Osprey Vacation Rentals

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Check prices for these dates

Tonight
Jan 11 - Jan 12
Tomorrow
Jan 12 - Jan 13
Next weekend
Jan 16 - Jan 18
In two weeks
Jan 23 - Jan 25

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 P5,867
P13,829 total
includes taxes & fees
Jan 19 - Jan 20
Tiny House Siesta
Property grounds
Tropical Beach Resorts

Aparthotel in South Village

Tropical Beach Resorts
3.5 star property
9.4 out of 10, Exceptional, (5,218 reviews)
"Great place to stay. Very nice getaway. "
United States
Joyeeta
The price is P8,512
P10,958 total
includes taxes & fees
Jan 12 - Jan 13
Tropical Beach Resorts
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 P4,849
P32,097 total
includes taxes & fees
Jan 12 - Jan 13
Chadwick Cove Resort & Marina
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 P9,064
P22,162 total
includes taxes & fees
Jan 12 - Jan 13
Siesta Heron Suites & Villas
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 P11,782
P13,313 total
includes taxes & fees
Jan 20 - Jan 21
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 P20,117
P25,745 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, (2,228 reviews)
"Very nice place !"
United States
Ivette
The price is P14,832
P16,760 total
includes taxes & fees
Feb 1 - Feb 2
Hibiscus Suites - Gateway to Siesta Key
Premium bedding, pillowtop beds, individually decorated
A Beach Retreat

Condo in Casey Key

A Beach Retreat
2.5 star property
9.2 out of 10, Wonderful, (584 reviews)
"Room was nice & staff was friendly. "
United States
Paula
A Beach Retreat
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

Hyatt Place Sarasota/Bradenton Airport

Hyatt Place Sarasota/Bradenton Airport

10/10 Excellent
"Everything was good. Easy check in. Room is nice. "
Theodore 2-night trip
Posted 2 days ago
Hyatt Place Sarasota/Bradenton Airport

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
  • Use the map to find apartments and other holiday homes in the Osprey neighbourhood you prefer
  • 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.