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.
$396 nightly
The price is $442
Sep 8 - Sep 9
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
Sep 3 - Sep 4
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
Sep 3 - Sep 4
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
Sep 7 - Sep 8
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
Sep 7 - Sep 8
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, (5,826 reviews)
"This place is awesome, super clean close to the beach and the pool small But completely renovated and great"
United States
Diana
$141 nightly
The price is $160
Sep 3 - Sep 4
Total with taxes and fees
Tropical Beach Resorts

7. Hibiscus Suites - Gateway to Siesta Key

Hibiscus Suites - Gateway to Siesta Key
2.5 star property
Sarasota
8.6 out of 10, Excellent, (2,434 reviews)
"This place was perfect!"
United States
Kat
$106 nightly
The price is $120
Sep 23 - Sep 24
Total with taxes and fees
Hibiscus Suites - Gateway to Siesta Key

8. Captiva Beach Resort

Captiva Beach Resort
3.0 star property
South Village
9.0 out of 10, Wonderful, (1,303 reviews)
"The proximity to the beach and the ambient of the place"
United States
natalia
$165 nightly
The price is $185
Sep 3 - Sep 4
Total with taxes and fees
Captiva Beach Resort

9. SeaSpray Resort

SeaSpray Resort
4.0 star property
Siesta Key
9.6 out of 10, Exceptional, (175 reviews)
"Beautiful hotel comfortable bed nice and friendly staff!!!!"
United States
Isabel
$217 nightly
The price is $245
Sep 8 - Sep 9
Total with taxes and fees
SeaSpray Resort

10. A Beach Retreat

A Beach Retreat
2.5 star property
Casey Key
9.2 out of 10, Wonderful, (671 reviews)
"Lovely place on a family beach."
United States
Robert
$205 nightly
The price is $231
Sep 7 - Sep 8
Total with taxes and fees
A Beach Retreat

11. 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
$197 nightly
The price is $223
Sep 18 - Sep 19
Total with taxes and fees
Tiny House Siesta

12. 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
Tropical Villas of Venice Beach

13. The Inn On Siesta Key

The Inn On Siesta Key
3.5 star property
Siesta Key
10.0 out of 10, Exceptional, (206 reviews)
"The property was perfect. Walk to down town and the beach. Loved the provisions for the beach which made it so convenient. Room was super clean and overall the property was well maintained."
United States
Stephen
$266 nightly
The price is $301
Sep 3 - Sep 4
Total with taxes and fees
The Inn On Siesta Key

14. 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
$295 nightly
The price is $333
Sep 7 - Sep 8
Total with taxes and fees
Siesta Key Island Rentals

15. Casey Key Beachfront Escape: Charming 1BR Cottage

Casey Key Beachfront Escape: Charming 1BR Cottage
Casey Key
9.4 out of 10, Exceptional, (131 reviews)
"A beautiful location and super comfortable!"
United States
K B.
$409 nightly
The price is $456
Sep 3 - Sep 4
Total with taxes and fees
Casey Key Beachfront Escape: Charming 1BR Cottage

16. Private Beach, Gulf View from Balcony, Heated Pools, $185 Free Activities Daily, Outdoor Workout

Private Beach, Gulf View from Balcony, Heated Pools, $185 Free Activities Daily, Outdoor Workout
South Village
9.8 out of 10, Exceptional, (97 reviews)
"It was all great, really enjoyed our stay."
United States
Roger K.
$707 nightly
The price is $789
Sep 4 - Sep 5
Total with taxes and fees
Private Beach, Gulf View from Balcony, Heated Pools, $185 Free Activities Daily, Outdoor Workout

17. 2BR Beach Style w Pool Beach Club Siesta 204C RVA

2BR Beach Style w Pool Beach Club Siesta 204C RVA
South Village
9.0 out of 10, Wonderful, (81 reviews)
"Good"
United States
Gelsy
$426 nightly
The price is $474
Sep 8 - Sep 9
Total with taxes and fees
2BR Beach Style w Pool Beach Club Siesta 204C RVA

18. Walk to the Beach and More from this Fully Renovated Unit W/ Heated Pool

Walk to the Beach and More from this Fully Renovated Unit W/ Heated Pool
Siesta Key
9.4 out of 10, Exceptional, (99 reviews)
"Great location"
United States
Daphane
$357 nightly
The price is $398
Sep 3 - Sep 4
Total with taxes and fees
Walk to the Beach and More from this Fully Renovated Unit W/ Heated Pool

19. 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)
$300 nightly
The price is $334
Sep 8 - Sep 9
Total with taxes and fees
Couple’s Escape-Beach Club at Siesta Key 106C by RVA

20. The Beach Club at Siesta Key #106D Resort by RVA

The Beach Club at Siesta Key #106D Resort by RVA
South Village
9.4 out of 10, Exceptional, (62 reviews)
"Everything was great. It was a good location to the beach."
United States
Angela A.
$433 nightly
The price is $483
Sep 3 - Sep 4
Total with taxes and fees
The Beach Club at Siesta Key #106D Resort by RVA
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 $120 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?

Jim Neville Marine Preserve and Turtle Beach are a couple of scenic spots to enjoy the outdoors, whereas Historic Spanish Point is one of the cultural attractions. 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.