Cottages & Houses

If you’re looking for unique, one-of-a-kind Siesta Key lodging consider a cottage, bungalow or quaint beach house. These small units offer tropical settings, privacy and everything you’ll need for your families Siesta Key vacation. Many of Siesta Key’s locally-owned and operated cottages and bungalows share in the historical charm of our island. We invite you to ask your innkeeper upon arrival.

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Hibiscus Hideaway
Tucked between Turtle and Crescent Beaches this one-story, 3 BR/2 BA waterfront home offers a screened pool. Dining and shopping …
Beach Place
Considered one of the finest Siesta Key vacation rentals, The Beach Place is a quiet oasis of cozy cottage apartments …
The Cottages at Siesta Key
Welcome to The Cottages at Siesta Key, a charming resort close to the white, powdery sand of a great Gulf …
Siesta Bungalows
We are a local family of three (Ali and Rich Light with our daughter Chloe! ???????? ) that rent …
My Old Florida LLC
Secluded 3 bedroom 2 bath home located on the Grand Canal with boating access to Sarasota Bay. An easy walk …
The Inn on Siesta Key
Looking for vintage Florida with coastal flair? The Inn on Siesta Key sits across the street from Siesta Beach, the …
A Home Away From Home
This charming tropical 1,320 sq.ft. 2 bedroom 2 bath home is located within the heart of Siesta Key Village and …
Siesta Leona House
Introducing, a deluxe vacation property in the Village of Siesta on the intercoastal waterway. Key features include, heated pool, enclosed …
Our House At The Beach
Our House at the Beach is a two bedroom/two bath condominium complex with 106 units total. Condos are fully furnished …
Siesta Palms by the Beach
Let the sweet smell of Plumeria greet you as you step into the charming paradise of their unique island accommodations. …
Siesta Key Bungalows
Siesta Key Bungalows is a ''peaceful tropical paradise, located a short distance from Siesta Key Beach'', surrounded in ''exotic palm …
All Sunnyside Properties
Sunnyside Properties is a family-owned and operated full service property Management Company specializing in vacation rentals on Siesta Key. We …
A Castle on the Key
This enchanting, two-story, canal-front ‘castle-like,’ private home with pool and spa is situated on Siesta Key within a block of …
Tiny House Siesta
Each Tiny House Siesta has it's own unique features that set it apart.
127 Beach Road
Beach Palms of Siesta Key Village
Enchanting Tropical Island Cottages and Beach View Suite on beautiful white Siesta Key Beach Florida with secluded patios with grills, …
Magnolia House
The Magnolia House is a tropical secluded oasis on Siesta Key. Each unit is a newly renovated 2 bedroom, 2 …
Siesta Key Inn
Siesta Key Inn is an intimate eight unit condominium complex which is operated with the ambiance of a family run …
Secrest Island Home in Paradise
Newly remodeled, single family home, 3 bedrooms, 2 baths, enclosed screened-in 27 x 13 heated outside pool(set to 82 degrees) …
Ringling Beach House
Our units range in size from adorable efficiencies to fresh and fun 2 bedroom units to spacious 3 bedroom units.

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