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Check prices for these dates

In two weeks
13 Feb - 15 Feb
In two months
27 Mar - 29 Mar
In three months
24 Apr - 26 Apr
In four months
22 May - 24 May

Our top choices for Osprey cottages

Exterior

Charming cottage for 2 across warm mineral springs park

Charming cottage for 2 across warm mineral springs park
Warm Mineral Springs
9.4 out of 10, Exceptional, (13 reviews)
"Property was perfect for the price."
United States
William M.
The price is €140
includes taxes & fees
1 Mar - 2 Mar
Charming cottage for 2 across warm mineral springs park
Interior

Stylish Retro Vibes Private BBQ & Beach Access

Stylish Retro Vibes Private BBQ & Beach Access
3.0 star property
Sarasota
The price is €333
includes taxes & fees
3 Feb - 4 Feb
Stylish Retro Vibes Private BBQ & Beach Access
Outdoor dining

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
10.0 out of 10, Exceptional, (1 review)
"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. "
United States
Jade C.
The price is €247
includes taxes & fees
5 Feb - 6 Feb
Charming 2-bedroom cottage in Englewood minutes to the Gulf Beaches-Dog Friendly
Exterior

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 €304
includes taxes & fees
1 Feb - 2 Feb
Escape near Siesta Key with Hot Tub, BBQ, and Fire pit
Exterior

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 €407
includes taxes & fees
7 Feb - 8 Feb
Cozy Beach Cottage
Exterior

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 €386
includes taxes & fees
8 Feb - 9 Feb
Explore Manasota Key, Walk to beach, bikes, kayaks in charming 1-bedroom cottage
Exterior

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 €251
includes taxes & fees
8 Feb - 9 Feb
Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.
Exterior

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
1-bedroom cottage in a park like setting! Close to Spring Training and Beaches.
The Cottage, 3 Bedroom 2 Bath (2 Kings, 1 Queen, 2 Twins) | Terrace/patio

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 Inn On Siesta Key
Outdoor dining

Tropical Treehouse · Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed

Tropical Treehouse · Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed
Siesta Key
9.4 out of 10, Exceptional, (6 reviews)
"We really enjoyed the cleanliness and location. Pool was great. Having our own deck was nice. Great views. Highly recommend. "
United States
Rolly N.
The price is €295
includes taxes & fees
1 Feb - 2 Feb
Tropical Treehouse · Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed
Exterior

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 €357
includes taxes & fees
2 Feb - 3 Feb
Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village
Interior

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 €529
includes taxes & fees
8 Feb - 9 Feb
Family Fun: Ping Pong, Bbq, Walk to Park Nearby
Terrace/patio

Casey Key Beachfront Escape: Charming 1BR Cottage

Casey Key Beachfront Escape: Charming 1BR Cottage
Casey Key
9.4 out of 10, Exceptional, (112 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 €376
includes taxes & fees
1 Feb - 2 Feb
Casey Key Beachfront Escape: Charming 1BR Cottage
1 bedroom, iron/ironing board, free WiFi, bed sheets

Light filled walk to bay 1 King BR,1 BA private cottage by the Ringling Museum

Light filled walk to bay 1 King BR,1 BA private cottage by the Ringling Museum
Indian Beach Sapphire Shores
9.6 out of 10, Exceptional, (34 reviews)
"Clean and everything was as advertised "
United States
alan m.
The price is €245
includes taxes & fees
1 Feb - 2 Feb
Light filled walk to bay 1 King BR,1 BA private cottage by the Ringling Museum
Terrace/patio

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
Terrace/patio

Direct Beachfront 2BR Cottage on Casey Key!

Direct Beachfront 2BR Cottage on Casey Key!
Casey Key
9.2 out of 10, Wonderful, (69 reviews)
"This is a great spot, this was our 2nd time staying and we will definitely be back. "
United States
Jason W.
The price is €822
includes taxes & fees
14 Feb - 15 Feb
Direct Beachfront 2BR Cottage on Casey Key!
Property grounds

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.
Haven cottage Across street from beach and Heated Pool
Interior

Siesta Heron 6 / Sunset

Siesta Heron 6 / Sunset
2.0 star property
Siesta Key
Siesta Heron 6 / Sunset
Interior

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

Lido Beach Resort

Lido Beach Resort

10/10 Excellent
"Location was great, staff so positive "
Heather 2-night trip
Posted 4 days ago
Lido Beach Resort

Find out more about Osprey

Osprey Cottages information

Number of reviews
587
Accommodation
325 Cottages
Lowest Price
€140
Highest Price
€822

Frequently asked questions

How much do cottages in Osprey cost?
Cottages in Osprey range between €140 and €822 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 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.