12 Best Hotels in The Florida Keys, Florida

In the heart of Old Town, this adults-only home away from home offers simple, clean, attractively priced accommodations. The high rollers and ladies of the night were chased away long ago, but this charming guesthouse revels in its past as a gambling hall and bordello. Units range from small rooms sharing a bath to spacious rooms with king beds and sleeper sofas. Built in 1899, the yellow-and-white clapboard building has second-floor porches, gabled roofs, and a white picket fence. The current owners prettied the rooms with flower-print curtains and linens and added homemade cinnamon rolls, which receive rave reviews in the guest book, to the breakfast bar. A lagoon-style pool, fountain, and old-brick walkways accent a lovely garden.

Elsewhere you'd pay big bucks for the wonderful views available at these three cabins, each of which has two two-bedroom units with full kitchens and baths, as well as air-conditioning (but no television, radio, or phone). All but one unit accommodate up to six (the other sleeps up to four and is accessible). The park also has popular campsites ($36 per night) suitable for either tents or motor homes. Some are directly on the beach—talk about a tent with a view! Cabins and campsites book up early, so reserve up to 11 months before your planned visit.

There's a congenial atmosphere at this lively, family-owned lodge-campground-marina—a happy mix of tent campers (who have the fabulous waterfront real estate), RVers (who look pretty permanent), and motel dwellers who like to mingle at the rooftop pool and play poker. Rooms have tile floors, wicker furniture, and doors that allow sea breezes to waft through. A skywalk joins the upper-story rooms with the pool and deck. Campsites range from rustic to full hookups. Everything is spotless—even the campground's bathhouse—and the service is good-natured and efficient. Satellite wireless means you can pick up a signal most places on the property, depending on the weather. The staff will book you a room, sell you bait, or hook you up with a fishing charter. There are plenty of family-oriented activities, so the youngsters will never complain about being bored. Discounts are available for week-long or longer stays.

You know what to expect from this chain hotel: well-maintained rooms, predictable service, and competitive prices. This one also happens to be on a 7-acre piece of property with ocean views next to the airport. Rooms are bright and modern with palm-frond patterns, crisp white linens, and mosaic-tiled bathrooms. Most have balconies. The palm-shaded pool and tiki bar looks over the Atlantic, and a covered picnic area with a large barbecue grill encourages socializing.

This little motel neatly packages three appealing characteristics—affordability, safety, and a pleasant location between Old Town and New Town at Garrison Bight. Units are boxy and basic, with little patios and lots of peace and quiet. For on-the-water living, book one of the four stationary houseboats with shiny new interiors; each sleeps four. Sportfishing charters are just a block away, and there's a fish-cleaning table on the dock. The pool is small but refreshing after a day exploring.

There are accommodations for every budget here, but the owners reason that budget travelers deserve as pleasant an experience (and as lavish a tropical continental breakfast) as their well-heeled counterparts. Local art—large, splashy canvases and a Gauguinesque mural—decorates the walls, while handmade textiles (owner Jody Carlson is a talented weaver) drape chairs, couches, and beds at this historic home. Less expensive rooms burst with bright colors (hand-painted dressers add a whimsical flourish) and balconies on the second-floor rooms overlook the gardens. Spacious, and more expensive, third-floor rooms are decorated with a paler palette and original furniture.

Almost every room at this budget-friendly option has a view of South Pine Channel, with the lovely curl of Big Pine Key in the foreground. Waterfront cottages, with decks or balconies, are spread out on 6 landscaped acres, where there's also a heated swimming pool and a putting green. There are water sports galore, and the staff will book you a kayak tour, a fishing trip, or a bike excursion, or tell you which local restaurants will deliver dinner to your room. So what if the decor feels a little like Grandma's house and you have to pay extra ($10 or more) if you want your room cleaned daily? It's clean and comfy.

Stylized metal herons mark the entrance to this 67-year-old family-run motel. The third and fourth generations of the Popp family are currently at the helm, taking care of the basic-but-clean units. Don't be discouraged by the building clutter around the office. Inside, the rooms have bright paint jobs, new floors, and modern kitchens. Room 9 is closest to the beach.

At this basic, budget lodging it's all about staying on the water for a song. But the resort is not without its charms, including draping bougainvillea and stately gumbo-limbos. There's a pond, hammocks, and a bridge that leads to the beach area; many rooms have water views, and some have private patios. Rooms 3, 4, and 5 are spacious and best for families. Unit 6, a one-bedroom cottage called the Beach House, has a large picture window with an awesome view of the bay. Each unit has its own charcoal grill and outdoor seating, and guests gather at the private beach and dock to watch the sun set.

During Prohibition, Raul Vasquez made this place popular by smuggling in rum from Cuba; today, its reputation is for having reasonably priced rooms within walking distance of the beach. Of course, the booze is legal now, and there's a bar in the lobby offering 350 brands of rum. Accommodations have kitchenettes that include a refrigerator, microwave, kitchen sink—everything you need. Pastel-painted walls are accented by bursts of color in rugs, pillows, and seat cushions. The rooms are basic, but some have nice touches like claw-foot tubs. Room 1A has a balcony that's good for people-watching.

This 1950s throwback recalls the days when parents packed the kids into the station wagon and headed to no-frills seaside motels. The owners have spiffed things up with cute, artsy touches and added a small sunning beach, but basically it's just a motel—nothing fancy but comfortable. Guests don't mind skimping on space (although larger waterfront cottages are available) and a few frills in favor of homey digs, socializing under the chickee, and reasonable rates.

This industrial-chic stunner—where spacious, airy rooms juxtapose crisp white linens with furnishings and fixtures in rich chocolate-browns and shades of gray—has made off-the-beaten-path Stock Island a Key West destination. The hotel is surrounded by water, so many of the rooms have truly wonderful views, and canine pals are welcome here, with pet-friendly amenities that include a dog park. Matt's Stock Island serves up some of the area's most creative food, with dishes such as crab beignets or grouper with cornbread gnudi (gnocchi-like dumplings).