Search Holiday Rentals in Osprey

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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

Mobile Home in Sarasota

Tiny House Siesta
2.0 star property
8.4 out of 10, Very good, (346 reviews)
"Enjoyable stay. "
United States
Lori
The price is 2.606.901 ₫
6.136.789 ₫ total
includes taxes & fees
27 Jan - 28 Jan
Tiny House Siesta
Property grounds
Tropical Beach Resorts

Aparthotel in South Village

Tropical Beach Resorts
3.5 star property
9.4 out of 10, Exceptional, (5,221 reviews)
"Great place to stay. Very nice getaway. "
United States
Joyeeta
The price is 3.773.111 ₫
4.857.371 ₫ total
includes taxes & fees
14 Jan - 15 Jan
Tropical Beach Resorts
Exterior
Chadwick Cove Resort & Marina

Condo in Manasota Key

Chadwick Cove Resort & Marina
4.0 star property
10.0 out of 10, Exceptional, (15 reviews)
"Great place and location "
United States
Cathy
The price is 2.149.446 ₫
14.227.079 ₫ total
includes taxes & fees
13 Jan - 14 Jan
Chadwick Cove Resort & Marina
House, Lakeside | Living area | 39-inch flat-screen TV with digital channels, TV, streaming services
Siesta Heron Suites & Villas

Holiday Home in Siesta Key

Siesta Heron Suites & Villas
3.5 star property
8.6 out of 10, Excellent, (38 reviews)
"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 4.379.593 ₫
10.232.083 ₫ total
includes taxes & fees
14 Jan - 15 Jan
Siesta Heron Suites & Villas
Terrace/patio
Kon Tiki Inn

Aparthotel in Venice Island

Kon Tiki Inn
2.5 star property
10.0 out of 10, Exceptional, (250 reviews)
"Great place! "
United States
Michelle
The price is 5.222.206 ₫
5.901.094 ₫ total
includes taxes & fees
20 Jan - 21 Jan
Kon Tiki Inn
Property grounds
The Residences at Siesta Key Beach by Hyatt Vacation Club

Aparthotel in South Village

The Residences at Siesta Key Beach by Hyatt Vacation Club
3.5 star property
9.6 out of 10, Exceptional, (306 reviews)
"The rooms were perfect, and the staff was great. The location was perfect and peaceful"
United States
Marybeth
The price is 8.916.782 ₫
11.411.589 ₫ 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

Aparthotel in Sarasota

Hibiscus Suites - Gateway to Siesta Key
2.5 star property
8.6 out of 10, Excellent, (2,230 reviews)
"Very nice place !"
United States
Ivette
The price is 6.574.118 ₫
7.428.754 ₫ total
includes taxes & fees
1 Feb - 2 Feb
Hibiscus Suites - Gateway to Siesta Key
Beachside One Bedroom Suite | Premium bedding, pillow-top beds, individually decorated
A Beach Retreat

Condo in Casey Key

A Beach Retreat
2.5 star property
9.2 out of 10, Wonderful, (584 reviews)
"Room was nice & staff was friendly. "
United States
Paula
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 Hotel Reviews

Tropical Breeze Resort

Tropical Breeze Resort

10/10 Excellent
"My only main complaint was the coffee bar in the room was horrible. Lavazza coffee is is just horrible "
Maria 6-night trip
Posted 4 days ago
Tropical Breeze Resort

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 18 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.