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

Osprey Holiday Rentals

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Our top choices for Osprey holiday 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.
The price is NZ$658
includes taxes & fees
13 Aug - 14 Aug
Charming Osprey Home

2. Charming Secluded Tented Cabin in Sarasota, Florida

Charming Secluded Tented Cabin in Sarasota, Florida
Sarasota
The price is NZ$584
includes taxes & fees
17 Aug - 18 Aug
Charming Secluded Tented Cabin in Sarasota, Florida

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

Incredible Tented Cabin with Stunning Forest Views in Sarasota, Florida
Sarasota
The price is NZ$584
includes taxes & fees
13 Aug - 14 Aug
Incredible Tented Cabin with Stunning Forest Views 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
The price is NZ$584
includes taxes & fees
18 Aug - 19 Aug
Enjoyable Secluded Tented Cabin with Fire Pit in Sarasota, Florida

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

Fantastic Tented Cabin with Fire Pit in Sarasota, Florida
Sarasota
The price is NZ$584
includes taxes & fees
18 Aug - 19 Aug
Fantastic Tented Cabin with Fire Pit in Sarasota, Florida

6. Hibiscus Suites - Gateway to Siesta Key

Hibiscus Suites - Gateway to Siesta Key
2.5 star property
Sarasota
8.6 out of 10, Excellent, (2,402 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
The price is NZ$248
includes taxes & fees
13 Aug - 14 Aug
Hibiscus Suites - Gateway to Siesta Key

7. Tropical Beach Resorts

Tropical Beach Resorts
3.5 star property
South Village
9.4 out of 10, Exceptional, (5,754 reviews)
"Great location, very close to the beach, very nice and helpful front desk."
United States
Airida
The price is NZ$304
includes taxes & fees
19 Aug - 20 Aug
Tropical Beach Resorts

8. Captiva Beach Resort

Captiva Beach Resort
3.0 star property
South Village
9.0 out of 10, Wonderful, (1,297 reviews)
"Very helpful staff and excellent beach!"
United States
Vania
The price is NZ$345
includes taxes & fees
13 Aug - 14 Aug
Captiva Beach Resort

9. A Beach Retreat

A Beach Retreat
2.5 star property
Casey Key
9.2 out of 10, Wonderful, (664 reviews)
"Lovely place on a family beach."
United States
Robert
The price is NZ$354
includes taxes & fees
27 Aug - 28 Aug
A Beach Retreat

10. SeaSpray Resort

SeaSpray Resort
4.0 star property
Siesta Key
9.6 out of 10, Exceptional, (166 reviews)
"Beautiful hotel comfortable bed nice and friendly staff!!!!"
United States
Isabel
The price is NZ$380
includes taxes & fees
1 Sept - 2 Sept
SeaSpray Resort

11. 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
The price is NZ$398
includes taxes & fees
20 Aug - 21 Aug
Tiny House Siesta

12. The Inn On Siesta Key

The Inn On Siesta Key
3.5 star property
Siesta Key
10.0 out of 10, Exceptional, (203 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 price is NZ$514
includes taxes & fees
13 Aug - 14 Aug
The Inn On Siesta Key

13. 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
Walk to the Beach and More from this Fully Renovated Unit W/ Heated Pool

14. 2BR Beach Style w Pool Beach Club Siesta 204C RVA

2BR Beach Style w Pool Beach Club Siesta 204C RVA
South Village
8.8 out of 10, Excellent, (80 reviews)
"Beautiful place"
United States
Chad
The price is NZ$793
includes taxes & fees
13 Aug - 14 Aug
2BR Beach Style w Pool Beach Club Siesta 204C RVA

15. 2BR Cook, Relax, Walk to Beach at The Beach Club Siesta Key #101E by RVA

2BR Cook, Relax, Walk to Beach at The Beach Club Siesta Key #101E by RVA
South Village
9.2 out of 10, Wonderful, (75 reviews)
"Great short stay. Close walk to the beach! "
United States
Tera S.
The price is NZ$774
includes taxes & fees
24 Aug - 25 Aug
2BR Cook, Relax, Walk to Beach at The Beach Club Siesta Key #101E by RVA

16. Siesta Key Master suite 1 Lg BR & 1 large bonus rm w bed Heated Pool & Pets ok

Siesta Key Master suite 1 Lg BR & 1 large bonus rm w bed Heated Pool & Pets ok
Ridge Wood Heights
9.4 out of 10, Exceptional, (125 reviews)
"very convenient, it was right in front of the event center that my daughter was dancing."
United States
erica
The price is NZ$483
includes taxes & fees
16 Aug - 17 Aug
Siesta Key Master suite 1 Lg BR & 1 large bonus rm w bed Heated Pool & Pets ok

17. Dream Sunsets & Coastal Bliss–Beach Club 108A / RVA

Dream Sunsets & Coastal Bliss–Beach Club 108A / RVA
South Village
9.0 out of 10, Wonderful, (77 reviews)
"We found this property to be delightful. We loved the balcony for enjoying our evenings. I would have liked to see a table on the balcony for eating at, it is FL, and I wanted to sit outside for my meals. It was a very close walk to the beach, the pool and hot tub were in excellent working condition. We enjoyed the property. We had a problem, but they had maintenance there within an hour to fix it, I call that a win for the property. "
United States
Jackie J.
The price is NZ$751
includes taxes & fees
13 Aug - 14 Aug
Dream Sunsets & Coastal Bliss–Beach Club 108A / RVA

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.
The price is NZ$557
includes taxes & fees
13 Aug - 14 Aug
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.
The price is NZ$637
includes taxes & fees
24 Aug - 25 Aug
Siesta Key Village-Suite #1: A block to the Beach!
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

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Osprey holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Osprey. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Osprey. Seeing all the best attractions is bound to make you fall in love with Osprey. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Osprey short-term rentals, that won’t be hard to do.

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Frequently asked questions

Can I find holiday rentals in Osprey?

Yes, there are holiday rentals in Osprey close to Jim Neville Marine Preserve, or you can select a more secluded option if you're looking for a relaxing stay. 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 holiday rentals that Osprey has to offer?

Siesta Key Island Rentals: This holiday home rental outside of Osprey comes with WiFi so that you can feel at home during your trip. This holiday rental also comes with free parking to give you added peace of mind.

How many holiday rentals are there in Osprey?

With 13 Expedia holiday rentals, you're guaranteed 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 such as Siesta Key Beach and Venice Beach.

What’s a holiday rental in Osprey like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Osprey. Holiday rentals feature extras such as kitchens and laundry facilities so you'll feel just like you're staying in your own home. If you're concerned about cleanliness, holiday rentals can provide a sense of security away from shared hotel lifts and lobbies bustling with people while still allowing you the experience of travel. You'll also have more space in a holiday rental than in a standard hotel, which makes a holiday rental a popular choice for families.