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

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 27 - Aug 28
Total with taxes and fees
Charming Osprey Home

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

Fantastic Tented Cabin with Fire Pit in Sarasota, Florida
Sarasota
10.0 out of 10, Exceptional, (1 review)
$318 nightly
The price is $354
Aug 27 - Aug 28
Total with taxes and fees
Fantastic Tented Cabin with Fire Pit in Sarasota, Florida

3. Charming Secluded Tented Cabin in Sarasota, Florida

Charming Secluded Tented Cabin in Sarasota, Florida
Sarasota
$318 nightly
The price is $354
Aug 27 - Aug 28
Total with taxes and fees
Charming Secluded Tented Cabin in Sarasota, Florida

4. 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 27 - Aug 28
Total with taxes and fees
Enjoyable Secluded Tented Cabin with Fire Pit 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 27 - Aug 28
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, (5,794 reviews)
"Great place to visit!"
United States
Margaret Lai Ling
$134 nightly
The price is $152
Aug 27 - Aug 28
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, (384 reviews)
"Great place"
United States
Mario
$198 nightly
The price is $224
Sep 1 - Sep 2
Total with taxes and fees
Tiny House Siesta

8. Siesta Key Island Rentals

Siesta Key Island Rentals
3.0 star property
Siesta Key
9.6 out of 10, Exceptional, (80 reviews)
"Great location, very clean and spacious."
United States
Jason
$290 nightly
The price is $328
Aug 27 - Aug 28
Total with taxes and fees
Siesta Key Island Rentals

9. Tropical Villas of Venice Beach

Tropical Villas of Venice Beach
3.5 star property
Venice Island
9.6 out of 10, Exceptional, (268 reviews)
"It was amazing and way beyond what I thought. Easy walk to beach(0.4 mikes) and shops. Private location with small pool. Just what you need."
United States
Christina
$118 nightly
The price is $133
Aug 27 - Aug 28
Total with taxes and fees
Tropical Villas of Venice Beach

10. Captiva Beach Resort

Captiva Beach Resort
3.0 star property
South Village
9.0 out of 10, Wonderful, (1,300 reviews)
"The proximity to the beach and the ambient of the place"
United States
natalia
$163 nightly
The price is $182
Sep 10 - Sep 11
Total with taxes and fees
Captiva Beach Resort

11. Hibiscus Suites - Gateway to Siesta Key

Hibiscus Suites - Gateway to Siesta Key
2.5 star property
Sarasota
8.6 out of 10, Excellent, (2,425 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
$124 nightly
The price is $140
Sep 1 - Sep 2
Total with taxes and fees
Hibiscus Suites - Gateway to Siesta Key

12. A Beach Retreat

A Beach Retreat
2.5 star property
Casey Key
9.2 out of 10, Wonderful, (670 reviews)
$205 nightly
The price is $231
Aug 27 - Aug 28
Total with taxes and fees
A Beach Retreat

13. [escape to paradise] siesta key beach getaway

[escape to paradise] siesta key beach getaway
Siesta Key
9.8 out of 10, Exceptional, (32 reviews)
"We appreciated the excellent location and good service. However, the listing should provide clearer and more accurate information about the layout, especially that the only bathroom is located inside one of the bedrooms. This arrangement significantly reduces privacy and makes the two-bedroom setup less convenient than expected. The additional $40-per-person bicycle fee should also be clearly stated in the listing."
United States
Tatyana
$315 nightly
The price is $321
Aug 30 - Aug 31
Total with taxes and fees
[escape to paradise] siesta key beach getaway

14. SeaSpray Resort

SeaSpray Resort
4.0 star property
Siesta Key
9.6 out of 10, Exceptional, (174 reviews)
"Beautiful hotel comfortable bed nice and friendly staff!!!!"
United States
Isabel
$198 nightly
The price is $224
Sep 1 - Sep 2
Total with taxes and fees
SeaSpray Resort

15. 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
$302 nightly
The price is $342
Aug 27 - Aug 28
Total with taxes and fees
The Inn On Siesta Key

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

[lounge like locals] walk to siesta beach +bikes
Siesta Key
9.8 out of 10, Exceptional, (37 reviews)
"Thanks for a great stay, Jayme! Perfect location and extremely accurate Vrbo listing! Beds super comfy!"
United States
Sue H.
$325 nightly
The price is $332
Aug 27 - Aug 28
Total with taxes and fees
[lounge like locals] walk to siesta beach +bikes

17. Dolphin Villa - Pool - Steps to Siesta Key Village

Dolphin Villa - Pool - Steps to Siesta Key Village
Siesta Key Village
9.4 out of 10, Exceptional, (17 reviews)
"Great location to downtown, beach. Kitchen and furnishing updated and in great condition. Negatives would be the lock on the backdoor, air conditioning from the ceiling that could not be controlled from our apartment. The pool was great and had plenty of seating. Only issue with the Dolphin apartment is the many windows, which kind of made it feel like living in a fish bowl. That might not be an issues for others. "
United States
Sandra C.
$353 nightly
The price is $369
Aug 31 - Sep 1
Total with taxes and fees
Dolphin Villa - Pool - Steps to Siesta Key Village

18. 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
Sep 2 - Sep 3
Total with taxes and fees
Couple’s Escape-Beach Club at Siesta Key 106C by RVA

19. Siesta Key Village-Suite #1: A block to the Beach!

Siesta Key Village-Suite #1: A block to the Beach!
Siesta Key Village
9.8 out of 10, Exceptional, (47 reviews)
"Great place to stay"
United States
Brad S.
$358 nightly
The price is $386
Aug 30 - Aug 31
Total with taxes and fees
Siesta Key Village-Suite #1: A block to the Beach!

20. 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.
$303 nightly
The price is $337
Aug 27 - Aug 28
Total with taxes and fees
Siesta Key, Walk to Beach. POOL VIEW. King Bed. Daily Rentals
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 $133 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 13 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.