Compare Villas, Resorts, & Rentals in Old Town, Key West, Florida, USA
About Casai's Private Villas and Holiday Rentals in Old Town
Discover more than 3536 vacation rentals available in Old Town. These rentals, ranging from vacation rentals to Casai Homes and other short-term private accommodations, offer top-notch amenities with unbeatable value, ensuring both comfort and luxury. Enjoy more space and value when you stay at a Casai property in Old Town.
Seeking last-minute deals or the best available offers for cottages, condos, private villas, and spacious vacation homes? With Casai in Old Town, you can effortlessly compare various deals with just a click. Whether you're looking for a Casai with exceptional swimming pools, hot tubs, pet-friendly options, or large master suite bedrooms equipped with large screen televisions, you'll find a variety of options near Old Town. On average, places to stay near Old Town offer 769.99 ft², with nightly prices averaging US $729.
With Casai, finding and comparing holiday rentals in Old Town is easy and secure, often at a 30-40% discount compared to hotel prices. Simply 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 holiday 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
- PINEAPPLE COTTAGE, 2BR/2BA-Pvt Pool, 1/2 block to Duval
- Bright & Modern Condo—7 MinWalk to the Beach! Pool, Bikes & 2 Furnished Porches!
- ~ Chick-A-Pea Cottage ~ Enjoy Key West’s charisma, with a pool, and parking!
- LOST SHAKER OF SALT ~ 3 Bed, 2 Bath Pet Friendly with 40' Private Heated Pool
- 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
How many Casai.com holiday rentals are available in Old Town?
As of 2026, Casai boasts over 3536 properties listed in the Old Town area, with more being added continually. By consolidating listings from various websites, Casai provides an extensive selection of the finest Casai properties in Old Town.
Nearby Neighborhood (11)
| Neighborhood | Property Count |
|---|---|
| Key West Historic District Vacation Rentals in Key West, Florida | 2225 |
| Downtown Vacation Rentals in Key West, Florida | 896 |
| Uptown - Upper Duval Vacation Rentals in Key West, Florida | 719 |
| Historic Seaport Vacation Rentals in Key West, Florida | 354 |
| Truman Annex Vacation Rentals in Key West, Florida | 328 |
| Meadows Vacation Rentals in Key West, Florida | 107 |
| The Meadows Vacation Rentals in Key West, Florida | 107 |
| Bahama Village Vacation Rentals in Key West, Florida | 84 |
| Midtown Vacation Rentals in Key West, Florida | 48 |
| White St. Gallery Vacation Rentals in Key West, Florida | 3797 |
| White Street Gallery District Vacation Rentals in Key West, Florida | 3796 |
