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Our top choices for Osprey holiday rentals

1. Timberline Glamping Sarasota Site 106

Timberline Glamping Sarasota Site 106
Sarasota
The price is £351
includes taxes & fees
13 Oct - 14 Oct
Timberline Glamping Sarasota Site 106

2. Timberline Glamping Site 20

Timberline Glamping Site 20
Sarasota
The price is £351
includes taxes & fees
13 Oct - 14 Oct
Timberline Glamping Site 20

3. Timberline Glamping Sarasota Site 19

Timberline Glamping Sarasota Site 19
Sarasota
10.0 out of 10, Exceptional, (1 review)
The price is £351
includes taxes & fees
13 Oct - 14 Oct
Timberline Glamping Sarasota Site 19

4. Timberline Glamping Sarasota Site 105

Timberline Glamping Sarasota Site 105
Sarasota
The price is £351
includes taxes & fees
13 Oct - 14 Oct
Timberline Glamping Sarasota Site 105

5. Tropical Beach Resorts

Tropical Beach Resorts
3.5 star property
South Village
9.4 out of 10, Exceptional, (5,962 reviews)
"Amazing resort,"
United States
kurt
The price is £128
includes taxes & fees
20 Oct - 21 Oct
Tropical Beach Resorts

6. Captiva Beach Resort

Captiva Beach Resort
3.0 star property
South Village
9.0 out of 10, Wonderful, (1,318 reviews)
"Clean room, beach access, easy parking, friendly staff"
United States
Karla
The price is £146
includes taxes & fees
15 Oct - 16 Oct
Captiva Beach Resort

7. Hibiscus Suites - Gateway to Siesta Key

Hibiscus Suites - Gateway to Siesta Key
2.5 star property
Sarasota
8.8 out of 10, Excellent, (2,465 reviews)
"This place was perfect!"
United States
Kat
The price is £106
includes taxes & fees
15 Oct - 16 Oct
Hibiscus Suites - Gateway to Siesta Key

8. Tiny House Siesta

Tiny House Siesta
2.0 star property
Sarasota
8.4 out of 10, Very good, (387 reviews)
"It's a very cute tiny house in a great location. Walking distance to Siesta Keys beach and numerous restaurants. I loved the decor in the sea turtle house. I would definitely stay here again next time I'm in Florida."
United States
Staci
The price is £154
includes taxes & fees
15 Oct - 16 Oct
Tiny House Siesta

9. A Beach Retreat

A Beach Retreat
2.5 star property
Casey Key
9.2 out of 10, Wonderful, (688 reviews)
"Great stay!!"
United States
Genghis
The price is £157
includes taxes & fees
4 Nov - 5 Nov
A Beach Retreat

10. SeaSpray Resort

SeaSpray Resort
4.0 star property
Siesta Key
9.6 out of 10, Exceptional, (191 reviews)
"Best short vacation"
United States
Rommel
The price is £170
includes taxes & fees
4 Nov - 5 Nov
SeaSpray Resort

11. Casey Key Resort

Casey Key Resort
3.0 star property
Casey Key
8.4 out of 10, Very good, (284 reviews)
"Nice little property,very well kept.Host was very nice and helpful.Will be back again."
United States
Greg
The price is £173
includes taxes & fees
28 Oct - 29 Oct
Casey Key Resort

12. Siesta Key, Sea Horse Villa, Pool. Daily rentals

Siesta Key, Sea Horse Villa, Pool. Daily rentals
South Village
9.4 out of 10, Exceptional, (54 reviews)
"Perfect weekend getaway stay for my husband and I! The cottage had everything we needed, was thoroughly cleaned and location was perfect for restaurant hopping and beach going. Would definitely stay again!"
United States
Allie A.
The price is £193
includes taxes & fees
14 Oct - 15 Oct
Siesta Key, Sea Horse Villa, Pool. Daily rentals

13. 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.
The price is £196
includes taxes & fees
11 Oct - 12 Oct
Siesta Key, Walk to Beach. POOL VIEW. King Bed. Daily Rentals

14. 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.
The price is £231
includes taxes & fees
21 Oct - 22 Oct
Sand Dollar Studio, King bed, Pool. Daily Rentals, Walk to Beach.

15. 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 £257
includes taxes & fees
27 Oct - 28 Oct
Bright & Beachy–Beach Club Siesta Key 100A by RVA

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.
The price is £250
includes taxes & fees
21 Oct - 22 Oct
Couple’s Escape-Beach Club at Siesta Key 106C by RVA

17. 2 miles to #1 Beach Siesta Key

2 miles to #1 Beach Siesta Key
Sarasota
9.8 out of 10, Exceptional, (85 reviews)
"Clean and convenient"
United States
Scott H.
The price is £263
includes taxes & fees
18 Oct - 19 Oct
2 miles to #1 Beach Siesta Key

18. Romantic Getaway Beach Club Siesta 202B by RVA

Romantic Getaway Beach Club Siesta 202B by RVA
South Village
8.8 out of 10, Excellent, (57 reviews)
"Peaceful getaway. Throughly enjoyed the stay. "
United States
Anonymous traveller
The price is £277
includes taxes & fees
11 Oct - 12 Oct
Romantic Getaway Beach Club Siesta 202B by RVA

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

Jetties Pointe Cottage #5 - 408 “Casey Key”
Casey Key
9.6 out of 10, Exceptional, (37 reviews)
"Amazing view and beach access, really great stay."
United States
Evan T.
The price is £298
includes taxes & fees
14 Oct - 15 Oct
Jetties Pointe Cottage #5 - 408 “Casey Key”

20. 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
The price is £270
includes taxes & fees
22 Oct - 23 Oct
Siesta Key 1-Bedroom Condo | Unit 102B at The Beach Club – Steps 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

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, apart-hotels, 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 favorite 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 depends 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 £106 per night. Entering your travel dates in the search wizard you might find 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. 

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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?

Tropical Villas of Venice Beach: This holiday home rental outside of Osprey is located near the beach, and has an outdoor pool, a terrace and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a fridge, a microwave and kitchenware. Make the most of garden in this rental home to help you unwind.

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?

Turtle Beach and Nokomis 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.