Top 14 Cool and Unusual Hotels in Key West 2023

Eclectic style and contemporary elegance coexist in perfect harmony at The Havana Cabana Resort, a little spot of paradise steeped with charm and character.

At this funky boutique hotel, guests can enjoy a lush escape from reality, courtesy of the nostalgic influences from the art and culture of Cuba. Vibey poolside music, classic mojitos, Cuban cars out front, and hand-painted murals provide a vibrant representation of the history, romance, and beauty of one of the most celebrated Caribbean countries.

The rooms boast a variety of boutique amenities to compliment their tropical designs and feature extravagant views of the resort pool or the sparkling Ocean.

Easily one of the coolest hotels in Key West, the modern, minimalist style that defines this upscale hotel evokes a true feeling of paradise. Guests can feel the salt-water breeze upon entrance to the hotel’s rustic lobby, topped off with weathered, driftwood-style flooring and soft, sand-colored furnishing.

Chickens roam the property in typical Key West fashion. The hotel’s large L-shaped pool and coveted rum row bar are the focal points of the property; visitors also enjoy a diverse range of activities on offer, such as lawn games and table tennis, with outdoor concerts also taking place.

The lobby’s serene, beachy vibe extends into all the guest rooms, which also boast weathered-wood-style flooring.

Spanning a lush, landscaped campus in the heart of the Old Town, Winslow’s Bungalows are named after famous painter Winslow Homer, who resided in Key West around the turn of the 19th century.

An idyllic scene for families, friends, and couples alike, the expansive haven features three glimmering private pools, vibrant gardens, and a fantastic outdoor bar. The bohemian-style hotel boasts an eclectic bliss, characteristic of this gorgeous slice of island life, which balances revelry and relaxation.

Guests can enjoy games of corn hole, snap photos of the infamous ‘Instagram Tree,’ or wander down the brick walkways through the vibrant greenery of the hotel. The Kimpton hospitality adds a charm of pure enchantment to this lush hotel.

This one-of-a-kind, bohemian island hotel is situated only a mango-throw distance from the iconic Key West Lighthouse and Hemingway’s home.

Guests are brought together around a lively pool, bustling bar, and brick garden grounds. This hotel covers half a city block and boasts both artificial and natural beauty, hence its soaring popularity as a beguiling backdrop for wedding groups and impromptu gatherings.

Each room at this cheerful getaway is designed with every traveler in mind and is the most social of Kimpton Key West’s five hotels. The infamous Duval Street is only a five 5-minute walk from the hotel, while the island’s Southernmost Point is a 7-minute walk away.

A heavenly experience is on offer at this gem of a hotel located in the heart of ‘Old Town’ Key West, only a minute’s walk from the bustling nightlife of Duval Street.

Guests will experience exquisite comfort with huge attention to casual, tranquil luxury, courtesy of the hotel’s 36 guestrooms designed in the signature cobalt blue and white color scheme, accented with LED blue mood lighting and classic, white sheer drapes.

Under this snazzy façade are contemporary details, such as Niven Morgan toiletries and Frette linens. The ‘play naughty, sleep saintly’ slogan evokes a sexy vibe, hence this hotel’s soaring popularity amongst couples.

The essence of Key West is fully reflected at Margaritaville, a fun-focussed brand that caters to couples, families, and friend groups alike.

Upon entrance to this low-rise resort, you will be greeted by a giant flip-flop sculpture outside and a chandelier made of margarita glasses in the lobby.

The 178 guestrooms come equipped with a full range of high-end amenities to maintain a comfortable, luxurious stay. Adirondack chairs and hammocks dot the grounds and offer a lavish spot of respite by the gorgeous poolside area.

The hotel is ideally situated for those who don’t want to stay downtown but would like to remain close to a beautiful beach, with access to all of Key West’s offerings at their fingertips.

Water sports, including scuba diving, snorkeling, and sailing, are offered at this hotel, which is set on the only private natural sand beach in Key West.

Nautically inspired rooms and suites, all featuring balconies with picturesque views, give this hotel a chic charm, which is reflected by the oceanfront pool and signature restaurant ‘Four Marlins.’

The spa also offers deep tissue massages for guests who are in the mood for pampering. Conveniently located, a 15-minute walk would lead you directly to Duval Street, and the Earnest Hemingway Museum sits within a 10-minute walk.

This amenity-laden resort is a beautiful beach getaway for people of all profiles, especially those who enjoy the sand between their toes and dipping their feet in the stunning Ocean.

Set in 5 acres of award-winning landscaping and palm groves, the Parrot Key Hotel & Villas is set just a short drive from the historic Old Town Key West, to which guests can take the complimentary shuttle.

Four beautiful swimming pools are nestled in their garden paradises, offering a perfect spot of respite to incoming guests. Rooms are surrounded by lush foliage.

They feature 55-inch flat-screen TVs as well as small fridges and private terraces where guests can enjoy breathtaking views of the Ocean and the tropical landscape.

Visitors can get a real taste of the tropics at the Grove Kitchen & Bar, where they can sip their favorite island-inspired cocktails.

This beautiful waterfront boutique hotel boasts breezy, beachy vibes and sweeping bay views, all in the intimacy of a well-curated bed and breakfast.

A gorgeously landscaped pool and tiki bar, well-appointed accommodations, and delectable dining offerings reflect the serenity and natural beauty of the Florida Keys.

Meanwhile, the coastal-chic décor and comfy sofas set a blissful scene for your ocean getaway, making The Capitana a perfect launch pad for your Florida adventures.

The guestrooms come decked out with high-end amenities and are decorated with island-inspired furnishings. This pet-friendly, state-of-the-art hotel also provides large family rooms and cozy cottages, while epic experiences, such as parasailing and snorkeling, are on offer right on the hotel’s doorstep.

This adult-only hotel is situated only 200 meters from Duval Street and features an outdoor sun terrace and pool. H20 suites deliver a highly personalized lodging experience, with spacious suites featuring designer bath amenities and daily deliveries of fresh pastries and coffee.

The stand-out feature of this property, however, is its 11 individual plunge pools, which complement the water features and plush tropical landscaping that permeates the property.

This Oasis of luxury offers a relaxing ambiance with chic décor alongside the chance to sip island-inspired drinks in front of panoramic views. Your Florida trip will become a once-in-a-lifetime experience at this unique, state-of-the-art hotel.

Here, salt air and five-star service create an irresistible waterfront oasis. The lobby’s high, airy ceiling is fused with furnishings of raw concrete, exposed steel, and natural wood.

Its decidedly industrial aesthetic, nestled in an area known for Victorian mansions with ornamental gingerbread latticework, creates a beautiful, casual welcome.

This laid-back atmosphere has been thoughtfully cultivated in keeping with Key West’s maritime roots, and guests can watch the boats enter and exit the harbor.

Owing to its off-the-beaten-path location, it offers deep-water access to offshore pleasures such as diving and fishing. The layout of the pool is also serene, lined with white lounge chairs and copious palm trees.

Located in a neighborhood setting minutes from the Key West Historic Seaport, this authentic conch-house, bohemian lodging readily welcomes on-the-go explorers.

The hotel can hook guests up with fantastic excursions of all kinds, from sunset sailing to land-based outings such as cycling. The hotel boasts 44 guestrooms, including three suites, which are graciously updated with tropical touches yet retain its turn-of-the-19th-century beauty.

Fitch Lodge is the smallest and most intimate of Kimpton Key West’s five eclectic hotels and is refreshingly removed from non-stop Duval Street, offering the perfect respite for couples and explorers of land and sea.

Built in the 1880s as the ‘Gardens Mansion,’ this green-certified hotel is listed on the National Register of Historic Places. It has been embellished with many modern amenities to compliment its historic charm.

These include an outdoor heated pool and a self-serve D’vine Wine Gallery, the first enomatic wine tasting system in the Keys. The expansive grounds of The Gardens Hotel feature over an acre of tropical landscaping alongside 20 luxurious guest suites and is conveniently located mere steps away from the infamous Duval Street.

Guests can enjoy seasonal, live jazz music in the gardens, amongst a host of other live events in the Cabaret, at weekends.

Located on a patch of ground with a history of deep roots at the very crossroads of Old Town Key West, the 22 elegant, amenity-filled rooms at this gorgeous property are encircled by lush, skyward-reaching tropical landscaping.

Just a short stroll would take you to the finest Key West restaurants, local attractions, and even the Ocean or Gulf of Mexico. Guests can harvest the bounty of the efforts from the fantastic staff as they relax amid the peace of this Oasis of solitude and nurture themselves in a tropical paradise.

All rooms are equipped with an HD Plasma TV, gourmet coffee, a mini refrigerator, and a microwave, with complimentary continental breakfasts and happy hours also on offer.