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Local Experts' 10 Best Bed and Breakfasts



Looking for a hotel with great service, and a quiet, family atmosphere? Bed and breakfasts in Key West like the Caribbean House Key West are the perfect choice for you. Beyond the friendly hosts, a bed and breakfast will open your eyes to a new world of comfortable and more affordable accommodations. Leave the long lines and mazes of hotel floors to enjoy a private room just a few feet from the entrance at the Artist House Key West one of Key West's most popular B&Bs. These intimate lodgings often offer complimentary happy hour or other events that make it easy for guests to mingle and many also cater to gay and lesbian travelers. Here are our expert's choices for some of Key West's finest bed and breakfasts.

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Special touches in guestrooms like hand-quilted bedspreads, marble ceiling bathrooms, and canopy beds set this B&B apart. There are four types of rooms to choose from, some of which are pet-friendly (visit the website to see in-depth descriptions and photos of the rooms before booking). The second floor has a wraparound balcony, and - In true Key West style - breakfast is served on the porch each morning which consists of a selection of fresh fruits and yogurt, and pastries.

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This 17-room, gay-friendly guesthouse is doing everything right: from tasteful, room décor (think modern black-and-white furniture and over-sized portraits of animals), to the shaded pool and Jacuzzi, or clothing-optional sundeck. Each day complimentary happy hour is perfect for mingling with other guests. The staff truly embraces the "one human family" credo which make travelers return to this home-away-from-home.

Read more about Alexander's Gay and Lesbian Guesthouse - Adults Only →




A few streets away from the drunken debauchery and hustle and bustle of Duval is the Author's House, a compound consisting of two small cottages. The cottages were once the living quarters for cigar makers and remain in traditional Bahamian-Conch style with the main house fitted with beautiful French doors, decks, and terraces. Colorful tropical foliage surrounds the pool and each of the guest rooms are named after literary legends. Rates are some of the lowest in town – during the off season you can snag a room for two for just $100.

Read more about Authors of Key West →


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The Wicker Guest House


Six spacious and beautifully restored guesthouses spanning an entire block define this popular inn, set on the heart of Duval Street. An inviting heated pool with sundecks ideal for soaking in the rays, there's a garden playhouse for kids, and BBQ grills, patios, mini kitchens, and Jacuzzis are available with the vacation cottages. Guests can also choose from standard, deluxe, king, and suite rooms - all of which include microwaves and mini fridges. The B&B offers continental breakfast served poolside and free parking (which is priceless when staying on Duval Street).

Read more about The Wicker Guest House →


Simonton Court Historic Inn and Cottages Key West

Take a stroll through your own "Wonderland" on Simonton Court's garden pathway, and adults-only lodging that is hidden on a quiet side street near Duval. This lush hideaway offers guests several accommodation options: a historic mansion, private cottages, manor house, or townhouse. Free WiFi is available throughout, and complimentary breakfast is served poolside in the morning.

Read more about Simonton Court Historic Inn and Cottages Key West →




A rum bar and bed and breakfast combined, this cheerful Duval Street inn is a steal in Key West. Cozy up at the rum bar and try some of the Bahama Bob's famous "root juice." This rum connoisseur always has a captive audience waiting to try his tasty concoctions. Friendly owners make you feel at ease, and their home cooking is top-notch. Room sizes vary, and several have private patios. This inn is located on the south end of Duval (the quiet side), but Mallory Square, Sloppy Joes, and all the usual hot spots are easily accessible.

Read more about Speakeasy Inn →


Ambrosia Key West


This luxurious, yet affordable pet-friendly B&B offers both themed guestrooms and suites with private entrances to gardens and verandahs. The honeymoon suites are romantically decorated and fitted with four-poster canopy beds and in-room Jacuzzis. Amenities include lush gardens, a pool, WiFi and computer access and full breakfast. Be sure to check out the different combo packages including diving, dining, adventure, and arts.

Read more about Ambrosia Key West →


Southernmost House


As one of the few oceanfront B&B's on the island, the Southernmost House has been intertwines classic Key West style with modern amenities and has been housing the upper crust – from Presidents to Kings for decades. A zero-entry pool, complimentary island breakfast, valet laundry services, and pool bar, and wireless internet are available for guest use. The Southernmost is located on Duval Street, just steps away from the "Southernmost Point" marker.

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Artist House Key West
Photo courtesy of Artist House


As one of the most photographed guesthouses in Key West, the Artist House is undoubtedly appealing from the outside, and those that choose to stay here will find that being inside its walls is just as colorful. The interior of the Victorian-era home has been beautifully restored and features stunning woodwork and elegant furniture in the rooms. Its history goes beyond the regal décor – the home once contained "Robert the Doll," a spooky local legend that now resides at Martello Museum.

Read more about Artist House Key West →


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Duval Street
The Gardens Hotel
Photo courtesy of Amber Nolan


This high-end sanctuary consists of 17 luxurious guest suites set among one of the oldest tropical gardens in Florida. The estate's rooms feature private entrances, marble counter tops, verandahs, and plush spa robes. Amenities include a wine room gallery, a Jacuzzi and heated pool, expansive breakfast, trickling fountains, and an aviary.

Read more about The Gardens Hotel →


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Meet Amber Nolan

Originally from upstate New York, this restless traveler has a knack for befriending interesting characters. You can usually find her just about anywhere that has a hammock. Amber's favorite...  More About Amber

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