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

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Check prices for these dates

In two weeks
18 Sep - 20 Sep
In two months
30 Oct - 1 Nov
In three months
27 Nov - 29 Nov
In four months
25 Dec - 27 Dec

Our top choices for Osprey Village holiday rentals

Front of property – evening/night

1. Captiva Beach Resort

Captiva Beach Resort
3.0 star property
South Village
9.0 out of 10, Wonderful, (1,302 reviews)
"The proximity to the beach and the ambient of the place"
United States
natalia
The price is 3.924.218 ₫
4.876.388 ₫ total
includes taxes & fees
1 Sept - 2 Sept
Captiva Beach Resort
Property grounds

2. Tropical Beach Resorts

Tropical Beach Resorts
3.5 star property
South Village
9.4 out of 10, Exceptional, (5,815 reviews)
"Great place to visit!"
United States
Margaret Lai Ling
The price is 2.899.874 ₫
3.954.626 ₫ total
includes taxes & fees
2 Sept - 3 Sept
Tropical Beach Resorts
Cabin (Tiny House - The Siesta) | Living area | Flat-screen TV, Netflix, streaming services

3. Tiny House Siesta

Tiny House Siesta
2.0 star property
Sarasota
8.4 out of 10, Very good, (384 reviews)
"Great place"
United States
Mario
The price is 2.186.640 ₫
6.008.371 ₫ total
includes taxes & fees
9 Sept - 10 Sept
Tiny House Siesta
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
8.6 out of 10, Excellent, (2,433 reviews)
"This place was perfect!"
United States
Kat
The price is 3.548.694 ₫
4.010.024 ₫ total
includes taxes & fees
1 Sept - 2 Sept
Hibiscus Suites - Gateway to Siesta Key
Beachside One Bedroom Suite | Premium bedding, pillow-top beds, iron/ironing board (on request)

5. A Beach Retreat

A Beach Retreat
2.5 star property
Casey Key
9.2 out of 10, Wonderful, (671 reviews)
"Lovely place on a family beach."
United States
Robert
The price is 4.805.393 ₫
5.430.222 ₫ total
includes taxes & fees
1 Sept - 2 Sept
A Beach Retreat
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 Village Hotel Reviews

The Westin Sarasota

The Westin Sarasota

10/10 Excellent
"Great location excellent view front 19 floor from the pool"
Orlando 1-night trip
Posted 8 hours ago
The Westin Sarasota

Frequently asked questions

Can I find a holiday rental in Osprey Village?

Yes, there are holiday rentals close to the most popular sights in Osprey Village, or you can select a more secluded option if you're looking for a relaxing stay.

How many holiday rentals will I find in Osprey Village?

Expedia has 3 holiday rentals for your stay in Osprey Village.

What can I see and do in Osprey Village?

While exploring the area, visit family-friendly sights like Jim Neville Marine Preserve, or get outside and enjoy nature at Siesta Key Beach. Venice Beach and Lido Beach are other popular places to visit in the area.

What are holiday rentals like in Osprey Village?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Osprey Village. Holiday rentals offer extras such as laundry facilities and kitchens so you'll feel just like you're at home. If you're concerned about a sanitised environment, a holiday rental can provide a sense of safety away from public hotel lifts and busy front desks while still allowing you the experience of travel. You'll also get more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a popular choice for a family trip.