Alexander's Guesthouse


 Alexander’s Guesthouse is a lovingly restored Key West Conch house built in 1902, boasting beautiful, original pine floors and stately windows. Decorated with a tropical  elegance, a homey atmosphere is thoughtfully created.  

We are an LGBTQ guesthouse where we ALSO welcome ALL Friends of The LGBTQ Community.  We promote acceptance and respect for all.   Thank you everyone for your support over the years.


1118 Fleming Street, Key West, Florida 33040 

Almond Tree Inn


Think of us as a relaxed and serene Key West Inn, flowering with all the amenities, service and personal attention guests expect in a fine Bed & Breakfast in

Key West. Just imagine your next island trip. You can take short strolls to anyplace: fine Key West restaurants, local attractions, activities, pubs, even the Ocean or Gulf of Mexico.

Inside the privacy of our Key West resort, you'll harvest the bounty of our efforts as you relax amid the peace and quiet of your oasis of solitude. Nurture yourself in a tropical paradise. When you're recharged and ready to go again, all of Key West is blossoming just outside your door. We think you'll agree we're growing the perfect blend of serenity and activity.


512 Truman Avenue, Key West, Florida 33040 



Let us welcome you to Ambrosia Key West, a tranquil tropical resort that is nestled in the heart of the Southernmost City’s Old Town Historic District. Ambrosia is set in a former tropical nursery and offers a warm and welcoming atmosphere. Once you arrive, you can unwind by relaxing in our courtyard surrounded by palm trees before taking a dip in one of our three refreshing pools.

Because Ambrosia is centrally located it is walking distance to the Duval Street Entertainment District, Mallory Square and the Historic Seaport. At Ambrosia you will be just minutes from most of the island’s museums, beaches, water sports and attractions including dozens of world-class restaurants, galleries and shops.


622 Fleming Street, Key West, Florida 33040 

Angelina Guesthouse


The Angelina is friendly and clean, no phones or television, two blocks from Duval, within walking distance of the significant sights of old Key West.

The heated lagoon style pool, surrounded by lush tropical plants is a great place to relax and get away from it all.  Lay in our poolside hammock while the trickling waterfall lulls you to sleep. Enjoy a good book while sitting by the pool or just sip a drink while relaxing in the pool and watching the palms sway in a gentle breeze.

​Your hosts will greet you with warm southern hospitality that makes you feel like you are visiting long lost family members.  Start your morning with bagels, fruit, coffee, tea, juice and of course, our famous homemade cinnamon rolls.  ​ 


302 Angela Street, Key West, Florida 33040 

Avalon Bed & Breakfast


Located on the quieter end of historic Duval Street, walking distance to all Key West has to offer, our 19 room boutique hotel offers several room types. Stay just one block away from the Southernmost Point in the continental USA and only steps away from the beach. Whether you are looking for a romantic getaway or this is just one stop

 on your Florida tour we are 

sure to have the right accommodations for you.

Locally owned and operated for over 20 years, this circa 1885 property has been lovingly restored to offer modern amenities while maintaining the colonial ambiance that is Key West.



1317 Duval Street, Key West, Florida 33040 

Azul Key West


  Fall in love with our minimalist bed and breakfast in Key West, Florida, offering guests a peaceful oasis just steps from the activity of downtown. Imagine a classic Queen Anne mansion in the heart of Old Town, Key West where tri-level blue decks surround a shimmering swimming pool. Discover Azul Key West: your southernmost sanctuary; the perfect romantic getaway; a bed and breakfast in Key West with a serene atmosphere and a focus on personalized service.

Adults-only and completely smoke-free, our historic house hotel is just three and a half blocks from Duval Street and a five-minute walk from Hemmingway House. Experience a bold new look in Old Town. 


907 Truman Avenue, Key West, Florida 33040 

Coco Plum Inn

Key West, Bed and Breakfast, vacation, Key West Inns, Key West Bed and Breakfast, Guesthouse, Duval

 Come experience history and Old World charm in our 1891 and 1899 Victorian Homes. Nestled in the heart of Key West’s “Old Town” Historic District, that offers one of the finest locations of any guesthouse in Key West. We are conveniently located just 1 block from legendary Duval Street, and just 3 blocks from the historic home of Ernest Hemingway and the Key West Lighthouse. Walk to the Beach, and all of Key West's  infamous attractions, shops, entertainment and night-life. Our upscale Bed and Breakfast is one of only a few family owned and operated in Key West.


 305-295-2955 and 877-644-2955

611 Whitehead Street, Key West, Florida 33040 

The Conch House Heritage Inn


Listed on the National Register of Historic Places, The Conch House truly embodies the distinct character of Key West style. Guests can choose from spacious and elegant rooms in the main house, furnished with individually selected antiques, or our Keys- Caribbean themed rooms in the tropical poolside cottage and cozy cabana. Whichever you choose you will be only minutes away from Duval Street.


625 Truman Avenue, Key West, Florida 33040 

Courtney's Place


 Key West Bed & Breakfasts! 

Let us invite you into "Courtney's Place Key West Historic Cottages & Inns". Courtney's Place is tucked away on a quiet lane in The Heart of Old Key West - just 1-1/2 blocks from world famous "Duval Street" and 

7 blocks from Ocean to Ocean. 

Our Key West bed & breakfast

is only minutes from all Key 

West attractions. Courtney's 

Place Key West has bed & breakfast accommodations to meet just about any ones need - from Cottages to just a Private Room. Courtney's Place Key West offers lots of amenities along with great rates.


720 Whitmarsh Lane, Key West, Florida 33040 

The Curry Mansion


Amsterdam’s Curry Mansion Inn is comprised of 28 unique guest rooms in three different structures. The Mansion, built in 1869, is open for tours daily. Four guest rooms and the owner’s residence are located on the second floor. The Guest Wing wraps around the rear of the house and the 16 room either overlook or open onto the pool and deck area where breakfast and cocktails are served daily. The James House is located directly across Caroline Street. Each of the eight accommodations has either 

a porch or a balcony. Some have sitting rooms with daybeds and trundles which makes it perfect

for families.



511 Caroline Street, Key West, Florida 33040 

Douglas House


The Douglas House is your ticket to Paradise, offering the finest accommodations and the best location. And check out our affordable room rates. Located in the center of Old Town Key West, the Douglas House is literally footsteps away from world class Duval Street. We're also in walking distance to the Southernmost Point Monument, as well as the historic Ernest Hemingway House Museum, the sunset pier at Mallory Square, the Lighthouse Museum and many other museums and attractions. 



419 Amelia Street, Key West, Florida 33040 

Duval Gardens


Duval Gardens boasts charming, intimate accommodations, located in the heart of Old Town on Key West's famous Duval Street. Guest rooms possess tropical ambiance, with queen & king beds, AC, flat screen TV, refrigerators, private bathroom. Porch side continental breakfast buffet included. Walking distance to all Key West has to offer including restaurants, nightlife, attractions and beaches. 



1012 Duval Street, Key West, Florida 33040 

The Grand Guesthouse


Relax & Recharge in Key West Style Located in the heart of Old Town in a quiet residential neighborhood. 5 blocks from the world famous Duval Street, and the Atlantic beaches. A Frommer's Guidebook 'Find,' winner of the Superior Small Lodgings 'White Glove' award for excellence in cleanliness, and featured in National Geographic Traveler. Queen Rooms and Efficiency Suites.


1116 Grinnell Street, Key West, Florida 33040 

The Gardens Hotel


  Welcome to the prettiest hotel in Key West, where our elegant guestrooms, cottages, and suites are the only choice for visitors seeking the highest level of luxury….


526 Angela Street, Key West, Florida 33040 

Historic Hideaways


 Through Historic Hideaways, you can rent and enjoy a Key West Vacation Rental for the same amount of money...or less...than it costs to rent a hotel room! Choose from private and historic Key West Vacation Rental homes with private pools, or a cozy cottage, or condominiums or townhomes with a shared pool. Each of the unique and charming Key West Vacation Rentals on our website has a detailed description, along with great interior and exterior photos, a list of amenities, and a map location.


1109 Duval Street, Key West, Florida 33040 

Historic Key West Vacation Rentals


 Historic Key West Vacation Rentals offers luxury historic vacation rental homes in Key West Florida. One of our well-trained vacation specialists will guide you through the important process of selecting just the right property for your stay. Whether your party is one of friends or family, or a group celebrating a special occasion, we are eager to help you find the ideal property.


425 Eaton Street, Key West, Florida 33040 

The Inn on Fleming


 Visit our peaceful B&B near Duval Street….Find The Inn on Fleming nestled on a quiet residential street two blocks from the Historic Seaport. Built in 1894, and once home to board of education chair Glynn Archer, our inn served as a private home until we transformed it into a beautiful, modern Bed and Breakfast in the 2000's. From our quiet inn you can walk to the restaurants and bars by the Seaport or to Duval Street, featuring dining, shopping, and local events. Rent a bicycle from us and travel around the island with ease.


1016 Fleming Street, Key West, 

Florida 33040 

Island City House


 Located in the heart of Old Town, historic 24 suite property, three unique houses joined by brick pathways winding through lush tropical gardens. Lounge by our large pool or enjoy the view from our windows walk. Children of all ages welcome.
One of the best places to stay for families and groups, our Old Town Key West hotel has maintained a long-standing reputation for providing impeccable hospitality in a gorgeous setting with incredible amenities. Situated in Historic Old Town Key West, sits this unique property that is comprised of three separate buildings, The Arch House, The Cigar House, and the Island City House. The oldest operating Guest House in Key West, Island City House Hotel offers guests an exceptional experience.  


411 William Street, Key West, Florida 33040 

Island House for Men


 Island House was recently named "The best gay resort in the world" by OUT Traveler magazine, by BOYZ magazine, and by We are Key West's largest gay men's guesthouse. Newly renovated. Luxurious rooms with our Heavenly Bed. Private, clothing-optional compound with heated swimming pool. Poolside café and bar. Gym with machines, free weights, and aerobic equipment. Sauna & steam room.


1129 Fleming Street, Key West, 

Florida 33040

Key Lime Inn


Historic architecture with updated, modern rooms and amenities are what you will enjoy at our Key Lime Inn located in the center of the Old Town area of Key West. Key Lime Inn is a stylish, boutique hotel with 37 guest rooms located just two blocks from amazing Key West nightlife on the world famous Duval Street. You can walk to restaurants and nightlife and enjoy the quaint houses in Key West's historic neighborhoods. Rooms are situated in several buildings spread out on an acre of grounds, giving the property a very tranquil, spacious feel. Garden paths and tropical foliage separate buildings and quiet resting spots. A large heated pool is surrounded by palm trees, and has plenty of deck space for comfortable chaise lounges. Continental breakfast is served poolside each morning and guest parking is available.


725 Truman Avenue, Key West, 

Florida 33040

Key West Bed & Breakfast


Feel at home in Old Town. Key West Bed and Breakfast is a trendy, adult-only inn with historic ties to William Street. Our B&B is located in the William Russell House, which was originally built in 1898 by Bahamian shipbuilders, and is listed on the National Register of Historic Places. Stroll through our three-story Victorian and find evidence of our past in the exposed wood and shaded verandas.

Our inn is three blocks from both Duval Street and the Historic Seaport, as well as being within walking distance of many restaurants. Truman Little White House and the Mel Fisher Maritime Museum are half a mile away. Shop at Mallory Square and stick around for a sunset festival. We're also just a few minutes from the southernmost point in the continental U.S. 



415 William Street, Key West, 

Florida 33040

Key West Hospitality Inns: Wicker Guest House


 The Quiet Oasis in the Heart of Old Town Key West. Family owned and operated since 1984. Continental breakfast buffet served poolside. Balconies, sundecks, guest kitchens and lounge rooms. Walking distance to beaches. Ideally located on colorful Duval Street in the heart of the Historic District. Stroll out your front door where shops, restaurants, galleries and live music awaits you. 


913 Duval Street, Key West, Florida 33040

Last Key Realty Vacation Rentals


 We want each of our guests to come away feeling that same magic we felt ourselves the first time we came to Key West. Our collection of 5-star meticulously furnished homes, condos & villas include 24/7 concierge guest services. Daily, Weekly & Monthly. 


La Te De


  Known as LaTeDa (from “La Terraza de Marti” or “the Balcony of Marti”). LaTeDa is an Establishment with its own Key West History. The former residence is the Hotel lobby and popular evening Piano Bar. Adjacent to the Lobby is a world class restaurant, 2nd floor Cabaret Theater, the street side Terrace Bar and luxurious newly renovated guestrooms. Take a step back in time and experience the history of Key West and live the adventure of the most sophisticated accommodations, entertainment and dinning on the island.

Located on Duval Street in Key West, 

La Te Da welcomes adult guests with a restaurant and bar.


1125 Duval Street, Key West,

Florida 33040

L'Habitation Hotel


Privately owned, and operated by an enthusiastic team of "Local Lovers of Paradise", L'Habitation is in the ideal location for stepping out the front door and being right in the middle of all the action Key West has to offer. Less than a block from Duval Street, you'll find yourself a very short distance from fine dining, famous bars, local entertainment,  historical sites, and shopping. You're minutes away from the best sunset views of any island paradise, and access to any water activity you might want to enjoy. It's all here for you...footsteps away from the front door of our eleven room guesthouse. And, when it's time to take a break, and enjoy a short respite from the hustle and bustle of main street Duval, you won't have to walk far to find yourself back at L'Habitation. 


408 Eaton Street, Key West, 

Florida 33040

Marrero's Guest Mansion


 Step into Marrero's Guest Mansion and step back in time to a more relaxed era. Rich in history and steeped in mystique. Enjoy the grandeur of our elegant Victorian mansion, carefully updated and lovingly converted into a charming Marrero's Guest Mansion Porch Key West inn featuring true island hospitality, while maintaining the original architectural detail. 


410 Fleming Street, Key West,

Florida 33040

The Mermaid & the Alligator


In the heart of Old Town, our accommodations range from the intimate tropical feel of the Conch Cottage to the elegant Caribbean Queen Suite with its four poster bed, wraparound veranda and Roman soaking tub. Enjoy a relaxed vacation surrounded by lush tropical vegetation in a true Key West mansion.   

So much more than your everyday B&B, The Mermaid & The Alligator still retains the heart of its original features, such as Dade County Pine floors, the attractive staircase, and original windows with Victorian-style interior trim.

We invite you to be our guest at our lovely and romantic bed and breakfast, where you can truly relax, reconnect, and embrace the laid-back vibe that Key West is known for.


729 Truman Avenue, Key West,

Florida 33040

Old Town Manor


 Location! Location! Location! Ideally located just steps off of Duval Street in the heart of Old Town Key West, Old Town Manor offers a huge continental breakfast, beautiful historic gardens to host weddings, and a quaint atmosphere. Very few can compare to its classical setting. Built in 1886 the Old Town Manor is a true reminder of our rich history. 


511 Eaton Street, Key West,

Florida 33040

Orchid Key Inn


  The Orchid Key is located on Duval Street and Truman Avenue right at the very crossroads of Historic Old Town Key West. Everything the island is famous for is just foot steps outside our gates... We are one block from the Hemingway House, Historic Light House, and just a short walk to water sports, art galleries, theaters, bars, wonderful restaurants, and sandy beaches.

Upon entering the Inn, brick paths lead you through lush tropical landscapes which surround our 24 elegant, amenity-filled guest rooms and suites. Tranquil waterfalls and water features fill the air as you near our peaceful sun deck, heated pool, and spa. 


1004 Duval Street, Key West,

Florida 33040

Paradise Inn


 An elegant, luxury guest house in the heart of Old Town featuring 18 spacious suites and one and two bedroom cottages. Marble bathrooms (with telephones) and separate marble vanities. All feature A/C, TV, radio, telephone, safe, refrigerator, hair dryer, bathrobes, private balconies. A pool, spa, lily pond, on-site parking, complimentary continental breakfast and concierge service are part of list of amenities. 


819 Simonton Street, Key West,

Florida 33040

Rose Lane Villas


Nestled on a quiet lane in the heart of Old Town, Rose Lane Villas is easy to find but difficult to leave. It's as close to the action as you'll get without sacrificing a good night's sleep. Each of the 6 Villas is perfectly laid out for your family gathering, reunion, or destination wedding. 


511 Eaton Street, Key West,

Florida 33040

Silver Palms Inn and Suites


 Silver Palms Inn is a new boutique hotel. Come experience our brand new beautifully appointed guest rooms with a modern island décor and get pampered in Silver Palms style. Enjoy our luxurious double pillow- top mattresses draped in 310 thread count sheets, complimented by hypoallergenic pillows and duvets. From pool views to island views with your own private balconies. 


1075 Duval Street C11, Key West,

Florida 33040

The Southern Most House


 Plan your vacation in paradise at one of the most historic Key West Beach hotels, and surround yourself in upscale elegance at the magnificent Southernmost House. When you take a dip in the zero-entry pool that is perched directly on the oceanfront, it feels like the crystal-clear waters ebb and flow into the horizon. Find out why our famous bed and breakfast has been the Key West, Florida boutique hotel of choice for Presidents, royalty, and famous figures like Ernest Hemingway. 


1400 Duval Street, Key West,

Florida 33040

Southwinds Motel


  For charming, cozy accommodations located near the famous Southernmost Point in beautiful Old Town, Key West, Florida, Southwinds Motel has you covered.

Spend time enjoying the gorgeous natural landscape of Key West, and stay within walking distance of the incredible attractions, beautiful Key West beaches, shopping, watersports, and scooter rentals. You will love our location, just a few short blocks from world-famous Duval Street. Drop your bags off at Southwinds Motel and start enjoying your vacation Key West style! 


1321 Simonton Street, Key West,

Florida 33040

Sunset Key Guest Cottages


 Tucked away on an exclusive 27-acre island just 500 yards off Key West, Sunset Key Cottages embodies the relaxed luxury of island living. Bougainvillea-laced cottages, exquisite waterfront dining, and exclusive resort activities abound as guests enjoy the intimacy of a true tropical island getaway.
Sunset Key matches sophistication and elegance with exceptional intimacy and warmth. Nestled amidst the tropical paradise filled with vibrant bougainvillea and exotic orchids, you’ll find our private one, two, three and four bedroom cottages with charming details and panoramic views. 



245 Front Street, Key  West, 

Florida 33040

Travelers Palm Inn & Suites


 Three ALL-NEW conch-style cottages, each with a private Jacuzzi and off- street parking, are nestled in lush gardens surrounding our solar-heated pool. Each cottage offers 2 large bedrooms and 2 bathrooms with full kitchens and living room/dining areas. Our quiet and peaceful setting is just blocks from the excitement of Duval Street. 


815 Catherine Street, Key West,

Florida 33040

Tropical Inn


 Tropical Inn is an intimate, exclusively adult inn where independent bed and breakfast character meets the inspired design and understated grace of a stylish Key West, Florida boutique hotel. This oasis of tranquility is set in 

a lush, secret garden enclave, with only eleven rooms sharing the inn’s spacious but intimate grounds, assuring optimal privacy. The mellow vibe found throughout plays perfect counterpart to the high-energy scene that beckons just beyond the doors of its walk-to-everything location on 

Duval Street. 


812 Duval Street, Key West,

Florida 33040

Weatherstation Inn


 The newly renovated Weatherstation Inn is located in the exclusive Truman Annex of Old Key West. Eight distinctively different rooms with king and queen size beds with the exception of one room that has two singles, several balconies, lush tropical landscaping, secluded private pool, harbor views and complimentary continental breakfast. 


57 Front Street, Key West,

Florida 33040

Westwinds Inn


 A secluded getaway in the heart of Key West, the Westwinds Inn offers unparalleled rest and relaxation. Charming, clean, and comfortable rooms provide guests with everything they need to enjoy their stay. Lush, tropical foliage surrounds the onsite pools and a complimentary continental breakfast is offered daily. A superb location for those wanting to explore Duval Street and all that Key West has to offer. 


914 Eaton Street, Key West,
Florida 33040