Osprey Vacation Rentals

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Check prices for these dates

Tonight
Jan 9 - Jan 10
Tomorrow
Jan 10 - Jan 11
This weekend
Jan 9 - Jan 11
Next weekend
Jan 16 - Jan 18

Our top choices for Osprey vacation rentals

Living area
Tiny House Siesta

Mobile Home in Sarasota

Tiny House Siesta
2.0 star property
8.4 out of 10, Very Good, (346 reviews)
"Enjoyable stay. "
United States
Lori
The price is P5,860
P13,813 total
includes taxes & fees
Jan 16 - Jan 17
Tiny House Siesta
Living area
Siesta Heron Suites & Villas

Vacation Home in Siesta Key

Siesta Heron Suites & Villas
3.5 star property
8.6 out of 10, Excellent, (38 reviews)
"Clean pool great apartment could use more seating in living room. Beach chairs was cool patio was awesome parking good water pressure great bed clean and comfy "
United States
jason
The price is P8,972
P22,044 total
includes taxes & fees
Jan 11 - Jan 12
Siesta Heron Suites & Villas
Property grounds
Tropical Beach Resorts

Aparthotel in South Village

Tropical Beach Resorts
3.5 star property
9.4 out of 10, Exceptional, (5,214 reviews)
"Great place to stay. Very nice getaway. "
United States
Joyeeta
The price is P8,503
P10,946 total
includes taxes & fees
Jan 11 - Jan 12
Tropical Beach Resorts
In-room safe, iron/ironing board, free WiFi
SeaSpray Resort

Aparthotel in Siesta Key

SeaSpray Resort
4.0 star property
9.4 out of 10, Exceptional, (84 reviews)
"Very clean very quiet and a great location to the beach."
United States
Dave
The price is P20,065
P22,674 total
includes taxes & fees
Jan 11 - Jan 12
SeaSpray Resort
Exterior
Chadwick Cove Resort & Marina

Condo in Manasota Key

Chadwick Cove Resort & Marina
4.0 star property
10.0 out of 10, Exceptional, (15 reviews)
"Great place and location "
United States
Cathy
The price is P4,844
P32,060 total
includes taxes & fees
Jan 12 - Jan 13
Chadwick Cove Resort & Marina
Terrace/patio
Kon Tiki Inn

Aparthotel in Venice Island

Kon Tiki Inn
2.5 star property
10.0 out of 10, Exceptional, (250 reviews)
"Great place! "
United States
Michelle
The price is P11,768
P13,298 total
includes taxes & fees
Jan 29 - Jan 30
Kon Tiki Inn
Property grounds
The Residences at Siesta Key Beach by Hyatt Vacation Club

Aparthotel in South Village

The Residences at Siesta Key Beach by Hyatt Vacation Club
3.5 star property
9.6 out of 10, Exceptional, (306 reviews)
"The rooms were perfect, and the staff was great. The location was perfect and peaceful"
United States
Marybeth
The price is P20,094
P25,716 total
includes taxes & fees
Jan 19 - Jan 20
The Residences at Siesta Key Beach by Hyatt Vacation Club
Outdoor pool, a heated pool, open 7:00 AM to 8:00 PM, sun loungers
Hibiscus Suites - Gateway to Siesta Key

Aparthotel in Sarasota

Hibiscus Suites - Gateway to Siesta Key
2.5 star property
8.6 out of 10, Excellent, (2,227 reviews)
"Very nice place !"
United States
Ivette
The price is P14,815
P16,741 total
includes taxes & fees
Feb 1 - Feb 2
Hibiscus Suites - Gateway to Siesta Key
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
"The manager was very friendly, very helpful. He helped us check in early since we had our 5 month old and pet. They even went as far as allowing me to store my breastmilk in there freezer and providing a crib. We will stay there again! Also have great rates!"
Bryanna 2-night trip
Posted 20 hours ago
Kompose Boutique Hotel

Find out more about Osprey

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

  • View our selection of featured holiday rentals in Osprey
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  • Enter your travel dates to view the best deals on holiday rentals in Osprey while they last

Look no further and take a look at our great range of rental properties in Osprey!

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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 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?

Charming Florida Beach Home w King Bed Patio: Visitors give good reviews to this Osprey vacation home rental, which offers a garden and free WiFi to help you feel comfortable in your new surroundings. This vacation rental also comes with free parking to give you added peace of mind.

How many vacation rentals are there in Osprey?

With 18 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.