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
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

Our top choices for Osprey Village holiday rentals

A compact living space with a kitchen, a dining area, and a sofa with cushions.

1. Tiny House Siesta

Tiny House Siesta
2.0 star property
Sarasota
8.4 out of 10, Very good, (387 reviews)
"It's a very cute tiny house in a great location. Walking distance to Siesta Keys beach and numerous restaurants. I loved the decor in the sea turtle house. I would definitely stay here again next time I'm in Florida."
United States
Staci
The price is 1.432.588 ₫
5.103.191 ₫ total
includes taxes & fees
23 Oct - 24 Oct
Tiny House Siesta
A pool area with a waterfall feature, lounge chairs, and palm trees.

2. Tropical Beach Resorts

Tropical Beach Resorts
3.5 star property
South Village
9.4 out of 10, Exceptional, (5,979 reviews)
"This Resort is wonderful"
United States
Liliana
The price is 3.601.522 ₫
4.742.160 ₫ total
includes taxes & fees
19 Oct - 20 Oct
Tropical Beach Resorts
An outdoor patio with a grill, white chairs, and a red umbrella.

3. Hibiscus Suites - Gateway to Siesta Key

Hibiscus Suites - Gateway to Siesta Key
2.5 star property
Sarasota
8.8 out of 10, Excellent, (2,468 reviews)
"This place was perfect!"
United States
Kat
The price is 3.425.353 ₫
3.870.649 ₫ total
includes taxes & fees
22 Oct - 23 Oct
Hibiscus Suites - Gateway to Siesta Key
A large orange armchair against a white wall with a 'Captiva' sign. There are two potted plants beside the chair.

4. Captiva Beach Resort

Captiva Beach Resort
3.0 star property
South Village
9.0 out of 10, Wonderful, (1,321 reviews)
"Clean room, beach access, easy parking, friendly staff"
United States
Karla
The price is 4.425.912 ₫
5.439.827 ₫ total
includes taxes & fees
18 Oct - 19 Oct
Captiva Beach Resort
A living room with a view of the ocean, a ceiling fan, and a wooden coffee table.

5. A Beach Retreat

A Beach Retreat
2.5 star property
Casey Key
9.2 out of 10, Wonderful, (692 reviews)
"Enjoyed our stay"
United States
Robin
The price is 4.769.829 ₫
5.390.034 ₫ total
includes taxes & fees
4 Nov - 5 Nov
A Beach Retreat
A modern living room with a flat-screen TV on a wooden cabinet, a grey sofa with patterned cushions, and a large window with sheer curtains.

6. SeaSpray Resort

SeaSpray Resort
4.0 star property
Siesta Key
9.6 out of 10, Exceptional, (198 reviews)
"Best short vacation"
United States
Rommel
The price is 5.798.139 ₫
6.552.078 ₫ total
includes taxes & fees
2 Nov - 3 Nov
SeaSpray Resort
A wooden structure with a thatched roof overlooking a beach.

7. Casey Key Resort

Casey Key Resort
3.0 star property
Casey Key
8.4 out of 10, Very good, (284 reviews)
"Nice little property,very well kept.Host was very nice and helpful.Will be back again."
United States
Greg
The price is 4.830.659 ₫
5.941.902 ₫ total
includes taxes & fees
28 Oct - 29 Oct
Casey Key Resort
A beach with a clear sky and calm sea.

8. The Inn On Siesta Key

The Inn On Siesta Key
3.5 star property
Siesta Key
10.0 out of 10, Exceptional, (211 reviews)
"The property was perfect. Walk to down town and the beach. Loved the provisions for the beach which made it so convenient. Room was super clean and overall the property was well maintained."
United States
Stephen
The price is 5.846.645 ₫
8.039.961 ₫ total
includes taxes & fees
18 Oct - 19 Oct
The Inn On Siesta Key
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
"Nice hotel and a pleasant stay."
mike 4-night trip
Posted 6 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 Mote Marine Laboratory & Aquarium, or get outside and enjoy nature at Siesta Key Beach. Lido Beach and Turtle Beach are a couple of places you'll find in the wider 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.