
Anna Maria Island & Sarasota Vacation Rentals
byMainsail Vacation Rentals
In Joe’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 Joe’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.
Browse the Collection



Doyen of Mainsail Vacation Rentals

Joe Collier
Favorite Restaurants
Mar Vista, The Chateau Anna MariaFavorite Bar
The Doctor’s OfficeFavorite Coffee
Ginny and Jane’sFavorite Guest Experience
Fishing with Todd Romine out of Waterline MarinaFavorite Things to Do on Anna Maria Island
Biking around the island at sunrise or sunsetA native Floridian born in Miami, Joe Collier began immersing himself in the world of hotels and restaurants at just 13 years old. After studying hotel management and marketing at Florida State University, an internship in the European Hotel program, and 15 years at Marriott International in sales, marketing, and development, Joe started Mainsail Lodging and Development in 1998.
For more than 25 years, award-winning Mainsail 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.
Mainsail is 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. Through their support of numerous local organizations like Feeding Tampa Bay and Anna Maria Island Turtle Watch, Mainsail has taken a stewardship role on Anna Maria Island, preserving this pristine barrier island for generations to come.
With an eye for design and an understanding of practicality, Joe’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.

On the Southwest Florida Gulf Coast, Anna Maria Island’s crystal clear waters and pristine white sand beaches make it a premier destination for an unforgettable family vacation. Delicious seafood, unique shopping experiences, and endless aquatic adventures create a perfect blend of relaxation and adventure, while theaters, botanical gardens, sporting events, and cultural experiences in Sarasota provide something for everyone.
These are just some of the reasons Joe Collier, President of Mainsail Lodging and Development, loves Anna Maria Island and Sarasota.