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Nov 13 - Nov 15
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Nov 20 - Nov 22
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Dec 4 - Dec 6
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Jan 1 - Jan 3

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 ￥14,017
￥39,975 total
includes taxes & fees
Nov 14 - Nov 15
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 ￥31,183
￥76,027 total
includes taxes & fees
Nov 12 - Nov 13
Direct Beachfront 2BR Cottage on Casey Key!
A riverfront restaurant with outdoor seating and a view of the water.

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 ￥21,891
￥44,834 total
includes taxes & fees
Nov 8 - Nov 9
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
The price is ￥17,686
￥51,681 total
includes taxes & fees
Nov 8 - Nov 9
Beach Tree Cottage,Walk To Beach& Siesta
A modern house with a driveway, a tree with purple lighting, and a white car parked in front.

5. 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 ￥26,773
￥57,662 total
includes taxes & fees
Nov 8 - Nov 9
Escape near Siesta Key with Hot Tub, BBQ, and Fire pit
A residential house with a white fence, a palm tree, and a parked car.

6. 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.
Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.
A pool area with a blue deck, lounge chairs, a barbecue, and a view of buildings in the background.

7. The Inn On Siesta Key

The Inn On Siesta Key
3.5 star property
Siesta Key
10.0 out of 10, Exceptional, (213 reviews)
"Thank you Paige & Gabe! My husband & I had a wonderful stay last week in The Nook at your beautiful Inn. Absolutely loved the old Florida charm and perfect location. Your Inn is immaculately kept as well as comfortable. We especially loved our private patio with the fire pit at The Nook. The location of The Inn could not be more perfect being less than a 5 minute walk across the street to Siesta Key beach as well as a short 10 minute walk to town with all the restaurants & shops. Thanks again...
United States
Karen Jean
The price is ￥40,078
￥55,077 total
includes taxes & fees
Nov 10 - Nov 11
The Inn On Siesta Key
A yellow house with a porch, a mailbox, and a number 5306 on the door.

8. Yellow Palm Cottage, Heart of Siesta Key

Yellow Palm Cottage, Heart of Siesta Key
2.0 star property
Siesta Key Village
The price is ￥27,892
￥63,214 total
includes taxes & fees
Nov 8 - Nov 9
Yellow Palm Cottage, Heart of 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.
The price is ￥19,686
￥52,720 total
includes taxes & fees
Nov 10 - Nov 11
Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed
A patio with a sun lounger, a table with chairs, and an umbrella.

10. 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 ￥28,490
￥63,693 total
includes taxes & fees
Nov 11 - Nov 12
Beach View 100ft To Beach and SPA
A two-story building with a blue exterior and white railings.

11. 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.
The price is ￥29,953
￥62,310 total
includes taxes & fees
Nov 13 - Nov 14
Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village
A beachfront property with a single-story house, a paved driveway, and a palm tree in the foreground.

12. 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 ￥31,183
￥75,302 total
includes taxes & fees
Nov 9 - Nov 10
Casey Key Beachfront Escape: Charming 1BR Cottage
A small, single-story building with a porch, surrounded by tropical vegetation.

13. BlueDolphin Cottage Walk To Siesta Beach

BlueDolphin Cottage Walk To Siesta Beach
2.5 star property
Siesta Key Village
The price is ￥27,956
￥63,285 total
includes taxes & fees
Nov 8 - Nov 9
BlueDolphin Cottage Walk To Siesta Beach
A single-story house with a front porch, a small deck, and a garage.

14. 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 ￥42,837
￥96,302 total
includes taxes & fees
Nov 23 - Nov 24
Unwind Poolside + Walk to Beach! Sarasota Retreat
A covered outdoor seating area with a sofa, a chair, and a coffee table.

15. Nook Cottage Across street from beach and Heated Pool

Nook Cottage Across street from beach and Heated Pool
Siesta Key
10.0 out of 10, Exceptional, (4 reviews)
"They have really thought of everything and gone above and beyond to make our stay as comfortable as possible. Everything was very clean! Paige was a wonderful guide and host for the local area!"
United States
Derek N.
The price is ￥44,740
￥109,443 total
includes taxes & fees
Nov 8 - Nov 9
Nook Cottage Across street from beach and Heated Pool
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.
The price is ￥7,875
￥21,466 total
includes taxes & fees
Nov 13 - Nov 14
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 ￥16,379
￥39,974 total
includes taxes & fees
Dec 7 - Dec 8
Coastal Breeze Cottage in Sunny Sarasota. Pet friendly. King size bed.
A pool area with a blue deck, lounge chairs, a barbecue, and a view of buildings in the background.

18. Cabana Cottage Across street from Beach and Heated Pool

Cabana Cottage Across street from Beach and Heated Pool
Siesta Key
10.0 out of 10, Exceptional, (5 reviews)
"Wonderful property and fantastic location. Everything you need at your fingertips for an enjoyable beach stay without ever having to leave the island!"
United States
Meghan J.
The price is ￥45,255
￥156,128 total
includes taxes & fees
Nov 10 - Nov 11
Cabana Cottage Across street from Beach and Heated Pool
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.
The price is ￥17,009
￥43,411 total
includes taxes & fees
Nov 8 - Nov 9
Charming 2-bedroom cottage in Englewood minutes to the Gulf Beaches-Dog Friendly
A bathroom with a toilet, a glass-enclosed shower, and a framed picture on the wall.

20. 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.
The price is ￥23,378
￥60,396 total
includes taxes & fees
Nov 25 - Nov 26
Coastal Studio, Walk to St Armand's or Lido 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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Learn more about Osprey

Paddle through Oscar Scherer State Park's serene waterways where you might spot eagles, turtles, and alligators along the way. Nearby Sarasota's white-sand beaches and Myakka River State Park offer perfect day trips from this peaceful Gulf Coast community.

See all hotels in Osprey
A nest on a wooden platform by a lake at sunset with birds flying around.

Top reviews in Osprey

A pool area with a blue deck, lounge chairs, a barbecue, and a view of buildings in the background.
The Inn On Siesta Key

The Inn On Siesta Key

The Inn On Siesta Key
Siesta Key

10/10 Excellent

We just finished our fall break getaway at The Inn On Siesta Key, and we absolutely loved it! The owners are so friendly and accommodating, staying here was the best choice we could have made. We stayed in the Cottage, and it was awesome, so inviting and cozy, and perfect for our family of 4. The great service started on our check in day. We arrived very early, as we had taken an early morning flight into Sarasota. Paige gave us an introduction to the property and let us change in the Cottage,...
United States
Steven
Reviewed October 2, 2021
The Inn On Siesta Key

Frequently Asked Questions

How much do cottages in Osprey cost?

Cottages in Osprey range between ￥7,875 and ￥45,255 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 9.6. 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 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.