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

Osprey Vacation Rentals

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Check prices for these dates

In two weeks
Aug 14 - Aug 16
In two months
Sep 25 - Sep 27
In three months
Oct 23 - Oct 25
In four months
Nov 20 - Nov 22

Our top choices for Osprey vacation rentals

Outdoor pool, a heated pool, open 7:00 AM to 8:00 PM, sun loungers

1. Hibiscus Suites - Gateway to Siesta Key

Hibiscus Suites - Gateway to Siesta Key
2.5 star property
Sarasota
8.6 out of 10, Excellent, (2,389 reviews)
"Staff was helpful, and room were very clean"
United States
Doris Isabel
$115 nightly
The price is $129
Aug 9 - Aug 10
Total with taxes and fees
Hibiscus Suites - Gateway to Siesta Key
Property grounds

2. Tropical Beach Resorts

Tropical Beach Resorts
3.5 star property
South Village
9.4 out of 10, Exceptional, (5,705 reviews)
"Great location, very close to the beach, very nice and helpful front desk."
United States
Airida
$175 nightly
The price is $198
Aug 23 - Aug 24
Total with taxes and fees
Tropical Beach Resorts
Cabin (Tiny House - The Siesta) | Living area | Flat-screen TV, Netflix, streaming services

3. Tiny House Siesta

Tiny House Siesta
2.0 star property
Sarasota
8.4 out of 10, Very Good, (382 reviews)
"Great place"
United States
Mario
$200 nightly
The price is $226
Aug 6 - Aug 7
Total with taxes and fees
Tiny House Siesta
Beachside One Bedroom Suite | Premium bedding, pillowtop beds, iron/ironing board (on request)

4. A Beach Retreat

A Beach Retreat
2.5 star property
Casey Key
9.2 out of 10, Wonderful, (657 reviews)
"The beach is right there, very clean and nice place."
United States
Maryna
$205 nightly
The price is $231
Aug 3 - Aug 4
Total with taxes and fees
A Beach Retreat
Front of property - evening/night

5. Captiva Beach Resort

Captiva Beach Resort
3.0 star property
South Village
9.0 out of 10, Wonderful, (1,294 reviews)
"Very helpful staff and excellent beach!"
United States
Vania
$173 nightly
The price is $193
Aug 10 - Aug 11
Total with taxes and fees
Captiva Beach Resort
Outdoor wedding area

6. Casey Key Resort - Gulf Shores

Casey Key Resort - Gulf Shores
3.0 star property
Casey Key
8.4 out of 10, Very Good, (280 reviews)
"Is was a great place to stay, everything was perfect!"
United States
Tracie Costello
$189 nightly
The price is $213
Aug 8 - Aug 9
Total with taxes and fees
Casey Key Resort - Gulf Shores
House (2 Bedrooms) | Interior

7. Siesta Heron 6 / Sunset

Siesta Heron 6 / Sunset
3.0 star property
Siesta Key
$675 nightly
The price is $762
Aug 25 - Aug 26
Total with taxes and fees
Siesta Heron 6 / Sunset
Apartment (1 Bedroom) | Interior

8. Explore Sarasota: Condo w/ Pool Access, Near Dtwn

Explore Sarasota: Condo w/ Pool Access, Near Dtwn
3.5 star property
Sarasota
$261 nightly
The price is $295
Aug 3 - Aug 4
Total with taxes and fees
Explore Sarasota: Condo w/ Pool Access, Near Dtwn
House, Lakeside | Living area | 39-inch flat-screen TV with digital channels, TV, streaming services

9. 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
$296 nightly
The price is $334
Aug 3 - Aug 4
Total with taxes and fees
Siesta Heron Suites & Villas
Superior Suite, 2 Bedrooms | In-room safe, iron/ironing board, WiFi (free)

10. SeaSpray Resort

SeaSpray Resort
4.0 star property
Siesta Key
9.6 out of 10, Exceptional, (156 reviews)
"We love the hotel the cleaners the facility was amazing"
United States
yisel
$259 nightly
The price is $293
Aug 31 - Sep 1
Total with taxes and fees
SeaSpray Resort
Condo (Beach Club Modern Condo C Building) | Exterior

11. Beach Club Modern Condo C Bldg

Beach Club Modern Condo C Bldg
3.0 star property
South Village
$526 nightly
The price is $595
Aug 19 - Aug 20
Total with taxes and fees
Beach Club Modern Condo C Bldg
5365 Calle Florida, Siesta Key, FL W/Pool | Private kitchen

12. Siesta Key Island Rentals

Siesta Key Island Rentals
3.0 star property
Siesta Key
9.6 out of 10, Exceptional, (74 reviews)
"Great location, very clean and spacious."
United States
Jason
$335 nightly
The price is $378
Aug 2 - Aug 3
Total with taxes and fees
Siesta Key Island Rentals
Beach nearby, white sand, beach umbrellas, beach towels

13. The Inn On Siesta Key

The Inn On Siesta Key
3.5 star property
Siesta Key
10.0 out of 10, Exceptional, (201 reviews)
"We had a wonderful stay at The Inn on Siesta Key. The Cabana was perfect for our family of 4, very clean and well equipped kitchen. The beds are very comfortable, and we enjoyed our morning coffee on the porch area. The property is fully equipped for the beach with chairs, towels, umbrellas, coolers, ice, and these great wagons to haul it all to the beach. Beaches are a short walk and amazing. The property is also a very short walk to The Village for shopping and dining. Paige checked us in and...
United States
Lisa
$286 nightly
The price is $323
Aug 2 - Aug 3
Total with taxes and fees
The Inn On Siesta Key
House | 4 bedrooms, high-speed internet

14. Coastal Home w Hot Tub Firepit and Music Lounge

Coastal Home w Hot Tub Firepit and Music Lounge
2.0 star property
Siesta Key
$648 nightly
The price is $732
Aug 5 - Aug 6
Total with taxes and fees
Coastal Home w Hot Tub Firepit and Music Lounge
Classic Bungalow, 3 Bedrooms, Patio | Living area | 43-inch TV with digital channels

15. The Linwood Canopy

The Linwood Canopy
Sarasota Springs
$425 nightly
The price is $483
Aug 1 - Aug 2
Total with taxes and fees
The Linwood Canopy
Terrace/patio

16. Palm Haven at Cape Leyte

Palm Haven at Cape Leyte
2.0 star property
Siesta Key
$625 nightly
The price is $710
Aug 5 - Aug 6
Total with taxes and fees
Palm Haven at Cape Leyte
Interior

17. Beach Road - Bari

Beach Road - Bari
3.0 star property
Siesta Key
$525 nightly
The price is $593
Aug 8 - Aug 9
Total with taxes and fees
Beach Road - Bari
House (3 Bedrooms) | Interior

18. 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
$602 nightly
The price is $680
Aug 5 - Aug 6
Total with taxes and fees
Unwind Poolside + Walk to Beach! Sarasota Retreat
Outdoor pool, pool umbrellas, sun loungers

19. 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
$537 nightly
The price is $607
Aug 2 - Aug 3
Total with taxes and fees
Cedar Run Resort - Roam Hospitality
Luxury Condo, Beach View | Balcony

20. Gulf View Condominiums

Gulf View Condominiums
3.5 star property
Manasota Key
$896 nightly
The price is $973
Aug 8 - Aug 9
Total with taxes and fees
Gulf View Condominiums
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

Inn at the Beach

Inn at the Beach

10/10 Excellent
"What a fabulous experience we had! The location, staff and room were all perfect. The only thing that I would change is the check in time, 4 pm is a bit late. We were offered chairs, umbrellas and towels for the beach but opted to go downtown. Love the shops, food and cleanliness! Sorry we couldn’t stay another day. We highly recommend the Inn by the beach!"
Wendy 1-night trip
Posted 1 hour ago
Inn at the Beach

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 $129 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.