You’ll find plenty of vacation rentals here, but to make things super-easy try the Hyatt Siesta Key Beach resort—the only luxury hotel property on the six-mile stretch. Instead of traditional hotel rooms, this residence club offers rentals on one- to four-bedroom condo-style units with washer-dryers and kitchen that would make any Food Network chef feel at home. Plentiful chaises, umbrellas, sand toys and paddleboards make it easy to relax oceanside, and the waterfall/hot-tub combo and poolside cabanas will equally spoil you.
1. Complimentary bicycles let you cruise under the banyan trees on Midnight Pass Road at a leisurely pace. Along the way, you can peek into the backyards of some of the region’s most gorgeous beach houses.
2. Go north and peruse Siesta Key Village to shop at funky stores for hats and flip-flops. Later, indulge in a big scoop of Kahlua Krunch ice cream at Big Olaf’s Creamery. (We won’t tell anyone how fast you eat it.)
3. Nearby Ophelia’s on the Bay serves waterside romance and a luscious blue-crab bisque. Request a table on the outdoor terrace skirting Little Sarasota Bay, and take your time as you dine, keeping an eye out for dolphin and long-legged waterfowl.
4. No one understands the importance of slowing down more than Southerners, so don’t miss a meal at Owen's Fish Camp restaurant for a home-grown taste of the Gulf with cornmeal-crusted catfish and collard greens.