Like ground frost and incessant smartphone meeting alerts, mega-resorts are rare in the Florida Keys. Small and mid-size hotels are the rule here, not the exception. After all, the Florida Keys are as beloved for their easygoing island vibes and quaint accommodations as they are for their year-round temperate weather and amazing dolphin sightings. To really zero in on the region's charm, a cottage stay is a great way to go. Read on for nine properties with cottage options as picturesque as their surroundings.
About 1,500 feet off the coast of Key West, the 27-acre Sunset Key Cottages is a laid-back (but upscale) island resort, carefully landscaped with grassy lawns, palm trees, bougainvillea, and other tropical flowers. Its pristine, classic-Key-West buildings include an airy fine-dining destination restaurant (thought to be the best in Key West) with unobstructed Gulf of Mexico views and beachy, pastel-colored cottages with Victorian tin roofs and wraparound porches. Most cottages are set in the gardens surrounding the saltwater pool, but many of the three-bedroom cottages and both of the four-bedroom ones have partial ocean views. The Three-Bedroom Deluxe Oceanfront Cottage has uninterrupted ocean views from nearly every vantage point — especially its huge covered porch. All cottages have full kitchens, breakfast nooks, and living rooms with sofa beds. Breakfast baskets with pastries and fruit are delivered to the cottages every morning.
Even in a town filled with intimate, romantic, and historic boutique properties, the glorious Gardens Hotel still manages to shine. This was once Key West’s largest private estate, and an air of relaxed luxury is conveyed through gleaming wood floors, heavy brocade curtains, and swirling palm-leaf ceiling fans. There’s a big wraparound porch out front, and all 20 plantation-style rooms and cottages have comfortably furnished verandas or balconies, made more private by the Gardens’ dense foliage of black bamboo and several palm varieties. The cottage rooms feel more contemporary, particularly in the kitchens with their stainless-steel appliances and sleek cabinet hardware.
All of The Paradise Inn‘s 18 one- and two-bedroom suites are set in restored cigar-maker cottages or reproductions of Bahamian-style houses. Everything in the adults-only hotel is white, bright, and spotless, with plenty of windows and French doors welcoming in the southern Florida sunshine. Outside, there are several terraces, sundecks, and quiet patios amid the palms — inviting spots to curl up with a book and a plate from the afternoon wine and cheese hour. Rooms are as soothing as the pristine building and leafy grounds; all have thin-planked oak floors, white walls, ceiling fans, wood and wicker furniture, and natural-fiber fabrics. Standard amenities include flat-screen TVs with cable, coffeemakers, microwaves, mini-fridges, bottled water, and free Wi-Fi, and housekeeping includes nightly turndown service with chocolate.
Located on a little-known Middle Key called Tavernier, one of the more laid-back islands in the Florida Keys, Island Bay Resort is a romantic beach hideaway ideal for couples and diving enthusiasts (the area is known for its excellent reefs). Its 10 cottages stretch from the front office, right off of U.S. 1, down a brick-paved lane toward the private beach. Each cottage is decorated differently, but all have private decks and kitchens, as well as charming pale-teal stucco facades, wood-shingle siding, and blue tin roofs.
In its 90 years, Merlin Guest House Key West has served as military housing, a brothel, and a gambling den. These days, the property is well settled into its charming bed-and-breakfast self — clapboard siding and white porch railings and all. The location is one block from touristy Duval Street, but the inn’s lush tropical landscaping helps insulate it from the nearby din. The internal courtyard features a gazebo (where the free breakfast is served), a pool, and a hammock, and the front porch, facing Simonton Street, makes a nice perch for drinking iced tea and watching bicyclists leisurely cruise by. Each of the 22 rooms (of which about half are original) has a unique layout and cottage-chic furnishings. Dark wooden flooring and exposed wooden ceilings create a romantic atmosphere. All rooms have flat-screen TVs, free Wi-Fi, air-conditioning, and shared porches or patios. The one- and two-bedroom cottages have living rooms and kitchenettes or wet bars.
As its name suggests, Pine and Palms Resort is set on five acres of beachfront grounds thick with gumbo limbo trees, coconut palms, orchids, and other tropical vegetation. The resort has a quaint village-like vibe, with sandy paths leading to cottages, villas, and low-lying room buildings. All cottages are bright and airy, with modern kitchens, outdoor space, and daily housekeeping (a rarity in self-catered apartment hotels). Some even have attractive wood ceilings, adding to the charm factor. Cottages come in one-, two-, and three-bedroom configurations, and the one-bedroom Orchard Cottage and the two Ocean Front Cozy Cottages have ocean views. The three-bedroom Coconut Cottage has its own pool, plus the option of an additional one-bedroom guest cottage.
Handwritten notes welcome guests checking into their room, cottage, or bungalow at The Duval Inn. Rooms are housed in the circa-1895 main house, while four cottages (with names like Mango and Leaf) and five bungalows are arranged around the pool and patio. A big distinction between the cottages and bungalows is that cottages have private (and spacious) bathrooms, while bungalows share a bathroom at the end of the hall. Each room is equipped with a flat-screen TV, an individual air-conditioning wall unit, a mini-fridge, and towels. Wi-Fi is free everywhere in the property, including the courtyard where free happy hour drinks are doled out at a small bamboo bar and greenery is supplied by hanging ferns, potted plants, tall palms, and flowering trees. The seashell-floored outdoor space is filled with frilly wrought-iron seating and umbrella-shaded tables and chairs.
For travelers who can do without traditional hotel services, Coral Lagoon — a collection of 18 privately-owned homes that dwarf a typical hotel room — is a great option for families and sport fishermen in Marathon. Its units are immaculately clean and large, each with a big modern kitchen, two-and-a-half bathrooms, and at least one porch overlooking the marina or canal. Coral Lagoon faces the Atlantic, but has no on-site beach (only a pool); it’s a five-minute drive to the nearest stretch of sand. Marathon is a major sports-fishing destination on both the gulf and Atlantic sides, especially during the annual tarpon and marlin tournaments in May and July. Impressive reefs make it very popular for diving and snorkeling.
Okay, Beach Palms is in Siesta Key, which is not part of the Florida Keys at all. (Siesta Key is a barrier island in the Gulf of Mexico near Sarasota.) But we had to include this value property’s delightful little guest bungalows, each with a full kitchen and a private porch with a gas grill and hammock. Beach Palms’ biggest asset? It is right across the street from the unbelievably beautiful white-sand Siesta Key Beach (in terms of broadness and sand quality, the beaches of Siesta Key are superior to those throughout the Florida Keys, which can be slim, rocky, full of vegetation, or man-made).
To match those chill Keys vibes, bring along a flowy romper for an easy yet stylish cover-up option.
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