Holiday Rentals in Osprey

    calendar shield illustration
    Change your mind
    Book hotels with free cancellation
    deals illustration
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    bed illustration
    Be picky
    Search almost a million properties worldwide

Check prices for these dates

Next weekend
In two weeks

Holiday Rentals in Osprey

Tropical Beach Resorts

3.5 star property
9.4 out of 10, Exceptional, (4724)
"Great customer service and perfect spot to walk around beach and town "
The price is €211
includes taxes & fees
23 Jun - 24 Jun
Tropical Beach Resorts

Hibiscus Suites - Gateway to Siesta Key

2.5 star property
8.6 out of 10, Excellent, (2134)
"Clean,friendly, close to the beach and major shopping center."
Hibiscus Suites - Gateway to Siesta Key

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

Luxury Beach Home! Pool, Rooftop Deck & Fun Amenities! - Shell-Abrate Good Times

10.0 out of 10, Exceptional, (21)
"Outstanding. 10/10"
Luxury Beach Home! Pool, Rooftop Deck & Fun Amenities! - Shell-Abrate Good Times

Captiva Beach Resort

2.0 star property
9.0 out of 10, Wonderful, (1104)
"Perfect location close to the beach clean and cozy place"
Captiva Beach Resort

Tiny House Siesta

2.0 star property
8.4 out of 10, Very good, (294)
"Great place to stay. "
The price is €127
includes taxes & fees
24 Jun - 25 Jun
Tiny House Siesta

Siesta Key Island Rentals

3.0 star property
9.6 out of 10, Exceptional, (35)
"Great vacation stay "
Siesta Key Island Rentals

Kon Tiki Inn

2.0 star property
10.0 out of 10, Exceptional, (203)
"We loved staying at Kon Tiki!"
The price is €136
includes taxes & fees
23 Jun - 24 Jun
Kon Tiki Inn

SeaSpray Resort

4.0 star property
8.0 out of 10, Very good, (1)
"In general it was a good apartment almost deserving 4 stars. However, there are a couple of quite important negative moments. First, they lied in the description about washer machine, they do not have any. Second, unlike other providers they do not allow to move in even 30 minutes earlier and made us wait for this time under Florida sun despite the room was ready. Third, they locked their dumpsters and people just throw their garbage over the locked gates, so rats will be there in no time unless...
The price is €332
includes taxes & fees
13 Jul - 14 Jul
SeaSpray Resort

Venice Beach Villas

3.0 star property
9.4 out of 10, Exceptional, (414)
"Very nice quiet and clean. "
Venice Beach Villas

Sea Club I Beach Resort

3.0 star property
9.0 out of 10, Wonderful, (311)
"Best place ever "
Sea Club I Beach Resort

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 price is €287
includes taxes & fees
25 Jun - 26 Jun
The Inn On Siesta Key

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

Beach Cottage with a Private Hot Tub

10.0 out of 10, Exceptional, (61)
"This was a great little place to stay. It was immaculate and had everything we needed."
Beach Cottage with a Private Hot Tub

Barsala at Champions Walk

4.0 star property
7.2 out of 10, Good, (40)
"Overall great experience! "
Barsala at Champions Walk

Tranquil Siesta Key Retreat ~ Walk to Beach ~ Pool

9.4 out of 10, Exceptional, (12)
"We had a great stay at this property! We had five adults and one infant with plenty of room to be comfortable. We enjoyed the short walk to the beach and that beach chairs were provided by the HOA (umbrellas are not but there was one at the property). The owners were wonderful, fast responses to any messages and made sure we had everything we needed to have a great time! Definitely recommend this property if you’re in Siesta Key and looking to be very close to the beach!"
Tranquil Siesta Key Retreat ~ Walk to Beach ~ Pool

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 €346
includes taxes & fees
7 Jul - 8 Jul
Siesta Heron Suites & Villas

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

THE BEACH CONDO #107. DIRECLY ON GULF FULL VIEW

9.8 out of 10, Exceptional, (67)
"Perfect location for a nice 4 day get away! Walk out the back door and you are on the beach. "
The price is €386
includes taxes & fees
26 Jun - 27 Jun
THE BEACH CONDO #107. DIRECLY ON GULF FULL VIEW

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
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.
Save an average of 15% on thousands of hotels when you're signed in

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?

Siesta Key Island Rentals: This holiday home rental outside of Osprey comes with WiFi so that you can feel at home during your trip. 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.