Sunset Key Guest Cottages, a Westin Resort Rating: 4.5 Pearls
This 40-room resort caters to the upscale traveler with luxurious, beach-chic cottages and high-end amenities. It is located on Sunset Key, a residential island off Key West, and is affiliated to the Westin Key West, with which it shares some features, such as the fitness center and the restaurants. The hotel itself has wonderful amenities, including a lovely pool, a gorgeous beach with palm trees and clear waters, and a pleasant spa. Its location, though idyllic and exclusive, might be somewhat inconvenient for travelers who want to be close to shops and restaurants (the hotel only has one eatery on-site).
Cheeca Lodge & Spa Rating: 4.5 Pearls
The 114-room Cheeca Lodge was one of the original luxury properties on Islamorada, dating to 1946 and earning plenty of celebrity cachet over the years (high-profile guests have included George W. Bush). The property was rebuilt after a fire gutted its main building in 2009, and now has bright, spacious rooms with tropical-luxe decor and massive bathrooms. The lush grounds are especially pretty at night, with Tiki-torch-lit paths.
Casa Marina Resort - a Waldorf Astoria Resort Rating: 4.5 Pearls
The 311 rooms of the Casa Marina Resort have a light, sophisticated, but still island-y feel, with neutral tones, sheer curtains, and sleek hardwood or tiled floors. The resort also offers great in-room amenities, including free Wi-Fi, flat-screen TVs, and espresso machines. Although bathrooms aren't anything grand (just simple walk-in showers or shower/tub combos), they're clean and sleek. The resort's grounds are beautiful, with palm trees and lush foliage, and lead to a rare amenity in Key West -- a swimmable beach. Although it's too rocky to wade into the water, a long dock extends to sandier bottoms.
Hawks Cay Resort Rating: 4.5 Pearls
Hawks Cay Resort has the feel of a small village, due to its massive size and many features -- the property even has its own 85-slip marina. Many guests arrive by boat, as the resort is located on Duck Key, a secluded spot far from Key West's main airport. The property largely attracts families looking for a quiet vacation, thanks in part to family-friendly features such as a dolphin experience, kids' club, and multi-bedroom villas. Plus, the beach has calm waters which appeals to families, but its secluded location gives it a bit of a romantic feel as well. The long list of amenities, which are all gorgeous -- from the spa to the pool to the three restaurants -- and the upscale rooms earn the resort a spot on our list.
Little Palm Island Resort & Spa Rating: 4.5 Pearls
Reachable only by boat or seaplane, Little Palm Island Resort & Spa is located on a private island where wild key deer roam. It includes 30 luxurious suites, many with private oceanfront verandas. A favorite getaway for celebrities, it provides a secluded place to unplug from the world (use of technology is discouraged) and experience a romantic vacation in a lush, tropical environment. Indulgent spa treatments, such as the decadent Madrugada Water Massages, are offered at SpaTerre. The Dining Room serves a blend of French and Pan-Latin cuisine. The chef will pack gourmet picnic lunches for guests to take on seaplane or sailing excursions arranged by the hotel. Nestled in the center of the island, the pool is surrounded by lush vegetation, bubbling fountains, resort-style lounge chairs, and a tropical Tiki bar.
Marriott Key Largo Bay Beach Resort Rating: 4.0 Pearls
This 153-room property is located in northern Key Largo, a short drive from the John Pennekamp Coral Reef State Park, and close to shops and restaurants. Not a lot stands out, but it does feature an upscale vibe and there are a few perks -- like a diver's center on-site, an adequate spa, and a nice private beach (albeit a tiny one). Big rooms have flat-screen TVs, free Wi-Fi, and attractive decor that earns it a spot on our luxury list. Book a room with an ocean view to enjoy the beautiful Key Largo sunsets.