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
9 Oct - 11 Oct
In two months
20 Nov - 22 Nov
In three months
18 Dec - 20 Dec
In four months
15 Jan - 17 Jan

Our top choices for Osprey cottages

A small house with a porch, surrounded by a grassy yard and dense foliage.

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

Perfect Getaway – Lovely One Bedroom cottage House – Near Beaches
Nokomis
The price is €227
includes taxes & fees
25 Sept - 26 Sept
Perfect Getaway – Lovely One Bedroom cottage House – Near Beaches
A residential house with a white fence, a palm tree, and a parked car.

2. 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 €267
includes taxes & fees
7 Oct - 8 Oct
Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.
A yellow house with a white door and number 5306.

3. Yellow Palm Cottage steps from the beach

Yellow Palm Cottage steps from the beach
Siesta Key Village
10.0 out of 10, Exceptional, (2 reviews)
"This place was so cute and quaint! It was just a short walk to the village and to the beach. The grounds were beautiful! A little oasis in the backyard. . Would stay here again!!!"
United States
Tami B.
Yellow Palm Cottage steps from the beach
A hammock tied between two palm trees, a pink building with a red roof, and a bush with red flowers.

4. Pink Mango Cottage steps from the beach

Pink Mango Cottage steps from the beach
Siesta Key Village
10.0 out of 10, Exceptional, (1 review)
The price is €485
includes taxes & fees
30 Sept - 1 Oct
Pink Mango Cottage steps from the beach
A wooden pier leading to a beach with a clear blue sky.

5. Casey Key Beachfront Escape: Charming 1BR Cottage

Casey Key Beachfront Escape: Charming 1BR Cottage
Casey Key
9.4 out of 10, Exceptional, (132 reviews)
"A beautiful location and super comfortable!"
United States
K B.
Casey Key Beachfront Escape: Charming 1BR Cottage

6. 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.
Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed
A wooden deck with a glass door leading to a lake view, surrounded by greenery.

7. Siesta Heron 6 / Sunset

Siesta Heron 6 / Sunset
3.0 star property
Siesta Key
The price is €585
includes taxes & fees
28 Sept - 29 Sept
Siesta Heron 6 / Sunset
A small, single-story building with a blue roof and yellow walls, surrounded by a white picket fence and palm trees.

8. Blue Dolphin Cottage steps from the beach

Blue Dolphin Cottage steps from the beach
Siesta Key Village
Blue Dolphin Cottage steps from the beach
A modern house with a driveway, a tree with purple lighting, and a white car parked in front.

9. 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 price is €413
includes taxes & fees
8 Oct - 9 Oct
Escape near Siesta Key with Hot Tub, BBQ, and Fire pit
A patio with a table set for two, a blue umbrella, and a white fence.

10. Studio by Lido Beach w heated pool

Studio by Lido Beach w heated pool
Lido Key
The price is €287
includes taxes & fees
1 Oct - 2 Oct
Studio by Lido Beach w heated pool
A wooden deck with a view of the ocean, a barbecue grill, and a cart.

11. 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.
The price is €551
includes taxes & fees
29 Sept - 30 Sept
Direct Beachfront 2BR Cottage on Casey Key!
A rectangular pool with white lounge chairs and a white fence, surrounded by palm trees and a building with balconies.

12. Lido Key Casita w Pool Steps to the Beach

Lido Key Casita w Pool Steps to the Beach
Lido Key
The price is €306
includes taxes & fees
28 Sept - 29 Sept
Lido Key Casita w Pool Steps to the 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)
"Right across the beach Less then 5 minutes Good space - rooms nice ad clean "
United States
ASHISH
The price is €418
includes taxes & fees
2 Oct - 3 Oct
Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village
A single-story house with a blue exterior, a front door, and a small porch area.

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

Coastal Breeze Cottage in Sunny Sarasota. Pet friendly. King size bed.
Desoto Lakes
Coastal Breeze Cottage in Sunny Sarasota. Pet friendly. King size bed.
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
The price is €329
includes taxes & fees
17 Oct - 18 Oct
Cozy Lido Studio by Beach & St Armand's
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)
"We were enjoying our stay."
United States
Inna K.
The price is €125
includes taxes & fees
1 Oct - 2 Oct
Charming cottage for 2 across warm mineral springs park
A bathroom with a toilet, a glass-enclosed shower, and a framed picture on the wall.

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

Coastal Studio, Walk to St Armand's or Lido Beach
Lido Key
The price is €322
includes taxes & fees
4 Oct - 5 Oct
Coastal Studio, Walk to St Armand's or Lido Beach
A residential house with a garage, a front door, and a small front yard.

18. Home < 1-mi Walk to Warm Mineral Springs Park!

Home < 1-mi Walk to Warm Mineral Springs Park!
3.0 star property
North Port
The price is €390
includes taxes & fees
25 Sept - 26 Sept
Home < 1-mi Walk to Warm Mineral Springs Park!
A two-story building with a blue and white exterior, a balcony, and a sign that reads "Gidget's Coastal Preserve."

19. Beach Road

Beach Road
2.0 star property
Siesta Key
The price is €828
includes taxes & fees
2 Oct - 3 Oct
Beach Road
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)
"Very clean house, nice place to stay"
United States
Linda G.
The price is €222
includes taxes & fees
17 Oct - 18 Oct
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

The Ritz-Carlton, Sarasota

The Ritz-Carlton, Sarasota

10/10 Excellent
"Fabulous"
Mari-Andrée 3-night trip
Posted 1 hour ago
The Ritz-Carlton, Sarasota

Find out more about Osprey

Osprey Cottages information

Number of reviews
331
Accommodation
333 Cottages
Lowest Price
€125
Highest Price
€828

Frequently asked questions

How much do cottages in Osprey cost?
Cottages in Osprey range between €125 and €828 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 333 cottages in Osprey. Whether you're holidaying with the kids or organising 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 travellers 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 travelling 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 travelling 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.