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

Search Holiday Rentals in Osprey

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
27 Nov - 29 Nov
In two months
8 Jan - 10 Jan
In three months
5 Feb - 7 Feb
In four months
5 Mar - 7 Mar

Our top choices for Osprey holiday rentals

A pool area with a waterfall feature, lounge chairs, and palm trees.

1. Tropical Beach Resorts

Tropical Beach Resorts
3.5 star property
South Village
9.4 out of 10, Exceptional, (6,056 reviews)
"Great resort and location!"
United States
Christine
The price is 3.697.920 ₫
4.843.993 ₫ total
includes taxes & fees
12 Nov - 13 Nov
Tropical Beach Resorts
A living room with a view of the ocean, a ceiling fan, and a wooden coffee table.

2. A Beach Retreat

A Beach Retreat
2.5 star property
Casey Key
9.2 out of 10, Wonderful, (700 reviews)
"Enjoyed our stay"
United States
Robin
The price is 4.717.312 ₫
5.330.688 ₫ total
includes taxes & fees
6 Dec - 7 Dec
A Beach Retreat
An outdoor patio with a grill, white chairs, and a red umbrella.

3. Hibiscus Suites - Gateway to Siesta Key

Hibiscus Suites - Gateway to Siesta Key
2.5 star property
Sarasota
8.8 out of 10, Excellent, (2,484 reviews)
"This place was perfect!"
United States
Kat
The price is 3.499.221 ₫
3.954.120 ₫ total
includes taxes & fees
16 Nov - 17 Nov
Hibiscus Suites - Gateway to Siesta Key
A compact living space with a sofa, a television, a ceiling fan, and a door.

4. Tiny House Siesta

Tiny House Siesta
2.0 star property
Sarasota
8.4 out of 10, Very good, (392 reviews)
"It's a very cute tiny house in a great location. Walking distance to Siesta Keys beach and numerous restaurants. I loved the decor in the sea turtle house. I would definitely stay here again next time I'm in Florida."
United States
Staci
The price is 1.553.664 ₫
5.208.064 ₫ total
includes taxes & fees
22 Nov - 23 Nov
Tiny House Siesta
An outdoor dining area with clear plastic chairs and tables, surrounded by greenery and a building in the background.

5. Captiva Beach Resort

Captiva Beach Resort
3.0 star property
South Village
9.0 out of 10, Wonderful, (1,333 reviews)
"Great location that's very close to the beach, large and clean room with a kitchenette, and very helpful and friendly staff. Loved our stay here!"
United States
Bob
The price is 3.941.291 ₫
4.887.579 ₫ total
includes taxes & fees
12 Nov - 13 Nov
Captiva Beach Resort
A modern living room with a sofa, a dining area, and a kitchen area.

6. Casey Key Resort

Casey Key Resort
3.0 star property
Casey Key
8.4 out of 10, Very good, (288 reviews)
"My boyfriend and I had a wonderful time. Easy late check in. Nice clean room. Property beautiful. Private beach beautiful. We definitely plan to come back and have family join."
United States
Jamie
The price is 4.992.000 ₫
6.140.160 ₫ total
includes taxes & fees
10 Dec - 11 Dec
Casey Key Resort
A bedroom with a view of a swimming pool and outdoor seating.

7. SeaSpray Resort

SeaSpray Resort
4.0 star property
Siesta Key
9.6 out of 10, Exceptional, (208 reviews)
"The room was clean and the staff were very kind."
United States
Geraldine
The price is 5.721.049 ₫
6.464.787 ₫ total
includes taxes & fees
16 Nov - 17 Nov
SeaSpray Resort
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Osprey Hotel Reviews

DoubleTree by Hilton Sarasota Bradenton Airport

DoubleTree by Hilton Sarasota Bradenton Airport

10/10 Excellent
"We arrived at the hotel and greeted at the front desk with plenty of assurances we would have a shuttle from the airport to the hotel and back and forth. Room was ready no waiting - and spotless. Definitely would stay here again. Staff was very helpful with an early morning departure,"
MaryJane 1-night trip
Posted less than an hour ago
DoubleTree by Hilton Sarasota Bradenton Airport

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.

How many holiday rentals are there in Osprey?

With 13 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?

Turtle Beach and Nokomis Beach are a couple of scenic spots to enjoy the outdoors, whereas Historic Spanish Point is one of the cultural attractions. 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.