1129 Fleming Street
Key West, 33040
Ph:305- 294-6284
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Key West is an exciting destination for gay men.
Whether you are looking for relaxation, action, sightseeing or adventure we can help you find the experience you want.
We think that you'll find that Key West lives up to its reputation as a party town. Dine, drink, dance, meet, play. We know the scene and can help you decide where and when you want to go.
If you can motivate yourself to leave the pool in the daytime, we can recommend tours of the historic district. Key West boasts the largest collection of intact Victorian buildings in the United States...all within easy walking distance of Island House. A popular Trolley tour of 'gay Key West' is available.
Biplanes, bikes, mopeds, jet skis, parasails. There are numerous options for getting around, and above, Key West. We can arrange them all.
Or you may want to get out on the water. There are gay nude sailing trips to the reef. Gay snorkeling outings. Trips to secluded beaches. We can help you find exactly what you
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Pier House Resort & Caribbean Spa
1 Duval St.
Key West, 33040
Ph:305- 296-4600
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There is not now, may never have been, and probably never will be a place in the world quite like Key West, Florida If you're seeking an authentic taste of "Key West" you will find it at Pier House Resort and Caribbean Spa.
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1012 Duval Street
Key West, 33041
Ph:305-292-3379
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809 Truman Avenue
Key West, 33040
Ph:305-292-9923
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Key West Bed and Breakfast, La Pensione Guesthouse and Inn
La Pensione, a Key West Bed and Breakfast is located in the heart of Old Town Key West and is a favorite Guesthouse for many of our repeat clients. Key West, the southernmost point in the continental United States, is an oasis like no other. Set at the end of the Florida's archipelago, Key West's tropical landscape is dotted with stately frame residences, trimmed with scrolls of gingerbread. The island is a visual feast with the mélange of Bahamian, New England and Latin influences that characterize it's famed century-old architecture.
La Pensione, a grand Classic Revival mansion, dates from Key West's Victorian Age. Built in 1891 as the private residence of Walter S. Lightbourn, the Vice-President of the Cortez Cigar Company, the elegant 2 1/2 story home on Rocky Road, (later Division Street and still later Truman Avenue), stands today as a tribute to the island's vast cigar making empire.
Sun lo
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512 Truman Avenue
Key West, 33040
Ph:305-296-5415
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1004 Duval Street
Key West, 33040
Ph:305- 296-9915
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3444 N. Roosevelt Blvd.
Key West, 33040
Ph:305- 296-7593
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Zero Duval St.
Key West, 33040
Ph:305-) 296-7701
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815 Duval Street
Key West, 33040
Ph:305-292-9491
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Centrally located at the midpoint of Duval Street, in the heart of old Key West, Duval House* is just steps from the best restaurants, shopping and nightlife.
With 7 caribbean-style buildings overlooking beautiful, lush tropical gardens, an inviting picturesque courtyard, and a sunny, newly constructed pool, our Old Key West-style Bed & Breakfast is the perfect setting for romance, WEDDINGS, receptions, honeymoons, and special events.
Duval House is only a short walk from Hemingway House and other historical sites, including Jimmy Buffett's Margaritaville and other famous haunts.
Enjoy snorkeling, kayak and ecological tours as well as deep-sea fishing, sailing, and boat or plane trips to the Dry Tortugas and more; all easily arranged by experienced concierge staff -or- simply explore this heavenly two-by-four mile island on your own.
Whatever you elect to do, Duval House awaits, ready to make your stay in Paradise a true reality!
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Key West Marriott Beachside Resort
3841 No. Roosevelt Blvd.
Key West, 33040
Ph:305-296-8100
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The Key West Marriott Beachside Hotel is the premier vacation destination in Key West. Come explore paradise with resort style amenities, stunning accommodations and breathtaking views of the Gulf.
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3820 N. Roosevelt Blvd.
Key West, 33040
Ph:305-294-5511
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Doubletree Grand Key Resort
3990 S. Roosevelt Blvd
Key West, 33040
Ph:305-293-1818
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Welcome to DoubleTree by Hilton Grand Key Resort – Key West, where a friendly staff member is waiting to welcome you with a freshly baked chocolate-chip cookie. Everything you need is available in the hotel, from a 24-hour business center to three meals a day served in the full-service Palm Haven Restaurant.
Start your day with a delicious Wake Up DoubleTree Breakfast and enjoy complimentary high-speed internet access in your guest room. Upgrade to a superior room and enjoy a superb balcony view that overlooks lush tropical landscaping. The pool features a waterfall, whirlpool, and large sunbathing decks ideal for lounging while sipping a refreshing cocktail from the Tiki Bar. Hold your business meeting or social event for up to 300 guests in one of our seven venues.
Stay at our Key West resort, just 1 mile from Key West International Airport, and take advantage of the complimentary hotel shuttle service to the beaches, the marinas, and downtown Key West
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Simonton Court Historic Inn & Cottages
320 Simonton St.
Key West, 33040
Ph:305- 294-6386
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Our lushly landscaped two-acre, private compound consists of the two-story Inn, Manor House, Townhouse or Guest House Suites, The Mansion, six cottages and four pools nestled in between. In the heart of Old Town, our adults only resort is located just one block from Duval Street. Bed and Breakfast Key West Hotel Resort Cottage and Inn Accommodation at Simonton Court, Historic Boutique Hotel Resort in Old Town Key West.
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Marriott Courtyard Waterfront
3031 North Roosevelt Blvd.
Key West, 33040
Ph:305- 296-6595
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Get FREE high-speed Internet access at the Courtyard Key West Waterfront. This Key West hotel is located on the Gulf of Mexico in the "New Town" section of Key West. The Courtyard Key West is located within a 10 minute drive of any attraction on the island and features spacious guest rooms and suites. It features a large outdoor junior olympic size heated swimming pool and nearby jacuzzi, a Tiki Bar located adjacent to the pool, a private sunbathing beach, a 300 foot observation boardwalk, a free computer workstation in the lobby, complimentary in-room refrigerators and laptop size safes, and a concierge agent to help you plan your Key West vacation. Complimentary shuttle service is available to and from the downtown Key West area from 8am to 11pm.
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525 United Street
Key West, 33040
Ph:305- 292-1450
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About Pearl's Key West
It's not cookie-cutter. It's not a chain. It's comfortable, historic, relaxed, a little funky – it's the essence of Key West.
Ideally located a half block from the quiet end of Duval Street, and just two blocks from the Atlantic Ocean, you'll find an historic guesthouse with many of the trappings of a resort. Our collection of buildings includes a former cigar factory, cigar-makers’ cottages and a wood-frame motel, and makes Pearl’s among the largest properties in Old Town.
Pearl's Key West combines the best of old Key West with the amenities travelers expect today, all in the tropical surroundings of the American Caribbean.
Pearl's Key West is an all-welcoming, clothing-optional (tops only), adult-only, gay-friendly, straight-friendly (and, in some rooms, pet-friendly) resort. Pearl's embodies the true One Human Family spirit that makes Key West Key West.
With two heated swimming pools, two hot tubs, a gym, on-site massage, a poolside b
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1001 Von Phister
Key West, 33040
Ph:305- 292-4713
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Choose your suite
Check availability
Things to do
Welcome to Suite Dream Inn
Suite Dreams Inn is a boutique hotel and guest house nestled in the heart of the Casa Marina Area of Old Town Key West, Florida, just blocks from the beach and a 7 minute walk to the world famous Duval Street.
Our distinctive Key West Inn offers 1, 2, 3 and 4 bedroom suites. Suites include private entrance, living rooms, well equipped kitchens or kitchenettes, comfortable king and/or queen beds with designer bed linens and flat screen TVs.
Take a dip in our sparkling, heated, lagoon style dipping pool to relax and unwind. The secluded tropical garden at our boutique hotel is perfect for reading a newspaper with your morning coffee or enjoying a good book with an afternoon cocktail.
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57 Front Street
Key West, 33040
Ph:305- 294-7277
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Imbued with a tropical mood
and the colors of the islands,
The Weatherstation Inn maintains the integrity of traditional Key West style. Bahama shutters, gleaming hardwood floors and furnishings bring to mind the plantation homes of the British and Dutch West Indies. Eight distinctively different guest rooms, several balconies and a spacious sundeck all look out on the tropical landscaping which surrounds the handsome residence and private heated pool. Located on the grounds of the old Navy Yard, in what is now the private upscale gated community of Truman Annex, The Weatherstation Inn offers security and location unavailable elsewhere in Key West.
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601 Front St.
Key West, 33040
Ph:305- 809-1234
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611 Truman Ave.
Key West, 33040
Ph:305-296-6700
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1400 Duval Street
Key West, 33040
Ph:305- 296-3141
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A sophisticated setting at ocean's edge, The Southernmost House stands out as Key West's most striking oceanfront bed and breakfast, with 18 spacious, exquisitely appointed, air conditioned guestrooms and suites. Refresh in the cool water of a glistening zero-entry pool as you gaze out at the infinite sea. Enjoy peaceful moments soaking in the sun and a delightful complimentary breakfast. Stroll down Duval Street, towards all the spirit and character that embodies Key West's laissez-faire persona. The Southernmost House is located just footsteps away from Old Town Key West attractions, restaurants & bars, shops and art galleries
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3850 No. Roosevelt Blvd.
Key West, 33040
Ph:305-294-6681
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625 South Street
Key West, 33040
Ph:305-296-2829
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Ocean Breeze Inn provides an excellent location for your accommodations in Old Town Key West, with Duval Street and tropical South Beach just steps away. Our affordable accommodations bring guests to the Ocean Breeze Inn, the unique charm of this tropical retreat and hometown hospitality bring them back again and again.
Guests enjoy a free continental breakfast every morning and free off street parking and then can explore the wonders of Key West on foot, bicycle or moped. From our picturesque setting 2 blocks away from the Atlantic side of this island paradise, you have excellent access to four separate public beaches and all of the historic sites in Old Town Key West. And, of course, right around the corner are all the sights, sounds and tastes of Duval Street.
As a small inn, consisting of only 15 rooms in two separate buildings, you can easily find privacy and seclusion here from the busy Duval Street activities. Tropical landscaping encloses our pool and patio area where y
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625 Truman Avenue
Key West, 33040
Ph:305- 293-0020
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The Conch House, AAA-rated three diamonds, was meticulously restored to its original elegance with every modern amenity but retains the Victorian grace that truly embodies the distinct character of Key West’s architecture.
Constructed by Bahamian ship builders in 1889 and listed on the National Register of Historic Places, this Key West family home has been owned and operated through five generations. Spacious accommodations with traditional antique furnishings in the main house, tropical island décor in the cottages, a large pool and gardens and sprawling grounds await you in one of Key West's premier Bed and Breakfast Inns. Enjoy all that’s best in Key West, The Conch House.
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800 Washington Street
Key West, 33040
Ph:305- 296-6531
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El Patio is a clean and modest 29 room motel designed in the 1950's Art Deco style, located in a pleasant residential neighborhood in Old Town Key West. Our rooms feature original Cuban tile floors and jalousie windows, both of which have been appreciated and enjoyed by Key West residents for many generations! We have a saltwater swimming pool on the ground floor, as well as a rooftop deck for sunbathing and stargazing! We also have free parking for guests. We are a simple, yet charming place. We do not offer lots of extra "frills" which allows us, in turn, to keep our rates affordable for you, by Key West standards. Remember, this isn't the mainland!
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622 Fleming Street
Key West, 33040
Ph:305-296-9838
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Come to a Key West bed and breakfast that is nestled in the heart of the Southernmost City’s Old Town Historic District. Ambrosia Key West is just minutes from the Duval Street Entertainment District, Mallory Square and the Historic Seaport. Our Key West bed and breakfast is within walking distance to most of the island's attractions, museums, beaches and water sport activities. Enjoy the convenience of a Key West inn that is near to dozens of world-class restaurants, galleries and shops while having the tranquility of a tropical resort.
Ambrosia Key West is where luxury and affordability meet. We offer spacious, tropical-themed rooms, two-room suites, two-story town homes, and a two-bedroom, two-bath cottage. Each of our Key West bed and breakfast units have private baths and entrances (most with French doors) that open onto intimate outdoor spaces, including private verandas, pools, patios and luscious gardens accented with fountains and sculptures.
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603 Southard Street
Key West, 33040
Ph:305- 293-1177
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Built in 1858, Mango Tree Inn is a Key West Bahamian style mansion. This architectural gem, featuring Dade County pine (now extinct) floors and walls, crown moldings, and unique octagonal wing, sits under a wild orchid tree on Southard Street, just one block from Duval in Key West Old Town. Upper and lower porches under a tin roof overlook a large heated pool and garden deck. We are not like a typical Key West bed and breakfast accommodation inn. While we do not serve breakfast, as we are within 2 blocks of numerous cafes which specialize in serving real Key West style breakfasts to our guests.
And don't just take our word that our bed and breakfast-type inn is special, click here to see what the Key West Citizen Newspaper has to say about our Key West Inn.
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1319 Duval Street
Key West, 33040
Ph:305- 296-6577
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Southernmost Hotel Collection is a simple, yet sophisticated choice for your quest of Key West hotels, a Key West beach resort, Four Diamond small luxury inn and quaint oceanfront Key West Bed and Breakfast located in historic Old Town. Our oceanfront Key West beach resort offers luxury ocean view rooms with a resort like experience. Southernmost Beach Cafe’ Restaurant, located on South Beach, is surrounded by the Southernmost Hotel Collection properties and offers oceanfront dining and a venue for the perfect Key West Beach Wedding and Corporate Event. From breathtaking Key West beach fronts to quiet and charming environs, we have your Key West vacation covered.
If you’re considering a Key West Wedding or Business Conference in Key West, Southernmost Hotel Collection can accommodate you and your guests in style. The Southernmost Hotel Collection’s personal touch is unlike any other guest experience. You’ll even find our Key West accommodations “specials†that will s
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Fairfield Inn & Suites by Marriott
2400 N. Roosevelt Blvd.
Key West, 33040
Ph:305- 296-5700
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Experience the best of island living at our tropical hotel in Key West, Florida where Marriott's signature style and professional service meet the laid-back atmosphere of the Florida Keys. Our guest rooms and spacious suites offer an incredible value for your vacation, with plenty of special features and "little extras" to make your stay in Key West absolutely unforgettable. Located close to everything on the island, our charming hotel makes your vacation easy with on-site scooter rentals and in-room refrigerators and microwaves, free parking and deluxe continental breakfast served daily next to our fantastic 72,000-gallon free-form pool with Tiki Bar
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1500 Reynolds Street
Key West, 33040
Ph:305- 296-3535
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Opened on New Year's Eve of 1920, Casa Marina, A Waldorf Astoria Resort, is a flawless merging of old Key West ambiance and contemporary luxury. Immerse yourself in a restful haven where emerald lawns meet a blue Atlantic - welcoming stunning sunrises each day. Come to the "house by the sea" enveloped in breezy elegance and shaded by graceful palms.
The premier place to escape in Key West
Enjoy a taste of tropical living at the legendary Casa Marina, A Waldorf Astoria Resort. Nestled along the southern edge of the island – spanning more than 1,100 feet of private beach – our modern accommodations provide a luxurious hideaway for travelers. Listed in the National Register for Historic Places, this landmark resort has attracted business tycoons, artists, and dignitaries since the 1920’s. Be a part of this grand tradition
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3101 No. Roosevelt Blvd.
Key West, 33040
Ph:305- 296-1043
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As you can see, we're no chain hotel – we just want to be the right hotel for YOU. We take a lot of pride in our individuality, and we thrive on yours by bringing you the very best of Key West to suit your unique tastes. Whether you're an active adventure-seeker, a Hemingway-buff, or just want to fit in with the locals – you'll get a full-deck of options here. Ibis Bay is more than a resort, we're your destination.
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2001 S. Roosevelt Blvd.
Key West, 33040
Ph:305- 292-9800
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Sheraton Suites Key Westis centrally located across the street from the recently renourished Smathers Beach and a short complimentary shuttle service to bustling Duval Street, the Sheraton Suites Key West is truly an oasis in paradise.
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Travelers Palm Inn & Guest Houses
Key West, 33040
Ph:305- 304-1751
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Travelers Palm, a Key West Guesthouse and Inn, is the perfect getaway accommodation in the tropical island paradise of Key West, FL. Three ALL-NEW conch-style cottages are nestled in lush gardens surrounding our solar-heated pool. This quiet and peaceful setting is only three blocks from the excitement of Duval Street. Walk to restaurants, art galleries, shopping, nightclubs and more.
Travelers Palm is state of the art, eco-friendly certified Green Lodging. Features include solar hot water, which supplies the pool and the rooms. All building materials and paint are environmentally safe, and cistern-collected rainwater irrigates the landscaping, designed with native plants.
Our accommodations can be configured according to your needs and the number in your party. Cottage and one-bedroom configurations include a private Jacuzzi and off-street parking. All units have central air conditioning, and private decks. All bedrooms are equipped with king-size beds. The living rooms in Casa
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508 South Street
Key West, 33040
Ph:305-296-6577
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Southernmost Hotel Collection is a simple, yet sophisticated choice for your quest of Key West hotels, a Key West beach resort, Four Diamond small luxury inn and quaint oceanfront Key West Bed and Breakfast located in historic Old Town. Our oceanfront Key West beach resort offers luxury ocean view rooms with a resort like experience. Southernmost Beach Cafe’ Restaurant, located on South Beach, is surrounded by the Southernmost Hotel Collection properties and offers oceanfront dining and a venue for the perfect Key West Beach Wedding and Corporate Event. From breathtaking Key West beach fronts to quiet and charming environs, we have your Key West vacation covered.
If you’re considering a Key West Wedding or Business Conference in Key West, Southernmost Hotel Collection can accommodate you and your guests in style. The Southernmost Hotel Collection’s personal touch is unlike any other guest experience. You’ll even find our Key West accommodations “specials†that will s
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1015 Fleming Street
Key West, 33040
Ph:305-296-6868
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A tranquil, peaceful setting with all the amenities and none of the attitude. In historic old town Key West, just a short walk from Duval Street. Eden House hotel offers affordable rates, a heated pool, Jacuzzi, elevated sundeck, waterfalls, hammocks, swings, garden cafe, wi-fi internet service and friendly service - all in a lush, tropical setting.
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1320 Simonton Street
Key West, 33040
Ph:305- 294-2585
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The Blue Marlin Motel is located in the South Beach area of Key West, one block off of Duval Street. Walk to all attractions, restaurants, and bars. The Blue Marlin Motel is one short block from the Atlantic Ocean and centrally located to the island’s beaches and various watersports.
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Best Western Key Ambassador
3755 S. Roosevelt Blvd.
Key West, 33040
Ph:305- 296-3500
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Key West's best kept resort secret!
Best Western Key Ambassador Resort Inn - A colorful and uniquely charming Key West resort experience awaits you in America's southernmost city, where the Atlantic Ocean meets the Gulf of Mexico... Key West, Florida. Our resort is on the quiet side of the island - the exhilarating blues of sky and water, lush greens of the tropics and the vivid reds and purples of sunset ... all provide the background for a distinctive place and people.
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506 South Street
Key West, 33040
Ph:305-296-6577
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Welcome to Southernmost Hotel Collection:
Four Hotels in Historic Old Town, Where Duval Meets the Atlantic!
Southernmost Hotel Collection is a simple, yet sophisticated choice for your quest of Key West hotels, a Key West beach resort, Four Diamond small luxury inn and quaint oceanfront Key West Bed and Breakfast located in historic Old Town. Our oceanfront Key West beach resort offers luxury ocean view rooms with a resort like experience. Southernmost Beach Cafe’ Restaurant, located on South Beach, is surrounded by the Southernmost Hotel Collection properties and offers oceanfront dining and a venue for the perfect Key West Beach Wedding and Corporate Event. From breathtaking Key West beach fronts to quiet and charming environs, we have your Key West vacation covered.
If you’re considering a Key West Wedding or Business Conference in Key West, Southernmost Hotel Collection can accommodate you and your guests in style. The Southernmost Hotel Collection’s personal touc
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