Osprey Holiday Rentals

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Check prices for these dates

Tonight
28 Jul - 29 Jul
Tomorrow
29 Jul - 30 Jul
This weekend
1 Aug - 3 Aug
Next weekend
8 Aug - 10 Aug

Holiday 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, (2)
"The best place to stay! Super clean home and friendly service. I would stay here again. "
The price is S$422
includes taxes & fees
30 Jul - 31 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, (4807)
"Excellent location, cute and clean rooms!! "
The price is S$237
includes taxes & fees
6 Aug - 7 Aug
Tropical Beach Resorts
SeaSpray Resort
Living area

SeaSpray Resort

4.0 star property
8.8 out of 10, Excellent, (5)
"Nice place to stay in SK! "
The price is S$394
includes taxes & fees
4 Aug - 5 Aug
SeaSpray 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, (2153)
"The hotel rooms inside were super nice and right by the beach."
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, (316)
"Excellent property, excellent communication with Susan, i recommend it to anyone who wants to have an amazing vacation."
The Ringling Beach House
Tiny House Siesta
Living area

Tiny House Siesta

2.0 star property
8.4 out of 10, Very good, (305)
"Great place to stay. "
The price is S$188
includes taxes & fees
1 Aug - 2 Aug
Tiny House Siesta
Captiva Beach Resort
Front of property – evening/night

Captiva Beach Resort

2.0 star property
9.0 out of 10, Wonderful, (1118)
"We love the property, beautiful, clean and we love that you can walked to the beach, that is a plus. "
Captiva Beach Resort
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, (318)
"Nice place "
Sea Club I Beach Resort
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
9.8 out of 10, Exceptional, (273)
"Fun place to stay for family vacation "
The Residences at Siesta Key Beach by Hyatt Vacation Club
Kon Tiki Inn
Exterior

Kon Tiki Inn

2.0 star property
10.0 out of 10, Exceptional, (214)
"One of my fave places ever!"
The price is S$202
includes taxes & fees
30 Jul - 31 Jul
Kon Tiki Inn
Siesta Key Island Rentals
Private kitchen

Siesta Key Island Rentals

3.0 star property
9.6 out of 10, Exceptional, (38)
"I want use Expedia to select a vacation destination again."
The price is S$497
includes taxes & fees
30 Jul - 31 Jul
Siesta Key Island Rentals
Venice Beach Villas
Terrace/patio

Venice Beach Villas

3.0 star property
9.4 out of 10, Exceptional, (425)
"Everything was great. Great people to work with."
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, (181)
"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 price is S$458
includes taxes & fees
3 Aug - 4 Aug
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, (238)
"Great Location !!"
Tropical Villas of Venice Beach
Siesta Palms By the Beach
Garden

Siesta Palms By the Beach

3.5 star property
9.2 out of 10, Wonderful, (124)
"An outstanding experience — a place that leaves you with a strong desire to return."
Siesta Palms By the Beach
VH106AMelissa
Private kitchen

VH106AMelissa

3.0 star property
3.0 out of 10, (2)
VH106AMelissa
Bradenton Apartments by Landing
Exterior

Bradenton Apartments by Landing

4.0 star property
7.4 out of 10, Good, (42)
"Absolutely beautiful location has everything you need n makes you feel like home"
Bradenton Apartments by Landing
Siesta Heron Suites & Villas
Private kitchen

Siesta Heron Suites & Villas

3.5 star property
8.4 out of 10, Very good, (35)
"It was perfect for my family of 4 for our beach vacation!!"
The price is S$461
includes taxes & fees
16 Aug - 17 Aug
Siesta Heron Suites & Villas
Chadwick Cove Resort & Marina
Property grounds

Chadwick Cove Resort & Marina

4.0 star property
10.0 out of 10, Exceptional, (8)
"Wonderful place to stay, quiet, close to the beach and wonderful restaurants within walking distance! Highly recommend!!!"
The price is S$695
includes taxes & fees
19 Aug - 20 Aug
Chadwick Cove Resort & Marina
Paradise Cove at Lemon Bay
Exterior

Paradise Cove at Lemon Bay

3.5 star property
8.2 out of 10, Very good, (77)
"The property was outstanding. The owners were marvelous would definitely go back."
Paradise Cove at Lemon Bay
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

The Westin Sarasota

The Westin Sarasota

10/10 Excellent
"Hotel shuttled us to Lido Beach, St Armand’s, and the surround areas. "
Andrew 2-night trip
Posted 12 hours ago
The Westin Sarasota

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 30 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.