Vacation Rental Shopping in old town Key West

Old Town Key West is one of the hottest vacation spots in the world. It is also convenient to Fort Myers Beach with a ride on the Key West
Express. So, I decided to explore the possibility of owning a vacation rental.

Vacation rental property in Old Town is very controlled and limited.
The rental licenses are limited and nearly impossible to acquire. I worked with a local real estate agent looking for a property I could rent out for a week or less. The list was whittled down property by property. Some had too many restrictions, while others had never been a rental and did not possess a rental license.

The only property development that offered anything close to the type of rental I was looking for and was walking distance to all Of Old Town, is the Truman Annex. More specifically, the Shipyards Condo complex. It is located south of Southard St. and west of Thomas St.

We toured a 2 bedroom, 2 bath condo, on the second floor. The unit had been recently remodeled and would make a great vacation rental.

The property was not ideal in that it overlooked the parking lot. It does have a balcony, and two full bathrooms is rare in this complex.

We evaluated the numbers; cost, taxes and monthly fees in relation to neighboring rental incomes. We did not love it enough to jump. Ultimately, we decided to keep an eye on the complex, and shop a little farther out next time. How far away from Old Town do we need to get, to have more rental freedom?