Discover a selection of 125 vacation rentals in Leonards, Road Town that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including private pools and swimming pools. Prices start at $175 per night, and villas and houses are popular options for a stay in Leonards. Either way, you'll find a rental for everyone's needs.
Destination guide

Slip into island time in Leonards

Leonards is a laidback Caribbean community set in the Tortola hillsides. Its elevated setting means you'll be immersed in a wonderland of emerald-green rainforest and dazzling ocean views. You'll also be just a few miles from Tortola's best beaches. Whether you're planning a family reunion, a destination wedding or a romantic getaway, Leonards vacation rentals promise an utterly unforgettable stay. Lush gardens, sparkling infinity pools and ravishing ocean views will make up the icing on the cake.

Things to do

Sip on Caribbean rum in Leonards

If you can drag yourself off the beach, Tortola is strewn with unique attractions, including the Callwood Rum Distillery. It's one of the Caribbean's oldest distilleries and has been crafting luscious Arundel rum for over 300 years. With breezy decks and gorgeous ocean views, Leonards vacation rentals afford the perfect opportunity to pick up a bottle and mix your own sunset cocktails. Head over to Road Town and you'll find hidden gems like the JR O'Neal Botanic Gardens. The island oasis is filled with tropical orchids, exotic plants and sunbaked cactus groves.


Kaleidoscopic snorkeling in Leonards

Leonards vacation rentals put you just a few miles from Cane Garden Bay, a stunning stretch of photogenic sand. You can bask on the sand, relax at a beachfront bar or make a splash with kayaking and other water sports. You'll also be just 10 minutes from Brewers Bay, an aquamarine cove fringed by colorful coral reefs. For a quintessential Tortola experience, bundle the family into a taxi and head up to the Fireball Full Moon Party. Held once a month at Aragorn's Studio, the family-friendly event features fire jugglers, live calypso music and sumptuous seafood.


A tropical hat trick in Leonards

Winter sees legions of sun seekers descend on the British Virgin Islands. Like the rest of the Caribbean, Tortola enjoys a hat trick of clear skies, calm water and balmy temperatures. Virgin Islands veterans cite September to November as a sweet spot. You'll sidestep hurricane season and beat the winter crowds. If you're planning on diving, it's best to avoid summer, as visibility can be frustrating. March sees the archipelago host the BVI Spring Regatta, one of the Caribbean's biggest yachting festivals.

Natural features

Leonards – a gateway to the British Virgin Islands

Thanks to its central location, Leonards is a great base for exploring Tortola. It's part of the British Virgin Islands, a sun-drenched archipelago in the Caribbean Sea. As well as gorgeous sandy beaches, Tortola is home to Sage Mountain National Park, where rainforest hiking trails wind up to scenic lookouts. Keep an eye out for colorful frogs and lizards hiding in the foliage. Divers will jump at the chance to explore the coral-strewn RMS Rhone shipwreck. Needless to say, the wreck's resident lobsters, octopuses and sea turtles make great dive buddies.

How many vacation rentals are available around Leonards, Road Town?

Our 2021 property listings offer a large selection of 125 vacation rentals around Leonards. From 67 villa rentals to 90 house rentals, find a unique house rental for you to enjoy a memorable holiday or a weekend with your family and friends.

Can I rent Villas in Leonards?

Yes, of course. Vrbo has 67 Villas in Leonards. Our other popular types of vacation rentals in Leonards include:

  • Houses: 90 rentals available
  • Boats: 22 rentals available
  • Yachts: 16 rentals available

But you can also enjoy a great stay in one of our other vacation rentals including Cottages and more.

Can I find a vacation rental with pool in Leonards?

Yes, you can select your preferred vacation rental with pool among our 60 vacation rentals with pool available in Leonards. Please use our search bar to access the selection of vacation rentals available.