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

Osprey Village Vacation Rentals

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Check prices for these dates

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

Our top choices for Osprey Village vacation 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 P9,369
P11,643 total
includes taxes & fees
Sep 1 - Sep 2
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 P6,924
P9,442 total
includes taxes & fees
Sep 2 - Sep 3
Tropical Beach Resorts
Living area

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 P5,156
P14,269 total
includes taxes & fees
Sep 11 - Sep 12
Tiny House Siesta
Outdoor pool, a heated pool, open 7:00 AM to 8:00 PM, sun 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 P7,922
P8,952 total
includes taxes & fees
Sep 14 - Sep 15
Hibiscus Suites - Gateway to Siesta Key
Premium bedding, pillowtop 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 P11,473
P12,965 total
includes taxes & fees
Sep 1 - Sep 2
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 5 hours ago
The Westin Sarasota

Find out more about Osprey Village

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

  • View our selection of featured holiday rentals in Osprey Village
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Look no further and take a look at our great range of rental properties in Osprey Village!

Frequently asked questions

Can I find a vacation rental in Osprey Village?

Yes, we give you a choice of vacation rentals close to popular local attractions in Osprey Village, or you can go with a more secluded option if you're looking for a relaxing stay.

What's the top vacation rental that Osprey Village has to offer?

Siesta Key Island Rentals: This vacation home rental near Osprey Village comes with 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 will I find in Osprey Village?

Expedia has 3 vacation 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 vacation rentals like in Osprey Village?

Vacation rentals are privately owned accommodations you can book for a couple days or more in Osprey Village. Vacation rentals feature amenities such as patios, hot tubs, and fire pits so you'll be comfy for your stay. If you're concerned about a sanitized environment, vacation rentals can offer a sense of safety away from public hotel elevators and busy lobbies while still allowing you a great travel experience. You'll also have more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a popular option for a family getaway.