Florida Keys' Character-Rich Hotels & Resorts

If you want true Florida Keys charm (friendly deer! 1960s-style bungalows!), look no further than this handful of spots, all experienced by our editors. (It’s a tough job...)
Article: Erin Shaw Street

Kona Kai Resort, Gallery, and Botanic Gardens, Key Largo 
Why we love it: The resort’s 11 rooms are nestled in subtropical botanic gardens, where you can learn about the uses of tropical and native plants cared for by their on-site ethnobotanist.
Don’t miss: The resort’s fine art gallery, which houses international paintings and sculpture. Rooms start at $269. 97802 Overseas Highway, Key Largo; kkresort.com or 800/365-7829

Hawks Cay Resort, Duck Key
Why we love it: Hawks Cay is a great home base for a family trip, and the hotel offers visitors a chance to swim with dolphins and has an on-site program for kids and teenagers.
Don’t miss: The Key Lime Mojito Body Treatment at the Calm Waters Spa ($180). Cap it off with one of the seven varieties of mojitos served at the Alma Restaurant. (We like the mango mojito; $12.) Rooms start at $239. 61 Hawks Cay Blvd., Duck Key; hawkscay.com or 888/395-5539

Pines & Palms Resort, Islamorada
Why we love it: These 1960s bungalow-style units are equipped with modern amenities, so you get the best of both worlds.
Don’t miss: The bicycles. Rent one from the front desk and explore the area ($5/day), or take in a sunrise at the end of their dock. Efficiency rooms start at $149, villas at $569. 80401 Old Highway, Islamorada; pinesandpalms.com or 800/624-0964

Deer Run Bed & Breakfast, Big Pine Key
Why we love it: Its most famous residents are the tiny Key deer who roam the property and will gladly visit with you over morning coffee (yes, they’re friendly!). Owners Jen and Harry De Maria have created an eco-friendly travel experience at its best.
Don’t miss: Jen’s homemade vegan breakfast. Even the most devout carnivores agree: It’s delicious. Rooms start at $225. 1997 Long Beach Road, Big Pine Key; deerrunfloridabb.com or 305/872-2015

Southernmost Hotel Collection, Key West 
Why we love it: This group of four hotels is right in the middle of Old Town, so you can easily walk just about everywhere.
Don’t miss: La Mer Hotel and Dewey House, two Southernmost properties, are both turn-of-the-century homes. Rooms start at $229. 1319 Duval Street, Key West; southernmostresorts.com or 800/354-4455