Looking for your next cozy staycation spot? The web service AirBNB, founded in 2008 a group of San Francisco tech entrepreneurs, has revolutionized the way vacation rentals get booked in Southwest Florida. We scouted out some of the highest-rated places on the site for you to seek out in the listings.

Ohana Hale North.


Siesta Key Apartment

Midcentury Modern


After using AirBNB services to book trips to Russia, Italy and elsewhere, Sarasota couple Detlev von Kessel and Kristina Syromyatnitkova decided to list half of their Sarasota home on the site, and have found bountiful success. Guests have their own private entrance into this cream-colored paradise, and the landlords make sure to pamper visitors with care, including providing mixed drinks with tiny umbrellas popping resort-style out of the glass. The international couple can converse in four languages, so worldly discussion comes free with the booking But the real secret, von Kessel says, is “location, location, location.” “We are near the beach, but people don’t only want to go to the beach,” he says. “They want to go shopping in Downtown or go to the Everglades for a day. They want to have this as a home base.”

Vintage Beach Trailer in Bradenton Beach.


Ohana Hale North

This Holmes Beach island home provides a bright and heartwarming atmosphere for guests in need of a getaway. One of eight area locations owned by Palmetto couple Danny and Brenda Chin, the pastel color scheme was picked out by the landlords’ daughter, Katelyn. The couple want the island home to capture the spirit of Hawaii, a locale the two visited and loved during their own travels, and bears a name that translates to “family house.” “Everyone has a standard beachside listing,” Chin says. “We wanted to offer something that set us apart.” This unit boasts proximity to both the beach and Cortez Village, letting guests enjoy both the Florida captured in travel brochures and a trip to Old Florida in a single trip.

Midcentury Modern

Sarasota’s reputation as an architecture capital seems perfectly encapsulated in this modern home. The owner, username Wilburn, stays here all winter but rents the place out from May through December. Decorated with modern furniture to match the physical environment, it’s the sleek interior that attracts guests, the homeowner said. Different than some expect from a Florida home, he has found guests delighted to stay somewhere besides the cookie-cutter subdivisions and strip rental complexes. And since this house serves as Wilburn’s own home base four months of the year, you can expect it to be maintained in top condition.

Vintage Beach Trailer 

The days of rollaway trailers seem more nostalgic than posh, but this Bradenton Beach spot manages to mix the look of a 1950s camper with a Tommy Bahama aesthetic. Landlord and designer Erik MacPeek, who maintains a few Florida trailers and Connecticut cottages on AirBNB, painted the home in Caribbean blue and laid down bamboo flooring in this classic mix of Florida kitsch and Jamaica cool. But this AirBNB superhost most prides himself on the hospitality touches he provides for every guest, from providing easy-to-prepare meals for guests checking in late at night to making sure fresh flowers decorate the tables. “People notice the little details,” MacPeek says. “That’s what they remember.”