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Bed and Breakfast Hotels in Key West

New Orleans House
New Orleans House is a lively adults-only bed-and-breakfast located in the heart of Key West's iconic Duval Street. Offering charming accommodations with a spirited atmosphere, guests can enjoy comfortable rooms, a tropical courtyard and an on-site bar. Perfect for those seeking proximity to nightlife, dining, and local attractions, New Orleans House delivers a unique blend of relaxation and entertainment in a welcoming setting that celebrates the vibrant spirit of Key West.
New Orleans House is a lively adults-only bed-and-breakfast located in the heart of Key West's iconic Duval Street. Offering charming accommodations with a spirited atmosphere, guests can enjoy comfortable rooms, a tropical courtyard and an on-site bar. Perfect for those seeking proximity to nightlife, dining, and local attractions, New Orleans House delivers a unique blend of relaxation and entertainment in a welcoming setting that celebrates the vibrant spirit of Key West.
The Mansion of the Sea
Surround yourself in upscale elegance at the magnificent Southernmost House. When you take a dip in the zero-entry heated pool that is perched directly on the oceanfront, it feels like the crystal-clear waters ebb and flow into the horizon. Find out why this famous bed and breakfast has been the Key West, Florida boutique hotel of choice for Presidents, royalty, and famous figures like Ernest Hemingway. Relax, unwind, and escape from everyday life on the quieter end of Duval Street.
Surround yourself in upscale elegance at the magnificent Southernmost House. When you take a dip in the zero-entry heated pool that is perched directly on the oceanfront, it feels like the crystal-clear waters ebb and flow into the horizon. Find out why this famous bed and breakfast has been the Key West, Florida boutique hotel of choice for Presidents, royalty, and famous figures like Ernest Hemingway. Relax, unwind, and escape from everyday life on the quieter end of Duval Street.
Westwinds Inn
Hospitality is the hallmark of each stay at Westwinds Inn. Established circa 1900 and located in the Historic Seaport District of Old Town Key West, their Victorian-style bed and breakfast still retains its original, pre-WWII charm while adding modern amenities like free Wi-Fi, air-conditioned rooms, and HDTVs. They deliver the intimacy of a B&B with 26 cozy rooms with soft beds and private bathrooms, as well as a free continental breakfast each morning.
Hospitality is the hallmark of each stay at Westwinds Inn. Established circa 1900 and located in the Historic Seaport District of Old Town Key West, their Victorian-style bed and breakfast still retains its original, pre-WWII charm while adding modern amenities like free Wi-Fi, air-conditioned rooms, and HDTVs. They deliver the intimacy of a B&B with 26 cozy rooms with soft beds and private bathrooms, as well as a free continental breakfast each morning.
The Palms Hotel
This historic hotel is a prime example of old Key West architecture and features a heated pool, free breakfast, free WiFi, and pet-friendly rooms. Just a short walk or bike ride away from the famous Duval Street, The Palms Hotel has a perfect location for your visit to Key West.
This historic hotel is a prime example of old Key West architecture and features a heated pool, free breakfast, free WiFi, and pet-friendly rooms. Just a short walk or bike ride away from the famous Duval Street, The Palms Hotel has a perfect location for your visit to Key West.
The Cabana Inn
When tropical oasis meets Duval Street, you know you have arrived at The Cabana Inn. Located just a block from Duval Street, the inn is hidden amongst the shady trees to create a tranquil paradise. The historic conch estate, with cottages was converted into a comfortable inn, with modern designs throughout the interior and exterior. Though Duval Street is the hub for nightlife on the island, The Cabana Inn is far enough away that you can relax in the peace and quiet of the charming inn.
When tropical oasis meets Duval Street, you know you have arrived at The Cabana Inn. Located just a block from Duval Street, the inn is hidden amongst the shady trees to create a tranquil paradise. The historic conch estate, with cottages was converted into a comfortable inn, with modern designs throughout the interior and exterior. Though Duval Street is the hub for nightlife on the island, The Cabana Inn is far enough away that you can relax in the peace and quiet of the charming inn.
Caribbean House
The Caribbean House is a charming and unique Bed and Breakfast. It's located in historic Bahama Village, a hip location with a great vibe. At the Caribbean House, you'll have your high-speed internet and complimentary continental breakfast with complimentary mimosa. This beautiful B&B is located only two blocks from Duval street and is surrounded by many of Keys West's most popular attractions, restaurants, and shops.
The Caribbean House is a charming and unique Bed and Breakfast. It's located in historic Bahama Village, a hip location with a great vibe. At the Caribbean House, you'll have your high-speed internet and complimentary continental breakfast with complimentary mimosa. This beautiful B&B is located only two blocks from Duval street and is surrounded by many of Keys West's most popular attractions, restaurants, and shops.
The Grand Guesthouse
The Grand Guesthouse rooms are comfortable, sparkling clean, and all have private bathrooms and entrances, Queen or King size beds, A/C & ceiling fans, cable television, USB charging stations, a small refrigerator, and are non-smoking. Their suites feature a queen bedroom which opens into a separate dining and seating area with a microwave, dishes and small fridge. They also have 6 on-site free parking spaces (more nearby) and high speed wireless internet.
The Grand Guesthouse rooms are comfortable, sparkling clean, and all have private bathrooms and entrances, Queen or King size beds, A/C & ceiling fans, cable television, USB charging stations, a small refrigerator, and are non-smoking. Their suites feature a queen bedroom which opens into a separate dining and seating area with a microwave, dishes and small fridge. They also have 6 on-site free parking spaces (more nearby) and high speed wireless internet.
La Pensione Inn
Capturing the spirit of the Victorian era, La Pension Inn and Guesthouse, invites you to be their guest and discover bed and breakfast comfort and hospitality with warmth that is distinctly Key West.
Capturing the spirit of the Victorian era, La Pension Inn and Guesthouse, invites you to be their guest and discover bed and breakfast comfort and hospitality with warmth that is distinctly Key West.
Southernmost Point Guest House
Southernmost Point Guest House is a charming bed-and-breakfast nestled in the heart of Key West, steps away from the iconic Southernmost Point. Housed in a historic Victorian home, this inviting retreat offers beautiful rooms with modern amenities. Guests can enjoy a complimentary breakfast, a lush tropical garden and a relaxing pool area. Perfectly located within walking distance from Duval Street and local attractions, it's an ideal choice for a serene yet adventurous Key West getaway.
Southernmost Point Guest House is a charming bed-and-breakfast nestled in the heart of Key West, steps away from the iconic Southernmost Point. Housed in a historic Victorian home, this inviting retreat offers beautiful rooms with modern amenities. Guests can enjoy a complimentary breakfast, a lush tropical garden and a relaxing pool area. Perfectly located within walking distance from Duval Street and local attractions, it's an ideal choice for a serene yet adventurous Key West getaway.
Conch Republic Cottage Suites
Three separate bedrooms with king-sized beds, two queen sleeper sofas, and two private hot tubs! Located literally steps from Duval Street, you can take advantage of the vivid nightlife, fine dining, two nearby company pools, and plenty of shopping! Conch Republic Cottages are absolutely perfect for larger gatherings of friends and/or family. All together, this group property sleeps a total of ten.
Three separate bedrooms with king-sized beds, two queen sleeper sofas, and two private hot tubs! Located literally steps from Duval Street, you can take advantage of the vivid nightlife, fine dining, two nearby company pools, and plenty of shopping! Conch Republic Cottages are absolutely perfect for larger gatherings of friends and/or family. All together, this group property sleeps a total of ten.
Tropical Inn
Tropical Inn is an 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 location on Duval Street.
Tropical Inn is an 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 location on Duval Street.
Knowles House
Knowles House, a historic Key West bed and breakfast, has the personal touch that gives it a unique, charming and welcoming feel. Knowles House is set in the historic Old Town district and exemplifies classic, Key West, tropical architecture. They offer the traditional, personal service and genuine hospitality you should expect and provide an elegant, yet comfortable and homey atmosphere that is as cool as Key West, itself.
Knowles House, a historic Key West bed and breakfast, has the personal touch that gives it a unique, charming and welcoming feel. Knowles House is set in the historic Old Town district and exemplifies classic, Key West, tropical architecture. They offer the traditional, personal service and genuine hospitality you should expect and provide an elegant, yet comfortable and homey atmosphere that is as cool as Key West, itself.
Angelina Guest House
Set in former gambling spot and bordello dating from the 1920s, this quaint, adults-only guesthouse is 5 minutes' walk from the Hemingway Home and Museum, and 2 blocks from Duval Street. Accommodations range from simple rooms with shared bathrooms to 2-bedroom units with en suite facilities, microwaves and mini-fridges. All rooms have air-conditioning and ceiling fans. Some rooms offer private entrances to the property's courtyard. Amenities include a free continental breakfast with homemade cinnamon rolls, and a heated lagoon-style outdoor pool surrounded by tropical plants.
Set in former gambling spot and bordello dating from the 1920s, this quaint, adults-only guesthouse is 5 minutes' walk from the Hemingway Home and Museum, and 2 blocks from Duval Street. Accommodations range from simple rooms with shared bathrooms to 2-bedroom units with en suite facilities, microwaves and mini-fridges. All rooms have air-conditioning and ceiling fans. Some rooms offer private entrances to the property's courtyard. Amenities include a free continental breakfast with homemade cinnamon rolls, and a heated lagoon-style outdoor pool surrounded by tropical plants.
The Weatherstation Inn
The Weatherstation Inn maintains the integrity of traditional Key West style. Located on the grounds of the old Navy Yard, in what is now the private upscale gated community of Truman Annex. With eight distinctively different guest rooms with tropical landscape surrounding the residence and private heated pool. Just outside Truman Annex gates a wanderer's paradise awaits you, including Duval Street or the charming lanes and alleys of Old Town.
The Weatherstation Inn maintains the integrity of traditional Key West style. Located on the grounds of the old Navy Yard, in what is now the private upscale gated community of Truman Annex. With eight distinctively different guest rooms with tropical landscape surrounding the residence and private heated pool. Just outside Truman Annex gates a wanderer's paradise awaits you, including Duval Street or the charming lanes and alleys of Old Town.
The Conch House
Located in the heart of Old Town Key West, our historic Key West bed and breakfast is just 1.5 blocks from world-famous Duval Street and the Southernmost Point of the continental U.S.A. Offering charming and romantic accommodations, The Conch House is the ideal location for your Key West tropical island inn escape. They are only minutes away from the Historic Seaport, best sightseeing, beaches, water sports, and entertainment Key West has to offer.
Located in the heart of Old Town Key West, our historic Key West bed and breakfast is just 1.5 blocks from world-famous Duval Street and the Southernmost Point of the continental U.S.A. Offering charming and romantic accommodations, The Conch House is the ideal location for your Key West tropical island inn escape. They are only minutes away from the Historic Seaport, best sightseeing, beaches, water sports, and entertainment Key West has to offer.
Key West Hospitality Inns
Key West Hospitality Inns is a family of Key West accommodations. Family-owned and operated since 2006, our properties suit a wide range of guests and families.Our four properties are meticulously maintained and located in the heart of historic Old Town Key West. Ideally located, our accommodations are within walking distance of countless restaurants, shops, art galleries, beaches, Mallory Square and mile-long Duval Street.Within our family of accommodations, we have four unique and distinct properties. Whether you are seeking a quiet, romantic, secluded stay, or vacation rentals for a family retreat, we have you covered. Our properties include a tropical bed and breakfast on Duval Street, a cozy inn near the beach and Southernmost Point, a historic “Conch” house, and quaint vacation cottages and best site online casino österreich, and studio apartments.
Key West Hospitality Inns is a family of Key West accommodations. Family-owned and operated since 2006, our properties suit a wide range of guests and families.Our four properties are meticulously maintained and located in the heart of historic Old Town Key West. Ideally located, our accommodations are within walking distance of countless restaurants, shops, art galleries, beaches, Mallory Square and mile-long Duval Street.Within our family of accommodations, we have four unique and distinct properties. Whether you are seeking a quiet, romantic, secluded stay, or vacation rentals for a family retreat, we have you covered. Our properties include a tropical bed and breakfast on Duval Street, a cozy inn near the beach and Southernmost Point, a historic “Conch” house, and quaint vacation cottages and best site online casino österreich, and studio apartments.
Azul Key West
Fall in love with Azul's 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.
Fall in love with Azul's 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.
The Inn on Fleming
The Inn on Fleming is nestled on a quiet residential street two blocks from the Historic Seaport. Built in 1894, this inn served as a private home until it was transformed into a beautiful, modern bed and breakfast in the 2000s. From this quiet inn you can walk to the restaurants and bars by the Seaport or to Duval Street, featuring dining, shopping, and local events.
The Inn on Fleming is nestled on a quiet residential street two blocks from the Historic Seaport. Built in 1894, this inn served as a private home until it was transformed into a beautiful, modern bed and breakfast in the 2000s. From this quiet inn you can walk to the restaurants and bars by the Seaport or to Duval Street, featuring dining, shopping, and local events.
Coco Plum Inn
Feel the history and old-world charm at the tranquil Coco Plum Inn. The Coco Plum Inn is the perfect location for your Key West adventure. Their tucked away in the heart of the Old Town Historic District in two Victorian homes. Stroll one block to legendary Duval Street, or walk three to the Hemingway Home or Key West lighthouse. You can easily reach all the local attractions, shops, entertainment, and nightlife from the Coco Plum Inn.
Feel the history and old-world charm at the tranquil Coco Plum Inn. The Coco Plum Inn is the perfect location for your Key West adventure. Their tucked away in the heart of the Old Town Historic District in two Victorian homes. Stroll one block to legendary Duval Street, or walk three to the Hemingway Home or Key West lighthouse. You can easily reach all the local attractions, shops, entertainment, and nightlife from the Coco Plum Inn.
Old Town Manor
Constructed in the late 1800s, this Key West bed and breakfast is also a 21st century establishment. Pet-friendly, certified Green Lodging, and an all-natural breakfast, it’s a perfect retreat for great thinkers and lovers of life and high energy. Creating a calm and relaxing atmosphere that is welcome and open to all guests. It’s a great start to an ideal Key West vacation with an impeccable staff, perfect location, and affordable prices.
Constructed in the late 1800s, this Key West bed and breakfast is also a 21st century establishment. Pet-friendly, certified Green Lodging, and an all-natural breakfast, it’s a perfect retreat for great thinkers and lovers of life and high energy. Creating a calm and relaxing atmosphere that is welcome and open to all guests. It’s a great start to an ideal Key West vacation with an impeccable staff, perfect location, and affordable prices.
Seascape Tropical Inn
Nestled on a quiet side street just steps away from the Heat of Duval Street, you’ll find the lovely Seascape Tropical Inn, your home away from home in beautiful Key West, Florida. This historic bed and breakfast with their tropically decorated rooms and upgraded amenities like a heated pool and spa, and complimentary breakfast, features everything you need to start your day off right.
Nestled on a quiet side street just steps away from the Heat of Duval Street, you’ll find the lovely Seascape Tropical Inn, your home away from home in beautiful Key West, Florida. This historic bed and breakfast with their tropically decorated rooms and upgraded amenities like a heated pool and spa, and complimentary breakfast, features everything you need to start your day off right.
Key West Harbor Inn
This laid-back, adults-only inn is in a 19th-century mansion and is surrounded by a lush, tropical garden. Individually decorated rooms and suites feature wooden floors and en suite bathrooms, as well as free Wi-Fi and flat-screen TVs. Complimentary amenities include breakfast and happy hour. There’s also an outdoor pool, a sundeck and bike rentals.
This laid-back, adults-only inn is in a 19th-century mansion and is surrounded by a lush, tropical garden. Individually decorated rooms and suites feature wooden floors and en suite bathrooms, as well as free Wi-Fi and flat-screen TVs. Complimentary amenities include breakfast and happy hour. There’s also an outdoor pool, a sundeck and bike rentals.
The Artist House
Dating from the Victorian era, this famous, art-filled guesthouse is just a 2-minute walk from the famous Duval Street. Individually decorated with vintage-style furnishings, all rooms and suites offer free Wi-Fi, flat-screen TVs, coffeemakers and mini fridges. Many suites add pull-out sofas, private outdoor staircases, patios and decks. Amenities include a communal porch, an outdoor pool and a garden courtyard with tables. A complimentary happy hour is offered daily.
Dating from the Victorian era, this famous, art-filled guesthouse is just a 2-minute walk from the famous Duval Street. Individually decorated with vintage-style furnishings, all rooms and suites offer free Wi-Fi, flat-screen TVs, coffeemakers and mini fridges. Many suites add pull-out sofas, private outdoor staircases, patios and decks. Amenities include a communal porch, an outdoor pool and a garden courtyard with tables. A complimentary happy hour is offered daily.
Douglas House
The Douglas House offers the finest accommodations & the most convenient location within Historic Old Town Key West, just off of World Famous Duval Street. Their in walking distance to both the Ernest Hemingway House & the Southernmost Point Monument, as well as the Sunset Pier at Mallory Square, countless restaurants, bars & retail stores.
The Douglas House offers the finest accommodations & the most convenient location within Historic Old Town Key West, just off of World Famous Duval Street. Their in walking distance to both the Ernest Hemingway House & the Southernmost Point Monument, as well as the Sunset Pier at Mallory Square, countless restaurants, bars & retail stores.
Simonton Court Hotel

Hotels Near Mallory Square

Simonton Court Hotel is a tropical boutique bed and breakfast located in the heart of Old Town Key West. Whether you’re relaxing by one of their four pools, enjoying the lush secluded beauty of their gardens and restored Victorian and Conch architecture, or exploring the world famous historic attractions of Key West just steps from their property, how you enjoy Key West is entirely up to you. You’ll be conveniently located just off the beaten path.
Simonton Court Hotel is a tropical boutique bed and breakfast located in the heart of Old Town Key West. Whether you’re relaxing by one of their four pools, enjoying the lush secluded beauty of their gardens and restored Victorian and Conch architecture, or exploring the world famous historic attractions of Key West just steps from their property, how you enjoy Key West is entirely up to you. You’ll be conveniently located just off the beaten path.