Osprey Holiday Rentals

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Check prices for these dates

Tonight
10 Jun - 11 Jun
Tomorrow
11 Jun - 12 Jun
This weekend
13 Jun - 15 Jun
Next weekend
20 Jun - 22 Jun

Holiday Rentals in Osprey

Tropical Beach Resorts
Property amenity

Tropical Beach Resorts

3.5 star property
9.4 out of 10, Exceptional, (4700)
"Great stay"
The price is S$258
includes taxes & fees
11 Jun - 12 Jun
Tropical Beach Resorts
Hibiscus Suites - Gateway to Siesta Key
Outdoor pool, a heated pool, open 7:00 AM to 8:00 PM, pool loungers

Hibiscus Suites - Gateway to Siesta Key

2.5 star property
8.6 out of 10, Excellent, (2132)
"Spacious, clean, affordable and good location for a first trip to Sarasota. "
Hibiscus Suites - Gateway to Siesta Key
The Residences at Siesta Key Beach by Hyatt Vacation Club
Sports facility

The Residences at Siesta Key Beach by Hyatt Vacation Club

3.5 star property
9.6 out of 10, Exceptional, (260)
"Very nice, clean, everyone so helpful. We had a great experience. We will definitely come back! "
The price is S$1,039
includes taxes & fees
1 Jul - 2 Jul
The Residences at Siesta Key Beach by Hyatt Vacation Club
The Ringling Beach House
Front of property

The Ringling Beach House

3.5 star property
9.0 out of 10, Wonderful, (305)
"Very clean, wish I could have stayed longer!"
The Ringling Beach House
Captiva Beach Resort
Front of property – evening/night

Captiva Beach Resort

2.0 star property
9.0 out of 10, Wonderful, (1101)
"Great property! The room looked brand new. Was very clean!"
Captiva Beach Resort
Tiny House Siesta
Living area

Tiny House Siesta

2.0 star property
8.4 out of 10, Very good, (290)
"Great place to stay. "
The price is S$207
includes taxes & fees
11 Jun - 12 Jun
Tiny House Siesta
Kon Tiki Inn
Exterior

Kon Tiki Inn

2.0 star property
10.0 out of 10, Exceptional, (201)
"Great hotel, pool was lovely and the room was just what we needed. Clean and spacious with a great kitchenette. "
The price is S$202
includes taxes & fees
11 Jun - 12 Jun
Kon Tiki Inn
Siesta Key Island Rentals
Room amenity

Siesta Key Island Rentals

3.0 star property
9.8 out of 10, Exceptional, (34)
"Great vacation stay "
The price is S$536
includes taxes & fees
15 Jun - 16 Jun
Siesta Key Island Rentals
Venice Beach Villas
Terrace/patio

Venice Beach Villas

3.0 star property
9.4 out of 10, Exceptional, (412)
"Very nice quiet and clean. "
Venice Beach Villas
Sea Club I Beach Resort
On the beach, white sand

Sea Club I Beach Resort

3.0 star property
9.0 out of 10, Wonderful, (309)
"Best place ever "
Sea Club I Beach Resort
SeaSpray Resort
In-room safe, iron/ironing board, free WiFi

SeaSpray Resort

4.0 star property
The price is S$551
includes taxes & fees
9 Jul - 10 Jul
SeaSpray Resort
The Inn On Siesta Key
Balcony view

The Inn On Siesta Key

3.5 star property
10.0 out of 10, Exceptional, (179)
"A very accommodating property. Very clean and well maintained. The staff are extremely helpful and friendly. Great location."
The price is S$407
includes taxes & fees
11 Jun - 12 Jun
The Inn On Siesta Key
Barsala at Champions Walk
Exterior

Barsala at Champions Walk

4.0 star property
7.4 out of 10, Good, (38)
"Overall great experience! "
Barsala at Champions Walk
Tropical Villas of Venice Beach
Beach nearby, beach umbrellas, beach towels

Tropical Villas of Venice Beach

3.5 star property
9.6 out of 10, Exceptional, (233)
"The property was in a quiet area and was very pleasant and comfortable. "
Tropical Villas of Venice Beach
Siesta Heron Suites & Villas
Private kitchen

Siesta Heron Suites & Villas

3.5 star property
8.4 out of 10, Very good, (31)
"A very comfortable stay in Siesta Key. Our apartment had been fully redeveloped since Hurricane Milton. Excellent job. Pool was really good. Nikes to ride. Kayaks to addle in the lagoon. All in allan exceptional choice. "
The price is S$423
includes taxes & fees
11 Jun - 12 Jun
Siesta Heron Suites & Villas
Siesta Palms By the Beach
Beach nearby, white sand, sun-loungers, beach umbrellas

Siesta Palms By the Beach

3.5 star property
9.2 out of 10, Wonderful, (117)
"This resort was clean and convenient, would definitely stay here again"
Siesta Palms By the Beach
Longboat Bay Club
Beach nearby, white sand

Longboat Bay Club

3.5 star property
10.0 out of 10, Exceptional, (1)
"Great property with beach access across the street! 2 br unit was huge as were the balconies. Our unit 105 was quite dated but still nice."
Longboat Bay Club
Chadwick Cove Resort & Marina
Microwave

Chadwick Cove Resort & Marina

4.0 star property
10.0 out of 10, Exceptional, (7)
"Very nice and updated property with a great panoramic view of the bay and ocean. Easy check in and checkout. Close to everything in Montasota Key/Englewood. "
The price is S$692
includes taxes & fees
15 Jun - 16 Jun
Chadwick Cove Resort & Marina
Bradenton Breeze
Living area

Bradenton Breeze

4.0 star property
2.0 out of 10, (1)
"No pude pasar ni una noche por que la casa por dentro se siente a humedo y se siente en el clima polvo y tuve que yebar a un hotel ami familia por que no sentia segura ami Familia en esa casa y al yegar ala casa todo es diferente como esta en las fotos no beo respuesta sobre mi dinero "
The price is S$619
includes taxes & fees
12 Jun - 13 Jun
Bradenton Breeze
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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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 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 26 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.