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).

Visiting Key West for the first time, I wanted to stay somewhere right in the heart of the action—and Key to Paradise delivered and then some. Just a short walk from Duval Street, the location couldn’t have been more ideal. Everything I needed was close by, including a CVS just minutes away for any essentials—though I hardly needed anything extra, as the home was incredibly well-stocked and accommodating. One of the best parts about the location was the number of restaurants within walking distance. From casual bites to upscale dining, there was no shortage of amazing food options just steps away. Whether I was in the mood for seafood, Cuban cuisine, or just a good cup of coffee, everything was right around the corner. The home itself was thoughtfully designed for both comfort and fun. There were plenty of rooms to choose from, each with its own charm, and the colorful island-inspired decor brought a cheerful, vacation-ready energy to the entire space. In the evenings, I loved relaxing in either of the two cozy living rooms—both equipped with smart TVs that made it easy to stream all my favorite shows. During the day, the full kitchen had everything I needed to whip up meals, snacks, or a quick breakfast before heading out to explore. The property also featured a spacious layout indoors and outdoors, including a separate guest house and a refreshing pool—perfect for unwinding after a day of adventures. The neighborhood felt safe and walkable, which made getting around a breeze. Key to Paradise truly made my trip unforgettable. I couldn’t have asked for a better place to stay and will absolutely be booking again on future visits. Key West was amazing, and this home made it all the more special.