Book Holiday Homes in Road Town
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Featured Holiday Homes in Road Town

Spectacular clifftop house with hot tub next to sandy beach, stunning sea views

Beautiful beach house steps from a secluded section of beautiful Brewers Bay.

Spectacularly located beach front Spring Tide @ The Tides at Little Apple Bay

Well Equipped 1 bedroom

The view!!!

3BR Luxury Escape / Near Beach/With Workspaces

Experience Tranquility with Breathtaking Hillside Views overlooking Nanny Cay

Top of the Hill Blue Sunshine

New Construction Oceanfront Home/Pool Private Walk To Beach
Road Town Holiday Houses
Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Road Town vacation homes are the perfect way for you to wing it.
Holiday houses in Road Town let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Road Town in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Road Town adventures, obvs.
If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Road Town with your name on it.
No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Road Town vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.
Road Town Holiday Homes essential information
Accommodation | 43 Holiday Homes |
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Lowest Price | |
Highest Price | |
Popular accommodation | Spectacular clifftop house with hot tub next to sandy beach, stunning sea views, Beautiful beach house steps from a secluded section of beautiful Brewers Bay., Spectacularly located beach front Spring Tide @ The Tides at Little Apple Bay, Well Equipped 1 bedroom, The view!!! , 3BR Luxury Escape / Near Beach/With Workspaces , Experience Tranquility with Breathtaking Hillside Views overlooking Nanny Cay, Top of the Hill Blue Sunshine, New Construction Oceanfront Home/Pool Private Walk To Beach |
More accommodations in Road Town
Top trending hotels in Road Town

Village Cay Hotel and Marina

Maria's By the Sea Hotel

Fort Burt Hotel

Maxi Cooper Bay
More ways to explore Road Town
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^Subject to availability and chosen travel dates.