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
Aug 7 - Aug 9
In two months
Sep 18 - Sep 20
In three months
Oct 16 - Oct 18
In four months
Nov 13 - Nov 15

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, (381 reviews)
"Great place"
United States
Mario
The price is NT$2,518
NT$5,029 total
includes taxes & fees
Aug 4 - Aug 5
Tiny House Siesta
Property grounds

Tropical Beach Resorts

Tropical Beach Resorts
3.5 star property
South Village
9.4 out of 10, Exceptional, (5,687 reviews)
"Great location, very close to the beach, very nice and helpful front desk."
United States
Airida
The price is NT$4,911
NT$6,389 total
includes taxes & fees
Aug 10 - Aug 11
Tropical Beach Resorts
Front of property - evening/night

Captiva Beach Resort

Captiva Beach Resort
3.0 star property
South Village
9.0 out of 10, Wonderful, (1,290 reviews)
"Very helpful staff and excellent beach!"
United States
Vania
The price is NT$5,489
NT$6,752 total
includes taxes & fees
Aug 10 - Aug 11
Captiva Beach Resort
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, (655 reviews)
"The beach is right there, very clean and nice place."
United States
Maryna
The price is NT$5,948
NT$6,722 total
includes taxes & fees
Aug 5 - Aug 6
A Beach Retreat
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, (2,376 reviews)
The price is NT$4,348
NT$4,914 total
includes taxes & fees
Aug 2 - Aug 3
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
The price is NT$6,553
NT$15,070 total
includes taxes & fees
Jul 28 - Jul 29
Siesta Key Island Rentals
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

Siesta Key Palms Resort

Siesta Key Palms Resort

10/10 Excellent
"The resort is perfect for faimily with kids and travel with your car. The resort location is ok, a bit far away(1-2 miles) from the beach and town center but if family travel with kids + car like us, it's perfect. They have bikes so you can borrow for free. We had great times and love to come back again."
Hung 2-night trip
Posted 2 hours ago
Siesta Key Palms Resort

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.