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Check prices for these dates

Tonight
28 Jun - 29 Jun
Tomorrow
29 Jun - 30 Jun
Next weekend
4 Jul - 6 Jul
In two weeks
11 Jul - 13 Jul

Top Holiday Rentals in Osprey

Charming Florida Beach Home w King Bed Patio
House | Internet

Charming Florida Beach Home w King Bed Patio

2.0 star property
10.0 out of 10, Exceptional, (1)
"The best place to stay! Super clean home and friendly service. I would stay here again. "
The price is ₹12,455
₹29,202 total
includes taxes & fees
30 Jun - 1 Jul
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, (4733)
"Nice spot for an overnight stay!"
The price is ₹16,640
₹20,735 total
includes taxes & fees
29 Jun - 30 Jun
Tropical Beach Resorts
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, (2137)
"Clean,friendly, close to the beach and major shopping center."
Hibiscus Suites - Gateway to Siesta Key
The Residences at Siesta Key Beach by Hyatt Vacation Club
Exterior

The Residences at Siesta Key Beach by Hyatt Vacation Club

3.5 star property
9.8 out of 10, Exceptional, (264)
"Fun place to stay for family vacation "
The price is ₹43,933
₹54,002 total
includes taxes & fees
21 Jul - 22 Jul
The Residences at Siesta Key Beach by Hyatt Vacation Club
The Ringling Beach House
Front of property

The Ringling Beach House

3.5 star property
9.0 out of 10, Wonderful, (308)
"Very clean, wish I could have stayed longer!"
The Ringling Beach House
Captiva Beach Resort
Front of property – evening/night

Captiva Beach Resort

2.0 star property
9.0 out of 10, Wonderful, (1107)
"Perfect location close to the beach clean and cozy place"
Captiva 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, (296)
"Great place to stay. "
The price is ₹7,437
₹13,234 total
includes taxes & fees
30 Jun - 1 Jul
Tiny House Siesta
Kon Tiki Inn
Exterior

Kon Tiki Inn

2.0 star property
10.0 out of 10, Exceptional, (204)
"We loved staying at Kon Tiki!"
The price is ₹11,898
₹13,445 total
includes taxes & fees
2 Jul - 3 Jul
Kon Tiki Inn
Sea Club I Beach Resort
On the beach, white sand

Sea Club I Beach Resort

3.0 star property
9.0 out of 10, Wonderful, (312)
"Best place ever "
Sea Club I Beach Resort
SeaSpray Resort
2 bedrooms, in-room safe, iron/ironing board, free WiFi

SeaSpray Resort

4.0 star property
9.0 out of 10, Wonderful, (2)
"Nice place to stay in SK! "
The price is ₹28,980
₹32,748 total
includes taxes & fees
13 Jul - 14 Jul
SeaSpray Resort
Siesta Key Island Rentals
Barefoot Bungalow W/Pool | Private kitchen

Siesta Key Island Rentals

3.0 star property
9.6 out of 10, Exceptional, (35)
"Great vacation stay "
The price is ₹12,216
₹26,569 total
includes taxes & fees
1 Jul - 2 Jul
Siesta Key Island Rentals
Venice Beach Villas
Terrace/patio

Venice Beach Villas

3.0 star property
9.4 out of 10, Exceptional, (417)
"Outstanding stay. Great room and amenities with a great locatio. We will return!! "
Venice Beach Villas
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, (180)
"The Inn on Siesta Key was awesome. Paige and Gabe were friendly and always helpful and they provided everything you would need for the beach. The property was clean and well maintained. The beach is literally across the street with a 3 minute walk. We will definitely be coming back. "
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, (234)
"The property was in a quiet area and was very pleasant and comfortable. "
Tropical Villas of Venice Beach
Barsala at Champions Walk
Exterior

Barsala at Champions Walk

4.0 star property
7.4 out of 10, Good, (41)
"Absolutely beautiful location has everything you need n makes you feel like home"
Barsala at Champions Walk
Siesta Palms By the Beach
Garden

Siesta Palms By the Beach

3.5 star property
9.2 out of 10, Wonderful, (119)
"This resort was clean and convenient, would definitely stay here again"
Siesta Palms By the Beach
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, (32)
"A very comfortable stay in Siesta Key. Our apartment had been fully redeveloped since Hurricane Milton. Excellent job. Pool was really good. Nikes to ride. Kayaks to addle in the lagoon. All in allan exceptional choice. "
The price is ₹13,070
₹31,964 total
includes taxes & fees
27 Jul - 28 Jul
Siesta Heron Suites & Villas
Longboat Bay Club
Outdoor pool

Longboat Bay Club

3.5 star property
10.0 out of 10, Exceptional, (1)
"Great property with beach access across the street! 2 br unit was huge as were the balconies. Our unit 105 was quite dated but still nice."
Longboat Bay Club
Casey Key Resort - Gulf Shores
Deluxe Studio, Bay View | View from room

Casey Key Resort - Gulf Shores

3.0 star property
8.2 out of 10, Very good, (257)
"Love love love this place ! Work turns into a leisure ! Every single time I come by. Beach day and then up to work @7pm. Easy access to the beach and nature ! I would recommend bike rentals … TY "
Casey Key Resort - Gulf Shores
Chadwick Cove Resort & Marina
Property grounds

Chadwick Cove Resort & Marina

4.0 star property
10.0 out of 10, Exceptional, (7)
"Very nice and updated property with a great panoramic view of the bay and ocean. Easy check in and checkout. Close to everything in Montasota Key/Englewood. "
The price is ₹5,945
₹45,127 total
includes taxes & fees
2 Jul - 3 Jul
Chadwick Cove Resort & Marina
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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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.

What are some of the best holiday rentals that Osprey has to offer?

Charming Florida Beach Home w King Bed Patio: This highly rated holiday home rental in Osprey offers a garden and free WiFi to help you feel comfortable in your new surroundings. This holiday rental also comes with free parking to give you added peace of mind.

How many holiday rentals are there in Osprey?

With 29 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.