If you’re on a Florida Keys road trip and you haven’t left your cares behind by the time you reach Upper Matecumbe Key, make a sharp left at mile marker 82.7. That will take you straight to the gates of The Islands of Islamorada, a compound of 22 gracious villas huddled around a private beach. From the minute your tires crunch over the gravel-and-seashell roads, you’ll feel the decompression. And as soon as you enter your villa—with its airy, bright spaces and breeze-swept terraces with a view of the sea—you may just decide that island time is the best time of all.
Not surprisingly, The Islands of Islamorada was developed by the Frisbie Group, one of Palm Beach’s most well-known family- owned businesses. The tight-knit Frisbies are all about multigenerational gatherings, and that ethos has driven the design of the villas. With four bedrooms and more than 3,100 square feet across three levels, these homes away from home have every creature comfort imaginable (down to a fully stocked laundry room) and multiple areas for families to spread out. Best of all, they’re perched directly on the water’s edge, so access to the beach, pools, and marina couldn’t be easier.
The mood here is definitely relaxed, but that’s the idea. Gather at your ground-level alfresco dining room for breakfast, then grab a paddleboard or kayak (both are complimentary to guests) and explore the shoreline. Later, play a game of volleyball or take an outdoor fitness class. At day’s end, enjoy cocktails at the Ocean House tiki bar or kick back on Adirondack chairs and watch the sunset while the kids play cornhole. If it sounds idyllic—a step back in time, even—that’s because it is.
Although the temptation is to do a whole lot of nothing, active types won’t be disappointed. There’s a pickleball court on property and a 24-hour gym for those who like to work up a sweat. An on-site concierge can help arrange fishing outings, especially when the tarpon are biting, as well as day trips to other Keys by boat, car, or seaplane. The Islands is committed to conservation and sustainability, and even offers guests eco-themed excursions like exploring Big Pine Key to see the precious, endangered Key deer. Memories, and good vibes, guaranteed.