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Check prices for these dates

Next weekend
22 Aug - 24 Aug
In two weeks
29 Aug - 31 Aug
In one month
12 Sep - 14 Sep
In two months
10 Oct - 12 Oct

Cottages in Osprey

The Inn On Siesta Key
Outdoor pool, a heated pool, open 8:00 AM to 8:00 PM, pool umbrellas

The Inn On Siesta Key

3.5 star property
10.0 out of 10, Exceptional, (182)
"Great place to stay! "
The price is AED 858
AED 1,107 total
includes taxes & fees
20 Aug - 21 Aug
The Inn On Siesta Key
Direct Beachfront Cottage-Casey Key/Nokomis Beach-2 bedrooms
On the beach, sun loungers, beach towels

Direct Beachfront Cottage-Casey Key/Nokomis Beach-2 bedrooms

9.2 out of 10, Wonderful, (60)
"Was easy to grab this little oasis in a pristine location to grab some much needed getaway time with the family. The surrounding area is low key and relaxed, plenty to do and see or just walk out and enjoy the beach!"
The price is AED 654
AED 1,655 total
includes taxes & fees
17 Aug - 18 Aug
Direct Beachfront Cottage-Casey Key/Nokomis Beach-2 bedrooms
Direct Beachfront Cottage-Casey Key/Nokomis Beach-1 Bedroom
On the beach, sun loungers, beach towels

Direct Beachfront Cottage-Casey Key/Nokomis Beach-1 Bedroom

9.2 out of 10, Wonderful, (95)
"We have stayed at this cottage before- just love this beach."
The price is AED 654
AED 1,579 total
includes taxes & fees
25 Aug - 26 Aug
Direct Beachfront Cottage-Casey Key/Nokomis Beach-1 Bedroom
Big Roomy Beach Cottage: 4 bd/3 ba -2,000 sq ft; 100 ft to beach path; priv pool
On the beach, sun loungers, beach towels

Big Roomy Beach Cottage: 4 bd/3 ba -2,000 sq ft; 100 ft to beach path; priv pool

10.0 out of 10, Exceptional, (125)
"We had an awesome vacation! The house beach and pool were outstanding. Hope to return next year!!"
Big Roomy Beach Cottage: 4 bd/3 ba -2,000 sq ft; 100 ft to beach path; priv pool
Best Location on Manasota Key, Cottage Sleeps 3, Kayaks and Wi-Fi
Outdoor dining

Best Location on Manasota Key, Cottage Sleeps 3, Kayaks and Wi-Fi

10.0 out of 10, Exceptional, (135)
"We have stayed at this cottage before, and it’s always been obvious how much love the owners put into the cottage, and how much effort they put into making your stay an enjoyable one. Knowing how much work they had to do to get it rehabbed after last year’s hurricanes makes you appreciate it even more. The cottage is very clean and has everything you need for your stay. You are right on the beach with a spectacular view of the sunset. Communication with the hosts is a breeze and they are quick...
Best Location on Manasota Key, Cottage Sleeps 3, Kayaks and Wi-Fi
Island Life! King Bed Studio-Steps to beach
Beach nearby

Island Life! King Bed Studio-Steps to beach

9.6 out of 10, Exceptional, (165)
"This is a fantastic place to stay. We will be back next year without a doubt. Thank you!!!"
Island Life! King Bed Studio-Steps to beach
Island-Life-Steps to Stunning Beach! Pool!
Beach nearby

Island-Life-Steps to Stunning Beach! Pool!

9.4 out of 10, Exceptional, (11)
"Oir host was amazing and on point. She quckly answered any all questions and immediately addressed any issues. Had an amzing workation. 10 out of 10 stars."
Island-Life-Steps to Stunning Beach! Pool!
Private Gulf Beach-4 BRs- Luxury Cottage, Pet Friendly-Kayaks & SUPs-Grill
On the beach, sun loungers, beach towels

Private Gulf Beach-4 BRs- Luxury Cottage, Pet Friendly-Kayaks & SUPs-Grill

10.0 out of 10, Exceptional, (34)
"Had a great family vacation. We spent lots of time on the beach & fishing off the dock. We were especially grateful for your turtle education thank you for letting us partake in that. "
Private Gulf Beach-4 BRs- Luxury Cottage, Pet Friendly-Kayaks & SUPs-Grill
Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village
Property grounds

Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village

9.0 out of 10, Wonderful, (174)
"Loved this place, very roomy and even had a coffee bar, cute style, and right by the beach."
The price is AED 562
AED 1,888 total
includes taxes & fees
24 Aug - 25 Aug
Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village
2Bd+2 Ba beach cottage w/private front/back yard, screened porch, firepit, grill
On the beach, sun loungers, beach towels

2Bd+2 Ba beach cottage w/private front/back yard, screened porch, firepit, grill

10.0 out of 10, Exceptional, (71)
"Wonderful quiet neighborhood property with very attentive property owners. Flamingo Cottage is ideally located for easy access to the beach as well as Shopping within walking distance. We look forward to our return next year!"
2Bd+2 Ba beach cottage w/private front/back yard, screened porch, firepit, grill
ONLY 2 WKS LEFT IN AUG 5 Min walk to Beach & Village, Private Pool,On the Canal
Sun loungers, beach towels

ONLY 2 WKS LEFT IN AUG 5 Min walk to Beach & Village, Private Pool,On the Canal

9.8 out of 10, Exceptional, (23)
"Perfect place to stay. 1 mile to the village and beach access. We loved making our own meals in the grill and swimming in the pool. "
ONLY 2 WKS LEFT IN AUG 5 Min walk to Beach & Village, Private Pool,On the Canal
1-bedroom cottage just 10 minutes from Siesta Key Beach
Terrace/patio

1-bedroom cottage just 10 minutes from Siesta Key Beach

9.0 out of 10, Wonderful, (36)
"We greatly enjoyed our stay. The yard is very secluded and quite large, which was ideal for us. The house was exceptionally clean, and is well laid out. Powerful a/c system, super welcome for hot florida days. It also has a very large screened in lanai, which is perfect for relaxing. "
1-bedroom cottage just 10 minutes from Siesta Key Beach
Across The Street From #1 Beach
Beach nearby, sun loungers, beach towels

Across The Street From #1 Beach

10.0 out of 10, Exceptional, (321)
"Very cute beach cottage! Great location,very clean ,no complaints,if ever in Siesta Key again would definitely stay here "
Across The Street From #1 Beach
Sarasota Vacation Rental w/ Private Pool & Lanai!
Interior

Sarasota Vacation Rental w/ Private Pool & Lanai!

3.0 star property
10.0 out of 10, Exceptional, (2)
"This home was great for our family. Everything was clean and well-kept. We enjoyed the pool and backyard. The home is also conveniently located with many stores and restaurants nearby."
Sarasota Vacation Rental w/ Private Pool & Lanai!
Oystercatcher at Shorebirds, Bikes and Kayaks 3 minutes walk to beach!
Outdoor dining

Oystercatcher at Shorebirds, Bikes and Kayaks 3 minutes walk to beach!

10.0 out of 10, Exceptional, (65)
"Our family of four had a fantastic stay at this condo. It was incredibly clean and had wonderful amenities. We loved the kayaks and bikes. The location was perfect and the beach access was close by. We look forward to booking here again! "
Oystercatcher at Shorebirds, Bikes and Kayaks 3 minutes walk to beach!
Villa Margarita Sparkles
Beach nearby

Villa Margarita Sparkles

9.8 out of 10, Exceptional, (145)
"Great location, easy beach access. Will definitely stay again."
Villa Margarita Sparkles
Venetian Vacation! Close To Beaches, Restaurants & Shopping!
Fridge, microwave, oven, stovetop

Venetian Vacation! Close To Beaches, Restaurants & Shopping!

10.0 out of 10, Exceptional, (110)
"Great place to stay. Very clean. "
Venetian Vacation! Close To Beaches, Restaurants & Shopping!
12 Mi to Beach: Home w/ Patio & Yard in Bradenton
House (3 Bedrooms) | Interior

12 Mi to Beach: Home w/ Patio & Yard in Bradenton

3.0 star property
10.0 out of 10, Exceptional, (1)
"Clean & close to the convention center"
12 Mi to Beach: Home w/ Patio & Yard in Bradenton
Country Cottage Home
Property grounds

Country Cottage Home

9.4 out of 10, Exceptional, (140)
"Perfect place for short stay. Great little cottage in a private quiet setting. Nothing super fancy but everything you need and exceptionally clean. "
Country Cottage Home
Remodeled Siesta Key Escape – Walk to the Beach!
Fridge, microwave, stovetop, coffee/tea maker

Remodeled Siesta Key Escape – Walk to the Beach!

10.0 out of 10, Exceptional, (11)
"The property was great and easy communication would recommend very peaceful didn’t want to leave to be honest"
Remodeled Siesta Key Escape – Walk to the Beach!
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

DoubleTree by Hilton Sarasota Bradenton Airport

DoubleTree by Hilton Sarasota Bradenton Airport

10/10 Excellent
"My hotel stay here was very pleasant, great staff- very clean. Hotel was up-to-date. Will definitely be staying here. Next time I come visit my grandfather. "
Josh Alonzo 3-night trip
Posted 1 day ago
DoubleTree by Hilton Sarasota Bradenton Airport

Frequently asked questions

How much do cottages in Osprey cost?
Cottages in Osprey range between AED 562 and AED 858 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 9.7. 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 322 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.