The Best Bed and Breakfasts to Book in Key West, Florida

Enjoy the warm weather of Florida with a dash of bohemian culture by staying in Key West
Enjoy the warm weather of Florida with a dash of bohemian culture by staying in Key West | Courtesy of Southernmost Beach Resort / Expedia
Photo of Tim Forster
15 December 2021

Wedged at the southernmost point of the continental United States, Key West is far more than just a magnet for warm weather and beautiful tropical scenery. The city has a firm bohemian streak that sets it apart from much of the rest of Florida. So, you can hit the ocean but also cultural attractions like the Ernest Hemingway House. There’s good seafood aplenty, as well. Here are a few of the friendliest and most colorful bed and breakfasts Key West has to offer. Book your break with Culture Trip.

Victorian vibes at the Guesthouses at Southernmost Beach Resort

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Southernmost Beach Resort | Courtesy of Southernmost Beach Resort / Expedia
Part of the neighboring Southernmost resort, these two guesthouses date back to the late 1800s. They’re set up in Victorian-style homes with wraparound porches in a classically Key West pastel color. Inside, they’re just as lovely; the airy rooms have wood floors, king or queen beds, and a few vintage touches. You also get access to the pools, cabanas and other amenities at the main resort next door. FYI: the Guesthouses were formerly known as Avalon and Duval Gardens.

The Gardens Hotel, for great gardens

The Gardens Hotel, Key West
Courtesy of the Gardens Hotel / Expedia
This historic hotel has been showered with accolades, thanks to its sprawling tropical garden and suites fitted out with gorgeous antique furniture. Between that furniture, the polished oak floors and the marble bathrooms, the rooms are high-class affairs; they all have private entrances, too. You’ll get full access to the hotel’s acre of gardens with two pools. Leave the premises and you’re just a few steps from Duval Street, where you’ll find a whole range of bars and restaurants.

Historic appeal at Heron House

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Heron House | Courtesy of Heron House / Expedia
Another formidable historic house to stay in is Heron House, a block away from busy Duval Street at the center of Key West’s Historic District. With rattan furniture and watercolor tones, its rooms feel perfectly tropical and are a bit more low-key than some flashier options around, but eminently airy and comfy. Expect a friendly, sociable vibe’ there’s a heated outdoor pool, hot tub and rooftop sun lounge, plus weekend happy hours to glide through. Take note: Heron House is adults-only, with all guests needing to be 21 or older.

Ambrosia Key West, for lazy days and nights

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Ambrosia Key West | Courtesy of Ambrosia Key West / Expedia
This bed and breakfast is made up of a few small cottages, with a central location in the city’s Historic District. With eclectically selected wood furniture and original artwork on the walls of its rooms and suites, Ambrosia feels like a homey hideaway for some much-needed détente after a day in the sun. You’ll want to spend some time in the gardens here: the property was formerly a plant nursery and is splendidly green. They also offer two pools and a spa.

Retro charm at Westwinds Inn

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Westwinds Inn | Courtesy of Westwinds Inn / Expedia
A sweeping Victorian-style wood building is the elegant setting for this inn, just two blocks from the waterfront and a short walk west to Duval Street. Its breezy rooms feel perfectly coastal with pastel tones and cane furniture; some come with French doors that open out onto spacious balconies. Furniture is simple, comfortable and retro. Not one but two pools are all yours for idling beside, in a palm-lined courtyard to boot.

Marrero’s Guest Mansion, for funky good looks

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Marrero’s Guest Mansion | Courtesy of Marrero’s Guest Mansion / Expedia
The former home of a 19th-century cigar-maker, Marrero’s overflows with character. Its 12 stylish rooms bring together time-honored rattan furniture and funky tropical-patterned wallpaper. Each unique room comes with a queen or king bed and, while mostly for couples, there are rooms for three or four guests, too. It’s an adults-only property, so you can mingle with other guests during a daily tiki happy hour on the front porch, or at the large, oasis-like pool that’s surrounded by palm trees out back.

Vintage elegance at Curry Mansion Inn

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Amsterdam's Curry Mansion Inn | Courtesy of Amsterdam's Curry Mansion Inn / Expedia
Even among the many elegant Key West bed and breakfasts, the 150-year-old Curry Mansion stands out for being particularly sophisticated, with a brilliant white-and-blue color scheme and huge wraparound veranda. Its 28 rooms feature antique canopy beds and an all-around vintage class. There’s a pool on-site and, unlike most Key West properties, there’s free parking too. If you’re not busy hitting the bars and restaurants on Duval Street, which is less than a block away, the Inn has a daily cocktail party, often with live music.

Weatherstation Inn, for atmospheric interiors

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Weatherstation Inn | Courtesy of Weatherstation Inn / Expedia
A former weather station now converted into a charming place to rest your head, this intimate inn is located on the grounds of a navy yard. The Weatherstation has just eight rooms, attractively decorated with vintage furniture, with one room getting a four-poster bed, and soothing pastel colours. Combine that with the shutters and hardwood floors and this is a classic piece of Key West architecture; enjoy it sitting by the pool or lush gardens, or from your balcony.

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