Top 15 Cool and Unusual Hotels in Key West 2022

Key West, Florida is everything you thought it would be – endless sunshine, sparkling turquoise waves, swaying palm trees, soft sandy beaches, a picturesque Old Town and characteristic dives once frequented by Ernest Hemingway and other writers and artists. All of this is packaged into an impossibly beautiful compact island that is just four miles square in size.

Take a trolley ride to explore museums, art galleries, live performances, excellent restaurants, great bars, shopping and nightlife. Discover the nearby nature preserves, take dolphin-watching trips and sunset cruises and go scuba diving and snorkeling around the coral reef.

There’s also a wide range of beautiful places to stay, all of them close to the ocean. From cute quirky-chic boutique inns to sleek, trendy and modern, here are our best cool and unusual hotels in Key West (in no particular order)…

1. Havana Cabana at Key West – a cool, hip and very Instagrammable design hotel that features a rock waterfall and a creative funky design

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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 of the sparkling ocean.

2. The Gates Hotel Key West – a trendy upscale hotel with a modern design perfect for partying Millenials and Gen Zs

The Gates Hotel Key West - an upscale hotel2

The Gates Hotel Key West - an upscale hotel The Gates Hotel Key West - an upscale hotel1

Easily one of the coolest hotels in Key West, the modern, minimalist style which 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-coloured 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 point of the property, however visitors also enjoy a diverse range of activities on offer, such as lawn games, 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.

3. Kimpton Winslow’s Bungalows, an IHG Hotel – a stylish boutique inn where pets are welcome

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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 simply 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.

4. Kimpton Lighthouse Hotel, an IHG Hotel – a cool and unusual lighthouse inn set in the heart of Key West

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This one-of-a-kind, bohemian island hotel is situated only a mango-throws distance to 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 manmade 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 for every traveller in mind, and is the most social of Kimpton Key West’s five hotels. The infamous Duval Street is only 5 minutes walk from the hotel, whilst the island’s Southernmost Point is a 7-minute walk away.

5. The Saint Hotel Key West, Autograph Collection – a hip and trendy hotel perfect for a uniquely-luxurious vacation

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

Guests will experience exquisite comfort with huge attention to casual, tranquil opulence, courtesy of the hotel’s 36 guestrooms designed in the signature cobalt blue and white colour 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.

6. Margaritaville Beach House Key West – one of the most Instagrammable hotels in Key West  

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The essence of Key West is fully reflected at Margaritaville, a fun-focussed brand which caters for 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, however, would like to remain close to a beautiful beach, with access to all Key West’s offerings at their fingertips.

7. The Reach Key West, Curio Collection by Hilton – a unique upscale boutique hotel based on the only private natural sand beach in Key West

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Water sports including scuba diving, snorkelling, 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.

8. Parrot Key Hotel & Villas – a chic and modern resort to stay in Key West nestled a lush garden paradise

Parrot Key Hotel & Villas - easily one of the coolest resorts to stay in Key West perfect for Millennials and Gen Zs Parrot Key Hotel & Villas - easily one of the coolest resorts to stay in Key West perfect for Millennials and Gen Zs1 Parrot Key Hotel & Villas - easily one of the coolest resorts to stay in Key West perfect for Millennials and Gen Zs2

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 own 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 favourite island-inspired cocktails.

9. The Capitana Key West – a boutique waterfront hotel close to local attractions

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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 cosy cottages, whilst epic experiences such as parasailing and snorkelling, are on offer right on the hotel’s doorstep.

10. H2O Suites- Adults Only – a cool, sleek and sexy hotel that offers a year-round outdoor rooftop pool with a sun terrace

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

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

This oasis of luxury offers a relaxing ambience 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.

11. The Perry Hotel & Marina Key West – a striking one-of-a-kind resort perfect for a very memorable stay

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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 welcoming.

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

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.

12. Kimpton Fitch Lodge, an IHG Hotel – a modern boutique inn steps away from the Key West Historic Seaport

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Located in a neighbourhood 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 3 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.

13. The Gardens Hotel – a charming and beautiful hotel housed in a historic 19th-century building that is travel sustainable certified

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Built in the 1880s as the ‘Gardens Mansion’, this green-certified hotel is listed on the National Register of Historic Places, and 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.

14. Almond Tree Inn – Adults Only – a colorful, kitsch, and fun party hotel to stay in Key West

Almond Tree Inn - Adults Only - a colorful, kitsch, and fun party hotel to stay in Key West Almond Tree Inn - Adults Only - a colorful, kitsch, and fun party hotel to stay in Key West1 Almond Tree Inn - Adults Only - a colorful, kitsch, and fun party hotel to stay in Key West2

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 and quiet of this Oasis of solitude, and nurture themselves in a tropical paradise.

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

15. Sunset Key Cottages – chic and modern beachside accommodation perfect for longer stays

Sunset Key Cottages

Sunset Key Cottages boasts a beachy vibe, which transcends into all guestrooms. This atmosphere is defined by its weathered-wood style flooring, white-washed furnishings and muted pops of blue, and plush amenities.

Uniquely located ‘Scene’ rooms are close to the live music stage, which provides some lucky guests with the chance to watch a concert from their very own patio, whilst other ‘Lifestyle’ rooms have a fantastic view of the pool.

Whilst a short 500-yard stroll takes you directly to bustling Key West, a seven-minute ferry ride to the island’s dock will greet guests with the ultimate, indulgent relaxation. An exclusive experience is ever-present at this distinctive, eclectic set of cottages.

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