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 family's 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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Siesta Leona House
Introducing, a deluxe vacation property in the Village of Siesta on the intercoastal waterway. Key features include, heated pool, enclosed …
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, …
127 Beach Road
Open floor plan brings game room (with pool table), living room and kitchen together. Two guest bedrooms on second level. …
All Sunnyside Properties
Sunnyside Properties is a family-owned and operated full-service property Management Company specializing in vacation rentals on Siesta Key. We have …
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 Key Bungalows
Siesta Key Bungalows is a ''peaceful tropical paradise, located a short distance from Siesta Beach'', surrounded by ''exotic palm trees, …
The Beach Place
Considered one of the finest Siesta Key vacation rentals, The Beach Place is a quiet oasis of cozy cottage apartments …
Siesta Bungalows
We are a local family of three that rents out cozy and private bungalows in Palm Island neighborhood in the …
Magnolia House
The Magnolia House is a tropical secluded oasis on Siesta Key. Each unit is a newly renovated 2 bedroom, 2 …
Pink Pineapple Properties
Select Pink Pineapple Properties for your ultimate gulf coast escape. Our beautiful beach homes are expertly chosen and professionally decorated …
Hibiscus Hideaway
Tucked between Turtle and Crescent Beaches this one-story, 3 BR/2 BA waterfront home offers a screened pool. Dining and shopping …
Siesta Key Inn
Siesta Key Inn is an intimate, eight-unit condominium complex operated with the ambiance of a family-run island inn a short …
Tiny House Siesta
Whether it is a 1st floor bedroom you seek, a 3 bedroom model, or a pet friendly tiny, we're sure …
Parrot Beach Cottages Siesta Key
Four-suite cottage steps to Siesta Beach. Enjoy spectacular sunsets, a romantic walk on the beach or relax at the pool. …
Altez Vacations
Every vacation should be unique, dynamic, and distinctive. Find our homes on the sugar sands of Siesta Key, and beyond. …
BeachPoint Cottages
Less than 100 feet to Siesta Beach Access 3B and only a 2-3 minute walk to Siesta Village, we're the …
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 …
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 Cottages at Siesta Key
Welcome to The Cottages at Siesta Key, a charming resort close to the white, powdery sand of a great Gulf …
Ringling Beach House
A private tropical paradise reminiscent of days gone by, steps from the powdery white sand and crystal-clear blue waters of …
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 …

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