Vacation rentals in Leonards

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Top-rated vacation rentals in Leonards

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Guest favorite

Apartment in Road Town, British Virgin Islands

4.87 out of 5 average rating, 210 reviews

Trunk Bay downstairs self-contained room

Hi! We paused this listing first because it was badly damaged by Hurricane Irma and then due to Covid 19, but we're back – repaired and upgraded! The outdoor shower that our guests loved is still there, only now it has hot water. There's also a new kitchen made of hardwood we were able to salvage after Irma. Great news! The beach is still there, too, and still a just ten minute walk away. Always popular for being simple and beautiful in a fantastic location, now it's the same, but even better!

Dec 5 – 12

$94 per night

Guest favorite

Cottage in Tortola, British Virgin Islands

5.0 out of 5 average rating, 8 reviews

New Listing: One Bedroom Cottage @ Botanica

New listing January 2024! Five minutes drive away from Cane Garden Bay and ten minutes from town, Botanica is a garden oasis spanning over an acre, with four standalone houses. By day, you will be amazed by the views of the hills, the bay and neighbouring islands. Sit on the patio under coconut trees and enjoy your coffee, or go for a walk in the tree-lined trail nearby. At night, you will be lulled to sleep by the sounds of nature - crickets, frogs and the whispering of the coconut fronds.

Dec 17 – 24

$190 per night

Guest favorite

Guesthouse in Coral Bay, U.S. Virgin Islands

4.96 out of 5 average rating, 140 reviews

Ocean Blue Cottage

Update: New mattress as of Fall 2022! Ocean Blue Cottage located in Upper Carolina, 400' above sea level, overlooking Coral Bay harbor, Bordeaux Mt, Carolina valley and a peek of the Caribbean Sea. 23 steps down from the road, it has a bedroom 9'x12', dining/kitchen area 6'x10', bathroom 3'x10', private outdoor shower 4'x5', deck 8'x4' with grill, furniture, umbrella. Pricing is $150 night. There’s also an $90 cleaning fee per reservation. 5 min drive to restaurants, 10 min to beaches.

Jun 28 – Jul 5

$150 per night

Guest favorite

Apartment in Mount Healthy

5.0 out of 5 average rating, 14 reviews

Shark Bay Views

Peaceful with beautiful surroundings, if your ideal is serene, quaint and quiet, our home fits your bill! This "apartment" was actually our one bedroom home before building an adjacent bedroom/bathroom and our new home above. The stairway leads to your private abode, where you can just enjoy the breeze, sit back and relax. About a 10 minute drive to Road Town, nestled high in the mountains, you'll find a tranquil setting and a clean apartment. Hope to see you soon!

Jan 23 – 30

$89 per night

Guest favorite

Guesthouse in Tortola, British Virgin Islands

4.96 out of 5 average rating, 46 reviews

The Anchorage- Studio apt above Cane Garden Bay

We are back with a newly renovated guest room! Charming studio apartment on lower level of provencal estate, centrally located in the hills above Cane Garden Bay w/view of Jost Van Dyke & surf at Cane Garden Bay. Private terrace w/outdoor dining. Includes use of shared pool. Small trail through 1 acre of undeveloped but landscaped jungle. 4WD vehicle required. Property is 10 min drive to Road Town & Cane Garden Bay, 5 min to Nanny Cay. 30 min to airport & west end.

Jan 15 – 22

$174 per night

Guest favorite

Home in Tortola, British Virgin Islands

5.0 out of 5 average rating, 8 reviews

Seaside 2 Bedroom Townhome with a Dock

Escape to your own private paradise at Coconut Tree, a one-of-a-kind vacation with a style all its own. Nestled on the water's edge just 15 minutes from Road Town this idyllic retreat offers breathtaking ocean views and an atmosphere of pure relaxation. Whether you're seeking adventure, romance, or simply a chance to unwind and recharge, Coconut Tree is the perfect destination for your next getaway. Book now and discover the magic!

May 25 – Jun 1

$275 per night

Guest favorite

Guesthouse in Tortola, British Virgin Islands

5.0 out of 5 average rating, 12 reviews

Long Bay Surf Shack

"Location, location, location!" This rustic yet charming guest studio is nestled on a hillside above one of the most sought-after and beautiful resorts in the Virgin Islands. Just a two-minute walk to Long Bay Beach and Resort, which offers an amazing spa, beach bar and restaurant. This guest studio is perfect for a couple or a family of three. Hosts have lived in the BVI for 30 years and love to share local insights.

Sep 20 – 27

$108 per night

Guest favorite

Villa in Greenbanks Estate, British Virgin Islands

5.0 out of 5 average rating, 6 reviews

Canefield House, 3 BR'S, APRIL 10% Off, Inquire

Welcome to Canefield House, a luxury three-bedroom villa, located high above Brewers Bay. Its ten acres of 17th century sugar plantation grounds, the original steps where the island’s world-famous rums were born, now offer breathtaking views of local tropical forest and dramatic “ghut”, the jewel-like crescent bay, and the expansive open Atlantic Ocean. Accommodation for up to 6 adults and 4 children.

Sep 5 – 12

$750 per night

Guest favorite

Apartment in Cane Garden Bay

4.92 out of 5 average rating, 53 reviews

Windy Hill Sea View

Windy Hill Sea View overlooks the beautiful Cane Garden Bay with a panoramic view of the ocean and neighboring islands. This spacious one bedroom ocean view apartment offers a comfortable atmosphere to stay in during your visit to the BVI. This apartment is located on Windy Hill in Tortola in a very quite low traffic neighborhood . Windy Hill Sea View is perfect for couples or just one person.

Dec 7 – 14

$113 per night

Guest favorite

Villa in Brewers Bay, British Virgin Islands

4.84 out of 5 average rating, 43 reviews

Villa Matija

Villa Matija is nestled comfortably into the hillside overlooking Brewers Bay on Tortola in the British Virgin Islands. Allow yourself a little luxury and be eco-friendly at the same time! Villa Matija (pronounced ma-TEE-ya) sits above Brewers Bay with an outstanding view of Jost Van Dyke and several other smaller cays & islands. On a clear day you can see Puerto Rico (about 70 miles away)!

Nov 11 – 18

$364 per night

Guest favorite

Hut in Tortola

4.94 out of 5 average rating, 135 reviews

Tiny Cozy Shack 8 minutes from Beef Island airport

Located in a breezy valley on the East End of Tortola overlooking Beef Island & Virgin Gorda. Nestled among boulders where you can enjoy the sun rise. Simple tiny room (8’x10’) with full size bed has a private bathroom + outdoor shower, no hot water.. Outdoor kitchenette with mini fridge, stove, kettle, toaster. Electricity, solar lights and WiFi available.

Dec 23 – 30

$93 per night

Guest favorite

Home in Tortola

4.93 out of 5 average rating, 122 reviews

Private One Bedroom Villa, HotTub, Amazing Views

Nestled on top of Cooten Bay in Tortola, British Virgin Islands, Cooten House has amazing views that will take your breath away. Whether you are looking for a romantic getaway, a place to relax and soak up the sun or all of that plus close proximity to great surfing spots, Cooten House will exceed your expectations.

Aug 13 – 20

$238 per night