3555+ The Oldest House - Key West Holiday Rentals & Private Villas

Find Family-Friendly Holiday Rentals in or near The Oldest House - Key West

Discover more than 3555 holiday rentals in The Oldest House - Key West. Rent By Owner holiday homes has everything you need to find a place to stay near The Oldest House - Key West, FL.

Whether you are looking for luxury villas in The Oldest House - Key West, furnished homes, unique style condos, flats, cozy cottages for a romantic getaway, spacious apartment for family holidays, or stylish accommodation for a business trip, we can help you find the perfect place. Our holiday rentals include top amenities such as indoor/outdoor swimming pools, kitchen facilities, gyms, hot tubs, Internet connectivity, and more.

If you are planning to travel to The Oldest House - Key West with a whole family or group, RBO holiday accommodations make your trip memorable. We have plenty of places to stay in The Oldest House - Key West for families, large parties, or private owner accommodations for long or short trips. The Oldest House - Key West Pet-friendly holiday rentals are available. Book your favorite vacation rentals in The Oldest House - Key West with Rent By Owner. RBO makes it easy to compare and book holiday rentals today.

Show more
Show less

Frequently Asked Questions About The Oldest House - Key West Holiday Rentals

There are a lot of options in The Oldest House - Key West. If you plan on staying in the The Oldest House - Key West area, consider making a reservation for a few nights at one of these properties as these have been rated the top Holiday Home Rentals in The Oldest House - Key West:

There are many holiday rentals available in The Oldest House - Key West; however, here are a few of the most popular holiday homes listed in The Oldest House - Key West on our website:
At Rent By Owner most of our places to stay are perfect for families. Check out the complete list of holiday homes in The Oldest House - Key West to find one that works for you.
Yes, there are 3555 self-catering family homes and holiday rentals in The Oldest House - Key West.
There are more than 3555 luxury holiday homes in or near The Oldest House - Key West, according to 2025 data from Rent By Owner. Consider these homes for your next holiday: