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Check prices for these dates

Tonight
11 Oct - 12 Oct
Tomorrow
12 Oct - 13 Oct
Next weekend
17 Oct - 19 Oct
In two weeks
24 Oct - 26 Oct

Top Holiday Rentals in Osprey

Charming Florida Beach Home w King Bed Patio
House | 2 bedrooms, Internet

Charming Florida Beach Home w King Bed Patio

2.0 star property
10.0 out of 10, Exceptional, (2)
"The best place to stay! Super clean home and friendly service. I would stay here again. "
Charming Florida Beach Home w King Bed Patio
Tropical Beach Resorts
Outdoor pool, a heated pool, open 8 AM to 10 PM, pool umbrellas

Tropical Beach Resorts

3.5 star property
9.4 out of 10, Exceptional, (5027)
"Great place and loved the closeness to the beach!"
The price is 3.335.961 ₫
4.365.065 ₫ total
includes taxes & fees
13 Oct - 14 Oct
Tropical Beach Resorts
Captiva Beach Resort
Front of property – evening/night

Captiva Beach Resort

3.0 star property
9.0 out of 10, Wonderful, (1142)
"2nd time and excellent as always..close to the beach and great surroundings "
Captiva Beach Resort
Hibiscus Suites - Gateway to Siesta Key
Outdoor pool, a heated pool, open 7:00 AM to 8:00 PM, pool loungers

Hibiscus Suites - Gateway to Siesta Key

2.5 star property
8.6 out of 10, Excellent, (2179)
"Friendly staff, room was really clean!"
Hibiscus Suites - Gateway to Siesta Key
SeaSpray Resort
Deluxe Suite, 2 Bedrooms | Living area

SeaSpray Resort

4.0 star property
9.6 out of 10, Exceptional, (47)
"I love everything about this place so beautiful with walking distance to the beach "
The price is 5.668.100 ₫
6.405.137 ₫ total
includes taxes & fees
26 Oct - 27 Oct
SeaSpray Resort
The Ringling Beach House
Front of property

The Ringling Beach House

3.5 star property
9.0 out of 10, Wonderful, (329)
"We liked the stay very much "
The Ringling Beach House
The Residences at Siesta Key Beach by Hyatt Vacation Club
Property amenity

The Residences at Siesta Key Beach by Hyatt Vacation Club

3.5 star property
9.6 out of 10, Exceptional, (292)
"Loved our stay! "
The price is 11.568.528 ₫
14.411.826 ₫ total
includes taxes & fees
10 Nov - 11 Nov
The Residences at Siesta Key Beach by Hyatt Vacation Club
Sea Club I Beach Resort
On the beach, white sand

Sea Club I Beach Resort

3.0 star property
9.2 out of 10, Wonderful, (328)
"Our room was on the beach! Beds and furniture were very comfortable!! Lots of outdoor seating and extremely close to the water!"
Sea Club I Beach Resort
Tiny House Siesta
Cabin (Tiny House - The Siesta) | Living area | Flat-screen TV, Netflix, streaming services

Tiny House Siesta

2.0 star property
8.4 out of 10, Very good, (330)
"We had a great time at Tiny House, location can not be better and everything was as described."
The price is 2.660.340 ₫
4.718.284 ₫ total
includes taxes & fees
15 Oct - 16 Oct
Tiny House Siesta
Siesta Palms By the Beach
Garden

Siesta Palms By the Beach

3.5 star property
9.2 out of 10, Wonderful, (132)
"We loved the condo. The distance to the beach was amazing. The wagon and beach chairs that were provided were so nice! The condo was clean and in great shape. The pool/ outdoor area was beautiful! We couldn’t have asked for a better place! "
Siesta Palms By the Beach
Bradenton Apartments by Landing
Exterior

Bradenton Apartments by Landing

4.5 star property
7.6 out of 10, Good, (46)
"Perfect place "
Bradenton Apartments by Landing
Kon Tiki Inn
Exterior

Kon Tiki Inn

2.5 star property
10.0 out of 10, Exceptional, (237)
"Charming, clean, and comfortable. Will definitely stay again when I'm the area. "
The price is 3.667.532 ₫
4.144.312 ₫ total
includes taxes & fees
13 Oct - 14 Oct
Kon Tiki Inn
Venice Beach Villas
Terrace/patio

Venice Beach Villas

3.0 star property
9.4 out of 10, Exceptional, (448)
"Staff was great. Room was very clean. Laundry onsite and the pool was wonderful! Will stay again!!!"
Venice Beach Villas
Siesta Key Island Rentals
322 Calle Miramar, Siesta Key, FL W/pool | Private kitchen

Siesta Key Island Rentals

3.0 star property
9.6 out of 10, Exceptional, (48)
"This place was incredible. We have traveled a lot with family and this was the best. Very comfortable and accommodating! I really cannot say enough good about this house. "
The price is 4.133.523 ₫
9.370.917 ₫ total
includes taxes & fees
13 Oct - 14 Oct
Siesta Key Island Rentals
The Inn On Siesta Key
Outdoor pool, a heated pool, open 8:00 AM to 8:00 PM, pool umbrellas

The Inn On Siesta Key

3.5 star property
10.0 out of 10, Exceptional, (184)
"clean and close proximity to beach and restaurants"
The Inn On Siesta Key
Tropical Villas of Venice Beach
Beach nearby, beach umbrellas, beach towels

Tropical Villas of Venice Beach

3.5 star property
9.6 out of 10, Exceptional, (239)
"Great Location !!"
Tropical Villas of Venice Beach
Paradise Cove at Lemon Bay
Exterior

Paradise Cove at Lemon Bay

3.5 star property
8.2 out of 10, Very good, (78)
"I loved the property and the host was also very professional. "
Paradise Cove at Lemon Bay
Siesta Heron Suites & Villas
Condo, Pool View | Private kitchen | Full-sized fridge, microwave, oven, stovetop

Siesta Heron Suites & Villas

3.5 star property
8.4 out of 10, Very good, (37)
"It was perfect for my family of 4 for our beach vacation!!"
Siesta Heron Suites & Villas
Chadwick Cove Resort & Marina
Property grounds

Chadwick Cove Resort & Marina

4.0 star property
10.0 out of 10, Exceptional, (14)
"Great place and location "
The price is 1.832.374 ₫
13.910.208 ₫ total
includes taxes & fees
15 Oct - 16 Oct
Chadwick Cove Resort & Marina
Casey Key Resort - Gulf Shores
Deluxe Studio, Bay View | View from room

Casey Key Resort - Gulf Shores

3.0 star property
8.4 out of 10, Very good, (261)
"Cute place and property! Cozy, quiet and clean. The property manager was very nice. We enjoyed the private beach on the property. It is walking distance to 2 restaurants. Would def go back, we had a nice relaxing weekend. "
Casey Key Resort - Gulf Shores
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
"Very Clean, comfortable, front desk service great!"
William 1-night trip
Posted 1 day 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 34 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.