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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 AU$607
includes taxes & fees
13 Sept - 14 Sept
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
The price is AU$504
includes taxes & fees
15 Sept - 16 Sept
Enjoyable Secluded Tented Cabin with Fire Pit 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 AU$504
includes taxes & fees
15 Sept - 16 Sept
Incredible Tented Cabin with Stunning Forest Views in Sarasota, Florida

4. 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)
The price is AU$504
includes taxes & fees
15 Sept - 16 Sept
Fantastic Tented Cabin with Fire Pit in Sarasota, Florida

5. Charming Secluded Tented Cabin in Sarasota, Florida

Charming Secluded Tented Cabin in Sarasota, Florida
Sarasota
The price is AU$504
includes taxes & fees
15 Sept - 16 Sept
Charming Secluded Tented Cabin in Sarasota, Florida

6. Tropical Beach Resorts

Tropical Beach Resorts
3.5 star property
South Village
9.4 out of 10, Exceptional, (5,858 reviews)
"This place is awesome, super clean close to the beach and the pool small But completely renovated and great"
United States
Diana
The price is AU$248
includes taxes & fees
27 Sept - 28 Sept
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
The price is AU$318
includes taxes & fees
12 Sept - 13 Sept
Tiny House Siesta

8. Hibiscus Suites - Gateway to Siesta Key

Hibiscus Suites - Gateway to Siesta Key
2.5 star property
Sarasota
8.8 out of 10, Excellent, (2,442 reviews)
"This place was perfect!"
United States
Kat
The price is AU$176
includes taxes & fees
17 Sept - 18 Sept
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, (1,306 reviews)
"Clean room, beach access, easy parking, friendly staff"
United States
Karla
The price is AU$249
includes taxes & fees
13 Sept - 14 Sept
Captiva Beach Resort

10. 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
Siesta Key Island Rentals

11. A Beach Retreat

A Beach Retreat
2.5 star property
Casey Key
9.2 out of 10, Wonderful, (677 reviews)
"Great stay!!"
United States
Genghis
The price is AU$288
includes taxes & fees
20 Sept - 21 Sept
A Beach Retreat

12. SeaSpray Resort

SeaSpray Resort
4.0 star property
Siesta Key
9.6 out of 10, Exceptional, (178 reviews)
The price is AU$326
includes taxes & fees
28 Sept - 29 Sept
SeaSpray Resort

13. 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.
The price is AU$824
includes taxes & fees
5 Oct - 6 Oct
Casey Key Beachfront Escape: Charming 1BR Cottage

14. 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 AU$462
includes taxes & fees
16 Sept - 17 Sept
Couple’s Escape-Beach Club at Siesta Key 106C by RVA

15. 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.
The price is AU$509
includes taxes & fees
29 Sept - 30 Sept
Dolphin Villa - Pool - Steps to Siesta Key Village

16. 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 AU$525
includes taxes & fees
23 Sept - 24 Sept
Siesta Key Village-Suite #1: A block to the Beach!

17. Siesta Key 1-Bedroom Condo w Private Patio | The Beach Club Vacation Rental

Siesta Key 1-Bedroom Condo w Private Patio | The Beach Club Vacation Rental
South Village
8.8 out of 10, Excellent, (89 reviews)
"Great location and easy access to the beach."
United States
Erica B.
The price is AU$487
includes taxes & fees
22 Sept - 23 Sept
Siesta Key 1-Bedroom Condo w Private Patio | The Beach Club Vacation Rental

18. Bright & Beachy–Beach Club Siesta Key 100A by RVA

Bright & Beachy–Beach Club Siesta Key 100A by RVA
South Village
9.0 out of 10, Wonderful, (119 reviews)
"The pool and proximity to the beach are great "
United States
Evan C.
The price is AU$475
includes taxes & fees
11 Sept - 12 Sept
Bright & Beachy–Beach Club Siesta Key 100A by RVA

19. Beachside Studio Located Across from Main Beach and Half Mile to Village

Beachside Studio Located Across from Main Beach and Half Mile to Village
Sarasota
8.8 out of 10, Excellent, (170 reviews)
"The rental had everything promised. The bed and couch were very comfortable. Everything was clean. Beach access was great. The chairs, cooler, and canopy were were just what was needed to maximize our enjoyment on a great beach."
United States
Karen G.
Beachside Studio Located Across from Main Beach and Half Mile to Village

20. [escape to paradise] siesta key beach getaway

[escape to paradise] siesta key beach getaway
Siesta Key
9.8 out of 10, Exceptional, (34 reviews)
"Easy process in and out. Would definitely do business with them again. A"
United States
Derek J.
The price is AU$423
includes taxes & fees
13 Sept - 14 Sept
[escape to paradise] siesta key beach getaway
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 holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Osprey holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favourite filters to narrow down your search. 

Osprey holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Osprey holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Osprey holiday rentals we have selected for you start as low as AU$176 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Osprey rentals

At Expedia, we put the best Osprey holiday 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 holiday.

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. 

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 free 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 15 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?

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 such as Siesta Key Beach and Lido 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.