Two Old Town houses, available by the month. Casa Catalina sits at 415 Catherine, half a block off Duval. Brisa Azul is at 806 Southard, a few blocks over and one of the rare Old Town houses with private off-street parking. Both are renovated, fully furnished, and walkable to most of what brings people down here.
Most of our guests are snowbirds escaping winter, remote workers stretching a long weekend into a month, or families down for a wedding or a project that keeps them on-island. A few are house-hunting and using the stay as a soft landing while they look. Whatever the reason, the calendar starts at 28 nights.
Why 28? Old Town is zoned to keep short-term rentals out of residential neighborhoods. Unless a house carries a transient license (most don’t), 28 nights is the shortest stay you can legally book. The trade-off is real: you settle in, get a routine, and pay a per-night rate that nightly bookings can’t touch.
Newly renovated historic Conch house half a block off Duval Street. Two bedrooms, two baths, sleeps six. Heated pool, outdoor bar, walkable to most of Old Town. 28-night minimum stay.
Prices start at: $17,500 for 28 nights (+taxes and fees)
Historic home in Old Town Key West with private pool and off-street parking. Two bedrooms plus a downstairs den, three baths, sleeps six. Heated/chilled saltwater pool, vaulted living room with fold-away doors. 28-night minimum stay.
Both houses are fully furnished and turnkey. You bring a suitcase; everything else is here.
The booking page on each property handles the quote, taxes, and fees in one shot. Pet policy and parking specifics are covered in the FAQ below.
YOUR KEYS
YOUR KEYS
Experience the best of island living with Your Keys Vacation Rentals and Your Keys Real Estate. Whether you’re planning a short-term stay in a charming cottage or ready to buy your dream home by the sea, our dedicated team provides the expertise and personal touch you need. Enjoy a seamless transition from unforgettable getaways to owning your own slice of paradise.
Old Town Key West restricts short-term rentals by ordinance. Unless a house has a specific transient license (most don’t), the shortest stay you can legally book is 28 nights. That’s why our calendars start at a month.
Ask before you book. We’ve had dogs in both houses, but it depends on the dog and the length of stay. There’s a pet fee. Anything bigger than medium needs more conversation.
Brisa Azul has private off-street parking. Casa Catalina doesn’t. You park on the street or pay for a nearby lot. Honestly most guests in Old Town don’t drive much. It’s bikes and golf carts.
Monthly rentals include utilities, internet, pool service, and landscape maintenance. There is a mandatory $550 cleaning fee, charged once per reservation and shown in your booking quote. Additional cleaning during a guest’s stay can be arranged for an additional fee.
Both houses are about 10-15 minutes from EYW by car. Uber and Lyft work fine. Catalina is closer to Duval but airport drive time is about the same from either house.
60 days out from your arrival, you can cancel for a full refund. Inside 60 days, the deposit doesn’t come back. The full terms are in the rental agreement. For a month-plus stay, travel insurance is usually worth the few hundred bucks.