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Anna Maria Island & Sarasota Vacation Rentals


Mainsail Vacation Rentals

In Andrew’s collection, you’ll find a handpicked selection of luxurious homes and 2- and 3-bedroom condos just steps from the mesmerizing turquoise waters of the Gulf of Mexico. In an incredible beachfront location, you’ll be treated to all the amenities of a five-star hotel, including heated pools, hot tubs, poolside grills, private beach lounge chairs and umbrellas, and bike rentals, but with ultimate comfort and privacy.

Inside, you’ll be delighted by elegant furnishings and fresh, bright designs blended with historically-inspired architecture and craftsmanship. Sunlight streams through large windows and sliders, polished pine floors gleam, and professionally designed rooms feature designer fabrics, comfortable furniture, and local artwork.

In fully-equipped, gourmet kitchens with open layouts, the chef in your group can dazzle with culinary creations while taking in mesmerizing Gulf views and enjoying marble countertops and stainless steel appliances. Or craft a cocktail and head out to your private beachfront balcony for a stunning sunset view.

These homes are like slipping on a favorite pair of shoes – welcoming, comfortable, and relaxing. But if you’re in the mood for a bit of Palm Springs, you’ll love Andrew’s one-of-a-kind, eclectic rentals directly on the beach, with a colorful design, terrace access, private patios, and a pool. No matter which style of home you choose, genuine hospitality awaits.

Doyen of Mainsail Vacation Rentals

Profile picture for Andrew Houghton
Andrew Houghton
Managing Partner
Favorite Restaurants
Tide Tables, The Chateau Anna Maria
Favorite Bar
The Doctor’s Office
Favorite Coffee
Rise and Nye’s in Sarasota
Favorite Guest Experience
Mote Marine
Favorite Things to Do on Anna Maria Island
Walking on the beach in the morning and participating in Turtle Watch

A hotelier by trade, Andrew Houghton lives and breathes hospitality. After working in the hotel business his entire life, including for Marriott in sales, marketing, and corporate roles across nine countries and four continents, Andrew retired. But he couldn’t stay away from hospitality for long.

Just a day into retirement, Andrew dove back in – this time into the vacation rental industry. Along with a longtime business partner, Andrew started Mainsail Vacation Rentals on Anna Maria Island and neighboring towns in the Sarasota area. Over the last three years, Andrew’s business has bought and developed land, operated hotels, and managed corporate housing and vacation rentals with an unwavering dedication to preserving the quiet confidence and authentic Florida experience that make Anna Maria Island and Sarasota so special.

A team of professional hoteliers with hospitality backgrounds, Mainsail approaches everything through that lens. They’re a local company that nurtures close relationships with the community in a way that benefits both local businesses and guests. They don’t just recommend a dolphin tour – they know the captain who keeps his boat in their basin, they work to protect his livelihood, and in turn, he treats their guests like family.

With an eye for design and an understanding of practicality, Andrew’s team transforms properties into the ultimate vacation experience. Whether young families and professionals looking for something unique, or guests looking for a more traditional beach home, Mainsail Vacation Rentals crafts an authentic American coastal experience they won’t soon forget.

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