Book Osprey, FL Cottages
Save an extra 10% or more on select hotels with Member Discounts
Access exclusive hotel deals, only with the Travelocity app
Top Cottages in Osprey

The Inn On Siesta Key

Charming 2-bedroom cottage in Englewood minutes to the Gulf Beaches-Dog Friendly

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

Casey Key Beachfront Escape: Charming 1BR Cottage

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

Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village

1-bedroom cottage just 10 minutes from Siesta Key Beach

2 bedroom, walk to beach-bikes-kayaks-grill-picnic-hot outdoor shower-beach gear

Venetian Vacation! Close To Beaches, Restaurants & Shopping!

Cottage Across The Street From #1 Beach

Kozy Kottage on private road. 2 minute walk to private beach. Pet friendly!
Top hotels in Osprey

Tropical Beach Resorts
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 | 376 Cottages |
|---|---|
Lowest Price | $85 |
Highest Price | $514 |
Popular accommodation | The Inn On Siesta Key, Charming 2-bedroom cottage in Englewood minutes to the Gulf Beaches-Dog Friendly, 5 Min walk to Beach & Village, Private Pool,On the Canal, Casey Key Beachfront Escape: Charming 1BR Cottage, 🌴 Palm Shade Cottage | Charming 1-Bedroom in SK, Access to Pool, Walk to Beach!, Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village, 1-bedroom cottage just 10 minutes from Siesta Key Beach, 2 bedroom, walk to beach-bikes-kayaks-grill-picnic-hot outdoor shower-beach gear, Venetian Vacation! Close To Beaches, Restaurants & Shopping!, Cottage Across The Street From #1 Beach, Kozy Kottage on private road. 2 minute walk to private beach. Pet friendly!, 🦩Book Me Baby! Pool, Pet-Friendly Paradise Near Downtown Sarasota🦩 |






