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Hotels in Key West
From resorts with all the amenities to seaside motels, quaint bed-and-breakfasts, and clothing-optional guesthouses, there’s a wide variety of lodgings in Key West. You can almost always find a place to stay at the last minute, unless you’re in town during the most popular holidays: Fantasy Fest (around Halloween), when Mardi Gras meets South Florida and most hotels have outrageous rates and 5-night minimums; Hemingway Days (in July), when Papa is seemingly and eerily alive and well; and Christmas, New Year’s and big fishing tournaments (many are held Oct–Dec) and boat-racing tourneys. As well, in winter prime properties fill up and many require 2- or 3-night minimum stays. Prices at these times are extremely high. Finding a decent room for less than $300 a night is a real trick.
There are many rentals available through Airbnb and VRBO. As always with these sites you can avoid extra fees by figuring out the name of the property manager and booking with them directly (easier on VRBO than Airbnb). LGBTQ+ travelers should check out the website of the Key West Business Guild (gaykeywestfl.com), which represents and recommends gay-friendly and gay-owned businesses. Be advised that many gay guesthouses have a clothing-optional policy.
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30 Results
- Hotel
Alexander’s Guesthouse
Key West has long ranked among the world’s top destinations for gay and lesbian vacationers. It’s still up there, but changing times, demographics, and trends have taken their toll, and while you’ll still see prominent gay nightspots, celebrations, and drag queens on Duval Street,…$$Around Town
- Hotel
Ambrosia Key West
Ambrosia is a a private compound set on 2 lush acres, hidden just a block from Duval Street. Three lagoon-style pools, suites, town houses, and a cottage are spread around the grounds. Town houses have living rooms, kitchens, and spiral staircases leading to master suites with…$$Around Town - Hotel
Angelina Guest House
The gambling and whoring of the Roaring [‘]20s are long gone at this distinctive two-story, double-gable yellow clapboard from the 1890s, located 2 blocks down from Duval. What’s left these days is a little charmer of a B&B that’s one of Key West’s best bedding-down bargains…$Around Town - Hotel
Caribbean House
A bargain guesthouse in another 19th-century clapboard, just two blocks from Duval Street, Caribbean House has been cheerily run for the past half-dozen years by the well-liked, Paris-born Marie Barrabes and her husband Michel. Its 10 spotless (though admittedly petite) rooms are…$Around Town - Hotel
Casa Marina
This pedigreed grande dame resort was conceived by Henry Flagler, the magnate whose railroad first opened up the island (and much else in Florida) to unprecedented commerce and well-heeled tourism, but finished only after his death. Its fortunes have waxed and waned since the doors…$$$Around Town - Hotel
Curry Mansion Inn
Back in the day, Bahamian immigrant William Curry became Key West’s first millionaire via the shady business of shipwreck salvaging, and used some of the boodle to start this big white pile just a half-block from Duval Street in 1869 (his son finally finished it 30 years later).…$$$Around Town - Hotel
Eden House
Owner and quirky Key West character Mike Eden bought the half-century-old Gibson Hotel in 1975 and turned it into Eden House. Today it’s one of those places that engender such loyalty and repeat business that on my last visit a front-desk staffer, once a frequent guest, had just 4…$$Around Town - Hotel
Island City House Hotel
Another charmer of a variation on the Key West theme of historic architecture and a fetching heated pool set amid palmy verdant gardens. Behind a striking, balustraded, triple-decker facade, Island City House also brings a particular distinction to the table: It’s the island’s oldest…$$$Around Town - Hotel
Key Lime Inn
An adorable old-fashioned complex that's just what you need for a fuss-free, affordable stay, the Key Lime lets you choose your own style. You can stay in one of the rooms gathered around the modest swimming pool for a classic motel-style stay or you can pick a self-contained cottage…$ - Hotel
La Concha Key West, Autograph Collection
Key West’s tallest building (a whopping seven stories) and one of its original hotel classics from way back (1926), this pale yellow-stucco landmark astride upper Duval Street has long depended on the kindness of both a loyal clientele and history made by the likes of Ernest…$$$Around Town - Hotel
La Mer & Dewey House
If we were to build a beach house, this is exactly what it would look like. And although it’s technically part of the sprawling, bustling Southernmost Beach Resort, the adults-only Victorian-style La Mer & Dewey House bed-and-breakfast are quaint and cottagey with separate…$$$Around Town - Hotel
La Pensione
Four blocks from Duval Street along Truman Avenue (which also happens to be the last stretch of 2,369-mile interstate U.S. 1), this quaint, low-key bed-and-breakfast occupies a handsome yellow-and-white Classic Revival manse built in 1891 by a bigwig in Key West’s once powerful…$$Around Town - Hotel
La Te Da
The name of this Duval Street institution isn’t high-falutin’ insouciance. It’s sort of short for La Terraza de Martí (“Martí’s Terrace”), named after the upper front porch, from which Cuba’s most revered independence hero speechified to drum up support from local Cubans—cigar…$$Around Town - Hotel
Marquesa Hotel
Back in 1986, a forward-thinking local transformed a lovely pair of 1880s clapboards into a four-building complex that today houses a pair of Key West’s most cozy, fetching, and pricey small hotels and restaurants that are close to, yet apart from, Duval Street’s bustle. Rooms are…$$$Around Town - Hotel
Ocean Key Resort & Spa
You can’t beat the location of this 100-room resort, at the foot of Mallory Square, the epicenter of the sunset ritual. Ocean Key also features a Gulf-side heated pool and the lively Sunset Pier, where guests can wind down with cocktails and live music. Guest rooms start at a…$$$On Mallory Square - Hotel
Pegasus International Hotel
After the best possible deal right on Duval Street? Here’s your home base, in the thick of it all. With a vaguely nautical, blue-and-white Deco-style facade, this latest incarnation of a hotel that’s occupied the corner since the 1940s was recently given an inside/out refresh by…$$Around Town - Hotel
Pier House Resort & Caribbean Spa
It’s fair to say that no hostelry is more “front and center” hereabouts than this former pineapple factory, which helped put Key West on the map as a vacation destination upon opening in 1968, provided a hangout for the likes of Truman Capote, and helped launch careers like those of…$$$Around Town - Hotel
Seascape Inn Bed & Breakfast
For a low-key, intimate, and adults-only stay just a half-block from Duval Street, the Seascape makes for a sweet little oasis. It was built from native pine in the Bahamas in the 1840s and transported by ship to Key West, where it was rebuilt in 1889. Fast-forward to 2025 and you…$$Around Town - Hotel
Seashell Motel & Key West Hostel
At the island’s only hostel, a bare-bones set-up three blocks from Higgs Beach and four blocks from the Atlantic end of Duval Street, the private rooms in particular are an okay option for those looking to economize, with some attempts to spiff them up in terms of amenities and decor…$Around Town - Hotel
Silver Palms Inn
Emerging from the wreckage of the mom-and-pop El Rancho Motel is this family friendly 50-room hotel on the edge of Duval Street featuring modern, immaculately clean rooms and suites surrounding a courtyard, deck, and saltwater pool. Amenities are aplenty here, including free parking…$$Around Town - Hotel
Simonton Court Historic Inn and Cottages
Behind the unassuming, palm-hidden facade of a onetime cigar factory is a lushly landscaped little world unto itself: converted Bahamian-style houses and cottages dating from the 1880s. Though all have the usual modern amenities, units vary quite a bit, from the rustic-feeling…$$$Around Town - Hotel
Southernmost Beach Resort
Why at the lower end of Duval Street is there a cluster of hostelries labeled “Southernmost”? Well, right down the block on South Street is that famous, garish, buoy-looking thingy marking the southernmost point in the continental U.S. (though actually, this is still true only if…$$$Around Town - Hotel
Southernmost Point Guest House
Why at the lower end of Duval Street is there a cluster of hostelries labeled “Southernmost”? Well, right down the block on South Street is that famous, garish, buoy-looking thingy marking the southernmost point in the continental U.S. (though actually, this is still true only if…$$Around Town - Hotel
Southernmost Point Guest House By the Beach
★★[em]One of the few inns here that welcomes children and pets, this romantic Victorian-era Queen Anne style guesthouse is a real find. Immaculately clean, modern coastal-style rooms are located either in the main guesthouse or in one of the adjoining buildings. The Pointe View Suite…$$Around Town - Hotel
Spanish Gardens Motel
On an island not exactly bursting with low-cost options, this modest family-owned motel, just a block from the Atlantic end of Duval Street, can offer a lifeline with 26 rooms that are small (and that goes for bathrooms and storage space, too), but clean and even with a touch of…$Around Town - Hotel
Sunset Key Guest Cottages - A Westin Resort
When I was a kid, when you went to Mallory Square to watch the sun set, it set behind a scraggly island full of huling fuel tanks. It was part of the charm. When the sun vanished behind the dilapidated rusty metal, the day was done.How things change. The onetime Tank Island was…$$$Mallory Square - Hotel
The Capitana
B&B meets boutique hotel at this chic, 75-room waterfront spot away from the Duval madness. It offers suites, cottages, and guest rooms decorated in, yep, coastal décor, but here it actually works because the water views complement, not contradict, the shiplap. Family rooms have…$$$Around Town - Hotel
The Gardens Hotel and Cottages
At last, the true Garden of Eden has been located…and it’s on Angela Street in Key West. Once Key West’s largest private estate–cum–botanical garden, created in the 1930s from an 1880s manse, and opened to the public in 1968, this has been an inn since the 1990s. Surrounding two…$$$Around Town - Hotel
The Grand Guesthouse
Built in the 1880s as a boarding house for workers at a nearby cigar factory, this guesthouse is tucked away on a quiet residential street a half-dozen blocks away from Duval. It’s also an easy several-block stroll from Higgs Beach—especially helpful because there’s no pool. Apart…$$Around Town - Hotel
Weatherstation Inn
Weather can be a big deal in the Gulf of Mexico, which is why the U.S. Navy built this two-story, neoclassical-style storm-tracking station in 1912. Presidents Truman, Eisenhower, and JFK all visited the station. By the 1990s, it had been transformed into a bed-and-breakfast of just…$$$Around Town
