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

Osprey Vacation Rentals

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Our top choices for Osprey vacation rentals

Hibiscus Suites - Gateway to Siesta Key

Hibiscus Suites - Gateway to Siesta Key
2.5 star property
Sarasota
8.6 out of 10, Excellent, (2,366 reviews)
"Excellent location, great place to stay! "
United States
Lynn
$127 nightly
The price is $144
Aug 3 - Aug 4
Total with taxes and fees
Hibiscus Suites - Gateway to Siesta Key

A Beach Retreat

A Beach Retreat
2.5 star property
Casey Key
9.2 out of 10, Wonderful, (647 reviews)
"Nice place ,clean and good location,quiet and relaxing."
United States
yohana
$184 nightly
The price is $208
Aug 3 - Aug 4
Total with taxes and fees
A Beach Retreat

Home < 1-mi Walk to Warm Mineral Springs Park!

Home < 1-mi Walk to Warm Mineral Springs Park!
3.0 star property
North Port
$395 nightly
The price is $446
Jul 12 - Jul 13
Total with taxes and fees
Home < 1-mi Walk to Warm Mineral Springs Park!

Tropical Beach Resorts

Tropical Beach Resorts
3.5 star property
South Village
9.4 out of 10, Exceptional, (5,647 reviews)
"perfect stay and location for a family!"
United States
Jessica
$175 nightly
The price is $198
Aug 9 - Aug 10
Total with taxes and fees
Tropical Beach Resorts

Casey Key Resort - Gulf Shores

Casey Key Resort - Gulf Shores
3.0 star property
Casey Key
8.4 out of 10, Very Good, (277 reviews)
"Is was a great place to stay, everything was perfect!"
United States
Tracie Costello
$179 nightly
The price is $202
Jul 12 - Jul 13
Total with taxes and fees
Casey Key Resort - Gulf Shores

SeaSpray Resort

SeaSpray Resort
4.0 star property
Siesta Key
9.6 out of 10, Exceptional, (148 reviews)
"Very nice room and easy access to an amazing beach."
United States
Michael
$299 nightly
The price is $338
Jul 19 - Jul 20
Total with taxes and fees
SeaSpray Resort

Tiny House Siesta

Tiny House Siesta
2.0 star property
Sarasota
8.4 out of 10, Very Good, (374 reviews)
"The house was clean and simple. Perfect for a couple to stay for a few nights. Not too far from the beach. Very quiet and safe area."
United States
bruno
$174 nightly
The price is $197
Jul 16 - Jul 17
Total with taxes and fees
Tiny House Siesta

Chadwick Cove Resort & Marina

Chadwick Cove Resort & Marina
4.0 star property
Manasota Key
9.4 out of 10, Exceptional, (22 reviews)
"Nic place to stay and enjoy the area"
United States
isabel
$558 nightly
The price is $601
Jul 17 - Jul 18
Total with taxes and fees
Chadwick Cove Resort & Marina

Gulf View Condominiums

Gulf View Condominiums
3.5 star property
Manasota Key
$896 nightly
The price is $973
Jul 12 - Jul 13
Total with taxes and fees
Gulf View Condominiums

Siesta Heron Suites & Villas

Siesta Heron Suites & Villas
3.5 star property
Siesta Key
8.6 out of 10, Excellent, (44 reviews)
"Clean rooms, convenient location, nice property and amenities. Simple check-in and check-out"
United States
Christopher Robert
$273 nightly
The price is $308
Jul 13 - Jul 14
Total with taxes and fees
Siesta Heron Suites & Villas

Cedar Run Resort - Roam Hospitality

Cedar Run Resort - Roam Hospitality
3.5 star property
South Bradenton
9.2 out of 10, Wonderful, (7 reviews)
"The room was very clean and well maintained/new. Staff was friendly and helpful. The air conditioner was great. The room we stayed at had lots of accessories for the beach like chairs and kid’s toys for the beach along with an umbrella. The surroundings are peaceful and beautiful. It was a great experience overall."
United States
Jose Luis Alberti
$554 nightly
The price is $626
Jul 12 - Jul 13
Total with taxes and fees
Cedar Run Resort - Roam Hospitality

Captiva Beach Resort

Captiva Beach Resort
3.0 star property
South Village
9.0 out of 10, Wonderful, (1,282 reviews)
$182 nightly
The price is $203
Aug 2 - Aug 3
Total with taxes and fees
Captiva Beach Resort

Waterfront Luxury Remodeled Studio! Pool Tiki Bar

Waterfront Luxury Remodeled Studio! Pool Tiki Bar
3.0 star property
Whitfield Estates
$194 nightly
The price is $219
Jul 13 - Jul 14
Total with taxes and fees
Waterfront Luxury Remodeled Studio! Pool Tiki Bar

The Ringling Beach House

The Ringling Beach House
3.5 star property
Siesta Key
9.0 out of 10, Wonderful, (371 reviews)
"Having everything within reach is the key to a great vacation.."
United States
Vakeshia
$274 nightly
The price is $309
Jul 12 - Jul 13
Total with taxes and fees
The Ringling Beach House

The Inn On Siesta Key

The Inn On Siesta Key
3.5 star property
Siesta Key
10.0 out of 10, Exceptional, (199 reviews)
"The room was clean and spacious with all the amenities. The location was perfect. I would highly recommend!"
United States
Amanda
$310 nightly
The price is $351
Jul 12 - Jul 13
Total with taxes and fees
The Inn On Siesta Key

Lulu's Crescent Cottage #2

Lulu's Crescent Cottage #2
2.5 star property
Siesta Key
$583 nightly
The price is $656
Jul 27 - Jul 28
Total with taxes and fees
Lulu's Crescent Cottage #2

Palm Haven at Cape Leyte

Palm Haven at Cape Leyte
2.0 star property
Siesta Key
$622 nightly
The price is $706
Jul 12 - Jul 13
Total with taxes and fees
Palm Haven at Cape Leyte

Sarasota Family Home Private Heated Pool Relax

Sarasota Family Home Private Heated Pool Relax
2.0 star property
Whitfield Estates
$482 nightly
The price is $545
Jul 16 - Jul 17
Total with taxes and fees
Sarasota Family Home Private Heated Pool Relax

Siesta Heron 6 / Sunset

Siesta Heron 6 / Sunset
3.0 star property
Siesta Key
$779 nightly
The price is $880
Aug 9 - Aug 10
Total with taxes and fees
Siesta Heron 6 / Sunset

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
$541 nightly
The price is $611
Jul 12 - Jul 13
Total with taxes and fees
Unwind Poolside + Walk to Beach! Sarasota 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 $144 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.

Explore a world of travel with Expedia

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 14 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.