Best Hotels in Islamorada

The Cheeca Lodge & Spa sits pretty on the skinny Florida key known as Upper Matecumbe, part of an incorporated village of islands called Islamorada. Travelers love this resort because it achieves a tropical getaway. But some mean this in a good way (transparent waters, calm Florida Bay breezes), while others mean this as an insult (too tropical to keep all the bugs away). There are several perks to staying at Cheeca Lodge, however. For one, the rooms feature screened-in balconies and rain showers, as well as flat-screen TVs, Illy espresso machines and wireless internet access (which is covered by the daily resort fee). Another plus, the bungalow-like setting is supremely romantic, and families will like that some of the accommodations have kitchens. If you don't feel like cooking, you can sit down to dinner at one of four on-site restaurants, which serve up fresh seafood and other tasty entrees. You'll find the Cheeca Lodge & Spa about 86 miles southwest of Miami and 80 miles northeast of Key West.

The oceanfront Amara Cay Resort is in the heart of the Florida Keys on the southern end of the town of Islamorada, which is home to shops, restaurants and the informative Keys History & Discovery Center. The beachy lobby features hanging basket chairs and driftwood accents, and its guestrooms and suites have neutral color schemes with seafoam and rattan accents. All rooms come with bathrobes and slippers, TVs with premium channels and rainfall showerheads in the bathroom; most rooms also have balconies. There’s daily resort fee that includes access to the fitness center, Wi-Fi, parking, use of beach chairs and towels, a shuttle into town and bike, kayak and paddleboard rentals. The hotel’s tiki bar, Reelburger, serves cocktails, milkshakes, fries and burgers for lunch and dinner by the free-form saltwater pool. Note that there is no late-night dining option or room service available at this pet-friendly resort.

A beachfront resort in Islamorada, Florida, Pelican Cove Resort & Marina offers a spectacular vantage point for visitors to enjoy the beauty of the Florida Keys. Guests will have no shortage of things to do on-site with an outdoor pool, a saltwater lagoon, a private beach, and a marina to explore. Particularly adventurous guests can participate in water sports and fishing. After they’ve tired themselves out, this resort has a restaurant and a cafe to refuel. (There is also a Starbucks relatively close.) The property recently renovated each of its 63 guest rooms with contemporary, clean decor, plus a flat-screen TV, a coffee maker, a minifridge, a private balcony and complimentary internet access. Recent guests rave about the spectacular views, helpful staff and multiple activities. Despite these pros, some visitors suggest that a few furniture pieces in the rooms prove to be more fashionable than comfortable. 

Postcard Inn Beach Resort & Marina is a retro, beachfront hotel that still manages to offer the contemporary perks travelers expect. The property’s location allows guests to access the breathtaking waters that surround the island of Islamorada. The accommodations at this hotel blend nostalgic decor with modern amenities, offering complimentary Wi-Fi access, flat-screen TVs and iPod docks in each of the 143 guest rooms. Plus, lodging options have extra perks like a private, furnished balcony with a marina view. There is a lot to do on-site, with a private beach, a resort-style outdoor pool, and diving and snorkeling trips, as well as other water sports. Recent guests love that everything food and fun related is nearby, with recreation, a raw bar, a restaurant and a Tiki bar all on-site. Travelers can’t help but bemoan the daily resort fee though.