Places to Stay Best Places to Stay in Key West
The Florida Keys have over 16,000 hotel rooms and thousands of Vacation Rental Properties. We are the Locals and we created this list of the best places to stay in Key West by Locale and Lifestyle.
Let us help you navigate all the lodging options to find the best Key West place to stay for you and your group. Our service is free and we love talking about Key West.
Best Key West Places to Stay by Locale
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Old Town
Old Town is filled with amazing and interesting places to stay and is home to an eclectic collection of historic homes and buildings. It is also the center of all the action: Duval Street, the Southernmost Point, Mallory Square and lots of boutique shopping, bars & restaurants. Accommodations include hotels, guesthouses, resorts and luxury vacation rentals.
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New Town
New Town is minutes to Old Town by bike or car. With quiet neighborhoods you will find locals walking their dogs and enjoying a cup of Cafe con Leche at the corner shop. Accommodations include affordable ocean view hotels, luxe oceanfront condos with proximity to the airport, golf course and grocery stores.
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Stock Island
Stock Island is only a short 5-minute drive to Old Town and is known for its mariners and eclectic local scene. Casual local restaurants, artist shops and galleries leave you with an authentic taste of the out-of-the ordinary Key West that locals appreciate. Accommodations include marina resorts and vacation rentals.
Best Key West Places to Stay by Lifestyle
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Lexi Roberts
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Old Town Key West
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Old Town Luxe Hotel
Designed with ultimate relaxation in mind, rooms and suites feature local art, hand-painted furnishings, and a private balcony with a view of the Gulf of Mexico or historic Duval Street. With the best location in town, you won't miss a thing. Accommodations include their boutique island spa, poolside lounging, fine dining, and waterfront cocktails and music. Epic Key West sunset included.
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Old Town Waterfront Resort
The resort is located on the corner of the Gulf of Mexico and Duval Street. Beautiful tropical gardens surround the pool in the center of the property and open directly onto the private beach. Secluded and private yet just steps from the energy and fun of Old Town Key West. Dining, dancing, historical architecture and wonderful galleries are at your doorstep, providing a taste of Key West’s irrepressible spirit.
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Old Town Standard Hotel
Explore the excitement of Duval Street and downtown Key West, then return to your cool spacious room at this great Key West hotel. Located at the southernmost point in the United States, visitors at this Key West hotel are here to enjoy paradise. Offering free parking and only one block from famous Duval Street. While parking is free, most guests don’t need a car since you can walk to the area’s best attractions. The beach is three blocks away and guests feel right at home in a quiet neighborhood that’s close to everything.
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Luxe Guest House
The transformation from 19th century “conch” houses to beautifully restored rooms, suites, and a fine-dining Café has brought this property many awards. With it’s Old Town Key West location it’s perfect for exploring – just one block from Duval Street, four blocks from Mallory Square and the Gulf of Mexico and a mile from the Atlantic Ocean. A car isn’t necessary – it’s all within walking distance.
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Old Town Standard Guesthouse
A lovingly restored Key West Conch house built in 1902 is home to a unique Key West guesthouse. Boasting beautiful, original pine floors and stately windows. Decorated with a tropical elegance, they have created a thoughtful, homey atmosphere. As a LGBTQ guesthouse they ALSO welcome ALL Friends of The LGBTQ Community. They promote acceptance and respect for all. Complimentary continental breakfast, poolside happy hour. 4 night minimum.
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Old Town Vacation Rentals
Imagine your vacation home being just steps in either direction from all of the shops, restaurants, and sites of Duval Street and the Historic Seaport. From homes steeped in history and built by ship’s captains to Key West’s famous “conch cottage” style, Old Town historic homes are tastefully restored and feature all the modern amenities.
New Town
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New Town Ocean View Hotel
Take it easy with Key West’s most affordable waterfront resort. Just minutes from downtown, this resort offers a free shuttle service to Old Town, Key West where you can enjoy all the best attractions and dining. Along with a restaurant, this resort has an outdoor pool and a 24-hour fitness center. Free continental breakfast is provided, as well as free WiFi in public areas, and free self parking. Other amenities include a bar/lounge, a poolside bar, and coffee/tea in a common area
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New Town Standard Hotel
This resort sits waterfront in Key West, a destination steeped with charm and character. Taking nostalgic influences from the art and culture of our neighbors in Cuba, this resort offers the perfect escape from reality. Mid-century cars greet resort guests as they arrive, birds of paradise punctuate the outdoor landscape, and the sweet sound of a Flamenco guitar can be heard poolside. Relax and unwind with a midday Mojito or explore the town on a bicycle or vintage Vespa, as you indulge in the marriage of old Havana's soul and the playful nature of our Key West island setting.
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New Town Vacation Rentals & Waterfront Condos
Imagine a home with floor-to-ceiling panoramic views of the Atlantic Ocean from every room. The modern, upscale furniture is complemented with splashes of color throughout the home. The balcony wraps 270 degrees around the condo, with seating for everyone in your group. Within walking or biking distance to all of your favorite Key West spots including beaches, restaurants, shopping, and the beautiful waters surrounding the island.
Stock Island
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Stock Island Ocean View Resort Suites
Those seeking the extraordinary will find this resort straight out of your get-away-from-it-all dreams. Surrounded by the clear and tranquil sea, this secluded resort offers a setting in which to unwind and recharge: exquisite ocean view suites with kitchenettes, swimming pools, on-site dining, and an array of water activities, all just a quick ride from downtown Key West aboard their complimentary shuttle. Includes a full service marina and a shuttle service
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Stock Island Standard
From the charming marina village that surrounds it to its many handcrafted touches, this hotel isn't just another boutique hotel - it's a one-of-a-kind Key West experience.Thoughtfully crafted with a unique blend of contemporary furnishings and rustic touches, each of the spacious guest rooms and suites comes with spectacular views of the marina and the ocean beyond. Other highlights include open air outdoor showers in select rooms, a state-of-the-art marina, two waterfront pools, dockside restaurants and bars, shuttle service to Old Town, on-site water activities, and a dog park
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Stock Island Vacation Rental
Each Stock Island vacation rental home reflects the laid-back, colorful and quirky island lifestyle of Key West. Located just just a short car or Uber ride from Old Town Key West.
Special Key West Accommodations Categories
Ocean Views
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Old Town Luxe Waterfront
Designed with ultimate relaxation in mind, rooms and suites feature local art, hand-painted furnishings, and a private balcony with a view of the Gulf of Mexico or historic Duval Street. With the best location in town, you won't miss a thing. Accommodations include their boutique island spa, poolside lounging, fine dining, and waterfront cocktails and music. Epic Key West sunset included.
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Old Town Waterfront Hotel
The resort is located on the corner of the Gulf of Mexico and Duval Street. Beautiful tropical gardens surround the pool in the center of the property and open directly onto the private beach. Secluded and private yet just steps from the energy and fun of Old Town Key West. Dining, dancing, historical architecture and wonderful galleries are at your doorstep, providing a taste of Key West’s irrepressible spirit.
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Old Town Waterfront Standard
This amazing resort is ideally located right on the waterfront of Old Town Key West within a working cruise ship port and just steps from the famous Mallory Square and one block from Duval Street - it is a hub of relaxation and luxury in the middle of all of the excitement that Key West is famous for.
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New Town Ocean View Hotel
Take it easy with Key West’s most affordable waterfront resort. Just moments from downtown, this resort offers a free shuttle service to Old Town, Key West where you can enjoy all the best attractions and dining. Along with a restaurant, this resort has an outdoor pool and a 24-hour fitness center. Free continental breakfast is provided, as well as free WiFi in public areas, and free self parking. Other amenities include a bar/lounge, a poolside bar, and coffee/tea in a common area.
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Vacation Rentals & Waterfront Condos
Imagine a home with floor-to-ceiling panoramic views of the Atlantic Ocean from every room. The modern, upscale furniture is complemented with splashes of color throughout the home. The balcony wraps 270 degrees around the condo, with seating for everyone in your group. Within walking or biking distance to all of your favorite Key West spots including beaches, restaurants, shopping, and the beautiful waters surrounding the island.
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Stock Island Ocean View Resort & Suites
Those seeking the extraordinary will find this resort straight out of your get-away-from-it-all dreams. Surrounded by the clear and tranquil sea, this secluded resort offers a setting in which to unwind and recharge: exquisite ocean view suites with kitchenettes, swimming pools, on-site dining, and an array of water activities, all just a quick ride from Downtown Key West on their complimentary shuttle. Full service marina and shuttle service.
Family Friendly
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Old Town Waterfront Resort
Immerse yourself in a fantastic family getaway on the only private beach in Key West. Enjoy a boutique resort feel with spectacular amenities, including oceanfront accommodations, two tropical pools, exquisite dining and thrilling water sports.
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Old Town Hotel
This amazing resort is ideally located right on the waterfront of Old Town Key West within a working cruise ship port and just steps from the famous Mallory Square and one block from Duval Street.- a hub of relaxation and luxury in the middle of all of the excitement that Key West is famous for.
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Old Town Vacation Rental
Spend your days soaking up the sun in the chaise lounges while you watch the kids splash and play. Fire up the grill for a poolside meal with your whole family gathered around the outdoor dining area. This is Key West living at it’s best.
Romantic Getaway
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Old Town Waterfront Hotel
Designed with ultimate relaxation in mind, rooms and suites feature local art, hand-painted furnishings, and a private balcony with a view of the Gulf of Mexico or historic Duval Street. With the best location in town, you won't miss a thing. Accommodations include their boutique island spa, poolside lounging, fine dining, and waterfront cocktails and music. Epic Key West sunset included.
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Old Town Hotel
Relax, unwind, and escape from everyday life on the quieter end of Duval Street in a gorgeous setting that stretches out around a charming, restored Victorian 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 our famous bed and breakfast has been the Key West, Florida boutique hotel of choice for Presidents, royalty, and famous figures like Ernest Hemingway.
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New Town Ocean View Hotel
Take it easy with Key West’s most affordable waterfront resort. Just moments from downtown, this resort offers a free shuttle service to Old Town, Key West where you can enjoy all the best attractions and dining. Along with a restaurant, this resort has an outdoor pool and a 24-hour fitness center. Free continental breakfast is provided, as well as free WiFi in public areas, and free self parking. Other amenities include a bar/lounge, a poolside bar, and coffee/tea in a common area.
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Old Town Vacation Rental
As Neptune was known as the Roman God of the Sea, "Neptune's Penthouse" is known as the crown jewel of the 1800 Atlantic complex overlooking the Sea. This Penthouse Condominium has a lavish wrap-around balcony that overlooks the Atlantic Ocean and Community Pool below. You'll be able to enjoy the refreshing Key West breezes from atop your own private balcony, with lofty vaulted ceilings surrounded by the palm tree tops. This home is located in an upscale private Community within walking or biking distance to all of your favorite Key West spots, including beaches, restaurants, shopping, and the beautiful waters surrounding the island.
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Stock Island Standard Hotel
From the charming marina village that surrounds it to its many handcrafted touches, this hotel isn't just another boutique hotel - it's a one-of-a-kind Key West experience.Thoughtfully crafted with a unique blend of contemporary furnishings and rustic touches, each of the spacious guest rooms and suites comes with spectacular views of the marina and the ocean beyond. Other highlights include open air outdoor showers in select rooms, a state-of-the-art marina, two waterfront pools, dockside restaurants and bars, shuttle service to Old Town, on-site water activities, and a dog park.
LGBTQ Fun
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Old Town Hotel
With an all-male, clothing optional environment that prides itself on guest privacy and comfort. Tucked away in the heart of Old Town Key West, this resort is just 3 blocks from Historic Duval Street, providing easy access to a city filled with history, culture, festivity and most of all relaxation.
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Old Town Guesthouse
A lovingly restored Key West Conch house built in 1902 is home to a unique Key West guesthouse. Boasting beautiful, original pine floors and stately windows. Decorated with a tropical elegance, they have created a thoughtful, homey atmosphere. As a LGBTQ guesthouse they ALSO welcome ALL Friends of The LGBTQ Community. They promote acceptance and respect for all. Complimentary continental breakfast, poolside happy hour. 4 night minimum.
Dog Friendly
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Old Town Luxe Hotel
The resort is located right on the corner of the Gulf of Mexico and Duval Street. Beautiful tropical gardens surround the pool in the center of the property and open directly onto the private beach. Secluded and private yet just steps from the energy and fun of Old Town Key West. Dining, dancing, historical architecture and wonderful galleries are at your doorstep, providing a taste of Key West’s irrepressible spirit.
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Old Town Standard Hotel
The resort is located right on the corner of the Gulf of Mexico and Duval Street. Beautiful tropical gardens surround the pool in the center of the property and open directly onto the private beach. Secluded and private yet just steps from the energy and fun of Old Town Key West. Dining, dancing, historical architecture and wonderful galleries are at your doorstep, providing a taste of Key West’s irrepressible spirit.
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Old Town Vacation Rental
Imagine your vacation home being just steps in either direction from all of the shops, restaurants, and sites of Duval Street and the Historic Seaport. From homes steeped in history and built by ship’s captains to Key West’s famous “conch cottage” style, Old Town historic homes are tastefully restored and feature all the modern amenities.
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New Town Ocean View Hotel
Take it easy with Key West’s most affordable waterfront resort. Just moments from downtown, this resort offers a free shuttle service to Old Town, Key West where you can enjoy all the best attractions and dining. Along with a restaurant, this resort has an outdoor pool and a 24-hour fitness center. Free continental breakfast is provided, as well as free WiFi in public areas, and free self parking. Other amenities include a bar/lounge, a poolside bar, and coffee/tea in a common area.
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Stock Island Ocean View Resort & Suites
Those seeking the extraordinary will find this resort straight out of your get-away-from-it-all dreams. Surrounded by the clear and tranquil sea, this secluded resort offers a setting in which to unwind and recharge: exquisite ocean view suites with kitchenettes, swimming pools, on-site dining, and an array of water activities, all just a quick ride from Downtown Key West on their complimentary shuttle. Full service marina and shuttle service.
-
Stock Island Standard Hotel
From the charming marina village that surrounds it to its many handcrafted touches, this hotel isn't just another boutique hotel - it's a one-of-a-kind Key West experience.Thoughtfully crafted with a unique blend of contemporary furnishings and rustic touches, each of the spacious guest rooms and suites comes with spectacular views. Other highlights include open air outdoor showers in select rooms, state-of-the-art marina, two waterfront pools, dockside restaurant, shuttle service to Old Town, on-site water activities, and dog park
Weddings, Bachelor/Bachelorette Parties
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Old Town Waterfront Resort
This amazing resort is ideally located right on the waterfront of Old Town Key West within a working cruise ship port and just steps from the famous Mallory Square and one block from Duval Street - a hub of relaxation and luxury in the middle of all of the excitement that Key West is famous for.
-
New Town Standard Hotel
This resort sits waterfront in Key West, a destination steeped with charm and character. Taking nostalgic influences from the art and culture of our neighbors in Cuba, this resort has a lush escape from reality. Mid-century cars greet resort guests as they arrive, birds of paradise punctuate the outdoor landscape, and the sweet sound of Flamenco guitar can be heard poolside. Relax and unwind with a midday Mojito or explore the town on a bicycle or vintage Vespa, as you indulge in the marriage of old Havana's soul and the playful nature of our island setting.
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Old Town Vacation Rental
A beautiful 5 bedroom 3500 sq ft townhome that is located directly on the water has everything you'll need while you're in Key West: luxurious accommodations, a dramatic water view from every floor, a private pool, your own boat slip, and even a 2 car garage. You will have your own little world, but you'll also be walking distance to all the restaurants and attractions of Old Town.
Budget Friendly
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Old Town Standard
Explore the excitement of Duval Street and downtown Key West, then return to your cool spacious room at this great Key West hotel. Located at the southernmost point in the United States, visitors at this Key West hotel are here to enjoy paradise. Offering free parking and only one block from famous Duval Street. While parking is free, most guests don’t need a car since you can walk to the area’s best attractions. The beach is three blocks away and guests feel right at home in a quiet neighborhood that’s close to everything.
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New Town Standard Hotel
This resort sits waterfront in Key West, a destination steeped with charm and character. Taking nostalgic influences from the art and culture of our neighbors in Cuba, this resort has a lush escape from reality. Mid-century cars greet resort guests as they arrive, birds of paradise punctuate the outdoor landscape, and the sweet sound of Flamenco guitar can be heard poolside. Relax and unwind with a midday Mojito or explore the town on a bicycle or vintage Vespa, as you indulge in the marriage of old Havana's soul and the playful nature of our island setting.
Bring Your Boat
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Stock Island Ocean View Resort & Suites
Those seeking the extraordinary will find this resort straight out of your get-away-from-it-all dreams. Surrounded by the clear and tranquil sea, this secluded resort offers a setting in which to unwind and recharge: exquisite ocean view suites with kitchenettes, swimming pools, on-site dining, and an array of water activities, all just a quick ride from Downtown Key West on their complimentary shuttle. Full service marina and shuttle service.
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Stock Island Standard Hotel
From the charming marina village that surrounds it to its many handcrafted touches, this hotel isn't just another boutique hotel - it's a one-of-a-kind Key West experience.Thoughtfully crafted with a unique blend of contemporary furnishings and rustic touches, each of the spacious guest rooms and suites comes with spectacular views. Other highlights include open air outdoor showers in select rooms, state-of-the-art marina, two waterfront pools, dockside restaurant, shuttle service to Old Town, on-site water activities, and dog park.
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Old Town Vacation Rental
A beautiful 5 bedroom 3500 sq ft townhome that is located directly on the water has everything you'll need while you're in Key West: luxurious accommodations, a dramatic water view from every floor, a private pool, your own boat slip, and even a 2 car garage. You will have your own little world, but you'll also be walking distance to all the restaurants and attractions of Old Town.
Stay on a Boat!
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Old Town Key West
60’ Viking Princess Motor Yacht in the heart of beautiful Key West, Florida ! Stay aboard overnight dockside which includes a Charter of your choice Sunrise, Daytime /Snorkel & Cruise or a Sunset Charter. Upon your arrival the very professional staff will greet you dockside at the Historical Seaport of Key West and will pamper you & your guest (up to 2 person maximum) for 1 overnight. During your exquisite stay the Captain & Stewardess will provide you with a luxurious atmosphere where you can relax, see the island & dine on fabulous foods, and a breakfast after your overnight stay.
Luxury Vacation Rentals
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Old Town Key West
Located in the Truman Annex, a gated community with some of the most impressive homes in Key West, this meticulously furnished estate occupies an entire block, making it the largest single property in the Annex. With three dwellings, two kitchens (one indoor, one outdoor), a very large pool and enough surrounding property to provide the ultimate in luxury and privacy right in the heart of Old Town Key West.
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About Us
Local since 1974, we create guest experiences that emphasize the natural world, art, music, food, history, and local characters. We provide premium concierge services, and serve as market-maker for a select pre-screened portfolio of the island’s best guest activity providers. We have a commitment to the highest hospitality standard, providing personalized guest support daily from 8am to 6pm.
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