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, (272 reviews)
"Very clean & spacious pet friendly room. Would definitely stay there again."
United States
Brittany
$117 nightly
The price is $132
Jun 2 - Jun 3
Total with taxes and fees
Kon Tiki Inn

Tropical Beach Resorts

Tropical Beach Resorts
3.5 star property
South Village
9.4 out of 10, Exceptional, (5,466 reviews)
"Great place to stay, beach 2 minute walk."
United States
Joseph
$209 nightly
The price is $236
May 25 - May 26
Total with taxes and fees
Tropical Beach Resorts

A Beach Retreat

A Beach Retreat
2.5 star property
Casey Key
9.2 out of 10, Wonderful, (630 reviews)
"Love this place"
United States
Marialis
$221 nightly
The price is $249
May 18 - May 19
Total with taxes and fees
A Beach Retreat

Hibiscus Suites - Gateway to Siesta Key

Hibiscus Suites - Gateway to Siesta Key
2.5 star property
Sarasota
8.6 out of 10, Excellent, (2,306 reviews)
"Excellent location, great place to stay! "
United States
Lynn
$145 nightly
The price is $164
Jun 4 - Jun 5
Total with taxes and fees
Hibiscus Suites - Gateway to Siesta Key

Gulf View Condominiums

Gulf View Condominiums
3.5 star property
Manasota Key
$896 nightly
The price is $973
May 6 - May 7
Total with taxes and fees
Gulf View Condominiums

Chadwick Cove Resort & Marina

Chadwick Cove Resort & Marina
4.0 star property
Manasota Key
10.0 out of 10, Exceptional, (17 reviews)
"Great place and location "
United States
Cathy
$535 nightly
The price is $576
May 7 - May 8
Total with taxes and fees
Chadwick Cove Resort & Marina

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
$207 nightly
The price is $233
May 6 - May 7
Total with taxes and fees
Tiny House Siesta

Captiva Beach Resort

Captiva Beach Resort
3.0 star property
South Village
9.0 out of 10, Wonderful, (1,245 reviews)
"Wonderful spot to stay! Traveled solo and Captiva was perfect "
United States
Angela
$207 nightly
The price is $232
May 6 - May 7
Total with taxes and fees
Captiva Beach Resort

Casey Key Resort - Gulf Shores

Casey Key Resort - Gulf Shores
3.0 star property
Casey Key
8.4 out of 10, Very Good, (273 reviews)
"Great place"
United States
tony
$225 nightly
The price is $254
May 10 - May 11
Total with taxes and fees
Casey Key Resort - Gulf Shores

Siesta Key Island Rentals

Siesta Key Island Rentals
3.0 star property
Siesta Key
9.6 out of 10, Exceptional, (66 reviews)
"Excellent location , minute walk to local bars and supermarket. Right across from beautiful siesta key beach."
United States
Alessandra
Siesta Key Island Rentals

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
$301 nightly
The price is $341
May 6 - May 7
Total with taxes and fees
Siesta Heron Suites & Villas

Minorga Sand Dollar on the Key

Minorga Sand Dollar on the Key
3.5 star property
Siesta Key Village
$483 nightly
The price is $544
May 10 - May 11
Total with taxes and fees
Minorga Sand Dollar on the Key

SeaSpray Resort

SeaSpray Resort
4.0 star property
Siesta Key
9.6 out of 10, Exceptional, (118 reviews)
"Amazing staff, and beautiful property. Very nice place to visit and kid friendly."
United States
Ahmad
$280 nightly
The price is $316
May 10 - May 11
Total with taxes and fees
SeaSpray Resort

Sarasota Family Home Private Heated Pool Relax

Sarasota Family Home Private Heated Pool Relax
2.0 star property
Whitfield Estates
$492 nightly
The price is $556
May 27 - May 28
Total with taxes and fees
Sarasota Family Home Private Heated Pool Relax

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
$323 nightly
The price is $365
May 10 - May 11
Total with taxes and fees
The Inn On Siesta Key

Unwind Poolside + Walk to Beach! Sarasota Retreat

Unwind Poolside + Walk to Beach! Sarasota Retreat
3.0 star property
South Village
8.0 out of 10, Very Good, (1 review)
"The location of the property was excellent. The home was clean and had everything we needed to prepare breakfast in the morning. The 3 bedrooms and 3 bathrooms made it easy for the six of us wash up and get ready for dinner after a fun fill day at the walkable beach. Beach was great. Having a pool at the property was great for the 2 youngsters. We also made use of the wagon that was available to carry items to the beach., The property is nothing fancy but a great value for the money. "
United States
Eleuterio
$480 nightly
The price is $538
May 17 - May 18
Total with taxes and fees
Unwind Poolside + Walk to Beach! Sarasota Retreat

FANCY RETREREAT

FANCY RETREREAT
3.0 star property
Bradenton
$621 nightly
The price is $702
May 26 - May 27
Total with taxes and fees
FANCY RETREREAT

Siesta Heron 6 / Sunset

Siesta Heron 6 / Sunset
3.0 star property
Siesta Key
$698 nightly
The price is $788
May 10 - May 11
Total with taxes and fees
Siesta Heron 6 / Sunset

Lulu's Key House Leatherback 2/2 Downstairs

Lulu's Key House Leatherback 2/2 Downstairs
4.0 star property
Siesta Key Village
$602 nightly
The price is $678
Jun 3 - Jun 4
Total with taxes and fees
Lulu's Key House Leatherback 2/2 Downstairs

Outdoor Kitchen & Gaming Garage: Bradenton Retreat

Outdoor Kitchen & Gaming Garage: Bradenton Retreat
3.0 star property
Bradenton
$596 nightly
The price is $669
May 21 - May 22
Total with taxes and fees
Outdoor Kitchen & Gaming Garage: Bradenton 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

Find out more about Osprey

Everything you need to know about Osprey vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Osprey vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Osprey vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Osprey vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Osprey. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Osprey in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $132 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Osprey rentals

At Expedia, we put the best Osprey vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Osprey rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Osprey vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Osprey. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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 free 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 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.