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. With an adults-only pool, a top-notch spa, and delicious on-site dining, it tops our list of most romantic hotels in the keys.
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 is idyllic and exclusive, adding to the romantic vibe.
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. The hotel also features several restaurants (serving up fresh seafood) and a spa with beachside treatment rooms.
Southernmost on the Beach Rating: 4.0 Pearls
Southernmost on the Beach is a Key West favorite. The hotel has lovely architectural details such as arched doorways, crown molding, bay window seats, and porthole windows. Many rooms have balconies, and some have corner, wrap-around balconies with ocean views that are truly spectacular. Polished rooms are decorated in soothing, beach-inspired tones. Highlights here include the spectacular beach, long pool, private sunbathing pier, spa, and sunny fitness center. The hotel is located on the far end of Duval street, giving guests easy access to Key West's famous bars and restaurants without the annoyance of nighttime noise. With hammocks strung between palm trees and Adirondack chairs looking out over the ocean, this 124-room hotel provides the perfect environment for romance.
Hawks Cay Resort Rating: 4.5 Pearls
Hawks Cay Resort has the feel of a small village, due to its massive size and many amenities -- 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. Though the property largely attracts families thanks in part to family-friendly features such as a dolphin experience and the kids club, its secluded location gives it a bit of a romantic feel as well. And all of the on-site amenities -- from the spa to the pool to the three restaurants -- are gorgeous.
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 a romantic 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. Book a room with an ocean view to enjoy the beautiful Key Largo sunsets.
The Weatherstation Inn Rating: 3.5 Pearls
This charming, 8-room property is housed in a historic building on a quiet street in Old Town Key West, within walking distance to some of the major tourist attractions, and to a couple of good beaches. Each of its rooms has a distinct character and few amenities (a flat-screen TV and little more), but they come with charming decor (four-poster beds, antique touches) and relaxing views of the well-tended grounds. The hotel has no amenities whatsoever -- just a tiny pool -- but there are some great freebies like free Wi-Fi, free parking, and a free quality continental breakfast, and the inn has a distinctly romantic vibe, in part due to the fact that children under 15 are not allowed.
Marquesa Hotel Rating: 4.0 Pearls
Refurbished from 1884 conch houses, the Marquesa Hotel is a compound of four buildings surrounding lovely interior gardens and two pools. A narrow staircase off the lobby leads to the individually decorated rooms. Light and airy rooms feature flat-screen TVs, mini-fridges, and cozy sitting areas with ottomans. Bathrooms are basic and clean with shower/tub combos and marble sinks. Suites have private terraces with cute wicker furniture and some are adjacent to one of the hotel's pools. An appealing on-site restaurant, Cafe Marquesa, serves fresh local seafood. No children under 14 are allowed at the hotel, adding to the quaint, romantic vibe. Free Wi-Fi and parking add value, and the Old Town location two blocks from Duval Street is convenient.
Casa Morada Rating: 4.0 Pearls
Inspired by a laidback Caribbean lifestyle, Casa Morada is an upscale 16-suite boutique hotel that’s perfect for couples looking for a romantic getaway, whether for a honeymoon or just because. Situated right next to the ocean in the middle of the Florida Keys on Islamorada, the hotel provides a peaceful and serene atmosphere with hanging hammocks and lots of fun and free activities like yoga classes, kayaking, and bicycle rentals. No kids under 16 are allowed. Compared to nearby hotels, this property offers great value with spacious and upscale rooms with water views.