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Check prices for these dates

In two weeks
12 Sep - 14 Sep
In two months
24 Oct - 26 Oct
In three months
21 Nov - 23 Nov
In four months
19 Dec - 21 Dec

Cottages in Osprey

Our top choices for Osprey cottages

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, (183)
"Great place to stay! "
The price is SAR 879
SAR 1,201 total
includes taxes & fees
1 Sep - 2 Sep
The Inn On Siesta Key
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)
"We enjoyed our stay so much! Just right for us with short walks to the Beach and Bay, peaceful back porch and comfy beds. It is a beautiful and clean house in the trees. Evan is a helpful host with great communication. We hope to go back again. "
Private Gulf Beach-4 BRs- Luxury Cottage, Pet Friendly-Kayaks & SUPs-Grill
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)
"We loved this little cottage and will absolutely go back in the future. Thank you so much for a wonderful retreat. "
The price is SAR 743
SAR 1,798 total
includes taxes & fees
13 Sep - 14 Sep
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, (96)
"We have stayed at this cottage before- just love this beach."
The price is SAR 931
SAR 1,940 total
includes taxes & fees
1 Sep - 2 Sep
Direct Beachfront Cottage-Casey Key/Nokomis Beach-1 Bedroom
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, (136)
"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
Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.
Sun loungers, beach towels

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

9.6 out of 10, Exceptional, (77)
"Its right next to everything we needed"
Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.
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
Island Life! King Bed Studio-Steps to beach
Beach nearby

Island Life! King Bed Studio-Steps to beach

9.6 out of 10, Exceptional, (166)
"Beautiful area and unit. We will be back."
Island Life! King Bed Studio-Steps to beach
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, (37)
"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
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
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
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
This cottage is a 2 bedroom(s), 2 bathrooms, located in Englewood, FL.
Beach nearby, beach towels

This cottage is a 2 bedroom(s), 2 bathrooms, located in Englewood, FL.

9.4 out of 10, Exceptional, (194)
"Cottages for my daughter and I were adjacent. Having a pool was nice. The free washer and dryer was a plus. "
This cottage is a 2 bedroom(s), 2 bathrooms, located in Englewood, FL.
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!
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, (127)
"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
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)
"my friends and I traveled from across the country to meet for our annual “girls” trip. Location is amazing. You can walk to the beach, you can rent cabanas and there are lounge chairs for your use. The pool is sparkling and the trolley stop is right outside the property entrance. I just love Siesta key and this is a wonderful place to get away from it all, but have easy access to all of the fun and shopping. "
The price is SAR 559
SAR 1,859 total
includes taxes & fees
24 Sep - 25 Sep
Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village
Kozy Kottage on private road. 2 minute walk to private beach. Pet friendly!
Beach nearby, sun loungers, beach towels

Kozy Kottage on private road. 2 minute walk to private beach. Pet friendly!

10.0 out of 10, Exceptional, (128)
"Owner easy to work with. Short walk to the beach and to restaurants in town."
Kozy Kottage on private road. 2 minute walk to private beach. Pet friendly!
Cozy Beach Cottage
On the beach, sun loungers, beach towels

Cozy Beach Cottage

9.4 out of 10, Exceptional, (21)
"Wonderful location for a peaceful getaway "
Cozy Beach Cottage
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
1 Bedroom Duplex On Intracoastal W/ Beach Access
Terrace/patio

1 Bedroom Duplex On Intracoastal W/ Beach Access

10.0 out of 10, Exceptional, (151)
"I would highly recommend staying here."
1 Bedroom Duplex On Intracoastal W/ Beach Access
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

Frequently asked questions

How much do cottages in Osprey cost?
Cottages in Osprey range between SAR 559 and SAR 931 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 9.3. 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 314 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.