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

Osprey Vacation Rentals

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Check prices for these dates

In two weeks
Jul 31 - Aug 2
In two months
Sep 11 - Sep 13
In three months
Oct 9 - Oct 11
In four months
Nov 6 - Nov 8

Our top choices for Osprey vacation rentals

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

Tiny House Siesta

Tiny House Siesta
2.0 star property
Sarasota
8.4 out of 10, Very Good, (377 reviews)
"The house was clean and simple. Perfect for a couple to stay for a few nights. Not too far from the beach. Very quiet and safe area."
United States
bruno
The price is NT$2,296
NT$6,523 total
includes taxes & fees
Jul 21 - Jul 22
Tiny House Siesta
Property grounds

Tropical Beach Resorts

Tropical Beach Resorts
3.5 star property
South Village
9.4 out of 10, Exceptional, (5,672 reviews)
"Great location, very close to the beach, very nice and helpful front desk."
United States
Airida
The price is NT$4,919
NT$6,399 total
includes taxes & fees
Aug 9 - Aug 10
Tropical Beach Resorts
Beachside One Bedroom Suite | Premium bedding, pillowtop beds, iron/ironing board (on request)

A Beach Retreat

A Beach Retreat
2.5 star property
Casey Key
9.2 out of 10, Wonderful, (652 reviews)
"The beach is right there, very clean and nice place."
United States
Maryna
The price is NT$5,347
NT$6,041 total
includes taxes & fees
Aug 3 - Aug 4
A Beach Retreat
Front of property - evening/night

Captiva Beach Resort

Captiva Beach Resort
3.0 star property
South Village
9.0 out of 10, Wonderful, (1,286 reviews)
"Very helpful staff and excellent beach!"
United States
Vania
The price is NT$5,031
NT$6,233 total
includes taxes & fees
Aug 10 - Aug 11
Captiva Beach Resort
Outdoor pool, a heated pool, open 7:00 AM to 8:00 PM, sun loungers

Hibiscus Suites - Gateway to Siesta Key

Hibiscus Suites - Gateway to Siesta Key
2.5 star property
Sarasota
8.6 out of 10, Excellent, (2,373 reviews)
"Excellent location, great place to stay! "
United States
Lynn
The price is NT$4,114
NT$4,648 total
includes taxes & fees
Aug 18 - Aug 19
Hibiscus Suites - Gateway to Siesta Key
5365 Calle Florida, Siesta Key, FL W/Pool | Private kitchen

Siesta Key Island Rentals

Siesta Key Island Rentals
3.0 star property
Siesta Key
9.6 out of 10, Exceptional, (73 reviews)
"Great location, very clean and spacious."
United States
Jason
Siesta Key Island Rentals
Superior Suite, 2 Bedrooms | In-room safe, iron/ironing board, WiFi (free)

SeaSpray Resort

SeaSpray Resort
4.0 star property
Siesta Key
9.6 out of 10, Exceptional, (152 reviews)
"Very nice room and easy access to an amazing beach."
United States
Michael
The price is NT$8,700
NT$9,831 total
includes taxes & fees
Jul 22 - Jul 23
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.
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Top Osprey Hotel Reviews

Carlisle Inn

Carlisle Inn

10/10 Excellent
"This hotel is very classy. I found a little far from where we wanted to spent our days but it worked well for us eventually. Staff are very friendly, rooms are big, but couch is full of stains, shower had a lot of pressure that could hurt sometimes, breakfast was great. Overall we had a great stay."
PRYSCILA 2-night trip
Posted less than an hour ago
Carlisle Inn

Find out more about Osprey

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

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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 vacation rentals in Osprey?

Yes, we have vacation rentals in Osprey near Jim Neville Marine Preserve, or you can go with a more secluded option if you're looking for extra privacy while you relax. 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 vacation rentals in Osprey?

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

How many vacation rentals are there in Osprey?

With 14 Expedia vacation rentals, you're sure 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 like Siesta Key Beach and Lido Beach.

What’s a vacation rental in Osprey like?

Vacation rentals are private properties you can stay in for a long or short time in Osprey. Vacation rentals provide amenities such as WiFi and washers and dryers so you'll have all the comforts of home. If you're concerned about a sanitized environment, a vacation rental can offer a sense of security away from shared hotel elevators and lobbies packed with people while still allowing you the enjoyment of travel. You'll also have more space in a vacation rental than in a hotel, which makes a vacation rental an attractive option for families.