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
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

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
$228 nightly
The price is $255
Oct 1 - Oct 2
Total with taxes and fees
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.
$270 nightly
The price is $301
Oct 4 - Oct 5
Total with taxes and fees
Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.
A hammock tied between two palm trees, a pink building with a red roof, and a bush with red flowers.

3. 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)
Pink Mango Cottage steps from the beach
Shared sunbathing deck by the pool, at the resort.

4. 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.
$285 nightly
The price is $318
Oct 1 - Oct 2
Total with taxes and fees
Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed
A wooden deck with a view of the ocean, a barbecue grill, and a cart.

5. 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 1 - Oct 2
Total with taxes and fees
Direct Beachfront 2BR Cottage on Casey Key!
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)
"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.
$414 nightly
The price is $461
Oct 8 - Oct 9
Total with taxes and fees
Escape near Siesta Key with Hot Tub, BBQ, and Fire pit
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
$622 nightly
The price is $702
Oct 4 - Oct 5
Total with taxes and fees
Siesta Heron 6 / Sunset
A patio with a table set for two, a blue umbrella, and a white fence.

8. Studio by Lido Beach w heated pool

Studio by Lido Beach w heated pool
Lido Key
$306 nightly
The price is $340
Oct 1 - Oct 2
Total with taxes and fees
Studio by Lido Beach w heated pool
A two-story building with a blue exterior and white railings.

9. 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.
$386 nightly
The price is $430
Oct 2 - Oct 3
Total with taxes and fees
Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village
A rectangular pool with white lounge chairs and a white fence, surrounded by palm trees and a building with balconies.

10. Lido Key Casita w Pool Steps to the Beach

Lido Key Casita w Pool Steps to the Beach
Lido Key
$297 nightly
The price is $331
Oct 5 - Oct 6
Total with taxes and fees
Lido Key Casita w Pool Steps to the Beach
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
$431 nightly
The price is $487
Oct 4 - Oct 5
Total with taxes and fees
Yellow Palm Cottage, Heart of Siesta Key
A beachfront property with a house, palm trees, and a view of the ocean.

12. Casey Key Beachfront Escape: Charming 1BR Cottage

Casey Key Beachfront Escape: Charming 1BR Cottage
Casey Key
9.4 out of 10, Exceptional, (132 reviews)
"Beautiful gulf view."
United States
Audrey B.
$539 nightly
The price is $601
Oct 9 - Oct 10
Total with taxes and fees
Casey Key Beachfront Escape: Charming 1BR Cottage
A single-story house with a blue exterior, a front door, and a small porch area.

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
$210 nightly
The price is $235
Oct 28 - Oct 29
Total with taxes and fees
Coastal Breeze Cottage in Sunny Sarasota. Pet friendly. King size bed.
A small, single-story building with a gray exterior, a white door, and a window with shutters.

14. 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.
$125 nightly
The price is $139
Oct 1 - Oct 2
Total with taxes and fees
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.

15. 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, (1 review)
"5 Stars: This cozy studio was exactly what we were looking for. Alexander was pleasant and friendly, the check in/check out process was easy. The location was fabulous- perhaps slightly too far to walk to St.Armand’s , but a quick ride on the rentable VEO bikes/scooters. The accommodations were clean, and beachy. We did not have an opportunity to use the pool, so I do have any objective comments for the pool. If we are in the area again, we would definitely stay here again!"
United States
lisa o.
$309 nightly
The price is $344
Oct 4 - Oct 5
Total with taxes and fees
Coastal Studio, Walk to St Armand's or Lido Beach
A residential house with a garage, a front door, and a small front yard.

16. 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 1 - Oct 2
Total with taxes and fees
Home < 1-mi Walk to Warm Mineral Springs Park!
A covered patio with a round table set for four, surrounded by wicker chairs.

17. 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.
$227 nightly
The price is $253
Oct 16 - Oct 17
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."

18. Beach Road

Beach Road
2.0 star property
Siesta Key
$753 nightly
The price is $851
Oct 2 - Oct 3
Total with taxes and fees
Beach Road
A two-story building with a covered patio area featuring outdoor seating.

19. 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
9.8 out of 10, Exceptional, (6 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 1 - Oct 2
Total with taxes and fees
2 bedroom, walk to beach-bikes-kayaks-grill-picnic-hot outdoor shower-beach gear
A covered outdoor area with a gravel ground, a covered seating area with chairs, and a building in the background.

20. Explore Manasota Key, Walk to beach, bikes, kayaks in charming 1-bedroom cottage

Explore Manasota Key, Walk to beach, bikes, kayaks in charming 1-bedroom cottage
Manasota Key
10.0 out of 10, Exceptional, (7 reviews)
"If you are looking for a quaint getaway in a quiet part of Manasota key, this is it. While you are close enough walk or bike to the beach and all the restaurant/bars, it’s just far enough away from all the congestion. The cottage was beautifully decorated, clean & updated. Truly a great host, they were responsive and provided more items to use than any other VRBO we’ve stayed at! "
United States
Brooke T.
$406 nightly
The price is $449
Oct 1 - Oct 2
Total with taxes and fees
Explore Manasota Key, Walk to beach, bikes, kayaks in charming 1-bedroom cottage
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 Westin Sarasota

The Westin Sarasota

10/10 Excellent
"There was a water leak in front of the window"
Cindy 3-night trip
Posted 4 hours ago
The Westin Sarasota

Find out more about Osprey

Osprey Cottages information

Number of reviews
343
Accommodation
396 Cottages
Lowest Price
$139
Highest Price
$851

Frequently asked questions

How much do cottages in Osprey cost?
Cottages in Osprey range between $139 and $851 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 9.5. 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.

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