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Check prices for these dates

In two weeks
23 Jan - 25 Jan
In two months
6 Mar - 8 Mar
In three months
3 Apr - 5 Apr
In four months
1 May - 3 May

Our top choices for Osprey holiday rentals

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

Tiny House Siesta

Tiny House Siesta
2.0 star property
Sarasota
8.4 out of 10, Very good, (346)
"Enjoyable stay. "
United States
Lori
The price is 2.554.621 ₫
6.078.753 ₫ total
includes taxes & fees
27 Jan - 28 Jan
Tiny House Siesta
House, Lakeside | Living area | 39-inch flat-screen TV with digital channels, TV, streaming services
Siesta Heron Suites & Villas

Siesta Heron Suites & Villas

Siesta Heron Suites & Villas
3.5 star property
Siesta Key
8.6 out of 10, Excellent, (38)
"Clean pool great apartment could use more seating in living room. Beach chairs was cool patio was awesome parking good water pressure great bed clean and comfy "
United States
jason
The price is 4.380.927 ₫
10.235.201 ₫ total
includes taxes & fees
11 Jan - 12 Jan
Siesta Heron Suites & Villas
Property grounds
Tropical Beach Resorts

Tropical Beach Resorts

Tropical Beach Resorts
3.5 star property
South Village
9.4 out of 10, Exceptional, (5211)
"Great place to stay. Very nice getaway. "
United States
Joyeeta
The price is 3.773.685 ₫
4.857.966 ₫ total
includes taxes & fees
12 Jan - 13 Jan
Tropical Beach Resorts
Deluxe Suite, 2 Bedrooms | In-room safe, iron/ironing board, free WiFi
SeaSpray Resort

SeaSpray Resort

SeaSpray Resort
4.0 star property
Siesta Key
9.4 out of 10, Exceptional, (84)
"Very clean very quiet and a great location to the beach."
United States
Dave
The price is 8.016.197 ₫
9.058.487 ₫ total
includes taxes & fees
25 Jan - 26 Jan
SeaSpray Resort
Exterior
Chadwick Cove Resort & Marina

Chadwick Cove Resort & Marina

Chadwick Cove Resort & Marina
4.0 star property
Manasota Key
10.0 out of 10, Exceptional, (15)
"Great place and location "
United States
Cathy
The price is 2.150.100 ₫
14.231.412 ₫ total
includes taxes & fees
12 Jan - 13 Jan
Chadwick Cove Resort & Marina
Terrace/patio
Kon Tiki Inn

Kon Tiki Inn

Kon Tiki Inn
2.5 star property
Venice Island
10.0 out of 10, Exceptional, (250)
"Great place! "
United States
Michelle
The price is 5.223.797 ₫
5.902.891 ₫ total
includes taxes & fees
20 Jan - 21 Jan
Kon Tiki Inn
Property grounds
The Residences at Siesta Key Beach by Hyatt Vacation Club

The Residences at Siesta Key Beach by Hyatt Vacation Club

The Residences at Siesta Key Beach by Hyatt Vacation Club
3.5 star property
South Village
9.6 out of 10, Exceptional, (306)
"The rooms were perfect, and the staff was great. The location was perfect and peaceful"
United States
Marybeth
The price is 8.919.498 ₫
11.415.065 ₫ total
includes taxes & fees
19 Jan - 20 Jan
The Residences at Siesta Key Beach by Hyatt Vacation Club
Outdoor pool, a heated pool, open 7:00 AM to 8:00 PM, pool loungers
Hibiscus Suites - Gateway to Siesta Key

Hibiscus Suites - Gateway to Siesta Key

Hibiscus Suites - Gateway to Siesta Key
2.5 star property
Sarasota
8.6 out of 10, Excellent, (2227)
"Very nice place !"
United States
Ivette
The price is 6.575.118 ₫
7.429.884 ₫ total
includes taxes & fees
8 Feb - 9 Feb
Hibiscus Suites - Gateway to 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 Hotel Reviews

Hyatt Place Sarasota/Bradenton Airport

Hyatt Place Sarasota/Bradenton Airport

10/10 Excellent
"The inside of the hotel looked like it was recently remodeled as everything looked new. The staff was friendly and helpful. I was pleased with the experience of staying there."
Joseph 9-night trip
Posted 3 days ago
Hyatt Place Sarasota/Bradenton Airport

Frequently asked questions

Can I find holiday rentals in Osprey?

Yes, there are holiday rentals in Osprey close to Jim Neville Marine Preserve, or you can select a more secluded option if you're looking for a relaxing stay. Visitors to Osprey speak positively about the popular beaches and top-notch restaurants in this destination. While you're in the area, you can also enjoy the lively bars and shops.

How many holiday rentals are there in Osprey?

With 19 Expedia holiday rentals, you're guaranteed 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 such as Siesta Key Beach and Lido Beach.

What’s a holiday rental in Osprey like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Osprey. Holiday rentals feature extras such as kitchens and laundry facilities so you'll feel just like you're staying in your own home. If you're concerned about cleanliness, holiday rentals can provide a sense of security away from shared hotel lifts and lobbies bustling with people while still allowing you the experience of travel. You'll also have more space in a holiday rental than in a standard hotel, which makes a holiday rental a popular choice for families.