Osprey, FL Cottage Rentals from $133

Q: How much do cottages in Osprey cost?

Cottages in Osprey range between $133 and $715 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.

Q: 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.

Q: 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.

Q: 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.

Q: 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.

Q: 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.

Q: 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.

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

$228 nightly

Oct 5 - Oct 6

Total with taxes and fees

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.

$270 nightly

Oct 5 - Oct 6

Total with taxes and fees

A beachfront property with a house, palm trees, and a view of the ocean.

3. Casey Key Beachfront Escape: Charming 1BR Cottage

Casey Key

Audrey B.

$543 nightly

Oct 17 - Oct 18

Total with taxes and fees

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

4. Siesta Heron 6 / Sunset

Siesta Key

$633 nightly

Oct 7 - Oct 8

Total with taxes and fees

A pair of stacked front-loading washing machines in a commercial setting.

5. Beach View 100ft To Beach and SPA

Siesta Key Village

Shared sunbathing deck by the pool, at the resort.

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

Siesta Key

Russ H.

$310 nightly

Oct 5 - Oct 6

Total with taxes and fees

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

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

Sarasota

Kandra R.

$414 nightly

Oct 8 - Oct 9

Total with taxes and fees

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

8. Yellow Palm Cottage, Heart of Siesta Key

Siesta Key Village

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

9. Charming cottage for 2 across warm mineral springs park

Warm Mineral Springs

Inna K.

$120 nightly

Oct 5 - Oct 6

Total with taxes and fees

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

10. Studio by Lido Beach w heated pool

Lido Key

$411 nightly

Oct 16 - Oct 17

Total with taxes and fees

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

11. Coastal Studio, Walk to St Armand's or Lido Beach

Lido Key

"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!"

lisa o.

$346 nightly

Oct 20 - Oct 21

Total with taxes and fees

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

12. Direct Beachfront 2BR Cottage on Casey Key!

Casey Key

Dominic C.

$565 nightly

Oct 12 - Oct 13

Total with taxes and fees

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

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

Englewood Central

Linda G.

$217 nightly

Oct 16 - Oct 17

Total with taxes and fees

A single-story house with a blue exterior, a front door, and a small porch area.

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

Desoto Lakes

$236 nightly

Oct 12 - Oct 13

Total with taxes and fees

A residential house with a garage, a front door, and a small front yard.

15. Home < 1-mi Walk to Warm Mineral Springs Park!

North Port

$395 nightly

Oct 9 - Oct 10

Total with taxes and fees

A covered outdoor area with a gravel ground, a covered seating area with chairs, and a building in the background.

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

Manasota Key

Brooke T.

$457 nightly

Oct 7 - Oct 8

Total with taxes and fees

A bedroom with a bed, a ceiling fan, a window with curtains, a wooden wardrobe, and a framed picture on the wall.

17. Cozy Lido Studio by Beach & St Armand's

Lido Key

$435 nightly

Oct 31 - Nov 1

Total with taxes and fees

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

18. Lido Key Casita w Pool Steps to the Beach

Lido Key

$291 nightly

Oct 5 - Oct 6

Total with taxes and fees

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

Manasota Key

Anabel P.

$508 nightly

Oct 5 - Oct 6

Total with taxes and fees

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Top Osprey Hotel Reviews

Spark by Hilton Sarasota Siesta Key Gateway

10/10 Excellent

"All the staff were very friendly and nice..my room was clean. There was a lamp that the bulbs had gone out and they immediately fixed. Would definitely stay here again. Oh and the breakfast was a bagel bar and super yummy."

DoubleTree by Hilton Sarasota Bradenton Airport

10/10 Excellent

"My experience at the hotel was very good overall. The staff was very friendly, and the hotel offered easy access, convenient parking, and great amenities. The room was well equipped and comfortable. I really enjoyed my stay and loved the experience."

Find out more about Osprey

Osprey Cottages information

Number of reviews	145
Accommodation	396 Cottages
Lowest Price	$133
Highest Price	$715

Frequently asked questions

How much do cottages in Osprey cost?

Cottages in Osprey range between $133 and $715 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 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

Things to do in Siesta Key

Room 1

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Upfront pricing

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.