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

Osprey Holiday Rentals

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Check prices for these dates

In two weeks
6 Nov - 8 Nov
In two months
18 Dec - 20 Dec
In three months
15 Jan - 17 Jan
In four months
12 Feb - 14 Feb

Our top choices for Osprey holiday rentals

A tented accommodation with a bed, pillows, a desk, and chairs.

1. 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 HK$2,255
HK$2,785 total
includes taxes & fees
26 Oct - 27 Oct
Fantastic Tented Cabin with Fire Pit in Sarasota, Florida
A cozy room with a bed, a small table with a welcome sign, a refrigerator, and a coffee maker.

2. Charming Secluded Tented Cabin in Sarasota, Florida

Charming Secluded Tented Cabin in Sarasota, Florida
Sarasota
The price is HK$2,255
HK$2,785 total
includes taxes & fees
26 Oct - 27 Oct
Charming Secluded Tented Cabin in Sarasota, Florida
A room with two beds, each with a black metal frame, white bedding, and striped pillows. There is a small table with a plant, a sign that says 'HAPPY CAMPING,' and a wooden floor.

3. Enjoyable Secluded Tented Cabin with Fire Pit in Sarasota, Florida

Enjoyable Secluded Tented Cabin with Fire Pit in Sarasota, Florida
Sarasota
The price is HK$2,255
HK$2,785 total
includes taxes & fees
26 Oct - 27 Oct
Enjoyable Secluded Tented Cabin with Fire Pit in Sarasota, Florida
A tent with a wooden platform, surrounded by trees and gravel.

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

Incredible Tented Cabin with Stunning Forest Views in Sarasota, Florida
Sarasota
The price is HK$2,255
HK$2,785 total
includes taxes & fees
2 Nov - 3 Nov
Incredible Tented Cabin with Stunning Forest Views in Sarasota, Florida
A pool area with a waterfall feature, lounge chairs, and palm trees.

5. Tropical Beach Resorts

Tropical Beach Resorts
3.5 star property
South Village
9.4 out of 10, Exceptional, (6,000 reviews)
"This Resort is wonderful"
United States
Liliana
The price is HK$1,159
HK$1,513 total
includes taxes & fees
26 Oct - 27 Oct
Tropical Beach Resorts
An outdoor patio with a grill, white chairs, and a red umbrella.

6. Hibiscus Suites - Gateway to Siesta Key

Hibiscus Suites - Gateway to Siesta Key
2.5 star property
Sarasota
8.8 out of 10, Excellent, (2,472 reviews)
"This place was perfect!"
United States
Kat
The price is HK$994
HK$1,123 total
includes taxes & fees
5 Nov - 6 Nov
Hibiscus Suites - Gateway to Siesta Key
A large orange armchair against a white wall with a 'Captiva' sign. There are two potted plants beside the chair.

7. Captiva Beach Resort

Captiva Beach Resort
3.0 star property
South Village
9.0 out of 10, Wonderful, (1,324 reviews)
"Clean room, beach access, easy parking, friendly staff"
United States
Karla
The price is HK$1,224
HK$1,515 total
includes taxes & fees
25 Oct - 26 Oct
Captiva Beach Resort
A compact living space with a kitchen, a dining area, and a sofa with cushions.

8. Tiny House Siesta

Tiny House Siesta
2.0 star property
Sarasota
8.4 out of 10, Very good, (390 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 HK$470
HK$1,588 total
includes taxes & fees
29 Oct - 30 Oct
Tiny House Siesta
A modern kitchen with a stainless steel sink, a dining area with a table and chairs, and a living room with a sofa and a TV.

9. Oceanfront home

Oceanfront home
Vamo
9.8 out of 10, Exceptional, (94 reviews)
"It looks just like the pictures and the sunset daily is absolutely gorgeous. The neighborhood is nice and the people are kind. We loved being short car rides away from stores, beaches and the legacy trail. The owners had great communication. Would definitely stay again."
United States
Ashley H.
The price is HK$2,069
HK$4,900 total
includes taxes & fees
28 Oct - 29 Oct
Oceanfront home
A modern living room with a flat-screen TV on a wooden cabinet, a grey sofa with patterned cushions, and a large window with sheer curtains.

10. SeaSpray Resort

SeaSpray Resort
4.0 star property
Siesta Key
9.6 out of 10, Exceptional, (200 reviews)
"The room was clean and the staff were very kind."
United States
Geraldine
The price is HK$1,756
HK$1,985 total
includes taxes & fees
2 Nov - 3 Nov
SeaSpray Resort
A living room with a view of the ocean, a ceiling fan, and a wooden coffee table.

11. A Beach Retreat

A Beach Retreat
2.5 star property
Casey Key
9.2 out of 10, Wonderful, (694 reviews)
"Enjoyed our stay"
United States
Robin
The price is HK$1,446
HK$1,634 total
includes taxes & fees
4 Nov - 5 Nov
A Beach Retreat
A wooden structure with a thatched roof overlooking a beach.

12. Casey Key Resort

Casey Key Resort
3.0 star property
Casey Key
8.4 out of 10, Very good, (284 reviews)
"Close to the water."
United States
jay
The price is HK$1,464
HK$1,801 total
includes taxes & fees
28 Oct - 29 Oct
Casey Key Resort
A beach with clear turquoise water, people swimming and sunbathing, and a sailboat in the distance.

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 HK$839
HK$2,106 total
includes taxes & fees
27 Oct - 28 Oct
Siesta Key, Walk to Beach. POOL VIEW. King Bed. Daily Rentals
A beach with clear turquoise water and gentle waves.

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

Siesta Key, Sea Horse Villa, Pool. Daily rentals
South Village
9.4 out of 10, Exceptional, (55 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 HK$838
HK$2,103 total
includes taxes & fees
26 Oct - 27 Oct
Siesta Key, Sea Horse Villa, Pool. Daily rentals
A beach path leading to the sea with grass on either side.

15. 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 HK$1,214
HK$3,007 total
includes taxes & fees
24 Oct - 25 Oct
Jetties Pointe Cottage #5 - 408 “Casey Key”
A beach with clear turquoise water, people swimming and walking along the shore, and a sailboat in the distance.

16. 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 HK$1,007
HK$1,997 total
includes taxes & fees
24 Oct - 25 Oct
Sand Dollar Studio, King bed, Pool. Daily Rentals, Walk to Beach.
A beach scene with a large sandcastle and people around it.

17. Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.

Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.
South Village
9.6 out of 10, Exceptional, (90 reviews)
"Would definitely stay here again. Great location and great house! Owner was quick and helpful with communication."
United States
Clarissa S.
The price is HK$777
HK$2,362 total
includes taxes & fees
25 Oct - 26 Oct
Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.
A beach with rows of umbrellas and beach chairs, a sandy shoreline, and a clear view of the ocean.

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 HK$1,193
HK$2,596 total
includes taxes & fees
24 Oct - 25 Oct
Couple’s Escape-Beach Club at Siesta Key 106C by RVA
A beach with rows of umbrellas and beach chairs, a sandy shoreline, and a clear view of the ocean.

19. 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 HK$1,248
HK$2,701 total
includes taxes & fees
27 Oct - 28 Oct
Bright & Beachy–Beach Club Siesta Key 100A by RVA
A beach with rows of umbrellas and beach chairs, a sandy shoreline, and a clear view of the ocean.

20. 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)
"Great beach! "
United States
Annie B.
The price is HK$1,569
HK$3,693 total
includes taxes & fees
24 Oct - 25 Oct
Dream Sunsets & Coastal Bliss–Beach Club 108A / 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

Tropical Beach Resorts

Tropical Beach Resorts

10/10 Excellent
"Beautiful property with easy access to the beach. We will return!"
Jenny 1-night trip
Posted less than an hour ago
Tropical Beach Resorts

Find out more about Osprey

Search for holiday rentals in Osprey on Expedia! You can easily find your home rentals, villas, holiday apartments in Osprey using one of the methods below:

  • View our selection of featured holiday rentals in Osprey
  • Use the map to find apartments and other holiday homes in the Osprey neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Osprey while they last

Look no further and take a look at our great range of rental properties in Osprey!

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.