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Check prices for these dates

Next weekend
25 Jul - 27 Jul
In two weeks
1 Aug - 3 Aug
In one month
15 Aug - 17 Aug
In two months
12 Sep - 14 Sep

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, (181)
"The Inn on Siesta Key was awesome. Paige and Gabe were friendly and always helpful and they provided everything you would need for the beach. The property was clean and well maintained. The beach is literally across the street with a 3 minute walk. We will definitely be coming back. "
The Inn On Siesta Key
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, (133)
"Our stay was great. Everything was as advertised and expected. "
Best Location on Manasota Key, Cottage Sleeps 3, Kayaks and Wi-Fi
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 SAR 709
SAR 2,101 total
includes taxes & fees
16 Jul - 17 Jul
Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village
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 were extremely happy with our stay and Evan as our host. He went out of his way to make sure everything went smoothly including helping us find all the beach amenities. The house was excellent and just what we needed, just a short walk across the road to the beach. We would definitely stay here again!"
Private Gulf Beach-4 BRs- Luxury Cottage, Pet Friendly-Kayaks & SUPs-Grill
Country Cottage Home
Property grounds

Country Cottage Home

9.4 out of 10, Exceptional, (139)
"Loved our stay at the property. Would book it again!"
Country Cottage Home
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
1 Bedroom Duplex On Intracoastal W/ Beach Access
Terrace/patio

1 Bedroom Duplex On Intracoastal W/ Beach Access

10.0 out of 10, Exceptional, (150)
"I would highly recommend staying here."
1 Bedroom Duplex On Intracoastal W/ Beach Access
Chic cottage, Vamo area, close to beaches, pet friendly, kayaks
Outdoor dining

Chic cottage, Vamo area, close to beaches, pet friendly, kayaks

9.8 out of 10, Exceptional, (19)
"Nice place "
Chic cottage, Vamo area, close to beaches, pet friendly, kayaks
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)
"We loved it. Our second stay at this house. The owners are amazing. We are coming back next year already reserved the house "
2Bd+2 Ba beach cottage w/private front/back yard, screened porch, firepit, grill
Villa Mojito Dazzles
Beach nearby

Villa Mojito Dazzles

9.8 out of 10, Exceptional, (142)
"Clean"
Villa Mojito Dazzles
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)
"The house was immaculate! Great location and easy walk to beach.The host was wonderful!!!!Can’t wait to go back!!!"
ONLY 2 WKS LEFT IN AUG 5 Min walk to Beach & Village, Private Pool,On the Canal
#4 Charming cottage across of warm mineral springs great for 2 person
Exterior

#4 Charming cottage across of warm mineral springs great for 2 person

8.8 out of 10, Excellent, (5)
"Excellent place for what we was looking for The host was very friendly and always helpful Thank you so much "
The price is SAR 186
SAR 539 total
includes taxes & fees
16 Jul - 17 Jul
#4 Charming cottage across of warm mineral springs great for 2 person
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!
Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed
Beach

Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed

9.2 out of 10, Wonderful, (5)
"We really enjoyed the cleanliness and location. Pool was great. Having our own deck was nice. Great views. Highly recommend. "
The price is SAR 484
SAR 1,193 total
includes taxes & fees
21 Jul - 22 Jul
Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed
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, (91)
"Very nice"
The price is SAR 1,118
SAR 2,155 total
includes taxes & fees
15 Aug - 16 Aug
Direct Beachfront Cottage-Casey Key/Nokomis Beach-1 Bedroom
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
Mermaid Cottage
Beach

Mermaid Cottage

10.0 out of 10, Exceptional, (18)
"Loved the decor and separate spaces. Liked that there was everything needed to prepare meals there. Nice stay."
Mermaid Cottage
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!
Laughing Gull at Shorebirds 3min walk to beach Sunsets! Kayaks Bikes and More!
Outdoor dining

Laughing Gull at Shorebirds 3min walk to beach Sunsets! Kayaks Bikes and More!

10.0 out of 10, Exceptional, (76)
"Was a great stay. Short walk to beach and short walk to put kayaks in. Was great to have beach supplies all there. "
Laughing Gull at Shorebirds 3min walk to beach Sunsets! Kayaks Bikes and More!
Island-Life-Steps to Stunning Beach! Pool!
Beach nearby

Island-Life-Steps to Stunning Beach! Pool!

9.4 out of 10, Exceptional, (9)
"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!
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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Frequently asked questions

How much do cottages in Osprey cost?
Cottages in Osprey range between SAR 186 and SAR 1,118 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 310 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.