Given the impending publication of my Moon Florida Keys  guide later this month, I've decided to offer a few posts about that unique archipelago south of Miami. Of course, this isn't the first time I've written about the Florida Keys  on this blog. Since last year, I've covered several related attractions, restaurants, and resorts, from Key Largo's Dolphins Plus  to the Eden House  in Key West. Even Islamorada , a town popular with sportfishing enthusiasts but less well known among average tourists, has received its fair share of attention here, with posts about Theater of the Sea  and the History of Diving Museum .
But, for today's post, I thought I'd turn the spotlight on one of Islamorada's finest lodging options. As with other parts of the Florida Keys, Islamorada offers a wide range of accommodations, from the pet-friendly Casa Thorn Bed & Breakfast  (114 Palm Ln., Plantation Key, 305/852-3996, $79-239 d), which provides five comfortable rooms, a lovely tropical garden, and a refreshing swimming pool, to the spacious Holiday Isle Resort & Marina  (84001 Overseas Hwy., Windley Key, 305/664-2321 or 800/327-7070, $149-229 d), which features oceanfront suites, a private beach, an on-site restaurant, six tropical bars, and various sportfishing charters, scuba-diving trips, and snorkeling excursions.
In addition, Islamorada presents some of the most upscale resorts in the entire Florida Keys island chain. One such option is the tranquil Chesapeake Beach Resort  (83409 Overseas Hwy., Upper Matecumbe Key, 305/664-4662 or 800/338-3395, rooms $210-340 d, villas $225-450), a luxurious, well-landscaped property that features a 6.5-acre tropical garden, two heated oceanfront pools, a hot-water spa, tennis and shuffleboard courts, a tiki-style observation deck, and a variety of accommodations. Another well-favored resort is the lavish Cheeca Lodge & Spa  (81801 Overseas Hwy., Upper Matecumbe Key, 305/664-4651 or 800/327-2888, rooms $209-490 d, suites $259-899, two-bedroom suites $559-998, bungalows $319-597), which has lured an array of U.S. presidents and movie stars since its opening in 1946. Today, the recently renovated resort includes tennis courts, a fishing pier, a private beach, an on-site spa, an adults-only pool, two fine restaurants, and an array of Caribbean-style rooms, suites, and adults-only bungalows.
In my opinion, though, the best example of Islamorada's luxury and seclusion is The Moorings Village Resort  (123 Beach Rd., Upper Matecumbe Key, 305/664-4708), a serene, splendidly lush property situated on the ocean side of U.S. 1, near mile marker 81.6 but far from the hustle and bustle of the Overseas Highway. Once part of a coconut plantation in the 1930s, this verdant 18-acre resort offers 18 private homes and cottages (which greatly range in price depending on the season), from several brightly painted Caribbean bungalows tucked amid the foliage ($250-750 daily) to a three-bedroom, French Colonial-style plantation house ($7,700-10,500 weekly) directly beside the ocean. Other options include a two-bedroom oceanfront bungalow ($3,150-4,550 weekly), seven two-bedroom inland homes ($3,850-5,600 weekly), a one-bedroom oceanfront home ($4,200-5,775 weekly), and two two-bedroom oceanfront homes ($6,650-9,100 weekly). These self-sufficient residences, many of which lure the same travelers year after year, contain televisions, telephones, well-equipped kitchens, luxurious beds, and, sometimes, washers and dryers. All lodgings require a two-night or one-week minimum stay, and all are only a short stroll from a private Polynesian-style beach – complete with swaying palm tress, cushioned lounge chairs, relaxing hammocks, and complimentary kayaks. It's no wonder, then, that this stunning beach has often been used as a backdrop for catalog photo shoots and in various movies, including Repo Men (2010).
Other on-site amenities include tennis courts, a relaxing pool area, kite-surfing lessons, and the Island Body & Söl Spa  (305/664-3264, by appt. daily, $50-190 per treatment), which offers a selection of rejuvenating facials, massages, and beachside yoga lessons. The family-owned resort also boasts two of the finest eateries in the Keys – the Morada Bay Beach Café , ideal for light lunches beside the beach, and Pierre's Restaurant , perfect for a romantic dinner. Both restaurants lie on the bay side of the Overseas Highway, only a short drive from the Moorings.
Although The Moorings Village Resort certainly doesn't fit every budget, its tropical seclusion and guaranteed tranquility make it well worth the cost for those who can afford it. For more information about other accommodations in the Islamorada area, plus details about local attractions, restaurants, events, and other diversions, consult the Islamorada Chamber of Commerce  (MM 83.2 BS U.S. 1, 305/664-4503 or 800/322-5397, 9 a.m.-5 p.m. Mon.-Fri., 9 a.m.-4 p.m. Sat., 9 a.m.-3 p.m. Sun.) or my soon-to-be-released Moon Florida Keys  guide. In the meantime, stay tuned for my next two posts, which explore the aforementioned Morada Bay  and Pierre's , two of my favorite dining options in Islamorada.
As always, I’m open to ideas for future posts. If you have any suggestions, burning questions, or destinations that you’d like me to explore in greater detail, please comment below or contact me via laura [at] wanderingsoles [dot] com.
Disclosure: While I occasionally accept free or discounted travel assistance when it coincides with my editorial goals, my opinion is never for sale, which means that everything written in my American Nomad  blog and my Moon travel guides is my unbiased reflection of the things that I see, do, and experience while traveling across the United States.
Photo of The Moorings Village  © 2010 Daniel Martone / Text © 2010 Laura Martone