Holiday Rentals in Osprey

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Holiday Rentals in Osprey

Our top choices for Osprey holiday rentals

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. "
The price is €267
includes taxes & fees
26 Aug - 27 Aug
Charming Florida Beach Home w King Bed Patio

Tropical Beach Resorts

3.5 star property
9.4 out of 10, Exceptional, (4900)
"Very Nice Resort!"
The price is €155
includes taxes & fees
1 Sept - 2 Sept
Tropical Beach Resorts

Hibiscus Suites - Gateway to Siesta Key

2.5 star property
8.6 out of 10, Excellent, (2164)
"Bed comfort , great location, friendly staff. "
Hibiscus Suites - Gateway to Siesta Key

SeaSpray Resort

4.0 star property
9.4 out of 10, Exceptional, (21)
"Renovated resort, a block away from the beach, very clean and friendly staff. Would stay there again. "
The price is €203
includes taxes & fees
1 Sept - 2 Sept
SeaSpray Resort

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

9.8 out of 10, Exceptional, (24)
"The house was in great condition and near everything. "
Luxury Beach Home! Pool, Rooftop Deck & Fun Amenities! - Shell-Abrate Good Times

The Ringling Beach House

3.5 star property
9.0 out of 10, Wonderful, (319)
"We loved the Villa!! It was spacious and stocked with every kitchen item you can imagine. "
The Ringling Beach House

Captiva Beach Resort

2.0 star property
9.0 out of 10, Wonderful, (1123)
"Everything was great and a walking distance to the beach❤️❤️❤️❤️❤️. Everyone was very friendly and kind, thank you so much."
Captiva Beach Resort

Tiny House Siesta

2.0 star property
8.4 out of 10, Very good, (314)
"Super helpful staff."
The price is €126
includes taxes & fees
3 Sept - 4 Sept
Tiny House Siesta

Sea Club I Beach Resort

3.0 star property
9.0 out of 10, Wonderful, (320)
"just an amazing staff and clean rooms! it was paradise will go back next year for sure!!"
Sea Club I Beach Resort

Kon Tiki Inn

2.0 star property
10.0 out of 10, Exceptional, (227)
"We love everything about this place Debbie and her husband are awesome from check in to check out this is a 5 star resort and we will be back many more times"
The price is €135
includes taxes & fees
24 Aug - 25 Aug
Kon Tiki Inn

Siesta Palms By the Beach

3.5 star property
9.2 out of 10, Wonderful, (126)
"An outstanding experience — a place that leaves you with a strong desire to return."
Siesta Palms By the Beach

The Residences at Siesta Key Beach by Hyatt Vacation Club

3.5 star property
9.8 out of 10, Exceptional, (282)
"Great location. Everyone was very friendly and accommodating!"
The price is €523
includes taxes & fees
25 Aug - 26 Aug
The Residences at Siesta Key Beach by Hyatt Vacation Club

Venice Beach Villas

3.0 star property
9.4 out of 10, Exceptional, (429)
"Easy walk or bike ride to beach. Property has plenty of bikes to borrow with locks. Overall just super place that I’ll stay again. "
Venice Beach Villas

Private Home Directly on Siesta Key Beach!

10.0 out of 10, Exceptional, (3)
"Beautiful place to stay… direct walk to the beach from your back door. Amazing view! Clean with all the amenities you need. "
Private Home Directly on Siesta Key Beach!

Bradenton Apartments by Landing

4.0 star property
7.4 out of 10, Good, (43)
"Absolutely beautiful location has everything you need n makes you feel like home"
Bradenton Apartments by Landing

Siesta Key Island Rentals

3.0 star property
9.6 out of 10, Exceptional, (46)
"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. "
Siesta Key Island Rentals

The Inn On Siesta Key

3.5 star property
10.0 out of 10, Exceptional, (183)
"Great place to stay! "
The price is €301
includes taxes & fees
23 Aug - 24 Aug
The Inn On Siesta Key

Tropical Villas of Venice Beach

3.5 star property
9.6 out of 10, Exceptional, (238)
"Great Location !!"
Tropical Villas of Venice Beach

Tranquil Siesta Key Retreat ~ Walk to Beach ~ Pool

9.6 out of 10, Exceptional, (17)
"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 Key Cottage – Best Value! Just Cross the Street to the Gulf!

9.4 out of 10, Exceptional, (34)
"Great location and experience"
Siesta Key Cottage – Best Value! Just Cross the Street to the Gulf!
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

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 31 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.