An Insider’s Guide to Vacation Rentals in Key West

Navigating the World of Vacation Rentals

Key West vacation rentals are actual homes that can be rented out to vacationers and usually have a minimum night stay. Some of the rentals are houses, and some are condos. Usually, people who rent vacation rentals are staying for a week or more, but some of the vacation rentals in Key West let you stay for as little as three nights.

You can rent by the month or even by the season, and lots of listings for vacation rentals are through real estate companies. Check out local classifieds, too, for listings. If you go with a realtor, be very specific about what you want, since there is a great diversity in vacation rentals, just as there is in guesthouses. Since they are privately owned, each one has its own personality. You can also invest in timeshare vacation properties ahead of time if you have some spare cash. A timeshare is a method for a group of individuals to share ownership of a property, usually a holiday property like a condominium unit in a resort area, according to the law. You simply need to be wary of holiday inn timeshare scams.

Options include private cottages in Old Town, which would mean easy access to dining and entertainment, such as Duval Street and the waterfront. It also means you might be staying in a historic conch house, which is an integral part of the Key West experience for lots of tourists.

Ocean Views & Huge Balconies: 1800 Atlantic Condominiums

1800 Atlantic Condominiums are situated right on the beach facing the Atlantic Ocean on Key West’s south side. The condos are often rented out as vacation rentals. The units are larger than most places in Key West, and they have expansive porches that overlook the beautiful courtyard and the ocean. The common grounds have a pool, hot tub, tennis courts, and a pool house. The area is lush with older palm trees. There is covered parking for guests and a parking lot for extra guest and resident cars. There’s an elevator for the upper floors and a 24-hour security guard who checks guests in and gives them info papers from the owners, as well as the key. 1800 Atlantic Condominiums are located within a short bicycle ride to Old Town, or a walk if you are feeling energetic. The condos are right on a private beach, although you wouldn’t want to swim in the ocean at this spot. The beach is lovely, however, and you can take long walks in the evening.

Inside, rooms at 1800 Atlantic Condominiums are large and have all the amenities you would need while on vacation. Although units are individually owned and therefore uniquely decorated and supplied, the owners all provide linens, kitchen dishes and pots and pans and even things like Tupperware containers, spices, and garbage bags. Some will have a video and book library for rainy or lazy days. Bedrooms are large and have sliding tekta glass doors out onto the deep balconies, all of which have at least a partial view of the ocean. There is central AC.

When to Rent 

Lots of Key West vacation rentals will mention a shoulder season, which refers to a slower season when rates are often lower. Typically, the shoulder season is May 1 to July 31. The summer season is even slower, and rates are often even lower than in the shoulder season. Summer season is roughly August 15 to December.

Then there are special events and week-long festivals such as Fantasy Fest that also drive up the rates for vacation rentals. Here’s a quick run-down of the special events in Key West, where rates typically go up:

• Christmas Week
• New Year’s Week
• Race Week (January)
• Easter Week
• Mini Lobster season in July
• Memorial Day Weekend
• Powerboat Races in November

Always call and check to see whether the time you want to visit Key West might be during a special event or holiday. There are more special events every year in Key West, which means rates can really fluctuate a lot.

Bringing Your Own Boat to Your Rental

If you have a boat and you’re bringing it to Key West, then you have lots of vacation rentals to choose from. There are dozens of properties for short-term rentals on the waterfront with boat slips.

One area of Key West with a number of condo-style vacation rentals with boat slips is on Eisenhower Drive. Eisenhower Drive properties are situated on Garrison Bight Marina, which has access from the middle of the island to the Gulf and driving around the tip of Key West, access to the Atlantic Ocean.

The only drawback is that you’re not really within easy walking distance to Old Town, but it is a quick bicycle ride away. You could walk it and be downtown in about half an hour. Garrison Bight Marina has gas, bait, and engine oil at their marine shop. You are, however, right next to charter dive operations, so if you plan to go scuba diving on a charter, you’re all set. There’s a small dive shop in the corner of Eisenhower and Truman (US 1). There’s also a community park across US 1 from Eisenhower Drive. There are tennis courts there.

A Final Note

Website conglomerates like VRBO do a fine job of consolidating vacation rentals and delivering a good experience for travelers. We recommend using a third-party website that gives you protection and assurances that you deserve when you travel so please beware of Craigslist ads and other classified-style methods of renting out homes in the Southernmost City.

Author

Catherine Tims is a travel writer who lives in Key West Florida