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Featured Cottages in Osprey

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

The Inn On Siesta Key

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

Country Cottage Home

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

Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village

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

Cozy Beach Cottage

Across The Street From #1 Beach

1-bedroom cottage just 10 minutes from Siesta Key Beach

Cozy 2 Bed, 1 Bath cottage close to Downtown Sarasota and the Beaches
Top trending hotels in Osprey

Carlisle Inn
Osprey Cottages For Rent
Dreaming of a getaway that’s reminiscent of a fairytale? Travelocity doesn’t have magic wands or talking animals in our inventory—at least, none that we can find—but we do have holiday cottages in Osprey that will make you feel like you’ve stepped inside your vacation dreams.
The word “cottage” may make you think of whitewashed walls, flower print curtains, and sprawling views of rolling green hills—lucky for you, we do offer tons of country cottages that were furnished with a rustic feel in mind. Appreciate the vase of daffodils on your dining room table, and peek out the window onto the private patio that surrounds yours and other rustic cottages in the area.
These charming “home away from homes” have long been a beacon for those who love the outdoors, so pick a spot peppered with hiking trails and spend lazy afternoons meandering through the gorgeous scenery Osprey is known for. Snap some pictures while you’re at it—you’ll want to remember sunset over this waterfall for the rest of your life. When the sun goes down, cuddle up in front of a cheerful fire, or head into town to explore the shops, restaurants, and art galleries that have sprung up over the years. Ah, it’s nice to return to civilization every once in a while, isn’t it?
Whether you select cottages minutes away from the bustling city center, or coastal cottages that are footsteps from the sand and surf, you’ll find the accommodation you’re looking for here on Travelocity. Just because you’re booking a place that reminds you of a fairytale doesn’t mean you need a fairy godmother to find the best deal around! Just a gnome…
Osprey Cottages essential information
Accommodation | 319 Cottages |
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Lowest Price | CA $146 |
Highest Price | CA $721 |
Popular accommodation | Direct Beachfront Cottage-Casey Key/Nokomis Beach-2 bedrooms, The Inn On Siesta Key, Direct Beachfront Cottage-Casey Key/Nokomis Beach-1 Bedroom, Country Cottage Home, Private Gulf Beach-4 BRs- Luxury Cottage, Pet Friendly-Kayaks & SUPs-Grill, Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village, ONLY 2 WKS LEFT IN AUG 5 Min walk to Beach & Village, Private Pool,On the Canal, Cozy Beach Cottage , Across The Street From #1 Beach, 1-bedroom cottage just 10 minutes from Siesta Key Beach, Cozy 2 Bed, 1 Bath cottage close to Downtown Sarasota and the Beaches, Big Roomy Beach Cottage: 4 bd/3 ba -2,000 sq ft; 100 ft to beach path; priv pool |