Osprey Cottages ￥20,445

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

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

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

Nokomis

￥39,624 total

includes taxes & fees

Sep 11 - Sep 12

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.

South Village

Clarissa S.

￥46,126 total

includes taxes & fees

Sep 10 - Sep 11

A wooden pier leading to a beach with a clear blue sky.

3. Casey Key Beachfront Escape: Charming 1BR Cottage

Casey Key

K B.

￥73,243 total

includes taxes & fees

Sep 11 - Sep 12

A modern house with a driveway, a tree with purple lighting, and a white car parked in front.

4. Escape near Siesta Key with Hot Tub, BBQ, and Fire pit

Sarasota

Kandra R.

￥71,221 total

includes taxes & fees

Sep 13 - Sep 14

A wooden deck with a glass door leading to a lake view, surrounded by greenery.

5. Siesta Heron 6 / Sunset

Siesta Key

￥106,220 total

includes taxes & fees

Sep 29 - Sep 30

A bathroom with a toilet, a glass-enclosed shower, and a framed picture on the wall.

6. Sunny Lido Studio - Modern Touches

Lido Key

￥51,371 total

includes taxes & fees

Sep 12 - Sep 13

A two-story building with a blue exterior and white railings.

7. Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village

Sarasota

ASHISH

￥64,058 total

includes taxes & fees

Sep 14 - Sep 15

A wooden deck with a view of the ocean, a barbecue grill, and a cart.

8. Direct Beachfront 2BR Cottage on Casey Key!

Casey Key

Dominic C.

￥76,974 total

includes taxes & fees

Sep 13 - Sep 14

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Top Osprey Hotel Reviews

The Westin Sarasota

10/10 Excellent

"El servicio de transporte a la playa es muy conveniente."

Cottages at Siesta Key Inn

10/10 Excellent

"Overall we had a good stay, Check in was quite difficult due to staff not being on scene that day. We had to make multiple phone calls and get transferred to numerous people before anyone could help us. Great location, easy parking, clean rooms. I will say, the rooms appear to be very recently updated but the wallpaper was already ripped off the walls, not sure if it's humidity or what but it did not affect the quality of our stay. I would recommend."

Find out more about Osprey

Osprey Cottages information

Number of reviews	543
Accommodation	390 Cottages
Lowest Price	￥20,445
Highest Price	￥171,314

Frequently asked questions

How much do cottages in Osprey cost?

Cottages in Osprey range between ￥20,445 and ￥171,314 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 9.4. 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 390 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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Room 1

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Osprey cottages

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

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

3. Casey Key Beachfront Escape: Charming 1BR Cottage