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, 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).
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, providing this property with a distinctly romantic feel. Free Wi-Fi and parking add value, and the Old Town location two blocks from Duval Street is convenient. Though it doesn't have quite as many amenities as the Sunset Key Cottages, some would argue that it has more of an authentic boutique vibe -- and many will prefer its Old Key West location to the Coral Lagoon's location on Marathon.
Casa Morada Rating: 4.0 Pearls
Originally opened in the 1950s, Casa Morada is an upscale and intimate boutique hotel that’s been completely renovated with elegant suite-style rooms, hammocks hanging between the trees, a serene pool deck and bar, and a Zen garden with rock grotto. The vibe is completely laidback and relaxed -- there are no children under 16 on the property, and the spa-like atmosphere is replete with landscaping designs by architect Raymond Jungles. The crown jewel of the hotel is its own private island, which is accessed by a footbridge and features a freshwater pool and secluded cabana with panoramic views of the Florida Bay.
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.
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.
Southernmost House Rating: 3.0 Pearls
The Southernmost House is an adult-only property in an historic Victorian home directly on the ocean and just off popular Duval Street. This 18-room, mid-range inn feels sophisticated but laid-back, and has hosted the likes of Hemingway and Capote. Its genteel sitting porches, antique furnishings, and original Tiffany-glass entrance canopy connect visitors with old Key West, while the spacious, individually designed guest rooms offer modern comforts, such as flat-screen TVs and mini-fridges. Free breakfast is served daily, and there's a lovely zero-edge pool overlooking the ocean. Noise from Duval Street can infiltrate some rooms, and service is not always as personalized as some might expect from a bed-and-breakfast.
Angelina Guest House Rating: 2.0 Pearls
The Angelina Guest House is a former 1920s bordello and gambling den turned into a charming Key West bed-and-breakfast teeming with Southern hospitality. The 13-room budget property welcomes adults only, and maintains a quiet, peaceful atmosphere; the owners request that guests leave their partying on nearby Duval Street. The Angelina offers a lovely lagoon-style pool, bike rentals, and homemade cinnamon rolls included in the free breakfast. Accommodations are clean and well cared for, ranging from simple rooms with shared bathrooms to efficiencies with refrigerators and microwaves; guest rooms don’t have phones, and only one has a TV.
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.
Ambrosia Key West Rating: 3.0 Pearls
This charming mid-range bed-and-breakfast is close enough to Key West action to be considered convenient, but secluded enough to still be a relaxing retreat. With the Ambrosia within fast walking distance of Duval Street, Mallory Square, and the historic seaport, guests often venture out after enjoying the free daily breakfast served in a gazebo, but they can also be seen relaxing in the hotel's two pools, hot tub, or courtyard. There are 20 rooms here, each with its own distinctive theme, size, and pricing. Situated in a former tropical nursery, the grounds are lush and a popular site for destination weddings.
Artist House Rating: 3.0 Pearls
Some guests might steer clear of the home of the haunted stuffed doll that inspired the movie "Chuckie," but Artist House, one of the most photographed houses in Key West, is immaculate, bright, colorful, and welcoming, with nothing spooky about it. This restored Victorian mansion serves European pastries at breakfast and hosts a free daily happy hour. It's located within a few minutes' walk of Duval Street and the heartbeat of Key West.
The Duval Inn Rating: 3.0 Pearls
The Duval Inn is about a block away from old Key West’s shops, restaurants, and bars but is an oasis of sorts with a jungle-like courtyard and small pool. Each room is rich in character and individually decorated. Families are welcome here and can stay in adjoining rooms. Some of the rooms have full kitchens. Priced similarly to other historic bed and breakfasts near Duval Street, the mid-range Duval Inn offers a free daily happy hour and breakfast. Be aware that parking is limited.
Cypress House Key West Rating: 3.0 Pearls
One of the six properties included in Historic Key West Inns, the tastefully renovated and mid-range Cypress House, on a quiet corner in old town, has 22 spacious rooms, and a comfortable outdoor pool area. It's a block from Duval Street, the seaport, and Key West’s many shops, restaurants, and bars. Free margaritas are served at a daily happy hour and breakfast is included in the rate. The historic hotel does not permit children.