When it comes to Key West, you’ll find a bit of something for everyone. From large resorts with sizable beaches to charming inns with personable owners and everything in between, I’ve tested out many properties on the dozen or so times I’ve visited. There’s even a luxe private island resort if you want to play “Swiss Family Robinson wins the lottery” for the weekend.
Of course, you’ll pay a premium for lodging near the popular Old Town area or on the water. But keep in mind that waterfront or oceanfront accommodations don’t necessarily imply that the property has a beach, so do your research accordingly.
Speaking of research, when booking a room, be aware that Key West has several adults-only hotels, some of which cater to the LGBTQ population and are clothing-optional. These websites are clear about their environment, though, so do your due diligence when booking if this isn’t the vibe you’re after. I’ve known people who carelessly booked an inn online to discover quite a different scene when they arrived.
As a longtime visitor, I suggest staying at an independently owned property if you want the authentic Key West experience at a decent price. They’re not often loaded with bells and whistles in terms of amenities, but they make up for it with personalized service, one-of-a-kind rooms, and an intimate atmosphere. The best ones make you feel like you’re staying at the house of a really cool friend.
Here are 10 lodging options in Key West that are sure to suit every taste and budget.
Sunset Key Cottages
Perhaps the most upscale resort in all of Key West, Sunset Key Cottages is located on a private island, accessible by a five-minute ferry ride from the mainland. The 40-unit property comprises pastel-colored cottages in Key West style. Choose from one to four bedrooms and oceanfront or garden views.
In addition to amenities like a toes-in-the-sand fine-dining restaurant, Latitudes; a pool with cabanas and a hot tub; a private beach; and a spa with individual treatment suites, the attention to detail truly elevates the experience at Sunset Key. Upon arriving, choose from a scented, chilled moist towel to freshen up, and head over to the free rum-tasting to get the party started.
Every morning, guests are greeted by a picnic basket on their front porch with locally baked pastries, orange juice, and Fiji water. At night, the OJ and H20 keep on coming, helping to hydrate you in the hot Florida sun. Other surprise goodies include fresh floral arrangements, locally made chocolates and cookies, and Nest toiletries and candles.
This is a special-occasion destination for sure, tailor-made for weddings, anniversaries, and reunions. My husband and I stayed in a three-bedroom cottage with two other couples, and it offered plenty of room for everyone with its full kitchen, seating area, and en suite guest rooms with balconies.
Heron House Hotel
The Heron House Hotel is an adults-only, independently owned property located just a block from Duval Street. Guests must be 21 years or older, but that doesn’t mean this is party central. The historic hotel is a quiet place for relaxation or romance.
This is a classic Key West guest house: I find it to be reasonably priced with guest rooms centered on a pool, and I appreciate that it serves complimentary breakfast alfresco. Its 24 rooms and suites are clean and well-appointed with original artwork, mini fridges, flat-screen TVs, and porches or patios. Don’t miss the daily happy hour, where you can mingle with other guests and pet the resident cat while sipping complimentary drinks.
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If you want to be close to all the action, you can’t do much better than Ocean Key Resort & Spa: It’s on Duval Street, just steps from the festivities of Mallory Square. Its Sunset Pier bar and restaurant, located on an actual small pier, offers live music and amazing waterfront and sunset views. Other dining options include the poolside Liquid and Hot Tin Roof, which I highly recommend.
Each of the high-end resort’s 200 guest rooms and suites is decorated with local art, and features a private balcony with views of either Duval Street or the Gulf of Mexico. Meanwhile, SpaTerre specializes in Thai body rituals and Balinese treatments to help you unwind.
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You’ll feel like you’ve arrived at your vacation home away from home at Casa 325, an affordable yet charming little guest house in the heart of Old Town. Each of the 11 guest rooms has a unique layout, ranging from one-bedroom studios to two-level suites, which makes it a great choice for a group getaway of couples, singles, and families.
Although the property is too small to serve breakfast or host happy hours like other inns, each guest room has a kitchenette, and with an address on Duval Street, some of the island’s best restaurants are just steps away. I also like that the hotel is set back from the street to provide a bit of privacy.
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Casa Marina Key West
Casa Marina Key West is a great option if you want to put some distance between yourself and the noise of Old Town. Located on the quieter southern shore of the island, the historic building is more than a century old, originally dreamed up by railroad magnate Henry Flagler. But it boasts modern amenities like WiFi and Nespresso machines in its public spaces and 311 guest rooms.
It also lays claim to the largest private beach on the island, where you can enjoy toes-in-the-sand dining or a workshop with the resident sand sculptor. There are also two pools — one for kids and one for adults — as well as spa treatments in private cabanas. For easy access to the pool and beach (not to mention the oceanfront bar), book an ocean-view suite with a walk-out patio.
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Margaritaville Beach House Key West
Jimmy Buffett first visited Key West on a lark in 1971 — and he never looked back. That’s where he developed the beach-bum persona and island-rock music that spawned a legendary career and eventually a hospitality empire, including Margaritaville Beach House Key West.
Sure, some may turn their noses up at a chain hotel, but there are many appealing aspects of this property. It’s great for families, not only because it’s located on a quieter part of the island, the southern shore, but it provides endless entertainment. Between the sizable beach, lagoon-style pool, and daily activities (e.g., fireside s’mores, sand-sculpting workshops, and coloring sessions), kids — and kids at heart — won’t ever get bored.
Coastal-chic vibes permeate the 186 guest rooms and suites, which feature beach-themed wall art and murals as well as pillows imprinted with the word “latitude” — a nod to Buffet’s famous song, “Changes in Latitudes, Changes in Attitudes.”
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Ibis Bay Beach Resort
The moment you arrive at Ibis Bay Beach Resort, on the eastern side of Key West, you’ll be offered a complimentary sarong to wrap around your waist and embrace the island lifestyle at this classic Old Florida resort.
Founded in 1956 but updated with modern amenities, the independently owned property features guest rooms in coral-rock cottages; private hammock gardens; brightly painted buildings; and a menagerie of birds, tortoises, and lizards. Daily shark feedings are a highlight for kids.
After enjoying complimentary breakfast and catching the hotel shuttle to downtown — which is about 3 miles away — cool off in the pool (with full bar service) or at the private white-sand beach.
Be sure to save one night for dinner at The Stoned Crab. Thanks to two private fishing boats that deliver their daily catch, the restaurant has some of the freshest seafood on the island. If you visit during stone-crab season (October 15 through May 1 annually), don’t miss out on this prized delicacy, the restaurant’s namesake. The claws are pricey, but it’s the only kind of crab I enjoy, thanks to its sweet, delicate flavor.
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The Perry Hotel & Marina
The Perry Hotel & Marina is a newer boutique hotel in the up-and-coming Stock Island area, just east of Key West proper but still in the city limits. Located alongside the 220-slip Stock Island Marina, the modern hotel — named for the famous US Navy commodore, Matthew Perry — boasts 100 rooms, each with a water view.
Enjoy a glass of Champagne at check-in before exploring the property: You’ll find two waterfront pools, fire pits, two dog parks, and an event lawn for live music and weekly yoga sessions. In addition to a coffee shop and a casual bar and grill, The Perry offers a dockside outpost of the world-famous Sloppy Joe’s bar as well as the signature restaurant, Matt’s Stock Island Kitchen & Bar, serving up what it calls “American coastal comfort food.”
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The Saint Hotel Key West
This 36-room boutique hotel is so chic that you might think you’ve been transported to Miami. But The Saint Hotel Key West is located in the heart of Old Town, comprising historic buildings that underwent a $22 million renovation in 2014. Despite its proximity to the main drag, the property was designed to provide a private, exclusive experience.
After lounging by the pool — serviced by a butler, no less — head over to the Burgundy Bar for a cocktail inspired by the Seven Deadly Sins while enjoying live jazz or a burlesque show. Then hit up the restaurant Tempt for an all-day menu of nouvelle fare. Don’t miss the Halo rooftop bar, open on weekends. Perched above Duval Street, it’s a prime spot for taking in special events like Fantasy Fest on Halloween.
Finally, retire to your stylish guest room or suite, decked out with a chandelier, dark-wood-paneled walls, a modern bathroom, and bed coverlets that alternately encourage you to “Sleep saintly” and “Play naughty.”
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Named for Winslow Homer, the famous painter and summertime Key West resident, Winslow’s Bungalows was created when the Kimpton hotel group combined the Chelsea House and the Key Lime Inn. The historic buildings across the property were previously owned by an Irish steamboat captain, a circus performer, and an Army officer.
That eclectic history is reflected in the 85 guestrooms, decorated in a combination of boho-chic and British colonial styles. The lushly landscaped property feels removed from its Old Town location, where winding pathways lead to three pools, two eateries, and an outdoor pavilion with daily treats.
The list of complimentary amenities goes on and on, including loaner bikes, daily continental breakfast, yoga mats in guest rooms, access to newspapers and books on a tablet, a boozy welcome beverage, and a snorkel kit.
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