Top Cottages in Osprey in 2026

Q: How much do cottages in Osprey cost?

Cottages in Osprey range between 12.728.964 ₫ and 41.493.873 ₫ 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 9.0. 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 226 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?

Many travellers 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 travelling 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 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

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

North Port

12.728.964 ₫ total

includes taxes & fees

23 Jun - 24 Jun

The Inn On Siesta Key

Siesta Key

Michele

14.444.397 ₫ total

includes taxes & fees

6 Jul - 7 Jul

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

16.048.980 ₫ total

includes taxes & fees

12 Jul - 13 Jul

Siesta Heron 6 / Sunset

Siesta Key

25.501.366 ₫ total

includes taxes & fees

13 Jul - 14 Jul

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Top Osprey Hotel Reviews

Lantern Inn & Suites

10/10 Excellent

"La habitación estaba super limpia,la ropa de cama,las toallas,baño y cocina en perfecto estado y muy higiénico todo.Un ambiente tranquilo.La atención fué muy buena,al final nos devolvieron los $ 150 del depósito.Solo estuvimos 1 día con su noche.No utilizamos la piscina y el bar.La relación calidad--precio es justa.Sin dudas la recomendaría y si volvemos a Sarasota nuevamente,volveríamos a quedarnos allí.Felicitaciones!"

Tropical Breeze Resort

8/10 Good

"This resort is very close to the beach, bars, restaurants and shopping. You can literally walk to everything. The room was very nice the only thing is you don’t get daily cleaning and need to request more towels. The people cleaning the rooms were very nice and hardworking though. Check in was not great as I had to wait nearly 45 minutes before my room was ready. The lady at the front desk was very nice and made she communicated well. Overall I enjoyed my stay and will stay again."

Carlisle Inn

10/10 Excellent

"I cannot recommend the Carlisle Inn Sarasota highly enough. From check-in to check-out, every staff member was genuinely warm, welcoming, and professional. They were always smiling, saying hello, and making sure guests had everything they needed. Their hospitality made the hotel feel family-run. This is, without question, the cleanest hotel I’ve ever stayed in. Spotless is an understatement. Every hallway, common area, and guest room was immaculate. Everything looked brand new, and I even saw a staff member touching up a wall with fresh paint. It’s obvious they take great pride in maintaining the property. The complimentary cookies served every evening were a delicious bonus. My king room was exceptionally well designed. The bathroom was separate from a large walk-in closet that included a second vanity and sink for getting ready. The closet also had a pocket door, creating a private dressing area. It’s a brilliant layout—one person can use the bathroom, another can get dressed in the bedroom, and another can get ready in the closet at the same time. The location was perfect—about 10–15 minutes from St. Armands Circle and a short drive to beaches, restaurants, and everything else we wanted to visit. The hotel felt quiet, safe, and exceptionally well cared for. I would absolutely stay here again and recommend it to anyone visiting Sarasota."

Embassy Suites by Hilton Sarasota, FL

8/10 Good

"Nice room, bar and wait staff excellent. Hotel was hosting families for a junior soccer tournament resulting in overcrowded pool area and coupled with one non operational elevator resulted in abnormally long waits for movement around facility. Kids were unattended by parents in pool and around facility playing with operational elevators. Parents were not chaperoning kids and hotel staff did not intervene and enforce posted rules. We have stayed here on numerous occasions and facility is normally first rate. My bad for not doing due diligence and checking if facility was hosting special event. Will definitely do it next time. Also thought $40 per day self parking fee was excessive"

Find out more about Osprey

Osprey Cottages information

Number of reviews	200
Accommodation	226 Cottages
Lowest Price	12.728.964 ₫
Highest Price	41.493.873 ₫

Frequently asked questions

How much do cottages in Osprey cost?

Cottages in Osprey range between 12.728.964 ₫ and 41.493.873 ₫ 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 9.0. 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 226 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?

Many travellers 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 travelling 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 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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Our top choices for Osprey cottages