Compare Vacation Rentals & Rent By Owner Homes in Old Town, Key West, Florida, USA
About Old Town Vacation Rentals
With more than 3503 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 768.57 ft² on average, with prices averaging US $768 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 Cay West Beautiful Tropical 3 bedrooms 2 KING suites - 2 miles to beach
- Condo in Old Town Key West's Truman Annex - Pool, Bicycle, Free Parking and WiFi
- Casa Capri Beautiful Tropical with 3 King Suites - 2 miles to beach
- Bright & Modern Condo—7 MinWalk to the Beach! Pool, Bikes & 2 Furnished Porches!
- PINEAPPLE COTTAGE, 2BR/2BA-Pvt Pool, 1/2 block to Duval
- ~ Chick-A-Pea Cottage ~ Enjoy Key West’s charisma, with a pool, and parking!
- Old Town 2 Bicycles, Grill, WiFi, 1st Floor, Pool! Rent 30 days get 20% discount
- LOST SHAKER OF SALT ~ 3 Bed, 2 Bath Pet Friendly with 40' Private Heated Pool
- Casa Cove Beautiful Tropical 3 KING SUITES Sleeps 8- 2 miles to beach
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 3503 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 | 2415 |
| Downtown Vacation Rentals in Key West, Florida | 994 |
| Uptown - Upper Duval Vacation Rentals in Key West, Florida | 761 |
| Historic Seaport Vacation Rentals in Key West, Florida | 389 |
| Truman Annex Vacation Rentals in Key West, Florida | 348 |
| Meadows Vacation Rentals in Key West, Florida | 100 |
| The Meadows Vacation Rentals in Key West, Florida | 100 |
| Bahama Village Vacation Rentals in Key West, Florida | 93 |
| Midtown Vacation Rentals in Key West, Florida | 50 |
| White St. Gallery Vacation Rentals in Key West, Florida | 24 |
| White Street Gallery District Vacation Rentals in Key West, Florida | 24 |
