Whether you’re looking for a relaxing beach vacation or a jam-packed water sports holiday, Key West has something for every mood.
Many visitors to Key West prefer to stay in Old Town, home to the island’s best restaurants and most popular shops, while others prefer beachfront hotels, which can give you easy access to sunset views and water-based fun. Looking for something more out of the box? Book a room or suite on a private island off the shores of Key West, which is the outermost island of the Florida Keys stretching into the Gulf of Mexico from the tip of Florida. Check out our comprehensive guide to the best places to stay in Key West.
Old Town hotels – Duval Street out your front door
Duval Street is the heart of Key West’s Old Town, the place you go for shopping, partying, and fun. These Key West hotels near Duval Street put you in the middle of the action.
Pier House Resort & Spa
Follow in Jimmy Buffett’s footsteps when you grab a drink at the Chart Room Bar in the Pier House Resort & Spa. Beautiful ocean views relax you as you gaze out from your room in this funky hotel that’s been catering to artistic types since the 1960s. From this resort and spa at the foot of Duval Street, you can enjoy the best of both worlds, with beachfront access as well as an easy stroll up the row of boutiques and restaurants.
Santa Maria Suites Resort
Want to spread out a bit? Then booking a suite at this all-suite hotel just off Duval Street might be the right choice. Fully equipped kitchens make it easy to grab a casual breakfast on your balcony — though you may not be hungry after enjoying the complimentary fresh fruit and smoothies by the pool, wine, and snacks at happy hour, and Dove ice cream bars delivered with your turndown service. Lounging at one of the two courtyard pools at Santa Maria Suites Resort lets you unwind and truly enjoy your vacation.
The Mermaid & the Alligator
This Key West bed-and-breakfast for adults-only is located in a stunning Victorian home that dates back to 1904 and features decor influences from Cuba, Hawaii, and the Mediterranean. The staff at this highly reviewed B&B encourage guests to mingle and are ready to direct you to great restaurants and make any reservations you need.
Tropical gardens welcome you every morning to enjoy your full breakfast, and the friendly owners of The Mermaid & the Alligator make sure you have everything you need to enjoy the best of Key West, from pool towels and beach chairs to sunscreen and sodas. The pool gives you space to relax, as does the complimentary wine poured every evening.
The Gardens Hotel
This smaller boutique hotel is situated in lush gardens that make you feel as if you’ve escaped from the hustle and bustle of the island, even though Duval Street is just a couple of blocks away.
A historic pool sets The Gardens Hotel apart, and an aviary lets you see the island’s bright bird population up close. Grab a drink at the hotel’s wine gallery or pool bar, or relax in the plantation furnishings of your guest room. If you want a little more space, opt for one of the secluded cottages, which share their own swimming pool. One of the cottages even features a private sauna.
La Concha Hotel & Spa
This historic hotel, which is nearing its 100th birthday, sits right on Duval Street in the middle of all the late-night action. Head to the rooftop spa to gasp at unparalleled views from the highest spot on all of Key West. As you enjoy bright Caribbean cuisine at the hotel’s 430 Duval restaurant or enticing cocktails at one of the hotel’s bars, you can revel knowing you’re following in the footsteps of Ernest Hemingway and Tennessee Williams, who also stayed at La Concha Hotel & Spa.
Ocean Key Resort & Spa
Choose a room overlooking Mallory Square, or gaze upon the Gulf of Mexico from your comfortably furnished balcony overlooking the Gulf of Mexico and Key West Harbor. At Ocean Key Resort & Spa, you can relax at Liquid, the private pool lounge, or enjoy Caribbean fusion cuisine (and an amazing Sunday brunch) at the Hot Tin Roof restaurant. Pamper yourself at Spa Terre, or stay in your suite to enjoy a private whirlpool bath.
This charming boutique inn situated in a restored Conch house caters to the gay and lesbian community. The shaded pool and hot tub are a great place to meet other guests or hang out on the clothing-optional sundeck to perfect your tan.
An expanded continental breakfast gets your day started off right, while the Pink Monkey Bar hosts a complimentary happy hour every day to transition you into the evening. With the kind, welcoming staff, you’ll feel as if you’re staying in the home of a good friend when you come to the adults-only Alexander’s Guesthouse.
As the first new hotel to be built in Old Town in 20 years, The Marker pairs modern amenities with a sense of timeless elegance. The ideal situation to give you the best of Key West, this boutique hotel is a quick walk from Duval Street while still providing a feeling of seclusion thanks to its 2-acre property and waterfront views. Poolside breakfasts are a great way to start the day, and the concierge will happily book you eco-adventures or sunset cruises to help you explore all Key West has to offer.
Margaritaville Resort & Marina
Sitting in the heart of Old Town’s waterfront district and only a block from Duval Street, Margaritaville Resort & Marina welcomes you to the best of Key West (and makes it easy to know what drink to order as you enjoy live music on the Sunset Deck).
This resort caters to families with plenty of activities including snorkeling and deep-sea fishing expeditions, while the beautifully landscaped pool invites you to simply relax if you prefer. Newly renovated suites pair plush furniture with state-of-the-art tech to indulge you with comfort.
Staying in the center of Old Town in a transformed Conch house from the 1800s gives you a sense of old Key West. This charming boutique hotel has landed a spot on numerous “World’s Best Hotel” lists, and when you experience its privacy and luxury, you’ll understand why.
Opt for guest rooms or small apartments in The Marquesa‘s four-building compound set in gardens that surround two swimming pools. The in-house restaurant, Cafe Marquesa, ranks as one of the highest-rated restaurants in Key West.
Beachfront hotels – sand and sea at your feet
While some Old Town hotels offer waterfront accommodations, sometimes you just want to focus on the beach. Take a look these hotels in Key West Florida on the beach.
The Gates Hotel
This lifestyle hotel aims for the millennial market with its laid-back vibe and retro styling. Hang poolside at the Rum Row Bar to enjoy fine cocktails that hearken back to the Prohibition era, or grab a meal from The Gates Hotel‘s resident food truck, The Blind Pig. Cabana rentals treat you to poolside privacy and luxury — and best of all, you can bring your pets.
Southernmost Beach Resort
The heady feeling of being at the very edge of the continent is what the Southernmost Beach Resort wants you to experience. The six acres of this resort provides privacy for relaxation. Stroll out on the dock to choose your favorite lounge chair, walk through the lushly landscaped gardens, or sink into an oceanfront hammock.
While the fun of Duval Street is only a few blocks away, the resort also offers entertainment. You don’t have to miss your yoga class when you stay here, and the fully equipped fitness center lets you work off all those craft cocktails. Simplicity with a sophisticated flair pairs with classic Key West architecture and stress-releasing ocean views to create a perfect stay.
The Reach Resort
The Reach offers all the luxury you’d expect from a Waldorf Astoria resort. Dine right by the water on Key West’s only private natural-sand beach, or stroll out to the end of the private dock to watch dolphins dancing in the crystal-blue water.
Luxury amenities in your ocean-view room include Nespresso machines and iPad docking stations. Concierges can arrange for any fun you want, from water skiing and scuba diving to stand-up paddleboarding, deep-sea fishing, and parasailing — or just relax on the beach as friendly staff members bring you popsicles and chilled towels. Reciprocal privileges with the Casa Marina resort expand your activity options.
This sister hotel to The Reach is also a Waldorf Astoria resort, but with a different point of view — literally. Casa Marina, unlike most of the more luxurious Key West hotels, faces the Atlantic Ocean rather than the Gulf of Mexico, placing you away from the crowds.
The beautiful old-world resort, about to celebrate its 100th birthday, is on the National Register of Historic Places and boasts the largest private beach (more than 1000 feet long) on the entire Key.
Indulge yourself at the Spa al Mare with an oceanside massage or a seaweed body wrap, or lounge in the two pools with an ocean view. A beach concierge is on hand to arrange for any and all water sports make this resort one of Key West’s best.
Off-island hotels – luxury away from the crowds
Key West Florida resorts sometimes plant themselves on islands adjacent to the Key so you can enjoy being surrounded by water on all sides.
Sunset Key Cottages
Taking a quick boat ride to Sunset Key puts you on a 27-acre private island populated with adorable luxury cottages with one to four bedrooms.
Each cottage has a full kitchen and a private wraparound veranda to facilitate your relaxation — and if you don’t want to cook, Latitudes restaurant will take care of you with a stunning view to boot. Want to go to Key West? A 24-hour ferry gets you to and from Sunset Key Cottages — or just stay on Sunset Key to enjoy the fitness center, pool, tennis courts, and private beach.
The Perry Hotel
This newer hotel on Stock Island, situated by a 220-slip marina, gives you respite from the hustle and bustle of Duval Street and Old Town — which is only minutes away, thanks to the hotel’s free shuttle.
No matter which room you choose at The Perry Hotel, you’ll enjoy an ocean view, and every room is individually decorated with artwork by local artists. If you plan to spend a lot of time on the beach, ask for a ground-floor room, where you can take advantage of an outdoor shower to wash off the sand. Two dog parks let your furry best friend have as much fun as you’re having, and outdoor fire pits provide a touch of coziness after the sun sets. Two restaurants serve sea-to-table cuisine and planned water activities help you enjoy the best Key West has to offer.
Parrot Key Hotel and Villas
Waterfront villas give you a sense of seclusion at this newly renovated hotel, which boasts four swimming pools to let you change your scenery daily.
Although Parrot Key Hotel and Villas is a couple of miles from the center of Key West, a daytime shuttle makes it easy to get to shopping and dining outlets, or you can rent a bike to enhance your freedom to explore. Guests who prefer to stay close to their home-away-from-home can enjoy a wide range of water activities, including kayaking, stand-up paddleboarding, and snorkeling, with equipment provided by the hotel. Travel + Leisure magazine named Parrot Key one of the Best New Hotels in the World for 2019.
Your luxurious vacation on Key West starts long before you take your first step onto the beach. Book a reliable Blacklane car service to start your vacation off right from the moment you deplane, and travel to your favorite hotel in comfort and style.