Old Road Town Vacation Rentals, Saint Thomas Middle Island Parish: house rentals & more

Scroll through and select from vacation rentals in Old Road Town to find one that's perfect for your trip. Whether you're traveling with family, friends, or just your furry companion, vacation rentals have the best amenities for spending time at your vacation home, which might include air conditioning and a pool. You'll be sure to find a rental to meet everyone's needs, including options that are accessible or non-smoking.

Find spaces that suit your style

Find properties near top attractions in Old Road Town

Romney Manor

Find the best place to stay - Old Road Town

Updated! Spacious Indoor/Outdoor living. Private pool. Amazing ocean views

Sleeps 6 · 2 bedrooms · 0+ bathrooms

Top rated rentals - Old Road Town

Premier Host

Beautiful Property

Peace of mind
Our Book with Confidence guarantee gives you 24/7 support
All the privacy of home
Enjoy full kitchens, laundry, pools, yards and more
More for less
More space, more privacy, more amenities — more value
A place for everyone
We stand for diversity, inclusion and families everywhere.
Learn more

Find the perfect vacation rental for your Old Road Town getaway

Learn about the unique charm of Old Road Town with a stay in a private vacation home. This city has something for everyone. Many rental homes come with outdoor spaces, separate dining areas and full kitchens, perfect if you want to enjoy some home-cooked meals.

Sightseeing in and around Old Road Town

Do you want to discover attractions to visit while you're in town? Venture out of your vacation home and check out everything that makes Old Road Town a one-of-a-kind vacation spot. Here are some of the most popular attractions to put on your list, all within 30 miles (48.2 km) of the city center:

Royal St. Kitts Golf Club (6.5 mi / 10.4 km)
Royal St. Kitts Golf Club (8.4 mi / 13.5 km)
Four Seasons Golf Course (16.9 mi / 27.3 km)
Clay Villa Plantation House & Gardens (6.7 mi / 10.7 km)
Cat Ghaut Chip 'n Putt (17.1 mi / 27.4 km)

Exploring the natural landscape of Old Road Town

Whether you're looking for fun outdoor activities or just want to spend some time taking in the scenery, Old Road Town is a great place to spend some time outside. Here are some of the area’s most eye-catching natural features, all within 30 miles (48.2 km) of the city center:

Frigate Bay Beach (8.7 mi / 14 km)
Frigate Bay (8.8 mi / 14.2 km)
South Friar's Beach (9.5 mi / 15.3 km)
Sandy Bank Beach (12.4 mi / 20 km)
Banana Bay Beach (13.4 mi / 21.5 km)
Turtle Beach (13.8 mi / 22.2 km)

Transportation options to and around Old Road Town

The nearest airport is in Robert L. Bradshaw Intl. Airport (SKB), located 6.4 mi (10.4 km) from the city center. If you can't find a flight that's convenient for your trip, you could also fly into Oranjestad (EUX-F.D. Roosevelt), which is 15.9 mi (25.6 km) away.

Frequently asked questions

What is the most popular type of vacation rental accommodation in Old Road Town?

The most in-demand types of vacation rentals in Old Road Town are apartments. Want something different? Vrbo has many options to match our guests' requirements, so you'll see vacation properties in all shapes and sizes, and for all budgets. The ideal fit is ready and waiting for you — get hold of yours today.

How much does it cost to rent a vacation rental in Old Road Town?

Season, property type and length of stay are some of the conditions that can influence the price of a vacation home. Simply click on your travel dates to find the ultimate escape. From comfy cabins to sprawling luxury villas, all Vrbo vacation rentals provide incredible value.

How much does it cost to rent a beach house in Old Road Town?

When you travel and the style and size of the property will influence the cost of your beachside escape. Put in your Old Road Town travel dates to see your options on Vrbo. Did someone just say "private pool"? Use the filters to pick the amenities and features you want.

What are popular rental amenities in Old Road Town?

When it comes to rental amenities that guests are on the lookout for in Old Road Town, an ocean view, mountain views and free WiFi rank highest. With Vrbo vacation rentals, you'll find options to match your taste and style, whether you're taking a trip with friends, relatives or even pets.

What are the top attractions for families in Old Road Town?

If you're searching for some entertainment for the family near the heart of Old Road Town, head over to Romney Manor.

How old do you have to be to rent a vacation rental in Old Road Town?

The minimum required age is normally 16, 18 or 21. It can differ between properties on Vrbo, so check the rules of your preferred Old Road Town stay before making a booking.

How long can I rent a vacation rental in Old Road Town for?

The amount of time you can stay in an Old Road Town vacation home for is up to each property. Simply put in your dates of travel to view available options offering longer term stays. They come with all you need to make your extended getaway more convenient and comfortable, like air conditioning and kitchens. Some vacation homes might also offer weekly or monthly discounted prices, so you can stay even longer for less.