Old Town Key West Vacation Rentals, Condo Rentals

Make Old Town Key West your next getaway

There’s just something special about staying in Old Town during your Key West vacation—and with our Old Key West rentals, you can do just that. This historic part of the Florida Keys includes many of the area’s most famous landmarks, like the iconic Hemingway House. The Conch Tour Train is a great way to explore the neighborhood with kids, but even if you don’t end up taking the train, the famous Southernmost Point is a must-see (and a great family photo opportunity).

We always enjoy renting a space that is larger than we need. This is a large 2/2 that gives a wonderful view of the water. Beautiful sunsets right off the balcony. It was updated and very clean. There are no staples in the kitchen except salt and pepper along with Folgers in filter packs. We didn't rent a car and everything you need is accessible with lots of restaurant options. We did rent a golf cart for 24hrs mid-week and toured the island and went to the Publix and bought a couple of days of meals to cook. We went to Fausto's and CVS a couple of times as well for conveniences. Things to note: Use the pool key to access the pool AND the back gate to the waterfront. In order to get into the back gardens and walkway, you need to access the pool area through the garage or go into 115 to get outside to the back gate. The key on the ring with the fob will work on the Truman access gate (one side) on Caroline Street. Our key didn't work on the other gates we tried. If you don't know about the back gate or the Caroline gate key, you will have to walk the long way around through the Southard entrance after 6pm. That is when the gates are closed. This was a bummer on day one because we hadn't figured out the key access. All said, I loved walking through Truman Annex. It is a pure oasis from the noise and crowds of the waterfront and Duval. Our week was great and we will rent again!!