Osprey Cottages

Get more for your budget and save up to 50% off select Secret Bargain hotels

Get even more value with CheapTickets Price Guarantee!

Change your flight without a fee on select flights

Cottages in Osprey

The Inn On Siesta Key

The Inn On Siesta Key

3.5 out of 5
515 Beach Road Siesta Key FL
$587 nightly
The price is $663 total per night
$663 total
Jun 19 - Jun 20
Total with taxes and fees
Located in Siesta Key, The Inn On Siesta Key is a 1-minute drive from Siesta Key Beach and 10 minutes from Turtle Beach.
Pool
Kitchen
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 FL
$216 nightly
The price is $241 total per night
$241 total
Jun 18 - Jun 19
Total with taxes and fees
With a stay at this cottage in Englewood (Englewood Central), you'll be within a 15-minute drive of Venice Beach and Manasota Beach.
Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village

Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village

Sarasota FL
$463 nightly
The price is $516 total per night
$516 total
Jun 17 - Jun 18
Total with taxes and fees
When you stay at this cottage in Siesta Key, you'll be by the sea, a 1-minute drive from Siesta Key Beach and 10 minutes from Turtle Beach.
Kitchen
Washer
🌴 Palm Shade Cottage | Charming 1-Bedroom in SK, Access to Pool, Walk to Beach!

🌴 Palm Shade Cottage | Charming 1-Bedroom in SK, Access to Pool, Walk to Beach!

Siesta Key FL
With a stay at this cottage, you'll be centrally located in Siesta Key, a 1-minute drive from Siesta Key Beach and 14 minutes from Turtle Beach.
Pool
Kitchen
Escape near Siesta Key with Hot Tub, BBQ, and Fire pit

Escape near Siesta Key with Hot Tub, BBQ, and Fire pit

Sarasota FL
With a stay at this cottage in Sarasota, you'll be a 4-minute drive from Siesta Key Beach and 9 minutes from Turtle Beach.
Hot Tub
Kitchen
Cottage Across The Street From #1 Beach

Cottage Across The Street From #1 Beach

Siesta Key FL
When you stay at this cottage in Siesta Key, you'll be by the sea, a 1-minute drive from Siesta Key Beach and 9 minutes from Crescent Beach.
Kitchen
Washer
Charming cottage for 2 across warm mineral springs park

Charming cottage for 2 across warm mineral springs park

North Port FL
$125 nightly
The price is $139 total per night
$139 total
Jun 22 - Jun 23
Total with taxes and fees
With a stay at this cottage in North Port (Warm Mineral Springs), you'll be a 1-minute drive from Warm Mineral Springs Pool and 7 minutes from North Port Performing Arts Center.
Kitchen
Washer
1-bedroom cottage just 10 minutes from Siesta Key Beach

1-bedroom cottage just 10 minutes from Siesta Key Beach

Sarasota FL
With a stay at this cottage, you'll be centrally located in Sarasota, a 2-minute drive from Sarasota Memorial Hospital and 10 minutes from St. Armands Circle.
Kitchen
Washer
Across The Street From #1 Beach

Across The Street From #1 Beach

Siesta Key FL
When you stay at this cottage in Siesta Key, you'll be by the sea, a 1-minute drive from Siesta Key Beach and 9 minutes from Turtle Beach.
Kitchen
Washer
Cozy 2Bd+2 Ba beach cottage; screened Florida rm, sleep porch; VR22-00059

Cozy 2Bd+2 Ba beach cottage; screened Florida rm, sleep porch; VR22-00059

Sarasota FL
A stay at this cottage places you in the heart of Sarasota, within a 10-minute walk of Lido Beach and St. Armands Circle.
5 Min walk to Beach & Village, Private Pool,On the Canal

5 Min walk to Beach & Village, Private Pool,On the Canal

Siesta Key FL
When you stay at this cottage in Siesta Key, you'll be on the waterfront, within a 15-minute drive of Siesta Key Beach and Turtle Beach.
Pool
Kitchen
Country Cottage Home

Country Cottage Home

Bradenton FL
Located in Bradenton, this cottage is in a rural location, within a 15-minute drive of The River Club and Mall at University Town Center.
Kitchen
Washer
Don't see what you're looking for?
See all available properties in Osprey
View all properties
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.

Osprey Cottages essential information

Accommodation
370 Cottages
Lowest Price
$139
Highest Price
$663
Popular accommodation
The Inn On Siesta Key, Charming 2-bedroom cottage in Englewood minutes to the Gulf Beaches-Dog Friendly, Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village, 🌴 Palm Shade Cottage | Charming 1-Bedroom in SK, Access to Pool, Walk to Beach!, Escape near Siesta Key with Hot Tub, BBQ, and Fire pit, Cottage Across The Street From #1 Beach, Charming cottage for 2 across warm mineral springs park, 1-bedroom cottage just 10 minutes from Siesta Key Beach, Across The Street From #1 Beach, Cozy 2Bd+2 Ba beach cottage; screened Florida rm, sleep porch; VR22-00059, 5 Min walk to Beach & Village, Private Pool,On the Canal, Country Cottage Home

Top Picks