Florida Keys Hotels › Historic Hotels
9 Hotels Found
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Cheeca Lodge & Spa

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. But the hotel's beach is manmade -- there's even a rock ledge on the water's edge -- making it muddy at times and less than ideal for swimmers and waders. And the family pool can get crowded; those traveling without children will probably prefer the much calmer adult-only pool.
The Mermaid & The Alligator

The Mermaid & The Alligator Rating: 4.0 Pearls

The Mermaid and The Alligator is a nine-room upscale bed and breakfast housed inside a historic Victorian estate. The owners have taken great care to renovate the home with bold and vibrant decor and updated furnishings. Located on Truman Street, three blocks from popular Duval Street, the home is a quiet and peaceful area that is steps from the heart of the entertainment district. There is a lush interior garden with hammock, lounge chairs, and plunge pool, but there are no on-site restaurants for lunch and dinner and the cancellation policy is strict.
Marquesa Hotel

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.
Key West Bed and Breakfast

Key West Bed and Breakfast Rating: 3.5 Pearls

Located inside a historic, late 19th-century house, the 10 rooms at the Key West Bed and Breakfast exude intimate luxury. Vibrant art and local flare converge in this Victorian-style property, which has a wide, Southern-style front porch and beautiful architecture. This charming property is a great fit for couples looking for a romantic getaway but who also want to be close to all the action on Duval Street and the sunset celebrations on Mallory Square. Rooms on the second floor share bathrooms, while rooms on the first and third floors are more spacious, and some have private sundecks.
Alexander's Guesthouse

Alexander's Guesthouse Rating: 3.5 Pearls

Alexander's Guesthouse is an intimate, 17-room bed and breakfast designed especially for the LGBT community and supporters. It’s a historic property that’s been completely renovated -- including the guest rooms, living room style lobby, pool area, and kitchen. The only meal served on property is the free breakfast, but there are tons of dining choices located within walking distance on lively Duval Street. Rates are comparable to competitors and rooms tend to book fast during the busy seasons, with a strict cancellation policy and minimum stay requirement at times.
The Weatherstation Inn

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 breakfast basket delivery.
Crowne Plaza Hotel Key West - La Concha

Crowne Plaza Hotel Key West - La Concha Rating: 3.5 Pearls

The Crowne Plaza is a National Historic Landmark dating to 1926, but today this mid-range chain is well past its prime, and lacks the charm of other historic hotels, like The Weatherstation Inn. The whole property is showing a bit of wear, and the 160 rooms are compact and frill-free (though white wicker chairs and honeycomb-tile bathroom floors do provide some classic charm). The best feature is, without a doubt, the location on lively Duval Street -- the main artery of Old Town Key West, lined with restaurants, shops, and bars. (It's a good 15-minute walk to the beach, though.) The rooftop deck is another highlight, with beautiful views of the ocean and the tops of palm trees dotting the landscape.
Eden House

Eden House Rating: 3.0 Pearls

Eden House has had the same owner for nearly 40 years, and numerous loyal customers return year after year for the affordable prices and friendly vibe. Rooms can be bare-bones, especially the semi-private ones with shared bathrooms and no TVs or mini-fridges. Even the higher-level rooms are fairly plain, though, with small bathrooms, simple (verging on bland) decor, and very little furniture (aside from the apartment-style rooms). This historic hotel does have a nice pool courtyard surrounded by palm trees, lovely grounds with deck areas, hammocks, and koi ponds throughout, and tons of freebies (Wi-Fi, parking, and happy hour) that make it a good value.
The Banyan Resort

The Banyan Resort Rating: 3.0 Pearls

Key West is a place that's steeped in history, and the Banyan Resort is no exception: its nine buildings are on the National Register of Historic Places. The 38 suites are clean and bright, but quality varies drastically. Most have dated, uninspired decor, with tube TVs, floral print sofas, and tacky lighting. But each suite has patios, balconies, and kitchens; the grounds are lush; and there are two shady (if small) outdoor pools. The hotel's biggest draw is its location just steps some of Key West's premier attractions, such as happening Duval Street and Mallory Square.

Dates


Oyster Pearl Rating

  • Award-Winning

What's Your Style?

  • Historic
  • Beach
  • Luxury
  • Resort
  • Romantic
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Locations

  • Duck Key
  • Islamorada
  • Key Largo
  • Key West
  • Little Torch Key
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Amenities

  • Air Conditioner
  • Babysitting Services
  • Balcony
  • Basic Television
  • Business Center
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Brands

  • Crowne Plaza
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