Villa Margarita

Villa Margarita located at 1109-1111 Crescent Street is a vibrant, festive newly decorated four bedroom/four bathroom/two kitchen home now available for vacation rentals with HomeAway Cottages. It’s the latest standout in our...

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Villa Fiesta

Villa Fiesta at 1115 Crescent Street is another beautifully decorated, exciting new 4BR/4BA/2Kit home recently added to our HomeAway Cottages collection of fine vacation homes. Villa Fiesta and its sister home, Villa Margarita...

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1670 Laurel Park

Centrally located in the heart of downtown Sarasota, and only minutes away from our Lido Key Beach, 1670 Laurel Park offers a bright and cheerful affordable luxury retreat within walking distance to the vibrant Main Street of...

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Villa Dom Brisa

Villa Dom Brisa or “Sun Breeze” at 1123-1125 Crescent Street is another beautifully decorated, exciting new 4BR/4BA/2Kit home recently added to our boutique collection of fine vacation homes at Homeaway Cottages....

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Villa Brisa Marina

Villa Brisa Marina or “Sea Breeze” at 1119-1121 Crescent Street is an exciting new 4BR/4BA/2Kit home just added to our boutique collection of fine vacation homes and it’s sure to be a standout. This home...

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Sophie’s Quartier

Welcome to Sophie’s Quartier! Two homes, side by side, combined together that can sleep up to 18!!! This is a perfect retreat for huge family gatherings and friends get-togethers! Enjoy the benefit of all the amenities of...

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Villa Mantequilla

Welcome to Villa Mantequilla, a lovely butter colored 4 bedroom, 2 bath pool cottage just 1 block from the Village and 3 blocks to the beach. This remarkable 4 bedroom home features a beautiful pool that overlooks the canal...

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Island Sol

Welcome to Island Sol, our exclusive 5+ bedroom, four and one-half [4.5] bath home with approximately 4,000SF of air conditioned space in Siesta Key. Across the open entry and living room, you look out beyond the exterior lanai...

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Casa De Suenos

Welcome to “Casa De Suenos”, one of the most fabulous vacation homes in Siesta Key. Newly constructed in 2013! The magic begins as you enter the foyer of this beautiful casa and gaze across the expansive living area, and deck...

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Harmony Cottage

Welcome to the Harmony Cottage, a truly remarkable three bedroom, two bath cottage with an absolutely mesmerizing outdoor pool and spa. This unique pool has a beach entrance like none you’ve seen before making it so pleasant for...

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Villa Champagne

Welcome to “Villa Champagne”, one of the most fabulous vacation homes in Siesta Key. It’s also one of the most popular favorites among our many guest families. The magic begins as you enter the foyer of this beautiful villa and...

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Old Oak Cottage

Welcome to the Old Oak Cottage located just one and a half blocks from the North Bridge to Siesta Key on the corner of Siesta Drive and Old Oak Road. With such a great location just off the Island, many of our families love to...

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Sophie’s Cottage

Sophie’s Cottage is a smart, sophisticated upscale waterfront retreat with an oversized hot tub, boat dock, and a short walk to Siesta Key Beach. Ideally, it accommodates 6 but can easily sleep up to 8 with 2 private bedrooms...

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Villa Espanola

Centrally located in the heart of Sarasota, and only minutes away from our world famous Siesta Key Beach, Villa Espanola offers a bright and cheerful retreat while not breaking the budget. Perfect for larger families that enjoy...

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Orchid/Hibiscus Villa

The Orchid and Hibiscus Villas are two separate units which can be uniquely configured to create “Villa Cascada,” an absolutely beautiful and stunning private pool home. (Please note: These units can be rented separately....

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Villa Cascada

Point of Rocks, located just south of the Stickney Point Bridge, the most notable location on Siesta Key, is blessed with the soft, white quartz sand found on Siesta Key beach, but geologically unique and named for the formation...

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Pura Vida Oasis

This spectacular bright cheerful, canal front cottage with heated pool & spa has 5 bedrooms/3 baths that can sleep up total of 13. As you enter Pura Vida Oasis, you will notice an eclectic wine storage rack and desk area...

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La Casa Verde

The waterfront cottage, ‘La Casa Verde’ is a very luxurious and large four [4] bedroom canal front heated pool home with two very large bathrooms in approximately 2,800SF of air conditioned living space. As you...

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The Topping Cottage

The Topping Cottage is a very luxurious and large five [5] bedroom, three and one-half [3.5] bath home with approximately 3,000SF of air conditioned space in Siesta Key. As you enter the foyer, you immediately notice the huge,...

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The Grand Canal

The Grand Canal Cottage, perhaps one of Siesta Key’s favorite luxury vacation homes, is a highly landscaped canal-front private luxury home featuring a heated pool with sun shelf and a separate 8-person spa. It is situated on...

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