"Winslow’s Bungalows is downright cool. The place just oozes a hip vibe with its retro-chic decor and intimate setting that makes you feel like you have the run of the place. It’s a boutique resort occupying several historic homes in the heart of Old Key West. Named for Winslow Homer, who wintered in town, it feels like it has a story behind it, and indeed the homes once belonged to a cast of characters. There may be 85 accommodations, but you’ll feel more like a guest in a private home than in a hotel. The resort fee covers the usual suspects, including towels at the resort’s three pools, but it also includes a kit with a mask and snorkel for getting up close and personal with the local marine life. Ask the concierge for the best snorkeling spots. —Nancy DePalma" - Jamie Spain