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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All Sunnyside Properties
Sunnyside Properties is a family-owned and operated full service property Management Company specializing in vacation rentals on Siesta Key. We …
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 …
BeachPoint Cottages
<100 feet to beach access 3B 2-3 min walk to Siesta Village Tropical cottages from studio to 2+ bedrooms All amenities included in …
127 Beach Road
Open floor plan brings game room (with pool table), living room and kitchen together. Two guest bedrooms on second level. …
Tiny House Siesta
Each Tiny House Siesta has it's own unique features that set it apart.
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 …
Hibiscus Hideaway
Tucked between Turtle and Crescent Beaches this one-story, 3 BR/2 BA waterfront home offers a screened pool. Dining and shopping …
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 Beach Place
Considered one of the finest Siesta Key vacation rentals, The Beach Place is a quiet oasis of cozy cottage apartments …
Siesta Key Bungalows
Siesta Key Bungalows is a ''peaceful tropical paradise, located a short distance from Siesta Key Beach'', surrounded in ''exotic palm …
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 Leona House
Introducing, a deluxe vacation property in the Village of Siesta on the intercoastal waterway. Key features include, heated pool, enclosed …
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 …
Ringling Beach House
Our units range in size from adorable efficiencies to fresh and fun 2 bedroom units to spacious 3 bedroom units.
Siesta Bungalows
We are a local family of three (Ali and Rich Light with our daughter Chloe! ???????? ) that rent …
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 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 Inn
Siesta Key Inn is an intimate eight unit condominium complex which is operated with the ambiance of a family run …

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