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

Search Osprey Cottages

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

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

Our top choices for Osprey cottages

A residential house with a white fence, a palm tree, and a parked car.

1. 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.
$270 nightly
The price is $301
Oct 25 - Oct 26
Total with taxes and fees
Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.
A small house with a porch, surrounded by a grassy yard and dense foliage.

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

Perfect Getaway – Lovely One Bedroom cottage House – Near Beaches
Nokomis
$228 nightly
The price is $255
Oct 22 - Oct 23
Total with taxes and fees
Perfect Getaway – Lovely One Bedroom cottage House – Near Beaches
A modern house with a driveway, a tree with purple lighting, and a white car parked in front.

3. 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)
"The house was truly lovely, and the hosts were exceptionally caring, kind, and attentive in their communication. It was wonderful to be so close to the beach, with stores conveniently nearby, making the stay feel comfortable and welcoming."
United States
Kandra R.
$337 nightly
The price is $375
Oct 25 - Oct 26
Total with taxes and fees
Escape near Siesta Key with Hot Tub, BBQ, and Fire pit
A blue house with a paved pathway leading to the entrance, surrounded by palm trees and tropical plants.

4. Direct Beachfront 2BR Cottage on Casey Key!

Direct Beachfront 2BR Cottage on Casey Key!
Casey Key
9.4 out of 10, Exceptional, (84 reviews)
"Great vacation!!"
United States
Dominic C.
$452 nightly
The price is $504
Oct 22 - Oct 23
Total with taxes and fees
Direct Beachfront 2BR Cottage on Casey Key!
A wooden deck with a glass door leading to a lake view, surrounded by greenery.

5. Siesta Heron 6 / Sunset

Siesta Heron 6 / Sunset
3.0 star property
Siesta Key
$619 nightly
The price is $699
Oct 26 - Oct 27
Total with taxes and fees
Siesta Heron 6 / Sunset
A pair of stacked front-loading washing machines in a commercial setting.

6. Beach View 100ft To Beach and SPA

Beach View 100ft To Beach and SPA
2.0 star property
Siesta Key Village
$373 nightly
The price is $421
Oct 24 - Oct 25
Total with taxes and fees
Beach View 100ft To Beach and SPA
A riverfront restaurant with outdoor seating and a view of the water.

7. 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, (33 reviews)
"Great location"
United States
Susan C.
$278 nightly
The price is $310
Oct 21 - Oct 22
Total with taxes and fees
NOKOMIS BEACH BUNGALOW 229 15 mins walk to the beach
A pool area with a blue deck, lounge chairs, a barbecue, and a view of buildings in the background.

8. The Inn On Siesta Key

The Inn On Siesta Key
3.5 star property
Siesta Key
10.0 out of 10, Exceptional, (212 reviews)
"The property was perfect. Walk to down town and the beach. Loved the provisions for the beach which made it so convenient. Room was super clean and overall the property was well maintained."
United States
Stephen
The Inn On Siesta Key
Shared sunbathing deck by the pool, at the resort.

9. 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.
$297 nightly
The price is $331
Oct 21 - Oct 22
Total with taxes and fees
Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed
A patio area with a grill, potted plants, and a building with a teal door.

10. Beach Tree Cottage,Walk To Beach& Siesta

Beach Tree Cottage,Walk To Beach& Siesta
2.0 star property
Siesta Key Village
$322 nightly
The price is $364
Oct 21 - Oct 22
Total with taxes and fees
Beach Tree Cottage,Walk To Beach& Siesta
A yellow house with a porch, a mailbox, and a number 5306 on the door.

11. Yellow Palm Cottage, Heart of Siesta Key

Yellow Palm Cottage, Heart of Siesta Key
2.0 star property
Siesta Key Village
$341 nightly
The price is $385
Oct 21 - Oct 22
Total with taxes and fees
Yellow Palm Cottage, Heart of Siesta Key
A kitchen with a sink, stove, microwave, and refrigerator.

12. BlueDolphin Cottage Walk To Siesta Beach

BlueDolphin Cottage Walk To Siesta Beach
2.5 star property
Siesta Key Village
$337 nightly
The price is $381
Oct 21 - Oct 22
Total with taxes and fees
BlueDolphin Cottage Walk To Siesta Beach
A two-story building with a blue exterior and white railings.

13. 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)
"Loved the location of this property! The property manager was easy to contact and the property was exactly as shown in the pictures. Would stay here again!"
United States
Tracie B.
$363 nightly
The price is $405
Oct 21 - Oct 22
Total with taxes and fees
Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village
A bathroom with a toilet, a glass-enclosed shower, and a framed picture on the wall.

14. Coastal Studio, Walk to St Armand's or Lido Beach

Coastal Studio, Walk to St Armand's or Lido Beach
Lido Key
10.0 out of 10, Exceptional, (2 reviews)
"This studio was perfect for a quick weekend getaway. The just was very responsive, and the property was very clean.We arrived after dark, and had to look around a bit to find the right unit (front of the office bldg.), but the host was available to assist. Good amenities and proximity to Lido Beach/ St. Armand Circle."
United States
Kevin C.
$363 nightly
The price is $405
Oct 25 - Oct 26
Total with taxes and fees
Coastal Studio, Walk to St Armand's or Lido Beach
A bedroom with a bed, a ceiling fan, a window with curtains, a wooden wardrobe, and a framed picture on the wall.

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

Cozy Lido Studio by Beach & St Armand's
Lido Key
$385 nightly
The price is $429
Oct 31 - Nov 1
Total with taxes and fees
Cozy Lido Studio by Beach & St Armand's
A residential area with houses, a gravel driveway, and palm trees.

16. Casey Key Beachfront Escape: Charming 1BR Cottage

Casey Key Beachfront Escape: Charming 1BR Cottage
Casey Key
9.4 out of 10, Exceptional, (134 reviews)
"Beautiful gulf view."
United States
Audrey B.
$659 nightly
The price is $734
Nov 3 - Nov 4
Total with taxes and fees
Casey Key Beachfront Escape: Charming 1BR Cottage
A small, single-story building with a gray exterior, a white door, and a window with shutters.

17. 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.
$125 nightly
The price is $139
Oct 24 - Oct 25
Total with taxes and fees
Charming cottage for 2 across warm mineral springs park
A single-story house with a blue exterior, a front door, and a small porch area.

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

Coastal Breeze Cottage in Sunny Sarasota. Pet friendly. King size bed.
Desoto Lakes
$221 nightly
The price is $247
Oct 21 - Oct 22
Total with taxes and fees
Coastal Breeze Cottage in Sunny Sarasota. Pet friendly. King size bed.
A covered patio with a round table set for four, surrounded by wicker chairs.

19. 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.
$215 nightly
The price is $240
Oct 24 - Oct 25
Total with taxes and fees
Charming 2-bedroom cottage in Englewood minutes to the Gulf Beaches-Dog Friendly
A two-story building with a blue and white exterior, a balcony, and a sign that reads "Gidget's Coastal Preserve."

20. Beach Road

Beach Road
2.0 star property
Siesta Key
Beach Road
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Osprey Hotel Reviews

Casey Key Resorts - Mainland

Casey Key Resorts - Mainland

8/10 Good
"Nicole at check in was really helpful. Great customer service! Ben in the evening was also really good. The pool was perfect and the room was very clean. Happy with the stay!"
Kathleen 3-night trip
Posted 4 hours ago
Casey Key Resorts - Mainland

Find out more about Osprey

Osprey Cottages information

Number of reviews
498
Accommodation
396 Cottages
Lowest Price
$139
Highest Price
$734

Frequently asked questions

How much do cottages in Osprey cost?
Cottages in Osprey range between $139 and $734 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 9.3. 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 396 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.
Are there any family-friendly cottages in Osprey?
Many travelers searching for a family-friendly cottage in Osprey choose The Inn On Siesta Key. With a 3.5-star rating and amenities including a nearby beach and a barbecue grill, you're sure to feel right at home here. Another superb option for traveling families is Flip Flop Cottages. A barbecue grill and a picnic area help make this 3-star cottage a comfortable base for your Osprey getaway. Osprey has tons of family-friendly attractions to check out that'll keep the kids entertained. Siesta Key Beach and Venice Beach promise a fun day out for both young and old.
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.
What is there to do in Osprey near my cottage?
The most useful travel accessory is a well-planned itinerary. Oscar Scherer State Park is a good spot to begin your sightseeing in Osprey.

Explore a world of travel with Expedia