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Our top choices for Osprey cottages

Family Fun: Ping Pong, Bbq, Walk to Park Nearby

Family Fun: Ping Pong, Bbq, Walk to Park Nearby
3.0 star property
Fruitville
The price is ¥17,594
¥73,592 total
includes taxes & fees
Jan 28 - Jan 29
Family Fun: Ping Pong, Bbq, Walk to Park Nearby

Charming cottage for 2 across warm mineral springs park

Charming cottage for 2 across warm mineral springs park
Warm Mineral Springs
9.2 out of 10, Wonderful, (12 reviews)
"Property was perfect for the price."
United States
William M.
The price is ¥10,899
¥25,986 total
includes taxes & fees
Jan 30 - Jan 31
Charming cottage for 2 across warm mineral springs park

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

Escape near Siesta Key with Hot Tub, BBQ, and Fire pit
Sarasota
10.0 out of 10, Exceptional, (1 review)
"Perfect vacation get away. Host are very good to work with. Everything was exactly as we wanted it! "
United States
Kara F.
The price is ¥23,355
¥54,456 total
includes taxes & fees
Jan 29 - Jan 30
Escape near Siesta Key with Hot Tub, BBQ, and Fire pit

Cozy Beach Cottage

Cozy Beach Cottage
Manasota Beach
9.4 out of 10, Exceptional, (24 reviews)
"Wonderful location for a peaceful getaway "
United States
pamela
The price is ¥29,272
¥74,805 total
includes taxes & fees
Feb 7 - Feb 8
Cozy Beach Cottage

The Inn On Siesta Key

The Inn On Siesta Key
3.5 star property
Siesta Key
10.0 out of 10, Exceptional, (194 reviews)
"Very charming place! Great location for the beach and restaurants. Would definitely stay again."
United States
Blaine
The price is ¥38,469
¥52,090 total
includes taxes & fees
Jan 28 - Jan 29
The Inn On Siesta Key

1-bedroom cottage in a park like setting! Close to Spring Training and Beaches.

1-bedroom cottage in a park like setting! Close to Spring Training and Beaches.
Bayou Oaks
The price is ¥9,217
¥16,695 total
includes taxes & fees
Feb 1 - Feb 2
1-bedroom cottage in a park like setting! Close to Spring Training and Beaches.

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

Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.
South Village
9.6 out of 10, Exceptional, (83 reviews)
"Great condo. The location is perfect. The pool was the best. Will stay here again."
United States
Jeanne J.
The price is ¥15,414
¥46,098 total
includes taxes & fees
Feb 11 - Feb 12
Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.

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

Charming 2-bedroom cottage in Englewood minutes to the Gulf Beaches-Dog Friendly
Englewood Central
The price is ¥21,020
¥43,581 total
includes taxes & fees
Feb 5 - Feb 6
Charming 2-bedroom cottage in Englewood minutes to the Gulf Beaches-Dog Friendly

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

Explore Manasota Key, Walk to beach, bikes, kayaks in charming 1-bedroom cottage
Manasota Key
10.0 out of 10, Exceptional, (1 review)
"This was a great stay. It was very clean and seemed like a brand new renovation. They provide plenty to do from two bicycles for cruising, a few kayaks and indoor games. The kitchen was stocked if you chose to stay in and cook. Lastly, the hosts were great to work with. We will stay again. "
United States
John C.
The price is ¥26,469
¥71,373 total
includes taxes & fees
Feb 8 - Feb 9
Explore Manasota Key, Walk to beach, bikes, kayaks in charming 1-bedroom cottage

Blue Dolphin Cottage steps from the beach

Blue Dolphin Cottage steps from the beach
Siesta Key Village
The price is ¥22,944
¥91,222 total
includes taxes & fees
Jan 27 - Jan 28
Blue Dolphin Cottage steps from the beach

Stylish Retro Vibes Private BBQ & Beach Access

Stylish Retro Vibes Private BBQ & Beach Access
3.0 star property
Sarasota
Stylish Retro Vibes Private BBQ & Beach Access

Yellow Palm Cottage steps from the beach

Yellow Palm Cottage steps from the beach
Siesta Key Village
Yellow Palm Cottage steps from the beach

Casey Key Beachfront Escape: Charming 1BR Cottage

Casey Key Beachfront Escape: Charming 1BR Cottage
Casey Key
9.4 out of 10, Exceptional, (111 reviews)
"Simple old-school beach shack - so hard to find these days, absolutely loved it. Right on the water, best location along Nokomis Beach/Casey Key...short walk to restaurants also....absolutely fantastic."
United States
HAYLEY S.
The price is ¥46,399
¥89,145 total
includes taxes & fees
Jan 31 - Feb 1
Casey Key Beachfront Escape: Charming 1BR Cottage

Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village

Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village
Sarasota
9.2 out of 10, Wonderful, (178 reviews)
"Wonderful property with an excellent location! Beach access was across the street and the trolley pick-up was at the end of the block. The village was within walking distance as well. The property was very clean and the beds were comfortable. The washer and dryer is located right outside of the unit and beach chairs and a cooler were provided. We look forward to booking this property again in the future! "
United States
Alison B.
The price is ¥48,111
¥84,509 total
includes taxes & fees
Feb 18 - Feb 19
Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village

Cabana Cottage Across street from Beach and Heated Pool

Cabana Cottage Across street from Beach and Heated Pool
Siesta Key
10.0 out of 10, Exceptional, (5 reviews)
"Wonderful property and fantastic location. Everything you need at your fingertips for an enjoyable beach stay without ever having to leave the island!"
United States
Meghan J.
Cabana Cottage Across street from Beach and Heated Pool

Haven cottage Across street from beach and Heated Pool

Haven cottage Across street from beach and Heated Pool
Siesta Key
9.8 out of 10, Exceptional, (7 reviews)
"It was a beautiful place. Great staff. Awesome experience."
United States
Nicholas M.
The price is ¥43,264
¥83,998 total
includes taxes & fees
Jan 29 - Jan 30
Haven cottage Across street from beach and Heated Pool

Direct Beachfront 2BR Cottage on Casey Key!

Direct Beachfront 2BR Cottage on Casey Key!
Casey Key
9.2 out of 10, Wonderful, (69 reviews)
"We enjoyed our stay at this ocean front property. Loved the fact that we were able to walk from the back door straight to the beach. We were able to find so many shark teeth on this beach and we watched dolphins most mornings. The property is in need of some love. Really wish there was an awning on the back porch to be able to enjoy an afternoon snack in some shade. "
United States
Cortney R.
The price is ¥93,109
¥150,584 total
includes taxes & fees
Feb 14 - Feb 15
Direct Beachfront 2BR Cottage on Casey Key!

Lookout Cottage Across street from Beach and Heated Pool

Lookout Cottage Across street from Beach and Heated Pool
Siesta Key
10.0 out of 10, Exceptional, (1 review)
"The place was beautiful, tastefully furnished and decorated, and so clean! Plenty of towels and nice sheets. Loved the amenities like the pool and the beach chairs. The best part is the location - right across the street from a fantastic beach, close enough to walk to the main business district but not so close that you have to deal with all the people of you don’t want to. Perfect place for a couple looking for some R&R!"
United States
Keeley L.
Lookout Cottage Across street from Beach and Heated Pool

Nook Cottage Across street from beach and Heated Pool

Nook Cottage Across street from beach and Heated Pool
Siesta Key
10.0 out of 10, Exceptional, (4 reviews)
"They have really thought of everything and gone above and beyond to make our stay as comfortable as possible. Everything was very clean! Paige was a wonderful guide and host for the local area!"
United States
Derek N.
Nook Cottage Across street from beach and Heated Pool

Beach Road

Beach Road
2.0 star property
Siesta Key
Beach Road
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Osprey Hotel Reviews

Find out more about Osprey

Osprey Cottages information

Number of reviews
549
Accommodation
325 Cottages
Lowest Price
¥25,986
Highest Price
¥150,584

Frequently asked questions

How much do cottages in Osprey cost?
Cottages in Osprey range between ¥25,986 and ¥150,584 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 9.5. 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 325 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.

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