Osprey Vacation Rentals

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Our top choices for Osprey vacation rentals

Kon Tiki Inn

Kon Tiki Inn
2.5 star property
Venice Island
10.0 out of 10, Exceptional, (276 reviews)
"Property is super cute and clean and has everything you need!"
United States
Vanessa
The price is CA $160
CA $181 total
includes taxes & fees
Jun 1 - Jun 2
Kon Tiki Inn

Cedar Run Resort - Roam Hospitality

Cedar Run Resort - Roam Hospitality
3.5 star property
South Bradenton
The price is CA $182
CA $459 total
includes taxes & fees
May 18 - May 19
Cedar Run Resort - Roam Hospitality

Tropical Beach Resorts

Tropical Beach Resorts
3.5 star property
South Village
9.4 out of 10, Exceptional, (5,483 reviews)
"This was such a great place to stay. The pool was GREAT and the beach access was fantastic"
United States
Laurie A
The price is CA $220
CA $285 total
includes taxes & fees
May 20 - May 21
Tropical Beach Resorts

Hibiscus Suites - Gateway to Siesta Key

Hibiscus Suites - Gateway to Siesta Key
2.5 star property
Sarasota
8.6 out of 10, Excellent, (2,311 reviews)
"Excellent location, great place to stay! "
United States
Lynn
The price is CA $204
CA $231 total
includes taxes & fees
May 25 - May 26
Hibiscus Suites - Gateway to Siesta Key

A Beach Retreat

A Beach Retreat
2.5 star property
Casey Key
9.2 out of 10, Wonderful, (633 reviews)
"Love this place"
United States
Marialis
The price is CA $272
CA $307 total
includes taxes & fees
May 18 - May 19
A Beach Retreat

Gulf View Condominiums

Gulf View Condominiums
3.5 star property
Manasota Key
The price is CA $518
CA $1,334 total
includes taxes & fees
May 30 - May 31
Gulf View Condominiums

Chadwick Cove Resort & Marina

Chadwick Cove Resort & Marina
4.0 star property
Manasota Key
9.6 out of 10, Exceptional, (19 reviews)
"Great place and location "
United States
Cathy
The price is CA $157
CA $793 total
includes taxes & fees
Jun 4 - Jun 5
Chadwick Cove Resort & Marina

Minorga Sand Dollar on the Key

Minorga Sand Dollar on the Key
3.5 star property
Siesta Key Village
The price is CA $268
CA $746 total
includes taxes & fees
May 20 - May 21
Minorga Sand Dollar on the Key

The Ringling Beach House

The Ringling Beach House
3.5 star property
Siesta Key
9.0 out of 10, Wonderful, (368 reviews)
"Having everything within reach is the key to a great vacation.."
United States
Vakeshia
The Ringling Beach House

Captiva Beach Resort

Captiva Beach Resort
3.0 star property
South Village
9.0 out of 10, Wonderful, (1,250 reviews)
"Wonderful spot to stay! Traveled solo and Captiva was perfect "
United States
Angela
The price is CA $305
CA $368 total
includes taxes & fees
Jun 11 - Jun 12
Captiva Beach Resort

Tiny House Siesta

Tiny House Siesta
2.0 star property
Sarasota
8.4 out of 10, Very good, (366 reviews)
"Cute place perfect for our holiday beach stay."
United States
Shelly
The price is CA $136
CA $320 total
includes taxes & fees
May 17 - May 18
Tiny House Siesta

Casey Key Resort - Gulf Shores

Casey Key Resort - Gulf Shores
3.0 star property
Casey Key
8.4 out of 10, Very good, (274 reviews)
"Great place"
United States
tony
The price is CA $243
CA $302 total
includes taxes & fees
May 21 - May 22
Casey Key Resort - Gulf Shores

The Inn On Siesta Key

The Inn On Siesta Key
3.5 star property
Siesta Key
10.0 out of 10, Exceptional, (198 reviews)
"This property was everything we wanted...although not on the beach, it was a short walk to the beach and chairs, umbrellas, coolers and wagons were provided to the beach. The pool area was very comfortable and clean. We like that there were only 6 units...each was unique and very clean. We stayed in "The Nook" which was perfect for our getaway."
United States
Michele
The price is CA $495
CA $635 total
includes taxes & fees
May 20 - May 21
The Inn On Siesta Key

5 Mi to Riverwalk: Bradenton Family Home w/ Yard

5 Mi to Riverwalk: Bradenton Family Home w/ Yard
3.0 star property
Bayshore Gardens
5 Mi to Riverwalk: Bradenton Family Home w/ Yard

Siesta Heron Suites & Villas

Siesta Heron Suites & Villas
3.5 star property
Siesta Key
8.4 out of 10, Very good, (42 reviews)
"Clean rooms, convenient location, nice property and amenities. Simple check-in and check-out"
United States
Christopher Robert
The price is CA $160
CA $457 total
includes taxes & fees
May 19 - May 20
Siesta Heron Suites & Villas

FANCY RETREREAT

FANCY RETREREAT
3.0 star property
Bradenton
The price is CA $480
CA $885 total
includes taxes & fees
May 26 - May 27
FANCY RETREREAT

Sarasota Family Home Private Heated Pool Relax

Sarasota Family Home Private Heated Pool Relax
2.0 star property
Whitfield Estates
The price is CA $377
CA $773 total
includes taxes & fees
May 18 - May 19
Sarasota Family Home Private Heated Pool Relax

Siesta Sands Beach Resort 4th Floor With Elevator

Siesta Sands Beach Resort 4th Floor With Elevator
3.5 star property
South Village
The price is CA $487
CA $1,070 total
includes taxes & fees
May 21 - May 22
Siesta Sands Beach Resort 4th Floor With Elevator

SeaSpray Resort

SeaSpray Resort
4.0 star property
Siesta Key
9.6 out of 10, Exceptional, (125 reviews)
"Enjoyed our stay great location easy walk to village and the beach"
United States
Gregory
The price is CA $394
CA $445 total
includes taxes & fees
Jun 10 - Jun 11
SeaSpray Resort

Siesta Heron 7

Siesta Heron 7
3.0 star property
Siesta Key
The price is CA $970
CA $1,602 total
includes taxes & fees
May 19 - May 20
Siesta Heron 7
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

Find out more about Osprey

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Osprey. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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 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 vacation rentals in Osprey?

Siesta Key Island Rentals: This vacation home rental near Osprey comes with WiFi so you can feel at home during your trip. This vacation rental also comes with free parking to give you added peace of mind.

How many vacation rentals are there in Osprey?

With 16 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 Venice 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.