Upper Duval Guesthouse ~ Our favorite Mid Range Guesthouse on Key West - Steps off Upper Duval - 2 Pools - Jacuzzi - Off-Street Parking - Children - Kitchenette Suites - Pool Breakfast Bar - Wide Variety of Units - Gardens & Ponds - Condo type units too. This Guesthouse is our favorite Inn in the Upper Duval Street area.  The combination of wonderful staff, the wide variety of really great and affordable guest rooms and suites, plus off street parking just steps from Upper Duval is unbeatable. We like staying in this section of Duval St. because you escape the craziness and noise of Lower Duval where you sleep. Douglas House consists of seven completely restored historic structures. The ambiance can be described as Casual Tropical Victorian. Douglas House has accommodations to fit nearly any need or any size party, from a good sized wedding party to just the two of you on that quick weekend escape. Call Now for Reservations & detailed info: 1-800-733-5397

Mansion Guesthouse ~ Opulence and history where the Atlantic Ocean meets Duval Street - On Atlantic at end of Duval, literally at the Southernmost Point. - Pool and Cabana Bar - Jacuzzi’s in 3 Suites - Children welcome - Giftshop, Gardens - Amazing Museum with Tremendous Tours - Presidential Helo Pad! We recently toured the museum and property... WOW! They have the most   fantastic collection of Presidential letters, documents & photographs and the largest collection of Hemingway letters known. This is without question, the most distinctive house in the Florida Keys!  When you’re on the island, even if you don’t stay in one of the 13 beautiful guest rooms, you have to take the tour & get an all day guest pass to lounge by the cabana bar and zero entry pool overlooking the Atlantic Ocean. The staff is very gracious and accommodating, the surroundings unique and nothing short of stunning. If you’re going to take the time to stay in Key West, make it this great mansion. Call Now for Reservations & detailed info: 1-800-733-5397

Charming Bed & Breakfast ~ Old World Charm, peacefully nestled in the heart of Old Town. - 400 Block of William St (3 blocks from Duval St.) - Tropical Garden and FishPond, dining area - Historic Registry - Adults only property - Full gourmet breakfast - Individualized rooms - 2 blocks to Waterfront - Old style kitchen, lobby We love this place for it’s quaintness and attention to detail; Every room is different and is individually named. Originally the Lowe House, built in 1845 by the son of one of Key West’s earliest Bahamian settlers, it is now one of the most original B&B’s on the island.  A full gourmet breakfast is served daily throughout the year, and is enjoyed in the breakfast nook or tropical gardens. The structure is listed on the National Register of Historic Places and sits on a beautiful, sleepy little street in the heart of Old Town, just two blocks from the Historic Seaport. We feel that this is the ideal choice for young couples or honeymooning newlyweds, call today for info. Call Now for Reservations & detailed info: 1-800-733-5397

Mid Duval Street Guesthouse ~ Heart of Duval Street... Children Welcome! - Steps away from corner of Duval and Truman. - Swimming Pool & deck - Continental Breakfast - Children Welcome - Family owns & operates - Balconies & sun decks - Duval Street Center - 5 blocks to Atlantic - Cool playhouse for kids What a tremendous location... just a few steps from the corner of Truman and Duval Street!  They have fully equipped guestrooms and suites that sleep four.  This is a large property, featuring a collection of new and restored houses. They have one of the largest open spaces for the swimming pool and sun decks in Old Town Key West. Just outside the front door is bustling Duval Street with great shops and restaurants just steps away.  This pretty guesthouse has been family owned and operated since 1984. They have constructed a “Historic” fun playhouse for visiting children. This House, one of the few Key West guesthouses or inns that allow children. Call Now for Reservations & detailed info: 1-800-733-5397

Eaton Street House ~ Small on Size, Big on Details & Hospitality - Near corner of Eaton and Grinnell - just 5 Key West blocks from Duval. - Pool & Deck area - Buffet Breakfast by pool - 8 indiv. guestrooms - Adults only please - 3 blocks to Historic Seaport This is a great little guesthouse! You know right away, when you walk in the front door that this Guesthouse stands out from many of the other gueshouses on the island.  The 8 guestrooms are each unique in style and furnishings. Their small size allows them to focus on the personal touch with both friendly service and overall ambience.  Very centrally located, being only five blocks from Duval and 2 tiny blocks from Key West’s Historic Seaport. We really like this area of Old Town and you almost feel like you’re staying at a friend’s house rather than a commercial operation.  This House, like many Key West guesthouses,  is an “all-welcome” property Call Now for Reservations & detailed info: 1-800-733-5397

Luxury Historic Court Guesthouse ~ The cigar maker’s never had it so good! - Lower Simonton Street 1 block from Duval St. - Brick center walkway lined with flowers & tropical plants - 3 swimming pools - color tv’s, cable, vcr’s - Some of the units also have Jacuzzi’s in them. - 3 blocks to KW Harbor - 2 acre compound. A truly stunning property, from the walk down the flower lined main path to the unique interiors of each special guestroom and cottage.  This courtyard was originally constructed in the 1880’s as a cigar factory and housing for the workers. Only 1 block from Duval, the interior of this little beautiful place is notably peaceful and nearly totally devoid of the insanity of Lower Duval just a couple hundred yards away.  If you appreciate the tropics and gorgeous architecture, you will fall in love with this property. Did we mention the mansion at the back of the property?... just take a left at the 3rd pool. Call for details & advance reservations are absolutely recommended. Call Now for Reservations & detailed info: 1-800-733-5397

Truman Street House ~ Come experience part of the Bahamian & Cuban Conch history books - Truman Ave, 2 blocks from Duval St & 5 blocks to the beach. - Pool & Deck - Spacious guestrooms - Off-Street Parking - Incredible History - Private baths, AC, TV - Complimentary breakfast every day. - In-Room refrigerators Listed on the National Register of Historic Places, this “Conch” House is a Key West classic and can be referred to as Victorian Styling with Bahamian influences in design.  This is a beauty, standing out on Truman Avenue as you roll into town, with its white picket fences, custom spindle railings on the wrap around porches and hurricane shutters.  Inside you’ll find gorgeous wood floors and high ceilings and the spacious guestrooms are beautifully furnished with originals and antiques. It was restored to it’s original glory in 1993.  What once was a private 2 story mansion home can now be yours to stay for the night or the week!  Rich with Key West history! Call Now for Reservations & detailed info: 1-800-733-5397

Duval Street House ~ Peaceful Tropical Gardens in a Great Central Location - Middle of Duval Street, walking distance to all. - Swimming Pool & deck - Tropical Breakfast with Fruit, Cereals, & Pastries - Beautiful Gazebo - Variety of guestrooms - Balconies & sun decks - 7 blocks to Mallory Sq - 6 blocks to Atlantic - Great Staff Nestled on a spacious island estate in the middle of Key West’s main street is a compound of beautifully restored wood frame 2.5 story Victorian style structures.  This Duval House is a classic mid-range 30 room Key West inn with a variety of guestrooms and suites. The pool, gazebo and fish ponds, all networked together by brick walkways, blend into the extensive tropical foliage and century old Banyan tree. A tropical breakfast is served every day by the pool by some of the nicest staff members on the island. The centralized location, walking distance to everything, on a very busy street with all it’s activity and bustle, stays outside, leaving the interior peaceful. Call Now for Reservations & detailed info: 1-800-733-5397

Two Hidden Private Lane Inns ~ Classic Key West Charm just steps off Duval Street - Middle of Duval Street, walking distance to all. - Swimming Pool & deck - Champagne Continental Breakfast - Bahama Style Structure - Variety of guestrooms - Balconies & sun decks - 7 blocks to Mallory Sq - 6 blocks to Atlantic - Hemingway neighbors Most visitors pass right by this lovely and humble property without notice as they make their way down Duval Street.  What a shame, since it is one of the cutest, most conveniently located Key West inns operating today. Family owned and operated for a number of years now, virually all of the guestrooms border on the lovely swimming pools.  Andrews in has it’s own long driveway, right off Middle Duval Street, leading directly into the center of one of the most historic blocks on the island.  Right over the fence is the Hemingway House and across the street is the Key West Lighthouse.  The propertys are accessed by either Olivia Street or Duval Street... Nice! Call Now for Reservations & detailed info: 1-800-733-5397