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Hotels in Upper and Middle Keys
Because the real beauty of the Keys lies mostly beyond the highways, there is no better way to see this area than by boat. So why not stay in a floating hotel? If you’re traveling with a group, houseboats are not only fun, they can be super economical. You’ll find plenty to rent on both Vrbo or Airbnb but if you go with a full service rental you’ll have someone to turn to if there are problems. We recommend KeySea Houseboats, in Key Largo (tel. 305/394-3096), which has slightly higher rates than you might find online ($970 for 2 nights to $2,485 for 7 nights), but that’s for a boat that can sleep up to six people and includes kayak rental, snorkel equipment, fishing equipment, and your first fill-up of ice. All KeySea boats have flat screen TVs, linens, bath amenities, touch screen GPS, and propane BBQ grill.
Or you could stay below the waves at Jules Undersea Lodge (51 Shoreland Dr., Key Largo; tel. 305/451-2353). Generally booked by honeymooners, and other celebrating events that make the high rates here palatable (they’re $1,350–$1,575 per person). This 2 guestroom hotel was once an underwater research station (it rests on pillars on the ocean floor, now operates as a two-room hotel. To get inside, guests scuba dive 21 feet under the structure and pop up into the unit through a 4 by 6-foot “moon pool” that gurgles soothingly all night long. Food, drink, and unlimited diving is part of the nightly rate here.
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Baker’s Cay Resort Key Largo, Curio Collection by Hilton
A short drive from Miami, this contemporary property is very peaceful, and actually quite beautiful, which you’d never guess from its motel-esque facade. Almost all rooms face the ocean, and the décor pulls from beachy places around the globe, with ikat (Indonesian) and…$$$Key Largo - Hotel
Casa Morada
The closest thing to a boutique hotel in the Florida Keys is the brainchild of a trio of New York women who used to work for hip hotelier Ian Schrager. The 16-suite Casa Morada is tucked off a sleepy lane, radiating serenity and style in an area where serenity abounds, but style not…$$$Islamorada - Hotel
Cheeca Lodge & Spa
Located on 27 acres of beachfront, this rambling resort has one of the only golf courses in the Upper Keys and much more. We’re talking two oceanfront family friendly pools and an adults-only lap pool; tennis, pickleball, basketball, and volleyball; eco-tours, sunset cruises, snorkel…$$$Islamorada - Hotel
Conch Key Cottages
Occupying their own private micro-island just off U.S. 1, these romantic, brightly painted cottages just steps from the ocean are a place to get away from it all, exuding what management touts as “bohemian luxury,” including Old Florida–style architecture with tin roofs and Dade…$$Marathon - Hotel
Hilton Key Largo Resort
A great escape for a weekend or longer, ensconced on 13 acres of forest and Gulf shore, and most rooms have water views. There are two pools, one for kids, one for grownups, but I’d recommend you spend most of your time on the private, white-sand beach, where you can do a variety of…$$Key Largo - Hotel
Isla Bella Beach Resort
Located off the beaten path and right before you head onto the Seven Mile Bridge, Isla Bella Beach Resort is truly an oasis away from the grit of Overseas Highway and smack on the water, with sandy beach, one mile of waterfront, and five oceanfront pools. Best of all, every room and…$$$Marathon - Hotel
John Pennekamp Coral Reef State Park
One of Florida’s best parks Pennekamp has 47 well-separated campsites, half of which are available by advance reservation. Tent and RV sites are small but equipped with restrooms, hot water, and showers. Note that it can get buggy, especially in late summer, so bring repellent. Two…$Key Largo - Hotel
Jules’ Undersea Lodge
Staying here is an experience of a lifetime—if you’re up to taking the plunge. Built as a research lab, this underwater habitat, which rests on pillars on the seabed, now operates as a pricey two-room hotel most popular with diving honeymooners. To get inside, guests swim 21 feet…$$$Key Largo - Hotel
Kona Kai Resort, Gallery & Botanic Garden
This little haven is an exquisite, adults-only property right on Florida Bay, offering stunning sunset views overlooking Everglades National Park. Guestrooms and suites are very comfortable, painted in cheerful sherbert colors, with quirky details (like a headboard made of oars, or a…$$$Key Largo - Hotel
Lime Tree Bay Resort
Just one of two spots to stay in the tiny town of Layton (pop. 183) sits on a pretty piece of waterfront, midway between Islamorada and Marathon, graced by hundreds of palm trees and tropical foliage. There are two pools, including one heated, a nice white sand beach, fishing pier,…$$Long Key - Hotel
Long Key State Park
The Upper Keys’ other main state park is more secluded than its northern neighbor—and more popular. All sites are located ocean-side and surrounded by narrow rows of trees and nearby restroom facilities. Reserve well in advance, especially in winter.$Long Key - Hotel
Pines and Palms of Islamorada Resort
Looking for a beachfront cottage or, better yet, oceanfront villa, without blowing half your kid’s college fund? Here’s the spot, with cheery, cozy one- to three-bedroom cottages, Atlantic views, and a private beachfront with hammocks and a pool, all in a relaxed tropical paradise…$$Islamorada - Hotel
Postcard Inn Beach Resort & Marina at Holiday Isle
The famously rough-and-tumble, rum-soaked Holiday Isle got a much-needed major makeover, and today it’s mostly whimsical surfer-chic with waterfront rooms awash in white woods and sand-colored stripes, with cute quotes from ocean lovers hand-stenciled on the walls. Around a…$$Islamorada - Hotel
Ragged Edge Resort
Honestly, I’m not sure where the “ragged’ thing comes in, because this oceanfront property’s units are spread along more than a half-dozen gorgeous, grassy waterfront acres. All are immaculately clean and comfy, and most are outfitted with full kitchens and pleasant if not fancy…$$Islamorada - Hotel
The Moorings Village & Spa
You may never see another soul at this pricey 18-acre resort, a former coconut plantation, if you choose not to (there isn’t even maid service unless you ask for it). The whitewashed units, from cozy cottages to three-bedroom houses, come with fully equipped kitchens and…$$$Islamorada - Hotel
Tranquility Bay Beachfront Hotel & Resort
On a tropically landscaped dozen Gulfside acres and worlds away from the busy, not-so-lovely Marathon stretch of U.S. 1, you’ll feel like you’re in your own beach house—literally, because besides the standard guestrooms the stars here are gorgeous two- and three-bedroom conch-style…$$Marathon



