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Check prices for these dates

In two weeks
19 Jun - 21 Jun
In two months
31 Jul - 2 Aug
In three months
28 Aug - 30 Aug
In four months
25 Sep - 27 Sep

Our top choices for Osprey holiday rentals

Terrace/patio

Kon Tiki Inn

Kon Tiki Inn
2.5 star property
Venice Island
10.0 out of 10, Exceptional, (283 reviews)
"Great place to stay!!!"
United States
Tara
The price is 3.296.019 ₫
3.724.501 ₫ total
includes taxes & fees
3 Jun - 4 Jun
Kon Tiki Inn
Interior

2 Mi to Englewood Beach! Home w/ Private Dock

2 Mi to Englewood Beach! Home w/ Private Dock
3.0 star property
Englewood
The price is 4.816.377 ₫
11.888.292 ₫ total
includes taxes & fees
12 Jun - 13 Jun
2 Mi to Englewood Beach! Home w/ Private Dock
Outdoor pool, pool umbrellas, pool loungers

Cedar Run Resort - Roam Hospitality

Cedar Run Resort - Roam Hospitality
3.5 star property
South Bradenton
8.0 out of 10, Very good, (3 reviews)
"I was extremely disappointed with this property. There was mold visible on the outside of the door, and the inside floors were absolutely filthy and appeared not to have been properly cleaned. The bathtub had pubic hair in it, and the shower was also dirty and unsanitary. I called to report the issues and requested to be moved to a different property. The representative who answered said she would call me back, but I didn't receive a return call until six hours later. By that time, I had no...
United States
Suzette
The price is 4.079.445 ₫
9.452.469 ₫ total
includes taxes & fees
3 Jun - 4 Jun
Cedar Run Resort - Roam Hospitality
Lobby

Venice Beach Villas

Venice Beach Villas
3.0 star property
Venice Island
9.4 out of 10, Exceptional, (482 reviews)
"Great location. Friendly staff nice pool Too much fabric softener fragrance in the linens"
United States
Marianne
Venice Beach Villas
Exterior

Chadwick Cove Resort & Marina

Chadwick Cove Resort & Marina
4.0 star property
Manasota Key
9.6 out of 10, Exceptional, (19 reviews)
"Great place and location "
United States
Cathy
The price is 2.272.438 ₫
14.385.981 ₫ total
includes taxes & fees
14 Jun - 15 Jun
Chadwick Cove Resort & Marina
House (2 Bedrooms) | Interior

Siesta Heron 6 / Sunset

Siesta Heron 6 / Sunset
3.0 star property
Siesta Key
The price is 17.554.773 ₫
26.781.175 ₫ total
includes taxes & fees
4 Jun - 5 Jun
Siesta Heron 6 / Sunset
Luxury Condo, Beach View | Balcony

Gulf View Condominiums

Gulf View Condominiums
3.5 star property
Manasota Key
The price is 8.951.683 ₫
24.498.035 ₫ total
includes taxes & fees
7 Jun - 8 Jun
Gulf View Condominiums
Beachside One Bedroom Suite | Premium bedding, pillow-top beds, individually decorated

A Beach Retreat

A Beach Retreat
2.5 star property
Casey Key
9.2 out of 10, Wonderful, (639 reviews)
"Best vacation"
United States
Lidiia
The price is 5.346.012 ₫
6.040.938 ₫ total
includes taxes & fees
7 Jun - 8 Jun
A Beach Retreat
Front of property – evening/night

Captiva Beach Resort

Captiva Beach Resort
3.0 star property
South Village
9.0 out of 10, Wonderful, (1,261 reviews)
"Very clean rooms, excellent location and a very nice staff"
United States
Yanseli
The price is 5.012.232 ₫
6.109.827 ₫ total
includes taxes & fees
3 Jun - 4 Jun
Captiva Beach Resort
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
2.5 star property
Sarasota
8.6 out of 10, Excellent, (2,326 reviews)
"great place to stay for a couple of nights. "
United States
Diana
The price is 3.920.149 ₫
4.429.768 ₫ total
includes taxes & fees
8 Jun - 9 Jun
Hibiscus Suites - Gateway to Siesta Key
Property grounds

Tropical Beach Resorts

Tropical Beach Resorts
3.5 star property
South Village
9.4 out of 10, Exceptional, (5,534 reviews)
"Clean room and convenient to the beach."
United States
Jacqueline
The price is 4.899.282 ₫
6.220.220 ₫ total
includes taxes & fees
8 Jun - 9 Jun
Tropical Beach Resorts
Interior

3 Mi to Beach! Englewood Family Gem + Private Pool

3 Mi to Beach! Englewood Family Gem + Private Pool
3.0 star property
Englewood
The price is 5.131.035 ₫
13.614.872 ₫ total
includes taxes & fees
11 Jun - 12 Jun
3 Mi to Beach! Englewood Family Gem + Private Pool
Condo (LuLu's Key House Leatherback 2/2 Down) | Exterior

Lulu's Key House Leatherback 2/2 Downstairs

Lulu's Key House Leatherback 2/2 Downstairs
4.0 star property
Siesta Key Village
The price is 7.544.341 ₫
16.607.291 ₫ total
includes taxes & fees
3 Jun - 4 Jun
Lulu's Key House Leatherback 2/2 Downstairs
House, Accessible | 4 bedrooms

Sarasota Family Home Private Heated Pool Relax

Sarasota Family Home Private Heated Pool Relax
2.0 star property
Whitfield Estates
The price is 6.748.844 ₫
13.841.953 ₫ total
includes taxes & fees
8 Jun - 9 Jun
Sarasota Family Home Private Heated Pool Relax
Deluxe Suite, 2 Bedrooms | In-room safe, iron/ironing board, free WiFi

SeaSpray Resort

SeaSpray Resort
4.0 star property
Siesta Key
9.6 out of 10, Exceptional, (132 reviews)
"Very nice room and easy access to an amazing beach."
United States
Michael
The price is 7.080.828 ₫
8.001.520 ₫ total
includes taxes & fees
9 Jun - 10 Jun
SeaSpray Resort
Interior

Beach Road - Capri

Beach Road - Capri
2.5 star property
Siesta Key
The price is 14.159.622 ₫
18.388.622 ₫ total
includes taxes & fees
4 Jun - 5 Jun
Beach Road - Capri
Terrace/patio

FANCY RETREREAT

FANCY RETREREAT
3.0 star property
Bradenton
The price is 21.050.400 ₫
30.365.202 ₫ total
includes taxes & fees
20 Jun - 21 Jun
FANCY RETREREAT
Outdoor wedding area

Casey Key Resort - Gulf Shores

Casey Key Resort - Gulf Shores
3.0 star property
Casey Key
8.4 out of 10, Very good, (275 reviews)
"Great place"
United States
tony
The price is 5.131.035 ₫
6.377.745 ₫ total
includes taxes & fees
10 Jun - 11 Jun
Casey Key Resort - Gulf Shores
5365 Calle Florida, Siesta Key, FL W/Pool | Private kitchen

Siesta Key Island Rentals

Siesta Key Island Rentals
3.0 star property
Siesta Key
9.6 out of 10, Exceptional, (68 reviews)
"Excellent location , minute walk to local bars and supermarket. Right across from beautiful siesta key beach."
United States
Alessandra
The price is 3.262.549 ₫
9.223.077 ₫ total
includes taxes & fees
3 Jun - 4 Jun
Siesta Key Island Rentals
House, Lakeside | Living area | 39-inch flat-screen TV with digital channels, TV, streaming services

Siesta Heron Suites & Villas

Siesta Heron Suites & Villas
3.5 star property
Siesta Key
8.4 out of 10, Very good, (43 reviews)
"Clean rooms, convenient location, nice property and amenities. Simple check-in and check-out"
United States
Christopher Robert
The price is 3.336.723 ₫
9.064.301 ₫ total
includes taxes & fees
3 Jun - 4 Jun
Siesta Heron Suites & Villas
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

Legacy Hotel at IMG Academy

Legacy Hotel at IMG Academy

10/10 Excellent
"Excellent"
Julius 1-night trip
Posted less than an hour ago
Legacy Hotel at IMG Academy

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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 lively bars in this destination. While you're in the area, you can also enjoy the top-notch restaurants and shops.

How many holiday rentals are there in Osprey?

With 15 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 Venice 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.