Want a place to call your own—if only for a weekend? Tradewinds Resort offers mini cottages and villas right near the Gulf that make the perfect home-away-from-home for lovebirds (and families, too, of course). Located on Anna Maria Island, Tradewinds is reminiscent of a Florida that has largely disappeared. With its bright, pastel-colored buildings surrounded by bougainvillea and jasmine, it’s easy to imagine that you have stumbled upon your own private paradise. Don’t miss a swim in the resort’s heated pool, which is nestled among palm trees and boasts its own view of the bay.
Nearby, in Longboat Key, Arbors by the Sea has lovely beach cottages (white picket fences included) that sit just steps away from a pristine beach. The property’s charm makes it easy to extend the vacation invite to the entire family, which is why the same broods return year after year (just be sure to sneak away for some couple time for yourselves). Whether it’s a quiet day of relaxation on a private Gulf of Mexico beach, a trip to the stellar restaurants and shops of nearby St. Armand’s Circle or an adrenaline-fueled afternoon at one of the area’s tennis resorts, Arbors by the Sea provides the perfect jumping-off point.