Picking the Perfect Key West Guesthouse

Key West Florida is known for its charming historic streets that are lined with trees, flowers, and hundred-year-old Victorian-style properties that were once private residences and have since been converted into Key West hotels, inns, and guesthouses, opening their doors to any visitor who wants to experience Old Key West during their vacation. These days, staying at a guesthouse during your Key West visit is the best way to not only immerse yourself in the history of Key West Florida, but also to conveniently place yourself within easy walking distance to all the best attractions and establishments in Key West. The historic guesthouses and inns line the streets of Downtown Key West, also known as Old Town Key West. This is the area where you can find all the famous Key West bars such as Sloppy Joe's and the Green Parrot, the great Key West museums such as the Pirate Soul and the Mel Fisher Museum, and the best Key West restaurantas such as Caroline's and the Grand Cafe. Staying in this area also puts you within walking distance to all the best Key West tours and activities, most of which depart from either the Key West Historic Bight Marina or the Westin Marina.

Guesthouses in the Heart of Downtown Key West

Staying anywhere in Downtown puts you with just a few blocks from Duval Street, the Schooner Wharf area, and all the best spots in Key West. There are, however, certain guesthouses that are right in the "heart" of everything. These are the ones that sometimes run a little pricier based on location alone, but they are also the ones that put you literally within a two-minute walk from almost anywhere you'd want to go. Most of these have the downfall of not being able to provide parking (you have to park your car along a side street or at one of the city parking lots or garages), but they have the advantage of placing you right in all the action. These Key West inns include the fabulous Garden House and the Key West Harbor Inn, both of which provide complimentary breakfast as well as a complimentary happy hour where guests get to interact with innkeepers and learn all the best secrets of Key West from locals. Other excellent properties in the heart of Old Town Key West include the luxurious Simonton Court, the homey Casa 325, and upscale Weatherstation Inn.

Luxury Guesthouses and Other Great Inns in Key West

Outside of the heart of Downtown you can find some of the guesthouses that have ample parking, larger pool areas, and more spacious rooms. One of the most famous of any these is the stunning Southernmost House, located at the south end of Duval Street overlooking the Atlantic Ocean. The Southernmost House was privately owned until the mid-90's, but is now the top in luxury Key West hotels, offering guests a gorgeous infinity pool, access to neighboring South Beach, and immaculately-decorated bedrooms. For more budget-friendly accommodations, the Wicker Guesthouse is an excellent choice with a tropical-style pool area, the Chelsea House, or the Conch House.

Exploring Old Town Key West

Really, the best way to experience Old Town Key West is on foot. Walking through the streets of Key West allows you to take in the unique architecture and landscaping of the narrow side streets. Walking allows you to take your time exploring Key West, stopping in at historical attractions like the Hemingway House on Whitehead Street, stopping it at the one-of-a-kind shops, grabbing a drink at one of the many bars, and taking in the warm island atmosphere that Key West is known for. If you need to get somewhere in a short amount of time, taxis are relatively inexpensive when traveling from one point in Downtown to another. Bikes, scooters, and electric cars are also an excellent and popular way of traveling through Key West.

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Free Sunset Cruise with Power Adventure

Come enjoy a complimentary Champagne Sunset Catamaran Sail as a gift for joining us on Key West's top Do-It-All excursion. Enjoy all the fun in the sun of the Power Adventure including kayaking, snorkeling, parasailing and jet skiing. Then enjoy a relaxing two-hour journey to watch the famous Key West sunset.