Osprey, FL Cottage Rentals from $128

Q: How much do cottages in Osprey cost?

Cottages in Osprey range between $128 and $868 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 9.3. 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 deck with a table and chairs, a blue umbrella, and a white fence.

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

Nokomis

$213 nightly

Nov 14 - Nov 15

Total with taxes and fees

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

2. Casey Key Beachfront Escape: Charming 1BR Cottage

Casey Key

kelly h.

$426 nightly

Nov 15 - Nov 16

Total with taxes and fees

A riverfront restaurant with outdoor seating and a view of the water.

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

Nokomis

Susan C.

$254 nightly

Nov 15 - Nov 16

Total with taxes and fees

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

Rocio S.

$327 nightly

Nov 15 - Nov 16

Total with taxes and fees

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

5. Beach View 100ft To Beach and SPA

Siesta Key Village

$374 nightly

Nov 16 - Nov 17

Total with taxes and fees

Shared sunbathing deck by the pool, at the resort.

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

Siesta Key

Russ H.

$285 nightly

Nov 15 - Nov 16

Total with taxes and fees

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

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

Sarasota

Tracie B.

$349 nightly

Nov 13 - Nov 14

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

$476 nightly

Nov 15 - Nov 16

Total with taxes and fees

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

9. 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

$541 nightly

Nov 23 - Nov 24

Total with taxes and fees

10. Direct Beachfront 2BR Cottage on Casey Key!

Casey Key

Tom K.

$448 nightly

Nov 15 - Nov 16

Total with taxes and fees

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

11. BlueDolphin Cottage Walk To Siesta Beach

Siesta Key Village

$445 nightly

Nov 15 - Nov 16

Total with taxes and fees

A small pink house with a white door, a blue car parked in front, and a white picket fence.

12. PinkMango Cottage Steps to Beach&Village

Siesta Key Village

$467 nightly

Nov 18 - Nov 19

Total with taxes and fees

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

13. Charming cottage for 2 across warm mineral springs park

Warm Mineral Springs

VIKTOR M.

$114 nightly

Nov 13 - Nov 14

Total with taxes and fees

A backyard with a tree, a wooden fence, a blue shed, and a house with a door.

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

Desoto Lakes

$216 nightly

Dec 2 - Dec 3

Total with taxes and fees

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

15. Lido Beach Studio with Heated Pool

Lido Key

Lorraine B.

$360 nightly

Nov 26 - Nov 27

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.

16. Lido Key Casita w Pool Steps to the Beach

Lido Key

Felecia P.

$361 nightly

Nov 18 - Nov 19

Total with taxes and fees

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

Englewood Central

Shawn G.

$246 nightly

Nov 13 - Nov 14

Total with taxes and fees

A two-story building with a blue and white exterior, a balcony, and a sign that reads "Gidget's Coastal Preserve."

18. Beach Road

Siesta Key

$768 nightly

Dec 8 - Dec 9

Total with taxes and fees

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

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

North Port

$420 nightly

Nov 15 - Nov 16

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.

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

Manasota Key

Brooke T.

$436 nightly

Nov 13 - Nov 14

Total with taxes and fees

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Top Osprey Hotel Reviews

Spark by Hilton Sarasota Siesta Key Gateway

8/10 Good

"Todo bien. Sugiero que los empleados hablen español también"

Siesta Key Beach Resort and Suites

10/10 Excellent

"I really enjoyed my stay at Siesta Key. It was just across the street from the beach access and I loved the live music in the afternoons! My room was right next to the bar area. But it really wasn’t loud and they quieted things down early. The amenities in the room were nice, and the pool and hot tub were appreciated. The fish tacos were absolutely delicious!"

DoubleTree by Hilton Sarasota Bradenton Airport

10/10 Excellent

"We arrived at the hotel and greeted at the front desk with plenty of assurances we would have a shuttle from the airport to the hotel and back and forth. Room was ready no waiting - and spotless. Definitely would stay here again. Staff was very helpful with an early morning departure,"

Find out more about Osprey

Osprey Cottages information

Number of reviews	517
Accommodation	396 Cottages
Lowest Price	$128
Highest Price	$868

Frequently asked questions

How much do cottages in Osprey cost?

Cottages in Osprey range between $128 and $868 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 9.3. 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

Search Osprey Cottages

Bundle & Save

OneKeyCash

Upfront pricing

Check prices for these dates

Our top choices for Osprey cottages

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

2. Casey Key Beachfront Escape: Charming 1BR Cottage

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

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

5. Beach View 100ft To Beach and SPA

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

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

8. Yellow Palm Cottage, Heart of Siesta Key

9. Unwind Poolside + Walk to Beach! Sarasota Retreat

10. Direct Beachfront 2BR Cottage on Casey Key!

11. BlueDolphin Cottage Walk To Siesta Beach

12. PinkMango Cottage Steps to Beach&Village

13. Charming cottage for 2 across warm mineral springs park

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

15. Lido Beach Studio with Heated Pool

16. Lido Key Casita w Pool Steps to the Beach

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

18. Beach Road

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

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

Find vacation rentals that suit your style

Top Osprey Hotel Reviews

Spark by Hilton Sarasota Siesta Key Gateway

Find out more about Osprey

Osprey Cottages information

Frequently asked questions

Explore a world of travel with Expedia