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

Osprey Vacation Rentals

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals
  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings
  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Osprey vacation rentals

1. Charming Osprey Home

Charming Osprey Home
Bay Acres
10.0 out of 10, Exceptional, (2 reviews)
"We had a positive experience staying at Linda’s duplex in Osprey. Linda was a lovely host and even furnished us with beach chairs and a cabana . The place was spotless & location was convenient for us as we explored most of the Sarasota, Venice & Naples area. Highly recommended staying at this lovely duplex. "
United States
Diane S.
$355 nightly
The price is $395
Aug 17 - Aug 18
Total with taxes and fees
Charming Osprey Home

2. Enjoyable Secluded Tented Cabin with Fire Pit in Sarasota, Florida

Enjoyable Secluded Tented Cabin with Fire Pit in Sarasota, Florida
Sarasota
$318 nightly
The price is $354
Aug 18 - Aug 19
Total with taxes and fees
Enjoyable Secluded Tented Cabin with Fire Pit in Sarasota, Florida

3. Fantastic Tented Cabin with Fire Pit in Sarasota, Florida

Fantastic Tented Cabin with Fire Pit in Sarasota, Florida
Sarasota
$318 nightly
The price is $354
Aug 18 - Aug 19
Total with taxes and fees
Fantastic Tented Cabin with Fire Pit in Sarasota, Florida

4. Charming Secluded Tented Cabin in Sarasota, Florida

Charming Secluded Tented Cabin in Sarasota, Florida
Sarasota
$318 nightly
The price is $354
Aug 17 - Aug 18
Total with taxes and fees
Charming Secluded Tented Cabin in Sarasota, Florida

5. Incredible Tented Cabin with Stunning Forest Views in Sarasota, Florida

Incredible Tented Cabin with Stunning Forest Views in Sarasota, Florida
Sarasota
$318 nightly
The price is $354
Aug 17 - Aug 18
Total with taxes and fees
Incredible Tented Cabin with Stunning Forest Views in Sarasota, Florida

6. Tropical Beach Resorts

Tropical Beach Resorts
3.5 star property
South Village
9.4 out of 10, Exceptional, (5,765 reviews)
"Clean quiet and close to the beach. Best place for a quiet weekend getaway in a cute quiet beach town"
United States
Lindy
$158 nightly
The price is $179
Aug 18 - Aug 19
Total with taxes and fees
Tropical Beach Resorts

7. Tiny House Siesta

Tiny House Siesta
2.0 star property
Sarasota
8.4 out of 10, Very Good, (383 reviews)
"Great place"
United States
Mario
$198 nightly
The price is $224
Aug 21 - Aug 22
Total with taxes and fees
Tiny House Siesta

8. Hibiscus Suites - Gateway to Siesta Key

Hibiscus Suites - Gateway to Siesta Key
2.5 star property
Sarasota
8.6 out of 10, Excellent, (2,407 reviews)
"We stayed for 2 nights, the location was perfect for our needs! The beds were very comfortable and the kitchen was a added bonus!"
United States
Justine
$116 nightly
The price is $131
Aug 24 - Aug 25
Total with taxes and fees
Hibiscus Suites - Gateway to Siesta Key

9. Captiva Beach Resort

Captiva Beach Resort
3.0 star property
South Village
9.0 out of 10, Wonderful, (1,298 reviews)
"Very helpful staff and excellent beach!"
United States
Vania
$177 nightly
The price is $198
Sep 9 - Sep 10
Total with taxes and fees
Captiva Beach Resort

10. A Beach Retreat

A Beach Retreat
2.5 star property
Casey Key
9.2 out of 10, Wonderful, (666 reviews)
"Lovely place on a family beach."
United States
Robert
$205 nightly
The price is $231
Aug 27 - Aug 28
Total with taxes and fees
A Beach Retreat

11. The Inn On Siesta Key

The Inn On Siesta Key
3.5 star property
Siesta Key
10.0 out of 10, Exceptional, (204 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
The Inn On Siesta Key

12. SeaSpray Resort

SeaSpray Resort
4.0 star property
Siesta Key
9.6 out of 10, Exceptional, (167 reviews)
"Beautiful hotel comfortable bed nice and friendly staff!!!!"
United States
Isabel
$206 nightly
The price is $233
Sep 2 - Sep 3
Total with taxes and fees
SeaSpray Resort

13. [lounge like locals] walk to siesta beach +bikes

[lounge like locals] walk to siesta beach +bikes
Siesta Key
9.8 out of 10, Exceptional, (36 reviews)
"Only 10 mins walking from the Village, so easy to check in, great communication, super clean. "
United States
John
$298 nightly
The price is $303
Aug 17 - Aug 18
Total with taxes and fees
[lounge like locals] walk to siesta beach +bikes

14. Siesta Key Village-Suite #3: A Block to the Beach!

Siesta Key Village-Suite #3: A Block to the Beach!
Siesta Key Village
9.2 out of 10, Wonderful, (77 reviews)
"We loved this suite. It had everything we needed! "
United States
Danielle F.
$352 nightly
The price is $379
Aug 17 - Aug 18
Total with taxes and fees
Siesta Key Village-Suite #3: A Block to the Beach!

15. Sand Dollar Studio, King bed, Pool. Daily Rentals, Walk to Beach.

Sand Dollar Studio, King bed, Pool. Daily Rentals, Walk to Beach.
South Village
9.8 out of 10, Exceptional, (34 reviews)
"Great stay."
United States
James J.
$193 nightly
The price is $215
Aug 17 - Aug 18
Total with taxes and fees
Sand Dollar Studio, King bed, Pool. Daily Rentals, Walk to Beach.

16. Couple’s Escape-Beach Club at Siesta Key 106C by RVA

Couple’s Escape-Beach Club at Siesta Key 106C by RVA
South Village
9.4 out of 10, Exceptional, (105 reviews)
"Great birthday weekend. Awesome location to the beach and nightlife. Highly recommend."
United States
Cindy F.
$301 nightly
The price is $335
Aug 17 - Aug 18
Total with taxes and fees
Couple’s Escape-Beach Club at Siesta Key 106C by RVA

17. Siesta Key 1-Bedroom Condo | Unit 102B at The Beach Club – Steps to the Beach

Siesta Key 1-Bedroom Condo | Unit 102B at The Beach Club – Steps to the Beach
South Village
8.8 out of 10, Excellent, (90 reviews)
"It was a great experience, definitely would come back."
United States
Alicia
$326 nightly
The price is $363
Aug 24 - Aug 25
Total with taxes and fees
Siesta Key 1-Bedroom Condo | Unit 102B at The Beach Club – Steps to the Beach

18. Siesta Key, Walk to Beach. POOL VIEW. King Bed. Daily Rentals

Siesta Key, Walk to Beach. POOL VIEW. King Bed. Daily Rentals
South Village
9.6 out of 10, Exceptional, (49 reviews)
"We enjoyed our stay alot of stores n restaurants nearby, don’t need to use the car. "
United States
maureen p.
$229 nightly
The price is $255
Aug 18 - Aug 19
Total with taxes and fees
Siesta Key, Walk to Beach. POOL VIEW. King Bed. Daily Rentals

19. Jetties Pointe Cottage #5 - 408 “Casey Key”

Jetties Pointe Cottage #5 - 408 “Casey Key”
Casey Key
9.8 out of 10, Exceptional, (32 reviews)
"Amazing view and beach access, really great stay."
United States
Evan T.
$357 nightly
The price is $397
Aug 26 - Aug 27
Total with taxes and fees
Jetties Pointe Cottage #5 - 408 “Casey Key”

20. Beach Club | Renovated Condo | Steps to Crescent Beach | Heated Pool & Hot Tub | Siesta Key

Beach Club | Renovated Condo | Steps to Crescent Beach | Heated Pool & Hot Tub | Siesta Key
South Village
9.4 out of 10, Exceptional, (38 reviews)
"It was a great location with easy access to the pool, beach and entertainment! The place was clean and nice, perfect for our family!"
United States
Emily
$521 nightly
The price is $581
Aug 19 - Aug 20
Total with taxes and fees
Beach Club | Renovated Condo | Steps to Crescent Beach | Heated Pool & Hot Tub | Siesta Key
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.
Save an average of 15% on thousands of hotels when you're signed in

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 $131 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 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?

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 12 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.