Deals on vacations and trips to Leonards

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Coconut Tree Villa

Coconut Tree Villa

3.5 out of 5
Price was $2,219, price is now $1,670 per person
$1,670
per person
May 31 - Jun 5
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to Tortola (EIS)
This hotel features a terrace, laundry facilities, and free self parking. A garden, concierge services, and barbecue grills are also on offer.
Long Bay Beach Resort

Long Bay Beach Resort

4.5 out of 5
Price was $7,720, price is now $6,099 per person
$6,099
per person
Apr 20 - Apr 25
found 7 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Tortola (EIS)
A private beach and a restaurant are featured at this luxury hotel. Enjoy beachfront dining and relax with free beach cabanas and sun loungers. Relax with a drink at one of the 2 beach bars and enjoy free perks like free self parking and WiFi in public areas.
Bitter End Yacht Club

Bitter End Yacht Club

3.5 out of 5
Save 100% on your flight
Price was $6,019, price is now $4,793 per person
$4,793
per person
May 10 - May 14
found 5 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Tortola (EIS)
This smoke-free hotel features a marina and 2 restaurants. Relax with free beach cabanas and sun loungers, and cool off with a drink at the beachside bar. There's fun for all ages with a free kid's club and kayaking, and babysitting is an added bonus.
Cane Garden Bay Beach Hotel

Cane Garden Bay Beach Hotel

3.5 out of 5
Price was $2,087, price is now $1,687 per person
$1,687
per person
May 31 - Jun 5
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to Tortola (EIS)
A full-service spa, a 24-hour gym, and a restaurant are all featured at this hotel. Relax with sun loungers and beach umbrellas, and cool off with a drink at the beachside bar. Enjoy the outdoor pool and free perks like continental breakfast and free self parking.
Sugar Mill hotel

Sugar Mill hotel

4 out of 5
Price was $2,296, price is now $1,860 per person
$1,860
per person
May 31 - Jun 5
found 1 day ago
Roundtrip non-stop flight included
Chicago (CHI) to Tortola (EIS)
A full-service spa, 2 restaurants, and an outdoor pool are all featured at this hotel. Relax with free beach cabanas and sun loungers, and cool off with a drink at the beachside bar. Relax with a drink at one of the 3 bars/lounges and enjoy free perks like cooked-to-order breakfast and free self parking.

Top Leonards hotels deals

Paradiso Ocean View. A perfect getaway. 10 mins drive to Smugglers Cove Beach..

Paradiso Ocean View. A perfect getaway. 10 mins drive to Smugglers Cove Beach..

St Bernard's Road Belmont State Tortola
Get rates
An outdoor pool is featured at this villa, along with laundry facilities and concierge services. Barbecue grills are provided for your convenience.
Pool
Kitchen
Wyndham Tortola BVI Lambert Beach Resort

Wyndham Tortola BVI Lambert Beach Resort

4.5 out of 5
East End East End Tortola
Free Cancellation
Reserve now, pay when you stay
$306 nightly
The price is $336 total per night
$336 total
Mar 31 - Apr 1
Total with taxes and fees
This hotel features a restaurant, an outdoor pool, and a bar/lounge. Traveling on business? Take advantage of the free WiFi in public areas and airport shuttle. Enjoy the 24-hour gym and perks like free self parking.
Pool
Pet friendly
Nanny Cay Resort and Marina

Nanny Cay Resort and Marina

3 out of 5
Nanny Cay Road Town NA
$246 nightly
The price is $269 total per night
$269 total
Apr 5 - Apr 6
Total with taxes and fees
A full-service spa, 2 restaurants, and an outdoor pool are all featured at this hotel. Enjoy beachfront dining and relax with sun loungers and beach umbrellas. Relax with a drink at one of the 2 bars/lounges and enjoy free perks like free self parking and WiFi in public areas.
Pool
Spa
Maria's By the Sea Hotel

Maria's By the Sea Hotel

3.5 out of 5
Road Town Road Town Tortola
$270 nightly
The price is $295 total per night
$295 total
Mar 27 - Mar 28
Total with taxes and fees
This hotel features a restaurant, an outdoor pool, and a bar/lounge. Traveling on business? Take advantage of the business center and free WiFi in public areas. Dry cleaning, concierge services, and wedding services are also on offer.
Pool
Free WiFi
Cane Garden Bay Beach Hotel

Cane Garden Bay Beach Hotel

3.5 out of 5
Rte 1 Cane Garden Bay Tortola
$409 nightly
The price is $444 total per night
$444 total
Apr 16 - Apr 17
Total with taxes and fees
A full-service spa, a 24-hour gym, and a restaurant are all featured at this hotel. Relax with sun loungers and beach umbrellas, and cool off with a drink at the beachside bar. Enjoy the outdoor pool and free perks like continental breakfast and free self parking.
Pool
Breakfast included
Sebastian's on the Beach

Sebastian's on the Beach

3 out of 5
Apple Bay West End Tortola
Free Cancellation
Reserve now, pay when you stay
$180 nightly
The price is $196 total per night
$196 total
Mar 26 - Mar 27
Total with taxes and fees
This hotel features a restaurant, a bar/lounge, and a beach bar. WiFi in public areas is free. A coffee shop, a terrace, and a garden are also on offer.
Free WiFi
Restaurant
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Popular places to visit

Trunk Bay Beach, St John, Virgin Islands National Park, Caribbean

Trunk Bay Beach

4.5/5(210 reviews)

If a restful vacation is part of your travel plans, Trunk Bay Beach might be the perfect place to seek out during your trip to Road Town. Stroll along the seaside or seek out the sailing opportunities.

Trunk Bay Beach
Island Roots is a great coffee shop if you're feeling a little home sick. They don't serve Nescafe and do make a good croissant breakfast sandwich. They still cook as fast as island time will allow however.

Main Street

You can find the perfect gifts to bring home at Main Street during your trip to Road Town. Stroll along the seaside or seek out the sailing opportunities.

Main Street

Tortola Cruise Ship Port

4/5(144 reviews)

Explore the waterfront in Road Town with a trip to Tortola Cruise Ship Port. Wander the beautiful beaches and seaside in this romantic area.

Tortola Cruise Ship Port

Frequently asked questions

How much are vacation packages to Leonards?
You can pick up a fantastic hotel and flight bundle from just $1,670. With a Travelocity vacation package, an escape to Leonards has never looked more enticing! Save both time and cash and then get a head start on packing those bags.
Where can I get the best vacation package deals for Leonards?
No matter what you enjoy doing, Travelocity can help you find a great Leonards package deal. The only thing you need to do is pick and choose between our 400 air carriers and 1,000,000 worldwide properties.
Why should I book my Leonards vacation bundle via Travelocity?
Nothing beats the feeling of knowing you've just scored the best deal available — that's our Price Match Guarantee. Add to that our impressively broad range of destinations and 24/7 team of customer service professionals and you've got the blueprint for a hassle-free vacation.
Can I save on my Leonards car rental if I bundle it with hotels and flights?
You most certainly can — and booking one of our Leonards vacation packages is the perfect way to go about this. Bundle any combination of a hotel, car, flight and experience and score serious discounts. The more you bundle, the more you save. There are loads of big-name sights around Leonards to put on your itinerary, including San Juan Gate (95 mi from Leonards). Nothing beats discovering amazing places like this with the freedom of your own set of wheels.

Photos of local treasures

Browse Leonards vacation photos for more inspiration

Sunset on Copper Island. Named from the days when they made barrels that transported the salt from Salt Island back to England. It is now home to the Cooper Island Resort which is an Eco-Friendly resort. Off of Cooper Island is some great diving and snorkeling including a great wreck and some beautiful large corals!