Where to Stay in Key West

What Type of Accommodations Would You Like?
Go Here for: Key West Guest Houses
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Key West accommodations cover a very wide range of choices-we have everything from quaint guest houses to chain hotels to deluxe waterfront resorts. If you’re vacationing in Key West for a month or more, there are also many longer-term vacation rentals, too. There are also lots of concierge services, realtors, and tourist information centers (online and in town) that will help you find just what you want in accommodations. Basically, the choices are in what type of Key West accommodations you want, and where you to be on the small island of Key West. That, of course, depends on how you plan to get around the island, and what you like to do.

Southernmost Point Area

Key West Southernmost Hotel If you stay in the vicinity of the Southernmost Point as your choice in Key West accommodations, you are still within walking distance to downtown (Old Town). However, it’s a little bit quieter and not quite as densely populated. There are moderately priced older motels here, as well as places on the ocean. Duval Street ends up in this Southernmost area, so can’t get lost if you go downtown for dinner or a museum.
Old Town Area
Old Town is everything Key West is famous for, and if you stay in this area, you can practically walk to everything. This is the original settled area of Key West, since it’s on slightly higher ground than the rest of the island. Therefore, the buildings are historical and, thanks to enthusiastic preservationists, lovingly restored. This is where rich wreckers in the eighteenth and nineteenth century built their dream homes, financed by the salvaged wreckage of unfortunate ships trying to navigate the reef and shoals around Key West. There are inns, guest cottages, and a few larger style Key West accommodations, but mostly smaller, unique establishments for which Key West is famous.

You can let the Innkeepers Association of Key West guide you to the right guest house, since they range in quality and style from superb to cluttered and disappointing. A “garden” can mean a jacuzzi in the back yard surrounded by wooden planks for a walkway. A “view” can mean you overlook someone else’s roof. Just be sure to investigate what you’re getting into before you sign up. Many have websites with pictures of their rooms and grounds.
Chain Hotel Area
An Old Town Conch House. Or a Beachfront Condo. Where will Your Key West Adventure Begin? If you drive to Key West, your first glimpse of the island will be the eastern tip, which is dotted with chain hotels, a popular choice in Key West accommodations. If you’ve never been to Key West before, you might feel a little disappointed as you drive up to a wall of large chain-style Key West accommodations that line the edge of the island as you drive in. After all, Key West is famous for Conch House guest houses, historical B & Bs, classy resorts and island charm. The good news is, these chain hotels are concentrated right where you first see them: the eastern edge of the island. It gets better as you drive further towards downtown Key West. The other good news is, these larger chain hotels, while not quaint and unique, are rather pleasant and convenient, especially if you arrive in town without a reservation for Key West accommodations. Some advertise their rates on large signs out front, encouraging walk-ins. Compared to other types of Key West accommodations, they have lots of amenities and many feature free shuttles to Old Town. They offer lots of free parking for guests, and easy access to chain restaurants as well. They do serve a purpose and many visitors to Key West have a great vacation while staying in these hotels, which range from Days Inn to Doubletree.
Beach Area
Along the southern edge of the island of Key West, on South Roosevelt Boulevard and Atlantic Avenue, there are newer condo buildings (newer than the buildings of Old Town, that is) that rent by the week, the month, or the weekend. The condo buidings face the ocean and Smathers Beach, or have their own beachfront space facing south towards the ocean. Pick this type of Key West accommodations if you plan on spending lots of time at the beach, and you don’t mind being a little bit outside of downtown, where the bars and nightlife and most shopping is found. It’s a quieter choice, and one that will require you to either bike, take a taxi, or drive and park (not a good idea) to Old Town, where you will definitely want to spend some time at some point.

These condos are inhabited by part-timers, other vacation-goers, and fulltime residents. They usually feature a swimming pool and landscaped grounds for the guests. Usually there’s an assigned parking spot that comes with the condo, where you can park. You’ll also find the occasional tennis courts, too. These rentals often have a three-night minimun stay and a checkout time deadline that’s pretty strict, since housecleaners have to come in and get the place ready for the next guests, often arriving in the afternoon after your morning checkout. The interiors range from seashell-and-flamingo trinket style to chic, professionally decorated style pads that you’d find in the pages of a style magazine. (Just FYI, it’s usually the former!). Somewhere there’s a shop in Key West that does a brisk business in wicker furniture, ceramic flamingoes, and palm tree-themed place settings for the table. But that’s ok, it’s a vacation! There are all sorts of Key West accommodations for all sorts of travelers.

Here are a few:

Crowne Plaza Key West
Fairfield Inn
Island City House
Island House