Boutique, Beachfront or B&B? Key West's Top 10 Hotels Embody Island Charm

Key West’s idyllic setting at the end of a sun-soaked archipelago has been drawing visitors long before Ernest Hemingway likened the island to St. Tropez. Demand for hotel rooms has only increased since then, and limited space means only so many places to lay your head. Bankrolling your stay in the Southernmost City may cost more than you anticipated, but what price can you really put on paradise?

Old Town is the most sought-after location for lodging with its historic B&Bs on shady side streets. It’s also home to Duval Street where you’ll find many of the boutiques, restaurants and late-night bars. One of the perks of staying here: you can park your car and walk to most places. Bookending the bustling thoroughfare, upscale properties like Ocean Key Resort and Spa and Southernmost Beach Resort offer waterfront views, sandy shores and luxury amenities. For the ultimate getaway, take the ferry across the Key West Harbor to Sunset Key where you can relax in a waterfront cottage on a private island. Outside of Old Town, you’ll find more competitive pricing at accommodations like The Gates, a new boutique hotel. While you might be able to show up and find a hotel last-minute, it’s not recommended. Festivals, weddings and holidays often leave every room on the island booked. You’d have to travel back up the Keys, possibly to Miami in search of a place to stay. So make your reservations early; you might even luck into a special discount.


This new boutique hotel at the entrance to Key West has partnered with local businesses, artists and designers to capture the unique character of the island. Their Rum Row bar features handcrafted cocktails made with Key West First Legal Rum Distillery, and at the Rodriguez Cigar lounge, smokers can enjoy the locally hand-rolled stogies. A permanent food truck, The Blind Pig, serves Conch fusion breakfast, tapas and bar snacks. The spacious rooms capture a beach feeling through whitewashed walls, floors and bed frame paired with pops of color from well-placed accessories and photos from local artist Jorge de la Torriente. Designed for the modern traveler, Wi-Fi is available across the property, and outlets are plentiful. In keeping with the clean contemporary aesthetic, all the information about hotel amenities, menus and local attractions has been loaded onto a Samsung tablet for in-room use.

Recommended for Best Hotels because: This chic boutique hotel at the entrance to Key West offers an immersive experience in the island's culture at competitive prices.

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The Pier House has all the ingredients for a perfect Key West vacation: waterfront views, private sandy beach, variety of dining options, award-winning spa and prime location near Mallory Square. Their 119 waterfront guestrooms and 23 expansive suites are decorated in a distinctly Florida fashion, with a mix of wicker and dark wood custom furniture, four poster beds, warm tropical colors, large tiled bathrooms, rain-style showers and local art. Dining options include a casual Caribbean cafe, a beachside bar and an upscale restaurant. Don't miss the Chart Room, their quirky dive bar. Other amenities include free Wi-Fi, beach and pool service with lounges and complimentary water, daily live music and a floating dock. They recently added the Duval Cruiser, guaranteed to save you some shoe leather. This complimentary shuttle takes guests down Duval Street to the resort's two sister properties La Concha and Southernmost House.

Recommended for Best Hotels because: The Pier House has all the ingredients for a perfect Key West vacation: waterfront views, private beach, award-winning spa and prime location near Mallory Square.

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Just one block away from Duval Street and the beach, Santa Maria Suites is a great alternative to a rental home with the added amenities of a luxury hotel. Perfect for those traveling with families or a large group, all of the 35 spacious one- and two-bedroom suites are equipped with state-of-the-art kitchens. (Think granite countertops, Sub-Zero refrigerator and Cuisinart cookware.) Don't feel like cooking? Just head to Ambrosia, their on-site sushi restaurant. The suites also have an in-room washer and dryer for those on longer getaways. Private balconies and terraces overlook the two garden-enclosed swimming pools, where you can cool off with complimentary smoothies, bottled water, popsicles and fresh fruit. Turn-down service comes with its own treats--Dove ice cream bars and fresh muffins. Free Wi-Fi and parking.

Recommended for Best Hotels because: The perfect alternative to renting a house, Santa Marina Suites has all the comforts of a home combined with the amenities of a luxury resort.

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This elegant boutique hotel boasts a large private natural-sand beach and a picturesque pier with a gazebo extending over the Atlantic. A Waldorf Astoria Resort, The Reach combines a casual atmosphere with top-notch customer service and amenities like private balconies, Wi-Fi, Nespresso coffee machines, iPod docking stations, mini-refrigerators and a fitness center. Located at the quiet end of Old Town, the property also features other fun activities like a life-size chess game, bocce ball court and watersport rentals. Relax in a lounge chair and let their staff pamper you with towels, popsicles, frozen eucalyptus towels and cocktails. On-site dining is available all day on the oceanfront veranda at Spencer's By the Sea. Guests receive reciprocal privileges at the sister resort, Casa Marina, just a few blocks away. There you can enjoy another sandy beach, two pools (one adults-only), Sun Sun restaurant and Spa al Mare.

Recommended for Best Hotels because: This boutique hotel offers Waldorf Astoria brand luxury with a casual Keys flare. Reciprocal privileges at the sister resort, Casa Marina, are a plus.

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The premier guesthouse for gay and lesbian couples, this 17-room inn is does everything right from the shaded pool and Jacuzzi to expanded continental breakfast and clothing-optional sundeck. In the heart of Old Town, this lovingly restored Key West Conch house, built in 1902, blends the original pine floors and stately windows with modern room decor. Black-and-white furniture is paired with zebra patterned rugs, over-sized animal portraits and splashes of red from Broadway posters and fresh flowers. Each day the complimentary happy hour at the Pink Monkey Bar is perfect for mingling with other guests. Ask anyone what makes Alexander's so special and they'll say that it is the kind, genuine, staff that truly embraces the "one human family" credo, which make travelers return again and again to this home-away-from-home. Note that Alexander's is adult's only--18 and over. Complimentary Wi-Fi is available throughout the property.

Recommended for Best Hotels because: In the heart of Old Town, this historic Conch house is the premier home-away-from home for gay and lesbian couples looking for a quiet getaway.

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

A cross between an inn and B&B, this gem is hidden in plain sight at Old Town's busiest intersection--Truman Avenue and Duval Street. Verdant gardens, tranquil waterfall and a privacy wall ensure that while all the action is just steps away, the noise is not. Almond Tree's 22 well-appointed rooms and suites have private balconies and patios and come equipped with free Wi-Fi, Keurig coffee makers, mini refrigerators and microwaves. Mornings bring a complimentary continental breakfast followed by a dip in the heated pool or whirlpool spa. Before dinner, mingle with the other guests at their happy hour that comes complete with complimentary wine, beverages and nibbles.

Recommended for Best Hotels because: Conveniently located near the halfway point on Duval Street, this cross between an inn and B&B blends the best of both worlds.

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On the less-crowded end of quirky Duval Street, rests Southernmost Beach Resort, an upscale (yet unpretentious) hotel. It boasts a private pier, sandy beach dotted with hammocks, oceanfront pool, Shores Bar and on-site restaurant. The rooms feature an understated modern decor in blue and neutral tones paired with stately dark wood furniture and nautical touches. Enjoy your morning coffee on a waterfront balcony while watching the sun rise from beneath the Atlantic's waves. A $25 resort fee gives you property-wide Wi-Fi, in-room bottled water daily, access to the fitness center, use of South Beach rental beach chairs and umbrellas and the use of beach towels on property. Since it's part of the Southernmost Hotel Collection, guests are also able to enjoy the Pineapple Bar and two additional pools (one adults-only) at the adjacent Southernmost Hotel. Check their website for specials and discounted rates for booking early.

Recommended for Best Hotels because: This upscale, yet unpretentious, resort offers sunrise views from oceanfront balconies, a private pier, sandy beach and on-site restaurant.

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Just three blocks from Duval Street, this charming adults-only B&B is tucked away in a lovingly restored Victorian home. The owners strive to make guests feel like they are staying at a good friend's home. The decor is an eclectic mix of art collected from Cuba, Costa Rica, Hawaii and Mediterranean countries that blends nicely with the original architectural features such as Dade county pine floors and pocket doors. The comfortable common areas encourage interaction with the other guests like the plush sofas, flat screen TV and games in the living room and evening wine on the outdoor pavilion. Each morning starts with with a full breakfast in the lush gardens, and parking and Wi-Fi are free. From pool towels, sunscreen, beach chairs, beach bags, toiletries, bottled water and sodas they have everything to make your stay in Key West more comfortable.

Recommended for Best Hotels because: At this adults-only historic B&B, the owners strive to make you feel as if you are staying at a good friend's home.

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For the ultimate getaway, board the ferry in Key West for a quick cruise to Sunset Key, a secluded 27-acre island. Dotted with 40 two-, three- and four-bedroom cottages, this recent addition to the Luxury Collection is laced with footpaths leading to private beaches, fitness center, two tennis courts, basketball court and zero-degree entry pool. The well-appointed cottages capture the essence on Conch architecture with porches, pastel wood finishes and Victorian-style tin roofs. Guests are welcomed by the resort's signature cocktail, frozen-sweet treats and personal concierge service. Each morning a breakfast basket, packed with freshly baked muffins, orange juice and a newspaper are delivered to your porch. Pamper yourself at their spa with treatments that include rejuvenating massages, body wraps and facials. At their on-site restaurant, Latitudes, feast on the local seafood artfully prepared by Chef Todd Holender, whose seasonal menu focuses on island fare with a Caribbean flair.

Recommended for Best Hotels because: The ultimate escape, Sunset Key offers a private-island experience with luxurious cottages, signature concierge service, beachfront dining and rejuvenating spa.

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Conveniently nestled between Key West Harbor and Mallory Square, Ocean Key Resort & Spa is the epitome of barefoot elegance. Their spacious rooms and suites offer understated tropical decor and luxurious comfort like whirlpool tubs and their own Spa Terre bath products. Large furnished balconies offer stellar views of the Gulf of Mexico or Mallory Square. Spend your days at LIQUID, their private pool, bar and lounge or head to the colorful Sunset Pier for casual dining and drinks. The upscale Hot Tin Roof restaurant offers Conch-fusion cuisine like lobster cocktail, pork empanadas and caramelized grouper. Don't miss their popular weekend brunch with unlimited mimosas and bloody Marys. At Spa Terre, Global Rituals like the Javanese Royal Treatment offer the utmost pampering. A $15 daily resort fee includes Wi-Fi, Liquid Lounge chilled pool towels, daily newspapers, in-room coffee, fitness center and off-site beach towels.

Recommended for Best Hotels because: Between Key West Harbor and Mallory Square, Ocean Key is the epitome of barefoot elegance replete with casual and upscale restaurants, pool bar and spa.

Read more about Ocean Key Resort - A Noble House Resort →


Meet Claudia Miller

Claudia Miller has been writing about South Florida for over 17 years--seven from Key Largo. A budding photographer, she can usually be found stalking a sunset. Despite being a tad...  More About Claudia