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

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Check prices for these dates

In two weeks
20 Nov - 22 Nov
In two months
1 Jan - 3 Jan
In three months
29 Jan - 31 Jan
In four months
26 Feb - 28 Feb

Our top choices for Osprey cottages

A deck with a table and chairs, a blue umbrella, and a white fence.

1. Perfect Getaway – Lovely One Bedroom cottage House – Near Beaches

Perfect Getaway – Lovely One Bedroom cottage House – Near Beaches
Nokomis
The price is AED 327
AED 932 total
includes taxes & fees
14 Nov - 15 Nov
Perfect Getaway – Lovely One Bedroom cottage House – Near Beaches
A beachfront property with a single-story house, a paved driveway, and a palm tree in the foreground.

2. Direct Beachfront 2BR Cottage on Casey Key!

Direct Beachfront 2BR Cottage on Casey Key!
Casey Key
9.4 out of 10, Exceptional, (86 reviews)
"Great vacation!!"
United States
Dominic C.
The price is AED 727
AED 1,839 total
includes taxes & fees
7 Nov - 8 Nov
Direct Beachfront 2BR Cottage on Casey Key!
A small, single-story building with a light beige exterior, a blue door, and a number '229' on the wall.

3. NOKOMIS BEACH BUNGALOW 229 15 mins walk to the beach

NOKOMIS BEACH BUNGALOW 229 15 mins walk to the beach
Nokomis
9.2 out of 10, Wonderful, (34 reviews)
"Great location"
United States
Susan C.
The price is AED 547
AED 1,094 total
includes taxes & fees
3 Dec - 4 Dec
NOKOMIS BEACH BUNGALOW 229 15 mins walk to the beach
An outdoor patio with green metal chairs and tables, a red umbrella, and a building with balconies in the background.

4. Beach Tree Cottage,Walk To Beach& Siesta

Beach Tree Cottage,Walk To Beach& Siesta
2.0 star property
Siesta Key Village
Beach Tree Cottage,Walk To Beach& Siesta
A residential house with a white fence, a palm tree, and a parked car.

5. 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
9.8 out of 10, Exceptional, (91 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 AED 364
AED 1,117 total
includes taxes & fees
10 Nov - 11 Nov
Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.
A modern house with a driveway, a tree with purple lighting, and a white car parked in front.

6. Escape near Siesta Key with Hot Tub, BBQ, and Fire pit

Escape near Siesta Key with Hot Tub, BBQ, and Fire pit
Sarasota
8.4 out of 10, Very good, (10 reviews)
"Very close drive to the beach! Nice place to stay!"
United States
Rocio S.
The price is AED 624
AED 1,345 total
includes taxes & fees
8 Nov - 9 Nov
Escape near Siesta Key with Hot Tub, BBQ, and Fire pit
A patio with a sun lounger, a table with chairs, and an umbrella.

7. Beach View 100ft To Beach and SPA

Beach View 100ft To Beach and SPA
2.0 star property
Siesta Key Village
10.0 out of 10, Exceptional, (1 review)
The price is AED 678
AED 1,500 total
includes taxes & fees
5 Nov - 6 Nov
Beach View 100ft To Beach and SPA
Shared sunbathing deck by the pool, at the resort.

8. Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed

Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed
Siesta Key
9.6 out of 10, Exceptional, (8 reviews)
"The most well maintained property I've ever stayed."
United States
Russ H.
The price is AED 459
AED 1,230 total
includes taxes & fees
10 Nov - 11 Nov
Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed
A hot tub surrounded by a wooden fence, with lounge chairs and an umbrella in the background.

9. PinkMango Cottage Steps to Beach&Village

PinkMango Cottage Steps to Beach&Village
2.0 star property
Siesta Key Village
PinkMango Cottage Steps to Beach&Village
A wooden deck with a glass door leading to a lake view, surrounded by greenery.

10. Siesta Heron 6 / Sunset

Siesta Heron 6 / Sunset
3.0 star property
Siesta Key
The price is AED 2,105
AED 3,347 total
includes taxes & fees
6 Nov - 7 Nov
Siesta Heron 6 / Sunset
A beachfront property with a single-story house, a paved driveway, and a palm tree in the foreground.

11. Casey Key Beachfront Escape: Charming 1BR Cottage

Casey Key Beachfront Escape: Charming 1BR Cottage
Casey Key
9.4 out of 10, Exceptional, (135 reviews)
"Cute little cottage right on the beach. Doesn’t get any better than that."
United States
kelly h.
The price is AED 727
AED 1,745 total
includes taxes & fees
5 Nov - 6 Nov
Casey Key Beachfront Escape: Charming 1BR Cottage
A small, single-story building with a porch, surrounded by tropical vegetation.

12. BlueDolphin Cottage Walk To Siesta Beach

BlueDolphin Cottage Walk To Siesta Beach
2.5 star property
Siesta Key Village
The price is AED 711
AED 1,538 total
includes taxes & fees
6 Nov - 7 Nov
BlueDolphin Cottage Walk To Siesta Beach
A yellow house with a porch, a mailbox, and a number 5306 on the door.

13. Yellow Palm Cottage, Heart of Siesta Key

Yellow Palm Cottage, Heart of Siesta Key
2.0 star property
Siesta Key Village
The price is AED 1,197
AED 2,088 total
includes taxes & fees
16 Nov - 17 Nov
Yellow Palm Cottage, Heart of Siesta Key
A modern kitchen with white cabinets, a built-in oven, and a microwave. There is a dining area with a wooden table set for two, blue plates, and wine glasses. A ceiling fan is visible in the living room area.

14. Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village

Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village
Sarasota
9.2 out of 10, Wonderful, (192 reviews)
"The property was perfect for our time in Siesta Key. Being right across the road from beach access and having the free trolly pick up/drop off right at the corner of the street was great! Only a quick few minute trolly ride to Siesta Key Village. We would definately stay here again!"
United States
Jacci W.
The price is AED 694
AED 1,429 total
includes taxes & fees
6 Nov - 7 Nov
Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village
A single-story house with a front porch, a small deck, and a garage.

15. Unwind Poolside + Walk to Beach! Sarasota Retreat

Unwind Poolside + Walk to Beach! Sarasota Retreat
3.0 star property
South Village
8.0 out of 10, Very good, (1 review)
"The location of the property was excellent. The home was clean and had everything we needed to prepare breakfast in the morning. The 3 bedrooms and 3 bathrooms made it easy for the six of us wash up and get ready for dinner after a fun fill day at the walkable beach. Beach was great. Having a pool at the property was great for the 2 youngsters. We also made use of the wagon that was available to carry items to the beach., The property is nothing fancy but a great value for the money. "
United States
Eleuterio
The price is AED 999
AED 2,246 total
includes taxes & fees
23 Nov - 24 Nov
Unwind Poolside + Walk to Beach! Sarasota Retreat
A small, single-story building with a gray exterior, a white door, and a window with shutters.

16. Charming cottage for 2 across warm mineral springs park

Charming cottage for 2 across warm mineral springs park
Warm Mineral Springs
9.0 out of 10, Wonderful, (29 reviews)
"Host responded quicklyWould stay again"
United States
VIKTOR M.
Charming cottage for 2 across warm mineral springs park
A backyard with a tree, a wooden fence, a blue shed, and a house with a door.

17. Coastal Breeze Cottage in Sunny Sarasota. Pet friendly. King size bed.

Coastal Breeze Cottage in Sunny Sarasota. Pet friendly. King size bed.
Desoto Lakes
The price is AED 344
AED 889 total
includes taxes & fees
24 Nov - 25 Nov
Coastal Breeze Cottage in Sunny Sarasota. Pet friendly. King size bed.
A rectangular pool with white lounge chairs and a white fence, surrounded by palm trees and a building with balconies.

18. Lido Key Casita w Pool Steps to the Beach

Lido Key Casita w Pool Steps to the Beach
Lido Key
10.0 out of 10, Exceptional, (1 review)
The price is AED 589
AED 1,495 total
includes taxes & fees
18 Nov - 19 Nov
Lido Key Casita w Pool Steps to the Beach
A bedroom with a bed, a ceiling fan, a window with curtains, a wooden wardrobe, and a framed picture on the wall.

19. Cozy Lido Studio by Beach & St Armand's

Cozy Lido Studio by Beach & St Armand's
Lido Key
The price is AED 589
AED 1,495 total
includes taxes & fees
15 Nov - 16 Nov
Cozy Lido Studio by Beach & St Armand's
A covered patio with a round table set for four, surrounded by wicker chairs.

20. Charming 2-bedroom cottage in Englewood minutes to the Gulf Beaches-Dog Friendly

Charming 2-bedroom cottage in Englewood minutes to the Gulf Beaches-Dog Friendly
Englewood Central
10.0 out of 10, Exceptional, (16 reviews)
"Great stay for our family of 5!"
United States
Shawn G.
The price is AED 397
AED 1,012 total
includes taxes & fees
6 Nov - 7 Nov
Charming 2-bedroom cottage in Englewood minutes to the Gulf Beaches-Dog Friendly
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

Hyatt Place Sarasota/Bradenton Airport

Hyatt Place Sarasota/Bradenton Airport

10/10 Excellent
"clean room"
Christina 2-night trip
Posted 5 hours ago
Hyatt Place Sarasota/Bradenton Airport

Frequently asked questions

How much do cottages in Osprey cost?
Cottages in Osprey range between AED 889 and AED 3,347 per night. These stays offer a chance to soak in nature's beauty — at a price you can afford. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
What are the best cottages in Osprey?
Osprey has multiple cottages with a total average guest review rating of 9.1. The Inn On Siesta Key is a terrific option if you're into nature and an easy-breezy pace. Guests of this 3.5-star stay will have access to a swimming pool and a garden. Flip Flop Cottages is another popular choice. This 3-star cottage features a swimming pool and a barbecue grill.
How many cottages are there in Osprey?
Take your pick of 390 cottages in Osprey. Whether you're vacationing with the kids or organizing a weekend break with close friends, Expedia can help you find the right space to get in touch with nature.
Why book your cottage in Osprey with Expedia?
We think that traveling should be simple, so if you're after cottages in Osprey at a competitive rate, Expedia has you covered. Keep the budget in check and stay in an economical option far away from the city rush, or book a 5-star cottage to spoil the ones you love most.
How can I find cheap cottages in Osprey?
The quickest way to track down cheap cottages in Osprey is with Expedia's useful filter tool. Refine your search by budget, amenities and star rating to grab unbeatable deals in just a few keystrokes.