Best Cottages in Osprey in 2026

Q: How much do cottages in Osprey cost?

Cottages in Osprey range between £106 and £1,019 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?

A traveller favourite is The Inn On Siesta Key . Base yourself at this 3.5-star stay which offers a barbecue grill and a memory foam mattress. Flip Flop Cottages is another popular option to consider. Spend your break at this 3-star cottage and make the most of amenities including a barbecue grill and a swimming pool. You'll have your pick of multiple cottages in Osprey with a total average guest review rating of 9.3.

Q: How many cottages are there in Osprey?

Take your pick of 365 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.

Q: Are there any family-friendly cottages in Osprey?

Holidaying with your group in Osprey couldn't be easier at The Inn On Siesta Key . With conveniences such as a nearby beach and an oven, you'll find all the comforts you need at this 3.5-star cottage. Flip Flop Cottages is another family-friendly property where you and the rest of the squad can take time out from the relentless pace of city life. This cottage has a 3-star rating and amenities including a picnic area and a barbecue grill. Once you've checked in and unpacked your suitcase, there are loads of family-friendly attractions to visit in and around Osprey. Manasota Beach and Heritage Oaks Golf and Country Club guarantee fun for all ages.

Q: 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.

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.

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Our top choices for Osprey cottages

Beach Road

Siesta Key

includes taxes & fees

21 Jun - 22 Jun

Charming cottage for 2 across warm mineral springs park

Warm Mineral Springs

Robert J.

includes taxes & fees

23 Jun - 24 Jun

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

North Port

includes taxes & fees

29 Jun - 30 Jun

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

Englewood Central

"We all had a wonderful stay!!! The home was clean, beautifully furnished and appointed with all sorts of amenities: coffee, tea, beach chairs, towels, laundry detergent and more. The fenced in yard was wonderful for privacy and the dogs. The owners were very responsive to our questions and needs. We would definitely stay here again!!! Not only was the home super cute, it was close to everything: grocery store, pharmacy, downtown, beaches and restaurants. "

Jade C.

includes taxes & fees

21 Jun - 22 Jun

2 bedroom, walk to beach-bikes-kayaks-grill-picnic-hot outdoor shower-beach gear

Manasota Key

Anabel P.

includes taxes & fees

1 Jul - 2 Jul

Entire Village! La Mia Casa out of Siesta Dr. Beach resort vibe!

Southgate

Chris R.

includes taxes & fees

30 Jun - 1 Jul

Waterfront Venice Nokomis FL Bay view Private Guest suite/house pet friendly

Nokomis

Bryan S.

includes taxes & fees

29 Jun - 30 Jun

Direct Beachfront 2BR Cottage on Casey Key!

Casey Key

Karen M.

includes taxes & fees

22 Jun - 23 Jun

The Inn On Siesta Key

Siesta Key

Michele

includes taxes & fees

22 Jun - 23 Jun

Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village

Sarasota

ASHISH

includes taxes & fees

21 Jun - 22 Jun

Siesta Heron 6 / Sunset

Siesta Key

includes taxes & fees

21 Jun - 22 Jun

Casey Key Beachfront Escape: Charming 1BR Cottage

Casey Key

K B.

includes taxes & fees

22 Jun - 23 Jun

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

12 Jul - 13 Jul

Siesta Heron 7

Siesta Key

includes taxes & fees

30 Jun - 1 Jul

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Top Osprey Hotel Reviews

Kompose Boutique Hotel

10/10 Excellent

"Limpieza"

Golden Host Resort - Sarasota

8/10 Good

"Staff was very nice. When we stayed the street outside was under construction, Not the Hotel's fault or anything they could do about that. The pool was very nice. we liked the the Hawaiian Feel. The facility is a little dated, but overall nice place. I would definitely stay again. Thank You Guys."

Find out more about Osprey

Osprey Cottages information

Number of reviews	638
Accommodation	365 Cottages
Lowest Price	£106
Highest Price	£1,019

Frequently asked questions

How much do cottages in Osprey cost?

Cottages in Osprey range between £106 and £1,019 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?

A traveller favourite is The Inn On Siesta Key. Base yourself at this 3.5-star stay which offers a barbecue grill and a memory foam mattress. Flip Flop Cottages is another popular option to consider. Spend your break at this 3-star cottage and make the most of amenities including a barbecue grill and a swimming pool. You'll have your pick of multiple cottages in Osprey with a total average guest review rating of 9.3.

How many cottages are there in Osprey?

Take your pick of 365 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?

Holidaying with your group in Osprey couldn't be easier at The Inn On Siesta Key. With conveniences such as a nearby beach and an oven, you'll find all the comforts you need at this 3.5-star cottage. Flip Flop Cottages is another family-friendly property where you and the rest of the squad can take time out from the relentless pace of city life. This cottage has a 3-star rating and amenities including a picnic area and a barbecue grill. Once you've checked in and unpacked your suitcase, there are loads of family-friendly attractions to visit in and around Osprey. Manasota Beach and Heritage Oaks Golf and Country Club guarantee fun for all ages.

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.

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