Just a half hour south of St. Petersburg on laid back Anna Maria Island, this intimate, delightfully old-fashioned (and also pet-friendly) colony of lowrise pastel cottages set amid lush greenery has a pool and lies on beautiful Tortuga Beach with an array of water sports. Apart from the pool and barbecue facilities, Tradewinds is fairly short on on-property amenities, but the town of Bradenton Beach in which it's located more than makes up for that in attractions, restaurants, shops, and a panoply of fun activities. This is definitely a sweet spot to get your chill on!

It's one of Tripatini member Ady Kang's 12 of Florida's Best Resorts.