Compare Vacation Rentals & Rent By Owner Homes in Old Town, Key West, Florida, USA
About Old Town Vacation Rentals
With more than 3594 Old Town vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Rent By Owner Homes (RBOs) and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at an RBO property in Old Town.
Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With RentByOwner Old Town, you have the flexibility of comparing different options of various deals with a single click. Looking for an RBO with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner (RBOs), and other popular Airbnb-style properties in Old Town. Places to stay near Old Town are 744.77 ft² on average, with prices averaging US $719 a night.
RentByOwner makes it easy and safe to find and compare vacation rentals in Old Town with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.
Other Places to Stay in Old Town, FL
Frequently Asked Questions About Old Town?
What are the top vacation rentals in Old Town?
- Almond Tree Inn Hotel - Adults Only
- Casa Capri Beautiful Tropical with 3 King Suites - 2 miles to beach
- Old Town 2 Bicycles, Grill, WiFi, 1st Floor, Pool! Rent 30 days get 20% discount
- Casa Calypso- Beautiful Tropical 3 KING Beds, 3 baths - 2 miles to beach
- Walkable Cottage w/Pool Access in Key West!
- Hidden away near the Southernmost Point, Louisa's Hideaway is it!
- ~ CLOUD 9 ~ It's heaven on earth in this 3B/3BA lavish home with pool/parking
- Boli Townhouse - Luxury WEEKLY Rental in gated Truman Annex-Saturday to Saturday
- MAJESTIC PARADISE @ Truman Annex - Heart of Old Town, Key West
- Everything Key West has to offer @ Mango Cottage
How many Rentbyowner vacation rentals are available in Old Town?
Currently, the total number of properties listed by Rent By Owner in 2026 is over 3594 in the Old Town area, and still counting. By aggregating listings from multiple websites, Rent By Owner offers an immense amount of choice of the best RBO properties in Old Town.
Nearby Neighborhood (11)
| Neighborhood | Property Count |
|---|---|
| Key West Historic District Vacation Rentals in Key West, Florida | 2107 |
| Downtown Vacation Rentals in Key West, Florida | 886 |
| Uptown - Upper Duval Vacation Rentals in Key West, Florida | 665 |
| Historic Seaport Vacation Rentals in Key West, Florida | 333 |
| Truman Annex Vacation Rentals in Key West, Florida | 248 |
| Meadows Vacation Rentals in Key West, Florida | 103 |
| The Meadows Vacation Rentals in Key West, Florida | 103 |
| Bahama Village Vacation Rentals in Key West, Florida | 64 |
| Midtown Vacation Rentals in Key West, Florida | 41 |
| White St. Gallery Vacation Rentals in Key West, Florida | 4477 |
| White Street Gallery District Vacation Rentals in Key West, Florida | 4473 |
