A marina with docked boats, a wooden bridge, and a building with a red roof.

Osprey Vacation Rentals

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Check prices for these dates

In two weeks
Nov 27 - Nov 29
In two months
Jan 8 - Jan 10
In three months
Feb 5 - Feb 7
In four months
Mar 5 - Mar 7

Our top choices for Osprey vacation rentals

A pool area with palm trees, lounge chairs, and a stone pathway.

1. Tropical Beach Resorts

Tropical Beach Resorts
3.5 star property
South Village
9.4 out of 10, Exceptional, (6,060 reviews)
"Great resort and location!"
United States
Christine
The price is ₩183,630
₩242,162 total
includes taxes & fees
Nov 16 - Nov 17
Tropical Beach Resorts
A living room with a view of the ocean, a ceiling fan, and a wooden coffee table.

2. A Beach Retreat

A Beach Retreat
2.5 star property
Casey Key
9.2 out of 10, Wonderful, (701 reviews)
"Enjoyed our stay"
United States
Robin
The price is ₩245,733
₩277,685 total
includes taxes & fees
Dec 6 - Dec 7
A Beach Retreat
An outdoor patio with a grill, white chairs, and a red umbrella.

3. Hibiscus Suites - Gateway to Siesta Key

Hibiscus Suites - Gateway to Siesta Key
2.5 star property
Sarasota
8.8 out of 10, Excellent, (2,485 reviews)
"This place was perfect!"
United States
Kat
The price is ₩182,788
₩206,550 total
includes taxes & fees
Nov 16 - Nov 17
Hibiscus Suites - Gateway to Siesta Key
A beach with white sand, wooden beach chairs, and a clear blue sky.

4. Captiva Beach Resort

Captiva Beach Resort
3.0 star property
South Village
9.0 out of 10, Wonderful, (1,337 reviews)
"Great location that's very close to the beach, large and clean room with a kitchenette, and very helpful and friendly staff. Loved our stay here!"
United States
Bob
The price is ₩205,309
₩254,604 total
includes taxes & fees
Nov 15 - Nov 16
Captiva Beach Resort
A beach with footprints in the sand and waves approaching the shore.

5. Casey Key Resort

Casey Key Resort
3.0 star property
Casey Key
8.4 out of 10, Very good, (288 reviews)
"My boyfriend and I had a wonderful time. Easy late check in. Nice clean room. Property beautiful. Private beach beautiful. We definitely plan to come back and have family join."
United States
Jamie
The price is ₩230,267
₩283,245 total
includes taxes & fees
Dec 10 - Dec 11
Casey Key Resort
A two-story house with a balcony, a visible air conditioning unit, and a driveway leading to the entrance.

6. SeaSpray Resort

SeaSpray Resort
4.0 star property
Siesta Key
9.6 out of 10, Exceptional, (209 reviews)
"The room was clean and had all of the necessities. The place was adorable and the location is great!"
United States
Dolores
The price is ₩298,849
₩337,699 total
includes taxes & fees
Nov 18 - Nov 19
SeaSpray Resort
A colorful playhouse with a green exterior and a blue chair with a striped umbrella nearby.

7. Tiny House Siesta

Tiny House Siesta
2.0 star property
Sarasota
8.4 out of 10, Very good, (392 reviews)
"It's a very cute tiny house in a great location. Walking distance to Siesta Keys beach and numerous restaurants. I loved the decor in the sea turtle house. I would definitely stay here again next time I'm in Florida."
United States
Staci
The price is ₩81,773
₩272,271 total
includes taxes & fees
Nov 22 - Nov 23
Tiny House Siesta
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

Kompose Boutique Hotel

Kompose Boutique Hotel

10/10 Excellent
"Excelente servicio e instalaciones"
Anibal 6-night trip
Posted 5 hours ago
Kompose Boutique Hotel

Find out more about Osprey

Search for Vacation rentals in Osprey on Expedia.co.uk! You can easily find your home rentals, villas, Vacation apartments in Osprey using one of the methods below:

  • View our selection of featured Vacation rentals in Osprey
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Look no further and take a look at our great range of rental properties in Osprey!

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 top-notch restaurants in this destination. While you're in the area, you can also enjoy the lively bars and shops.

What are some of the best vacation rentals in Osprey?

Tropical Villas of Venice Beach: This vacation home rental near Osprey is located near the beach and has an outdoor pool, a terrace, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a fridge, a microwave, and kitchenware. Make the most of the garden in this rental home to help you unwind.

How many vacation rentals are there in Osprey?

With 13 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?

Turtle Beach and Nokomis Beach are a couple of scenic spots to enjoy the outdoors, whereas Historic Spanish Point is one of the cultural attractions. 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.