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

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Our top choices for Osprey cottages

1. Siesta Heron 7

Siesta Heron 7
3.0 star property
Siesta Key
The price is €929
includes taxes & fees
12 Aug - 13 Aug
Siesta Heron 7

2. The Inn On Siesta Key

The Inn On Siesta Key
3.5 star property
Siesta Key
10.0 out of 10, Exceptional, (203 reviews)
"We had a wonderful stay at The Inn on Siesta Key. The Cabana was perfect for our family of 4, very clean and well equipped kitchen. The beds are very comfortable, and we enjoyed our morning coffee on the porch area. The property is fully equipped for the beach with chairs, towels, umbrellas, coolers, ice, and these great wagons to haul it all to the beach. Beaches are a short walk and amazing. The property is also a very short walk to The Village for shopping and dining. Paige checked us in and...
United States
Lisa
The price is €264
includes taxes & fees
10 Aug - 11 Aug
The Inn On Siesta Key

3. Casey Key Beachfront Escape: Charming 1BR Cottage

Casey Key Beachfront Escape: Charming 1BR Cottage
Casey Key
9.4 out of 10, Exceptional, (129 reviews)
"A beautiful location and super comfortable!"
United States
K B.
The price is €467
includes taxes & fees
14 Aug - 15 Aug
Casey Key Beachfront Escape: Charming 1BR Cottage

4. 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.
Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.

5. 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 €966
includes taxes & fees
13 Aug - 14 Aug
Cabana Cottage Across street from Beach and Heated Pool

6. Lookout Cottage Across street from Beach and Heated Pool

Lookout Cottage Across street from Beach and Heated Pool
Siesta Key
10.0 out of 10, Exceptional, (1 review)
"The place was beautiful, tastefully furnished and decorated, and so clean! Plenty of towels and nice sheets. Loved the amenities like the pool and the beach chairs. The best part is the location - right across the street from a fantastic beach, close enough to walk to the main business district but not so close that you have to deal with all the people of you don’t want to. Perfect place for a couple looking for some R&R!"
United States
Keeley L.
Lookout Cottage Across street from Beach and Heated Pool

7. Direct Beachfront 2BR Cottage on Casey Key!

Direct Beachfront 2BR Cottage on Casey Key!
Casey Key
9.4 out of 10, Exceptional, (80 reviews)
"Great vacation!!"
United States
Dominic C.
The price is €498
includes taxes & fees
8 Sept - 9 Sept
Direct Beachfront 2BR Cottage on Casey Key!

8. 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, (189 reviews)
"Right across the beach Less then 5 minutes Good space - rooms nice ad clean "
United States
ASHISH
The price is €362
includes taxes & fees
2 Sept - 3 Sept
Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village

9. 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 €607
includes taxes & fees
13 Aug - 14 Aug
Nook Cottage Across street from beach and Heated Pool

10. Cozy Lido Key Bungalow by Pool & Beach

Cozy Lido Key Bungalow by Pool & Beach
Lido Key
The price is €293
includes taxes & fees
10 Aug - 11 Aug
Cozy Lido Key Bungalow by Pool & Beach

11. Siesta Heron 6 / Sunset

Siesta Heron 6 / Sunset
3.0 star property
Siesta Key
The price is €646
includes taxes & fees
1 Sept - 2 Sept
Siesta Heron 6 / Sunset

12. Sunny Lido Studio - Modern Touches

Sunny Lido Studio - Modern Touches
Lido Key
The price is €306
includes taxes & fees
10 Aug - 11 Aug
Sunny Lido Studio - Modern Touches

13. Lido Bungalow Walk to Beach & St. Armand's Circle

Lido Bungalow Walk to Beach & St. Armand's Circle
Lido Key
The price is €293
includes taxes & fees
18 Aug - 19 Aug
Lido Bungalow Walk to Beach & St. Armand's Circle

14. Charming cottage for 2 across warm mineral springs park

Charming cottage for 2 across warm mineral springs park
Warm Mineral Springs
9.2 out of 10, Wonderful, (26 reviews)
"We were enjoying our stay."
United States
Inna K.
The price is €119
includes taxes & fees
16 Aug - 17 Aug
Charming cottage for 2 across warm mineral springs park

15. 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 €386
includes taxes & fees
10 Aug - 11 Aug
Home < 1-mi Walk to Warm Mineral Springs Park!

16. 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
9.6 out of 10, Exceptional, (5 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.
The price is €378
includes taxes & fees
22 Aug - 23 Aug
2 bedroom, walk to beach-bikes-kayaks-grill-picnic-hot outdoor shower-beach gear

17. 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, (6 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.
The price is €404
includes taxes & fees
1 Sept - 2 Sept
Explore Manasota Key, Walk to beach, bikes, kayaks in charming 1-bedroom cottage

18. Beach Road

Beach Road
2.0 star property
Siesta Key
The price is €716
includes taxes & fees
2 Sept - 3 Sept
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.
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Top Osprey Hotel Reviews

Find out more about Osprey

Osprey Cottages information

Number of reviews
658
Accommodation
380 Cottages
Lowest Price
€119
Highest Price
€966

Frequently asked questions

How much do cottages in Osprey cost?
Cottages in Osprey range between €119 and €966 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 9.7. 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 380 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.