Lesser Antilles Holidays

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Your Lesser Antilles Holiday

See and do more with a holiday package to Lesser Antilles. Whether you're going for the views, history, culture, or something else, our package deals make travel planning easy. With so many things to explore on a trip to Lesser Antilles, it can be difficult to know where to start. Kick off your journey in Charlotte Amalie at Bolongo Bay and Magens Bay Beach — two popular attractions here. Another great city to add to your itinerary is Philipsburg. Be sure not to miss Maho Beach and Great Bay Beach. Start packing your suitcase, because your Lesser Antilles holiday is just a few clicks away with Expedia.

Our guide on where to stay in Lesser Antilles

Find the best Lesser Antilles areas and neighborhoods for the activities you enjoy most. Learn more about Lesser Antilles
Esperanza

Esperanza

Stroll along the coastal boulevard and visit the collection of shops and restaurants on the main strip in the charming town.

Find hotels in Esperanza

Lesser Antilles Holiday

Lesser Antilles Essential Information

Closest Airport
Luis Munoz Marin Intl. Airport (SJU)
Top Sights
Maho Beach, Magens Bay Beach and Flamenco Beach

Our pick of the best Lesser Antilles Hotel Deals

The Morgan Resort Spa Village

The Morgan Resort Spa Village

4 out of 5
2 Beacon Hill Road Simpson Bay
The price is AU$608 per night from 11 Jan to 12 Jan
AU$608
11 Jan - 12 Jan
includes taxes & fees
8.8/10 Excellent! (1,926 reviews)
The was courteous and helpful with every situation that arose, the front desk did an excellent job, the pool and restaurant staff were always visible. Will definitely recommend the Morgan.

Reviewed on 4 Jan 2026

The Morgan Resort Spa Village
Margaritaville Vacation Club - St. Thomas

Margaritaville Vacation Club - St. Thomas

4 out of 5
6080 Estate Smith Bay St. Thomas
The price is AU$753 per night from 7 Jan to 8 Jan
AU$753
7 Jan - 8 Jan
includes taxes & fees
7.8/10 Good! (2,330 reviews)
We had a great time at Margaritaville! Couple things you should know: The beach at the resort is unusable due to the seaweed problem. The food is inconsistent-overall good but seems to depend on who is cooking. A lot of guests complained but our overall experience with the food was good. Need cash ...

Reviewed on 1 Jan 2026

Margaritaville Vacation Club - St. Thomas
Simpson Bay Resort, Marina & Spa

Simpson Bay Resort, Marina & Spa

4 out of 5
Billy Folly Road 37 Simpson Bay
The price is AU$590 per night from 25 Jan to 26 Jan
AU$590
25 Jan - 26 Jan
includes taxes & fees
8.8/10 Excellent! (1,554 reviews)
Fantastic property. Absolutely not one complaint.

Reviewed on 31 Dec 2025

Simpson Bay Resort, Marina & Spa
See all 14,582 properties in Lesser Antilles
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.
All Inclusive Holidays
All Inclusive Holidays
All Inclusive Holidays
Cheap Holidays
Cheap Holidays
Cheap Holidays
beach holidays
Beach Holidays
Beach Holidays

Discover the most popular places to visit in Lesser Antilles

Sapphire Beach which includes a sandy beach and tropical scenes

Sapphire Beach

Enjoy sunbathing, swimming and fun-filled watersports at this peaceful arched bay.

Sapphire Beach
Orient Bay Beach

Orient Bay Beach

Nothing says holiday like spending a lazy day at Orient Bay Beach, a popular beach in Orient Bay. Visit the top-notch restaurants or lively bars in this romantic area.

Orient Bay Beach
Trunk Bay which includes island images

Trunk Bay

Backed by palms, this stretch of sparkling white sand is regularly ranked as one of the most beautiful beaches in the world.

Trunk Bay

Frequently asked questions

Can I cancel my flight booking to Lesser Antilles due to COVID-19?
If you haven't booked yet, check the terms and conditions of the airfare you're considering. If you've already purchased your flight to Lesser Antilles, make use of our Customer Service Portal. The information here will help you work out which COVID-19 policies apply to your reservation and provide advice on the next steps.
What's the best way to find cheap flights to Lesser Antilles that have flexible change policies?
We know that travel schedules can change in a flash, so booking a flexible ticket with Expedia is a wise idea. Just tick the "No change fee" box below the "Flexible change policies" filter. Your low-priced, flexible flight to Lesser Antilles is just a few clicks away.
What are some of the general tips for travellers to Lesser Antilles during the COVID-19 outbreak?
With new safety guidelines in effect, travel looks a lot different these days. These are some handy things to know before you fly off to Lesser Antilles:
  • Investigate if any travel restrictions apply to your origin and destination before booking. Also check if there are any requirements you'll need to follow on arrival, such as health testing.
  • Wear a face mask during airport screening. A TSA employee will require you to temporarily lower your mask to verify your identity.
  • Instead of handing a TSA employee your boarding pass, position it straight on the reader yourself. Then, hold it up for inspection.
  • You're allowed to take one container of hand sanitizer up to 12 oz (350 ml) in your carry-on bag. This will need to be removed for screening.
  • Remove items from your pocket, such as your keys, phone and wallet, and place them in your carry-on instead of the bins. This will minimize handling during screening.
  • Separate any food you're carrying for X-ray screening. Placing it in a clear plastic bag and into a bin reduces the need for a TSA officer to touch and inspect your belongings.

Which airlines fly to Lesser Antilles?
Let American Airlines take you there. This prominent carrier runs 521 flights every month to Luis Munoz Marin Intl. Airport (SJU), a Lesser Antilles gateway.
How can I find cheap tickets to Lesser Antilles?
You'll always pick up an amazing deal with Expedia, but our "flexible dates" feature makes it even easier. Enter your preferred flight date, then click on the flexible dates link above to compare prices for nearby days. was the lowest price for a flight to Lesser Antilles in the last seven days.
How much is a flight to Lesser Antilles?
In the last seven days, return airfares to Lesser Antilles sold from just and reached a maximum of . For one-way journeys departing from (), the cheapest seat during this time was .
What are the most popular airports to fly into in Lesser Antilles?
Start arranging your Lesser Antilles journey by booking a ticket on one of the 4703 monthly flights to Luis Munoz Marin Intl. Airport (SJU). This is the region's primary gateway.
When is the cheapest time to fly to Lesser Antilles?
Flying on a Tuesday, followed by a Monday, is usually the best way to nab the cheapest airfare. Stay away from the weekends if possible, because Saturday is typically the most expensive day of the week. Spend the money you saved having a good time in Lesser Antilles instead!
How much is a plane ticket to Lesser Antilles?
In the last seven days, plane tickets to Lesser Antilles ranged between and . Prices depend on the time of departure, cabin class, airline and how early the fare is booked.
Which airlines with flights to Lesser Antilles employ COVID-19 cleanliness policies?
While flying during the COVID-19 pandemic can be slightly daunting, airlines are going above and beyond to ensure the well-being of their passengers and staff. These are some carriers that have implemented changes:
  • JetBlue - this airline is known for keeping the middle seat empty and capped capacity flights.
  • Cape Air - this airline is known for providing passenger masks and cleaning with disinfectant.
  • American Airlines - this airline is known for providing passenger masks and cleaning with disinfectant.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.