The Florida Keys aren't short on waterfront hotels, but this one built its own protected swimming cove instead of settling for a strip of sand. The Islands of Islamorada (rated 4.7/5 on Tripadvisor) is a boutique, 30-room resort about an hour from Miami, made up of villas and ocean suites rather than standard hotel rooms. It's a good fit for couples and families who want a quieter, more private property than the big Keys resorts, and after digging through the calendar, we found the best rates for this stay in September.
Guests can play pickleball or cornhole, grab beach toys for the kids, head out for scuba diving and other water activities, or settle in around the s'mores pit after sunset. There's a tiki bar for poolside drinks, too, which means it's very easy to spend an entire day here without getting back in the car. Villas come with full kitchens and BBQ grills if you'd rather cook than order in, and evenings can wind down with a sunset by the beach fire pit, a game of pickleball, or drinks by the water.
🏴☠️ Pirate Tip: Islamorada calls itself the "Sportfishing Capital of the World," and this stretch of the Keys is built for boat time. The resort's own marina puts you minutes from backcountry flats fishing and reef diving, and Robbie's Marina down the road (tarpon feeding included) is a classic stop even for non-anglers.
