When you live in a vacation destination, the winter months naturally invite out-of-town family and friends from northern climes to break bread with you under the sun. If you’ve got the space and budget for a well-appointed, free-standing guesthouse, you have the perfect setup. Guesthouses make visitors feel pampered and welcome in their own private space—and, just as importantly, help hosts keep their sanity. We’ve found three guesthouses, in three different styles, that offer luxurious touches inside and lush green spaces outside. The only problem? Your guests may never want to leave.

Midcentury Hospitality

The Revere Quality House

Most guesthouses don’t end up on The New York Times’ 52 places for a changed world list, but David Zaccardelli’s Siesta Key guest home was spotlighted for its midcentury modern design and history.

Designed by Sarasota School of Architecture greats Paul Rudolph and Ralph Twitchell, it was built in 1948 as part of an innovative program to meet the housing needs of returning World War II veterans. Considered the first iconic structure of the Sarasota School movement, the 1,000-square-foot, two-bedroom, single-story Revere Quality House, on Bayou Louise on Siesta Key, used the Sarasota School’s signature horizontal lines and flow-through ventilation that worked in a hot climate in the days before air conditioning. It’s also where Zaccardelli’s lucky family stays when they visit.

Zaccardelli, the CEO of pharmaceutical company Verona Pharma, bought the property in 2017 and lives in the larger, two-story Guy Peterson-designed home next door. Over the years, he has restored the guest home, even replacing the broken bricks at the base of the fireplace and burning them to match the other charred blocks for a seamless fit. The original copper hoods over the fireplace and stove gleam warmly, along with the cappuccino-colored terrazzo floors. The ceiling in the living area is painted peacock blue, to represent the sky, while the bedroom and kitchen walls are lemon yellow. The home makes guests yearn for a tropical drink with a parasol.

When guests aren’t in residence, it’s used “as a bit of a pool house,” says Zaccardelli. Other times, it welcomes architecture fans from far and wide who want to learn more about the midcentury modern movement.

Zaccardelli’s main tip for welcoming guests is “making sure to stock the fridge.” While he sourced a period proper stove for the kitchen, he went with a modern-day fridge “because we like to make ice,” he says—for those tropical drinks everyone wants.

Petite Retreat

Gillespie Park Guest House

This guest home in Gillespie Park, just north of downtown Sarasota, packs personal touches and function into 260 square feet. Built with her visiting father and stepmother in mind, Cathy Wilson, the CFO for the Sarasota Orchestra, made it mimic the main 1949 house where she and her partner live. Indeed, no one would guess the guesthouse was built in 2020.

Inside, two barn doors made of reclaimed cypress vats that once stored prunes date to the 1900s. To remove the patina, Wilson and her dad planed each plank, assembled them and applied a clear finish. A wall quilt she sewed shows colorful fish and says, “Welcome to a Coastal Place.”

She makes guests feel cherished by stocking their favorite treats. “My dad and stepmother love hot chocolate, so I leave a homemade mix for them along with a homemade loaf of my great-grandmother’s raisin bread,” she says.

Sea turtle coasters and runners hint at Wilson’s double life. “I did sea turtle volunteering with Mote Marine Laboratory for over 20 years. Now I mostly volunteer with the county’s turtle tagging program,” she says.

The Murphy bed, ordered through Miller’s Dutch Haus Furniture in Sarasota, was custom built in Ohio. It smartly stores a queen-sized bed, reading lights and a tabletop.

In the bathroom, vintage Florida postcards hang on the wall, and a collection of moon snail shells sits on the windowsill. A walk-in shower with handrails adds comfort. Outside, the porch overlooks a pool and lemon, lime and banana trees. Garden beds burst with herbs Wilson uses for cooking.

But the intangibles stick the most. “They’re always surprised how peaceful it is despite the close-to-downtown location,” says Wilson, “and they love sitting outside and enjoying the garden.”

The Casita

A Mediterranean Revival Cottage in Manatee County

The casita (Spanish for “little house”), as homeowner Dianne Glass calls it, is a getaway that gives guests the space to tune out the world. Along with the main home, the Mediterranean-revival cottage was built in 1926 as a maid quarters and two-car garage. Today it’s an 800-square-foot, one-bedroom guest home that, along with the main home, sits on a little more than an acre in Manatee County.

“When you have a space like that, it's easy to have people visit. There’s always someone coming and going,” says Glass, an acupuncture physician. “They love that it's private and tropical.”

It’s funky, too. Shelving along a wall holds a museum of kitsch, vintage pottery and barware collected from thrift shops over the years. Faraway finds from Glass’ travels include Indonesian art and masks on the wall, and she makes sure to include lots of books on travel, spirituality and art. Ambitious guests use her tried and true cookbooks.
Stocking local coffee from Java Dog and loose leaves from Local Tea Company are a thoughtful touch. “Guests can get a cup on and take advantage of the outdoors,” says Glass. Among the cobbled pathways and trees hung with Spanish moss, seating nooks invite sipping, conversation or quiet contemplation.

Glass’ secret for getting it right is “walking the walk. You have to live in the space,” says Glass, who sometimes stays there just to change it up. “Having throw blankets, flowers and candles make it feel cozy,” she adds. Vases of fresh-cut palm fronds from the garden bring the outdoors in, adding to the tropical vibe.

Maintaining an almost 100-year-old casita for guests takes work, but Glass admits she has help. Lily, her 14-year-old lab mix, “is the hostess with the mostest,” according to Glass, and greets everybody with a wagging tail.