, very clean and well equipped kitchen. The beds are very comfortable, and we enjoyed our morning coffee on the porch area. The property is fully equipped for the beach with chairs, towels, umbrellas, coolers, ice, and these great wagons to haul it all to the beach. Beaches are a short walk and amazing. The property is also a very short walk to The Village for shopping and dining. Paige checked us in and...
United States
Lisa
The price is ₹38,936
₹49,942 total
includes taxes & fees
7 Aug - 8 Aug
The Inn On Siesta Key
House | 4 bedrooms, Internet

14. Coastal Home w Hot Tub Firepit and Music Lounge

Coastal Home w Hot Tub Firepit and Music Lounge
2.0 star property
Siesta Key
Coastal Home w Hot Tub Firepit and Music Lounge
Classic Bungalow, 3 Bedrooms, Patio | Living area | 43-inch TV with digital channels

15. The Linwood Canopy

The Linwood Canopy
Sarasota Springs
The Linwood Canopy
Terrace/patio

16. Palm Haven at Cape Leyte

Palm Haven at Cape Leyte
2.0 star property
Siesta Key
Palm Haven at Cape Leyte
Interior

17. Beach Road - Bari

Beach Road - Bari
3.0 star property
Siesta Key
The price is ₹35,102
₹51,014 total
includes taxes & fees
2 Aug - 3 Aug
Beach Road - Bari
House (3 Bedrooms) | Interior

18. Unwind Poolside + Walk to Beach! Sarasota Retreat

Unwind Poolside + Walk to Beach! Sarasota Retreat
3.0 star property
South Village
8.0 out of 10, Very good, (1 review)
"The location of the property was excellent. The home was clean and had everything we needed to prepare breakfast in the morning. The 3 bedrooms and 3 bathrooms made it easy for the six of us wash up and get ready for dinner after a fun fill day at the walkable beach. Beach was great. Having a pool at the property was great for the 2 youngsters. We also made use of the wagon that was available to carry items to the beach., The property is nothing fancy but a great value for the money. "
United States
Eleuterio
The price is ₹31,850
₹65,079 total
includes taxes & fees
5 Aug - 6 Aug
Unwind Poolside + Walk to Beach! Sarasota Retreat
Outdoor pool, pool umbrellas, pool loungers

19. Cedar Run Resort - Roam Hospitality

Cedar Run Resort - Roam Hospitality
3.5 star property
South Bradenton
9.2 out of 10, Wonderful, (7 reviews)
"The room was very clean and well maintained/new. Staff was friendly and helpful. The air conditioner was great. The room we stayed at had lots of accessories for the beach like chairs and kid’s toys for the beach along with an umbrella. The surroundings are peaceful and beautiful. It was a great experience overall."
United States
Jose Luis Alberti
The price is ₹12,011
₹58,516 total
includes taxes & fees
2 Aug - 3 Aug
Cedar Run Resort - Roam Hospitality
Luxury Condo, Beach View | Balcony

20. Gulf View Condominiums

Gulf View Condominiums
3.5 star property
Manasota Key
The price is ₹32,539
₹89,049 total
includes taxes & fees
10 Aug - 11 Aug
Gulf View Condominiums
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

Lido Beach Resort

Lido Beach Resort

10/10 Excellent
"Everything was perfect the beach is beautiful everyone is good and very helpful the restaurant is really good too very fancy and tasty just went into a bad weather and couldn’t see that crystal clear water the breakfast was pretty good"
Yadier 3-night trip
Posted 3 hours ago
Lido Beach Resort

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
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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 lively bars in this destination. While you're in the area, you can also enjoy the top-notch restaurants and shops.

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

Siesta Key Island Rentals: This holiday home rental outside of Osprey comes with free WiFi so that you can feel at home during your trip. This holiday rental also comes with free parking to give you added peace of mind.

How many holiday rentals are there in Osprey?

With 14 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.