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 Cottages, a Luxury Collection Resort, Key West 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.
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.
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.
The Conch House Heritage Inn Rating: 3.0 Pearls
The 10-room Conch House Heritage Inn is an historic, competitively priced retreat in Old Town Key West in walking distance to Duval Street. This charming, mid-range property draws repeat guests with its warm hospitality, free homemade breakfast, daily happy hour, and tropically landscaped outdoor pool area. Guest rooms are individually decorated with antiques, and have mini-fridges and flat-screen TVs; the suite offers a full kitchen. The unheated pool, though, can be a bit chilly for comfort. Kids under age 12 aren't allowed, adding to the romantic environment.
La Mer Hotel and Dewey House Rating: 4.0 Pearls
The 19-room La Mer Hotel and Dewey House is an upscale, adults-only property built at the turn of the century on South Beach. With its breezy yet elegant style, beachfront dining terrace, and access to a sister hotels' pools, spa, and three bars, this property offers the features of a resort with a bed-and-breakfast atmosphere. Guest rooms are beautifully decorated in a classic style, and have flat-screen TVs, mini-fridges, and coffeemakers; some open to balconies. The property serves free breakfast, along with occasional treats like chocolate-covered strawberries, but there's a pesky resort fee and minimum stays are occasionally required.
The Paradise Inn Rating: 3.5 Pearls
The 18-room Paradise Inn is an adult-only boutique hotel with historic flair located in Key West’s Old Town close to Duval Street. The upper-middle-range inn is quaint and relaxed. Management is committed to preserving the peaceful elegance of the hotel and its restored cigar-maker cottages, and doesn’t allow bachelor or bachelorette parties or other raucous behavior. Rather, there is a civilized afternoon wine and cheese hour by the palm-shaded pool. Rooms, many of them suites with private balconies, are sunny, spotless and spacious.
Pier House Resort and Caribbean Spa Rating: 4.0 Pearls
A full-service, four-pearl hotel in a town filled with B&Bs, this property differentiates itself from the competition by providing more rooms and more amenities -- including an on-site spa, pool, restaurant/bar, and beach access -- in a convenient downtown location. Rooms are simple and comfy with premium bedding, rain-style showers, flat-screen TVs, mini-fridges, and free Wi-Fi; some have balconies and exquisite views. A well-stocked fitness center and ample event spaces are on hand as well. The oldest bar in Key West is also here and the proximity to Sunset Pier means guests can watch the sun go down in style.
Knowles House B&B Rating: 3.0 Pearls
The Knowles House B&B is an historic conch house near Duval Street and the waterfront with eight individually decorated guest rooms. This charming, mid-range property serves homemade breakfast on a tropical patio, and offers a tiny outdoor pool, hot tub, and rooftop sun deck. Guest rooms have TVs, mini-fridges, and antique touches; one has a whirlpool tub. Daily happy hour includes free wine and beer, and guests can help themselves to free coffee and baked goods throughout the day and night. Some rooms have dated decor and tube TVs, however.
Old Town Manor Rating: 3.0 Pearls
The 14-room, mid-range Old Town Manor is an adult-only bed-and-breakfast set in an historic Victorian mansion, just a block from Key West's popular Duval Street. The two-house Manor is cozy and warm with tons of character, including a grand front porch with rocking chairs, and lush gardens where guests can sit and relax. The ample free breakfast includes organic fruits and baked goods, and pets are enthusiastically welcomed. Guest rooms are large and individually decorated, with beautiful modern bathrooms and free Wi-Fi. In an area filled with guesthouses, the Old Town's quiet charm and attention to detail raise it above the rest.