Osprey Vacation Rentals

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Check prices for these dates

Tonight
Jun 24 - Jun 25
Tomorrow
Jun 25 - Jun 26
This weekend
Jun 27 - Jun 29
Next weekend
Jul 4 - Jul 6

Vacation Rentals in Osprey

Charming Florida Beach Home w King Bed Patio
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 P9,603
P21,046 total
includes taxes & fees
Jun 30 - Jul 1
Charming Florida Beach Home w King Bed Patio
Tropical Beach Resorts
Property amenity

Tropical Beach Resorts

3.5 star property
9.4 out of 10, Exceptional, (4727)
"Nice spot for an overnight stay!"
The price is P11,128
P13,867 total
includes taxes & fees
Jun 25 - Jun 26
Tropical Beach Resorts
Hibiscus Suites - Gateway to Siesta Key
Outdoor pool, a heated pool, open 7:00 AM to 8:00 PM, sun 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 Ringling Beach House
Front of property

The Ringling Beach House

3.5 star property
9.0 out of 10, Wonderful, (307)
"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
Living area

Tiny House Siesta

2.0 star property
8.4 out of 10, Very Good, (296)
"Great place to stay. "
The price is P4,609
P8,463 total
includes taxes & fees
Jun 25 - Jun 26
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 P7,957
P8,991 total
includes taxes & fees
Jun 25 - Jun 26
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, (311)
"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 P19,381
P21,900 total
includes taxes & fees
Jul 20 - Jul 21
SeaSpray Resort
Siesta Key Island Rentals
Exterior

Siesta Key Island Rentals

3.0 star property
9.6 out of 10, Exceptional, (35)
"Great vacation stay "
The price is P8,013
P17,646 total
includes taxes & fees
Jun 25 - Jun 26
Siesta Key Island Rentals
Venice Beach Villas
Terrace/patio

Venice Beach Villas

3.0 star property
9.4 out of 10, Exceptional, (416)
"Everything was great!"
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, (179)
"A very accommodating property. Very clean and well maintained. The staff are extremely helpful and friendly. Great location."
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)
"Overall great experience! "
Barsala at Champions Walk
Siesta Palms By the Beach
Beach nearby, white sand, sun loungers, beach umbrellas

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
Private kitchen

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 P9,686
P22,533 total
includes taxes & fees
Jul 2 - Jul 3
Siesta Heron Suites & Villas
Longboat Bay Club
Beach nearby, white sand

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
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
Microwave

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 P4,372
P30,822 total
includes taxes & fees
Jul 2 - Jul 3
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 vacation rentals in Osprey?

Yes, we have vacation rentals in Osprey near Jim Neville Marine Preserve, or you can go with a more secluded option if you're looking for extra privacy while you relax. 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 vacation rentals in Osprey?

Siesta Key Island Rentals: This vacation home rental near Osprey comes with WiFi so you can feel at home during your trip. This vacation rental also comes with free parking to give you added peace of mind.

How many vacation rentals are there in Osprey?

With 29 Expedia vacation rentals, you're sure 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 like Siesta Key Beach and Lido Beach.

What’s a vacation rental in Osprey like?

Vacation rentals are private properties you can stay in for a long or short time in Osprey. Vacation rentals provide amenities such as WiFi and washers and dryers so you'll have all the comforts of home. If you're concerned about a sanitized environment, a vacation rental can offer a sense of security away from shared hotel elevators and lobbies packed with people while still allowing you the enjoyment of travel. You'll also have more space in a vacation rental than in a hotel, which makes a vacation rental an attractive option for families.