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Our top choices for Osprey cottages

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
9.8 out of 10, Exceptional, (6 reviews)
"Very clean and nicely decorated condo. Appreciated the extras...dish soap, soap, shampoo and body wash, & TP. Also, beach chairs and towels! Nice outside area and short drive to beaches. Host is very responsive...issue with heat resolved same day. "
United States
Susan E.
The price is ¥11,986
¥38,864 total
includes taxes & fees
May 18 - May 19
Charming 2-bedroom cottage in Englewood minutes to the Gulf Beaches-Dog Friendly

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, (24 reviews)
"We liked how it was a quiet neighborhood and a short drive to stores and restaurants. "
United States
Luann F.
The price is ¥8,617
¥23,494 total
includes taxes & fees
May 14 - May 15
Charming cottage for 2 across warm mineral springs park

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

2 bedroom, walk to beach-bikes-kayaks-grill-picnic-hot outdoor shower-beach gear
Manasota Key
9.0 out of 10, Wonderful, (2 reviews)
"Beautiful decor, perfect location to the beach (5min walking). very thoughtful touches throughout the rental. The kitchen is well- equipped with all you need. Bedroom with excellent mattress. The patio with BBQ, kayaks, free parking, beach chair /loungers available, the property was immaculate.10/10. I would recommend""
United States
Anabel P.
The price is ¥25,069
¥70,381 total
includes taxes & fees
May 12 - May 13
2 bedroom, walk to beach-bikes-kayaks-grill-picnic-hot outdoor shower-beach gear

Direct Beachfront 2BR Cottage on Casey Key!

Direct Beachfront 2BR Cottage on Casey Key!
Casey Key
9.2 out of 10, Wonderful, (71 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 ¥38,857
¥82,828 total
includes taxes & fees
May 12 - May 13
Direct Beachfront 2BR Cottage on Casey Key!

Outdoor Kitchen & Gaming Garage: Bradenton Retreat

Outdoor Kitchen & Gaming Garage: Bradenton Retreat
3.0 star property
Bradenton
The price is ¥31,493
¥104,874 total
includes taxes & fees
May 16 - May 17
Outdoor Kitchen & Gaming Garage: Bradenton Retreat

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, (87 reviews)
"Great stay - flexible early check-in!"
United States
Jill P.
The price is ¥15,511
¥47,485 total
includes taxes & fees
May 30 - May 31
Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.

Yellow Palm Cottage steps from the beach

Yellow Palm Cottage steps from the beach
Siesta Key Village
10.0 out of 10, Exceptional, (1 review)
"This place was so cute and quaint! It was just a short walk to the village and to the beach. The grounds were beautiful! A little oasis in the backyard. . Would stay here again!!!"
United States
Tami B.
The price is ¥40,635
¥119,542 total
includes taxes & fees
May 12 - May 13
Yellow Palm Cottage steps from the beach

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

Tropical Treehouse · Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed
Siesta Key
9.6 out of 10, Exceptional, (8 reviews)
"The most well maintained property I've ever stayed."
United States
Russ H.
The price is ¥32,589
¥65,805 total
includes taxes & fees
May 26 - May 27
Tropical Treehouse · Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed

Lido Key Getaway - Bikes & Beach Gear

Lido Key Getaway - Bikes & Beach Gear
Lido Key
The price is ¥14,571
¥63,352 total
includes taxes & fees
May 31 - Jun 1
Lido Key Getaway - Bikes & Beach Gear

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, (6 reviews)
"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 ¥25,069
¥70,381 total
includes taxes & fees
May 15 - May 16
Explore Manasota Key, Walk to beach, bikes, kayaks in charming 1-bedroom cottage

The Inn On Siesta Key

The Inn On Siesta Key
3.5 star property
Siesta Key
10.0 out of 10, Exceptional, (198 reviews)
"This property was everything we wanted...although not on the beach, it was a short walk to the beach and chairs, umbrellas, coolers and wagons were provided to the beach. The pool area was very comfortable and clean. We like that there were only 6 units...each was unique and very clean. We stayed in "The Nook" which was perfect for our getaway."
United States
Michele
The price is ¥86,597
¥106,530 total
includes taxes & fees
May 22 - May 23
The Inn On Siesta Key

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

Waterfront Venice Nokomis FL Bay view Private Guest suite/house pet friendly
Nokomis
9.6 out of 10, Exceptional, (4 reviews)
"The property was very well stocked, had a bowl for our dog an very clean! It was the petfect place for our visit with local family. The "Florida Room" was lovely and the view was excellent. Very peaceful location."
United States
Marie W.
The price is ¥19,585
¥32,660 total
includes taxes & fees
May 26 - May 27
Waterfront Venice Nokomis FL Bay view Private Guest suite/house pet friendly

Miles of Private Gulf Beach-Luxury 4 BR-Pets Okay-Kayaks & SUPs-Best Shark Teeth

Miles of Private Gulf Beach-Luxury 4 BR-Pets Okay-Kayaks & SUPs-Best Shark Teeth
Englewood
10.0 out of 10, Exceptional, (39 reviews)
"Very private beach. Beautiful lodging and everything you need to have a great beach vacation. The host was wonderful and answered questions quickly. The whole package for a memorable vacation. "
United States
Anonymous traveler
The price is ¥86,174
¥157,518 total
includes taxes & fees
May 16 - May 17
Miles of Private Gulf Beach-Luxury 4 BR-Pets Okay-Kayaks & SUPs-Best Shark Teeth

Casey Key Beachfront Escape: Charming 1BR Cottage

Casey Key Beachfront Escape: Charming 1BR Cottage
Casey Key
9.4 out of 10, Exceptional, (122 reviews)
"It was a cool place. Best experience on the beach I have had in my life. The one thing is that they could use a few updates, you can tell it’s been some years since they took the photos till now. However, it was a great time for the family. You won’t regret it."
United States
James
The price is ¥38,857
¥78,973 total
includes taxes & fees
May 13 - May 14
Casey Key Beachfront Escape: Charming 1BR Cottage

5 Mi to Riverwalk: Bradenton Family Home w/ Yard

5 Mi to Riverwalk: Bradenton Family Home w/ Yard
3.0 star property
Bayshore Gardens
The price is ¥21,779
¥61,410 total
includes taxes & fees
May 12 - May 13
5 Mi to Riverwalk: Bradenton Family Home w/ Yard

Blue Dolphin Cottage steps from the beach

Blue Dolphin Cottage steps from the beach
Siesta Key Village
The price is ¥38,603
¥116,818 total
includes taxes & fees
May 12 - May 13
Blue Dolphin Cottage steps from the beach

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.
The price is ¥64,960
¥112,497 total
includes taxes & fees
May 14 - May 15
Lookout Cottage Across street from Beach and Heated Pool

Siesta Heron 7

Siesta Heron 7
3.0 star property
Siesta Key
The price is ¥94,835
¥164,908 total
includes taxes & fees
May 14 - May 15
Siesta Heron 7

Nest Cottage Across street from beach and Heated Pool

Nest Cottage Across street from beach and Heated Pool
Siesta Key
10.0 out of 10, Exceptional, (2 reviews)
"Clean, modern and staff is amazing. Room ready before noon received text notification from owners. This is now our new go to after 19 years of staying up the street. All of everything is provided in rooms and for beach life, well maintained and fun atmosphere no pressures except to make memories here."
United States
Marti C.
The price is ¥81,995
¥134,252 total
includes taxes & fees
May 22 - May 23
Nest Cottage Across street from beach and Heated Pool

Unwind Poolside + Walk to Beach! Sarasota Retreat

Unwind Poolside + Walk to Beach! Sarasota Retreat
3.0 star property
South Village
8.0 out of 10, Very Good, (1 review)
"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. "
United States
Eleuterio
The price is ¥28,672
¥84,361 total
includes taxes & fees
May 17 - May 18
Unwind Poolside + Walk to Beach! Sarasota Retreat
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
531
Accommodation
364 Cottages
Lowest Price
¥23,494
Highest Price
¥207,673

Frequently asked questions

How much do cottages in Osprey cost?
Cottages in Osprey range between ¥23,494 and ¥207,673 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 9.6. 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 364 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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