A Caribbean getaway can mean good things like relaxing on an island, soaking up the sun, and swimming in clear blue water. But it can also mean long flights, passport hassles, and endless customs lines. What if you could get the magic of the Caribbean minus the trouble? We have some good news: The Florida Keys has all that magic and more. These seven beachfront places to stay harness the laid-back vibe that a Caribbean vacation is known for. Get ready to crack some conch, drink some rum, and enjoy some world-class sunsets at one of these great hotels and resorts in the Florida Keys.
Lush tropical foliage at Casa Morada
Courtesy of Casa Morada
1. Casa Morada
- Location: Islamorada
- Book now
Designed to impart the owners’ love of nature and wildlife to visitors, Casa Morada, on Islamorada, is perfect for those who appreciate lush tropical flora. Guests who arrive expecting only palm trees are in for a surprise. This all-suite boutique hotel celebrates its place in the tropics through landscape design by Raymond Jungles, whose signature style lends a, well, jungle ambience reminiscent of famously green Caribbean islands like St. Lucia and Dominica. An added bonus: Many of the guest rooms feature outdoor showers and Jacuzzis, so staying outside is almost always an option.
Enjoy sunset from the resort’s fleet of fishing boats.
Courtesy of Cheeca Lodge & Spa
2. Cheeca Lodge & Spa
- Location: Islamorada
- Book now
Fishing is a pastime and a profession in the Caribbean. Cheeca Lodge & Spa, on Islamorada, Florida’s sportfishing capital, communicates its own stateside enthusiasm for this water-loving pastime with everything from their logo (a giant tarpon) to their gorgeous new fishing pier. The hotel is famous for expert-led fishing excursions that take place on its own fleet—skiffs, bay boats, and sportfishing boats—and guests can choose between fly or reel fishing on reefs or offshore. The resort hosts several fishing competitions, including the prestigious Presidential Sailfish Tournament, founded by former president George H.W. Bush in 1990 and held at Cheeca Lodge every January.
Ocean Key Resort is the place to be for Key West’s sunset celebrations.
Courtesy of Ocean Key Resort
3. Ocean Key Resort & Spa
- Location: Key West
- Book now
Home to Key West’s famous Sunset Pier, Ocean Key Resort & Spa has sunset-watching on lockdown, giving islands like the Bahamas, Turks and Caicos, and Antigua a run for their money. Sunset Pier is considered the best place in Key West to enjoy spectacular gulf sunsets, an experience that’s sweetened by the resort’s tropical and Caribbean cocktails and cuisine. Keep the vibe going and join the nightly post-sundown party for music and dancing. Alternatively, the idea of watching the flaming sun sink into the Gulf of Mexico from your private balcony doesn’t sound half bad, either.
Replace gray winter days with the brilliant sun of Key West.
Courtesy of The Reach
4. The Reach
- Location: Key West
- Book now
Key West’s beachfront resort The Reach offers a truly luxurious, Caribbean-style sun-worshipping experience with powdery sand and crystal clear water. The beach will remind you of islands like St. Bart’s and Grand Cayman. Sprawled across a private stretch of pristine white sand lapped by cerulean gulf waters, this five-star property has everything you need (hello, pool concierge) and nothing you don’t (bye-bye, crowds). Also important: lots of inviting hammocks.
Island spices infuse the dishes in the Florida Keys, too.
Courtesy of Moorings Village
5. Moorings Village
- Location: Islamorada
- Book now
The dressed-down resort of Moorings Village has two restaurants for its 18 guest cottages. The more casual of the two—the toes-in-the-sand Beach Café—serves an eclectic menu packed with Caribbean specialties. Try the Bahamian conch chowder, conch fritters, or conch salad. An order of whole fried snapper with tostones, cilantro rice, and sofrito criollo offers a taste of the Dominican Republic; or go whole hog for island flavor by requesting the spicy mojo-marinated roasted pig. The bar’s signature Man Overboard cocktail hits all the tropical notes with Cruzan rum, blue curaçao, and fresh tropical juices.
The Gulf of Mexico, a private lagoon, and six swimming pools keep you refreshed at Hawks Cay.
Courtesy of Hawks Cay
6. Hawks Cay Resort
- Location: Duck Key
- Book now
Lots of people head to the Caribbean hoping for an easy family vacation with entertainment for everyone. For a similar vacation stateside, look no further than Hawks Cay in the Middle Keys. The resort takes family-focused fun pretty seriously: In addition to six swimming pools (one with a pirate ship), there’s a freshwater lagoon, daily pirate shows, a hands-on dolphin program with free dolphin watching, and an eco-focused kids’ club. Adults will be kept interested, too, of course, with every water sport you can think of (yes, they have SNUBA), a tennis program, a spa and fitness center, and multiple restaurants.
Lime juice and rum taste like island life.
Courtesy of the Gates Hotel
7. Gates Hotel
- Location: Key West
- Book now
No trip to the Caribbean is complete without swigging some rum, but the Keys has plenty of the golden stuff on hand as well. The hip Gates Hotel in Key West is home to Rum Row, a hopping bar next to the L-shaped swimming pool. Through an exclusive partnership with Key West’s own First Legal Rum Distillery, the bar slings cocktails like the Up in Smoke, made with aged Key West Raw and Unfiltered Rum, mezcal, ginger, and lime juice. To partake in a scene with an even stronger pirate vibe, head to the hotel’s cigar lounge.
>> Next: Plan Your Trip with AFAR’s Guide to the Florida Keys
