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

Osprey Holiday Rentals

  • 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
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

Our top choices for Osprey holiday rentals

Living area

1. Tiny House Siesta

Tiny House Siesta
2.0 star property
Sarasota
8.4 out of 10, Very good, (385 reviews)
"Great place"
United States
Mario
The price is S$266
includes taxes & fees
5 Oct - 6 Oct
Tiny House Siesta
Property grounds

2. Tropical Beach Resorts

Tropical Beach Resorts
3.5 star property
South Village
9.4 out of 10, Exceptional, (5,904 reviews)
"Loved our stay! Definitely recommend"
United States
Alexander
The price is S$228
includes taxes & fees
27 Sept - 28 Sept
Tropical Beach Resorts
Front of property – evening/night

3. Captiva Beach Resort

Captiva Beach Resort
3.0 star property
South Village
9.0 out of 10, Wonderful, (1,308 reviews)
"Clean room, beach access, easy parking, friendly staff"
United States
Karla
The price is S$245
includes taxes & fees
22 Sept - 23 Sept
Captiva Beach Resort
Outdoor pool, a heated pool, open 7:00 AM to 8:00 PM, pool loungers

4. Hibiscus Suites - Gateway to Siesta Key

Hibiscus Suites - Gateway to Siesta Key
2.5 star property
Sarasota
8.8 out of 10, Excellent, (2,450 reviews)
"This place was perfect!"
United States
Kat
The price is S$172
includes taxes & fees
22 Sept - 23 Sept
Hibiscus Suites - Gateway to Siesta Key
Private kitchen

5. Siesta Key Island Rentals

Siesta Key Island Rentals
3.0 star property
Siesta Key
9.4 out of 10, Exceptional, (81 reviews)
"The property was clean and had great decor! They provide everything you need for the beach and the pool is a great added bonus. Perfect location with being so close the restaurants and the beach. We are already planning our next stay!"
United States
Meghan
The price is S$415
includes taxes & fees
30 Sept - 1 Oct
Siesta Key Island Rentals
Premium bedding, pillow-top beds, iron/ironing board (on request)

6. A Beach Retreat

A Beach Retreat
2.5 star property
Casey Key
9.2 out of 10, Wonderful, (681 reviews)
"Great stay!!"
United States
Genghis
The price is S$266
includes taxes & fees
23 Sept - 24 Sept
A Beach Retreat
In-room safe, iron/ironing board, free WiFi

7. SeaSpray Resort

SeaSpray Resort
4.0 star property
Siesta Key
9.6 out of 10, Exceptional, (181 reviews)
"Property and room were beautiful!! Right across the street from the beach ⛱️"
United States
Michelle Suzanne
The price is S$320
includes taxes & fees
22 Sept - 23 Sept
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

Kompose Boutique Hotel

Kompose Boutique Hotel

10/10 Excellent
"I stay here all the time because it’s a terrific value."
Corey 2-night trip
Posted 1 hour ago
Kompose Boutique Hotel

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?

Tropical Villas of Venice Beach: This holiday home rental outside of Osprey is located near the beach, and has an outdoor pool, a terrace and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a fridge, a microwave and kitchenware. Make the most of garden in this rental home to help you unwind.

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?

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.