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

Search Osprey Cottages

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 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
$228 nightly
The price is $255
Oct 24 - Oct 25
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.

2. 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.
$344 nightly
The price is $383
Oct 30 - Oct 31
Total with taxes and fees
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.

3. 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 patio with a sun lounger, a table with chairs, and an umbrella.

4. Beach View 100ft To Beach and SPA

Beach View 100ft To Beach and SPA
2.0 star property
Siesta Key Village
$346 nightly
The price is $391
Oct 25 - Oct 26
Total with taxes and fees
Beach View 100ft To Beach and SPA
A riverfront restaurant with outdoor seating and a view of the water.

5. 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 25 - Oct 26
Total with taxes and fees
NOKOMIS BEACH BUNGALOW 229 15 mins walk to the beach
A beachfront property with a single-story house, a paved driveway, and a palm tree in the foreground.

6. Direct Beachfront 2BR Cottage on Casey Key!

Direct Beachfront 2BR Cottage on Casey Key!
Casey Key
9.4 out of 10, Exceptional, (85 reviews)
"Great vacation!!"
United States
Dominic C.
$449 nightly
The price is $501
Oct 26 - Oct 27
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.

7. Siesta Heron 6 / Sunset

Siesta Heron 6 / Sunset
3.0 star property
Siesta Key
$665 nightly
The price is $751
Oct 26 - Oct 27
Total with taxes and fees
Siesta Heron 6 / Sunset
An outdoor patio with green metal chairs and tables, a red umbrella, and a building with balconies in the background.

8. Beach Tree Cottage,Walk To Beach& Siesta

Beach Tree Cottage,Walk To Beach& Siesta
2.0 star property
Siesta Key Village
$346 nightly
The price is $391
Oct 25 - Oct 26
Total with taxes and fees
Beach Tree Cottage,Walk To Beach& Siesta
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.
$311 nightly
The price is $347
Nov 10 - Nov 11
Total with taxes and fees
Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed
A small pink house with a white door, a blue car parked in front, and a white picket fence.

10. PinkMango Cottage Steps to Beach&Village

PinkMango Cottage Steps to Beach&Village
2.0 star property
Siesta Key Village
$344 nightly
The price is $389
Oct 26 - Oct 27
Total with taxes and fees
PinkMango Cottage Steps to Beach&Village
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
$383 nightly
The price is $433
Oct 26 - Oct 27
Total with taxes and fees
Yellow Palm Cottage, Heart of Siesta Key
A two-story building with a blue exterior and white railings.

12. 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.
$365 nightly
The price is $407
Oct 26 - Oct 27
Total with taxes and fees
Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village
A backyard with a wooden fence, a blue trash bin, and a hammock.

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

Coastal Breeze Cottage in Sunny Sarasota. Pet friendly. King size bed.
Desoto Lakes
$225 nightly
The price is $251
Oct 24 - Oct 25
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.

14. 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 small, single-story building with a gray exterior, a white door, and a window with shutters.

15. 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.
$135 nightly
The price is $150
Nov 13 - Nov 14
Total with taxes and fees
Charming cottage for 2 across warm mineral springs park
A wooden pier leading to a beach with a clear blue sky.

16. Casey Key Beachfront Escape: Charming 1BR Cottage

Casey Key Beachfront Escape: Charming 1BR Cottage
Casey Key
9.4 out of 10, Exceptional, (135 reviews)
"Beautiful gulf view."
United States
Audrey B.
$652 nightly
The price is $727
Nov 3 - Nov 4
Total with taxes and fees
Casey Key Beachfront Escape: Charming 1BR Cottage
A rectangular pool with white lounge chairs and a white fence, surrounded by palm trees and a building with balconies.

17. 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)
$370 nightly
The price is $412
Nov 4 - Nov 5
Total with taxes and fees
Lido Key Casita w Pool Steps to the 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
$395 nightly
The price is $446
Oct 24 - Oct 25
Total with taxes and fees
Home < 1-mi Walk to Warm Mineral Springs Park!
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
$366 nightly
The price is $408
Oct 31 - Nov 1
Total with taxes and fees
Cozy Lido Studio by Beach & St Armand's
A two-story building with a covered patio area featuring outdoor seating.

20. 2 bedroom, walk to beach-bikes-kayaks-grill-picnic-hot outdoor shower-beach gear

2 bedroom, walk to beach-bikes-kayaks-grill-picnic-hot outdoor shower-beach gear
Manasota Key
9.2 out of 10, Wonderful, (7 reviews)
"Beautiful decor, perfect location to the beach (5min walking). very thoughtful touches throughout the rental. The kitchen is well- equipped with all you need. Bedroom with excellent mattress. The patio with BBQ, kayaks, free parking, beach chair /loungers available, the property was immaculate.10/10. I would recommend""
United States
Anabel P.
$508 nightly
The price is $562
Oct 24 - Oct 25
Total with taxes and fees
2 bedroom, walk to beach-bikes-kayaks-grill-picnic-hot outdoor shower-beach gear
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

Spark by Hilton Sarasota Siesta Key Gateway

Spark by Hilton Sarasota Siesta Key Gateway

8/10 Good
"The property was nice. It would have been better if the hot tub was in working condition."
Rebecca 2-night trip
Posted 8 hours ago
Spark by Hilton Sarasota Siesta Key Gateway

Find out more about Osprey

Osprey Cottages information

Number of reviews
497
Accommodation
396 Cottages
Lowest Price
$150
Highest Price
$751

Frequently asked questions

How much do cottages in Osprey cost?
Cottages in Osprey range between $150 and $751 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 9.2. 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