3709+ Private Villas and Holiday Rentals in Old Town |
  1. USA
  2. Florida
  3. Key West
  4. Old Town

Old Town Holiday Rentals

About Casai's Private Villas and Holiday Rentals in Old Town

Discover more than 3709 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 758.68 ft², with nightly prices averaging US $740.

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.

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Top Accommodation Types in Old Town

Type Count
Vacation Homes1770
Holiday Apartments437
Cottages92
Villas36

Use these Quick Filters to Find a Holiday Rental in Old Town

★ Pro Tip: Casai simplifies the process of comparing the finest listings across various online vacation rental platforms, including Booking.com and more. Utilize the Advanced Filter feature located at the top to effortlessly switch between Casai homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals, eco-friendly properties, and different property types. Explore various cancellation policies, prices, and numerous options to find the ideal accommodation for your next vacation in Old Town.

Weather in Old Town, FL

View the weather forecast for Old Town before booking your Old Town Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

Other Places to Stay in Old Town, FL


Key West Wildlife Center 4,284 Properties
Studios of Key West 4,247 Properties
Key West Burlesque Theater 4,247 Properties
Higgs Beach 4,246 Properties
Key West Garden Club 4,238 Properties
Key West 2,852 Properties
Key West Historic District 2,297 Properties
Duval Street 1,681 Properties
Downtown 941 Properties
Uptown - Upper Duval 740 Properties
Truman Annex 287 Properties
Bahama Village 74 Properties

Frequently Asked Questions About Old Town?

What are the top holiday rentals in Old Town?

With numerous options available in Old Town, planning to stay in the area? Consider booking a few nights at one of these properties, rated as the Top Holiday Rentals in Old Town:

How many holiday rentals have private pools in Old Town?

Discover a selection of holiday rentals with private pools near Old Town with Casai. Experience the epitome of luxury and relaxation in our top-rated villas and holiday homes, where you can enjoy exclusive access to refreshing swimming pools.

Which holiday homes in Old Town are best for families?

If you're searching for a family-friendly holiday home in Old Town, consider one of the following properties. Each comes highly recommended, with excellent reviews for families or groups staying in Old Town:

How many Casai.com holiday rentals are available in Old Town?

As of 2026, Casai boasts over 3709 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) 
NeighborhoodProperty Count
Key West Historic District Vacation Rentals in Key West, Florida 2297
Downtown Vacation Rentals in Key West, Florida 941
Uptown - Upper Duval Vacation Rentals in Key West, Florida 740
Historic Seaport Vacation Rentals in Key West, Florida 365
Truman Annex Vacation Rentals in Key West, Florida 287
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 74
Midtown Vacation Rentals in Key West, Florida 41
White St. Gallery Vacation Rentals in Key West, Florida 4531
White Street Gallery District Vacation Rentals in Key West, Florida 4527

People Also Ask

There are 3709 Old Town, FL Holiday Rentals

Recently Booked Holiday Rentals in Old Town