Osprey Cottages

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Our top choices for Osprey cottages

An outdoor patio with green metal chairs and tables, a red umbrella, and a building with balconies in the background.

1. Beach Tree Cottage,Walk To Beach& Siesta

Siesta Key Village

includes taxes & fees

10 Nov - 11 Nov

A deck with a table and chairs, a blue umbrella, and a white fence.

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

Nokomis

includes taxes & fees

14 Nov - 15 Nov

A yellow house with a porch, a mailbox, and a number 5306 on the door.

3. Yellow Palm Cottage, Heart of Siesta Key

Siesta Key Village

includes taxes & fees

10 Nov - 11 Nov

A beachfront property with a single-story house, a paved driveway, and a palm tree in the foreground.

4. Casey Key Beachfront Escape: Charming 1BR Cottage

Casey Key

kelly h.

includes taxes & fees

10 Nov - 11 Nov

A small, single-story building with a light beige exterior, a blue door, and a number '229' on the wall.

5. NOKOMIS BEACH BUNGALOW 229 15 mins walk to the beach

Nokomis

Susan C.

includes taxes & fees

10 Nov - 11 Nov

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

Sarasota

Rocio S.

includes taxes & fees

11 Nov - 12 Nov

A residential house with a white fence, a palm tree, and a parked car.

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

South Village

Clarissa S.

A pool area with a blue deck, lounge chairs, a barbecue, and a view of buildings in the background.

8. The Inn On Siesta Key

Siesta Key

"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...

Karen Jean

includes taxes & fees

10 Nov - 11 Nov

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

9. Beach View 100ft To Beach and SPA

Siesta Key Village

includes taxes & fees

11 Nov - 12 Nov

Shared sunbathing deck by the pool, at the resort.

10. Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed

Siesta Key

Russ H.

includes taxes & fees

10 Nov - 11 Nov

A small, single-story building with a porch, surrounded by tropical vegetation.

11. BlueDolphin Cottage Walk To Siesta Beach

Siesta Key Village

includes taxes & fees

10 Nov - 11 Nov

A single-story house with a front porch, a small deck, and a garage.

12. Unwind Poolside + Walk to Beach! Sarasota Retreat

South Village

"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. "

Eleuterio

includes taxes & fees

23 Nov - 24 Nov

13. Direct Beachfront 2BR Cottage on Casey Key!

Casey Key

Tom K.

includes taxes & fees

12 Nov - 13 Nov

A modern kitchen with white cabinets, a built-in oven, and a microwave. There is a dining area with a wooden table set for two, blue plates, and wine glasses. A ceiling fan is visible in the living room area.

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

Sarasota

Tracie B.

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

Warm Mineral Springs

VIKTOR M.

includes taxes & fees

13 Nov - 14 Nov

A rectangular pool with white lounge chairs and a white fence, surrounded by palm trees and a building with balconies.

16. Lido Key Casita w Pool Steps to the Beach

Lido Key

Felecia P.

includes taxes & fees

18 Nov - 19 Nov

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.

Desoto Lakes

includes taxes & fees

24 Nov - 25 Nov

18. Cabana Cottage Across street from Beach and Heated Pool

Siesta Key

Meghan J.

A patio with a table set for two, a blue umbrella, and a white fence.

19. Lido Beach Studio with Heated Pool

Lido Key

Lorraine B.

A covered patio with a round table set for four, surrounded by wicker chairs.

20. Charming 2-bedroom cottage in Englewood minutes to the Gulf Beaches-Dog Friendly

Englewood Central

Shawn G.

includes taxes & fees

10 Nov - 11 Nov

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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.

Frequently Asked Questions

How much do cottages in Osprey cost?

Cottages in Osprey range between NZ$245 and NZ$1,103 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.

How many cottages are there in Osprey?

Take your pick of 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.

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.

Book a Osprey Cottage

Change your mind

Treat yourself

Be picky

Find holiday rentals that suit your style

Check prices for these dates

Our top choices for Osprey cottages

1. Beach Tree Cottage,Walk To Beach& Siesta

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

3. Yellow Palm Cottage, Heart of Siesta Key

4. Casey Key Beachfront Escape: Charming 1BR Cottage

5. NOKOMIS BEACH BUNGALOW 229 15 mins walk to the beach

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

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

8. The Inn On Siesta Key

9. Beach View 100ft To Beach and SPA

10. Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed

11. BlueDolphin Cottage Walk To Siesta Beach

12. Unwind Poolside + Walk to Beach! Sarasota Retreat

13. Direct Beachfront 2BR Cottage on Casey Key!

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

15. Charming cottage for 2 across warm mineral springs park

16. Lido Key Casita w Pool Steps to the Beach

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

18. Cabana Cottage Across street from Beach and Heated Pool

19. Lido Beach Studio with Heated Pool

20. Charming 2-bedroom cottage in Englewood minutes to the Gulf Beaches-Dog Friendly

Learn more about Osprey

Frequently Asked Questions

How much do cottages in Osprey cost?

How many cottages are there in Osprey?

What is there to do in Osprey near my cottage?