Lesser Antilles Vacation Packages

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Your Lesser Antilles Vacation

See and do more with a vacation 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 vacation is just a few clicks away with Expedia.

Top Lesser Antilles Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Princess Heights Luxury Boutique Condo Hotel

Princess Heights Luxury Boutique Condo Hotel

3.5 out of 5
Oyster Pond
Price was CA $1,722, price is now CA $1,060 per person
CA $1,060
per person
May 28 - Jun 1
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Philipsburg (SXM)
9.2/10 Wonderful! (1,007 reviews)
Beautiful location, and get ready for some nice walks.

Reviewed on Mar 23, 2026

The Villas at Simpson Bay Resort

The Villas at Simpson Bay Resort

4 out of 5
Pelican Key
Price was CA $4,290, price is now CA $1,823 per person
CA $1,823
per person
May 9 - May 16
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Philipsburg (SXM)
9.2/10 Wonderful! (1,387 reviews)
Nice room. Great view. Staff could be a bit friendlier overall - at the bar, beach staff putting out chairs, etc. overall nice stay

Reviewed on Mar 22, 2026

Simpson Bay Resort, Marina & Spa

Simpson Bay Resort, Marina & Spa

4 out of 5
Pelican Key
Price was CA $2,323, price is now CA $1,153 per person
CA $1,153
per person
May 28 - Jun 1
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Philipsburg (SXM)
9/10 Wonderful! (1,629 reviews)
Everything was fabulous. Room faced the Marina.

Reviewed on Mar 23, 2026

The Morgan Resort Spa Village

The Morgan Resort Spa Village

4 out of 5
Price was CA $2,147, price is now CA $1,426 per person
CA $1,426
per person
May 28 - Jun 1
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Philipsburg (SXM)
9/10 Wonderful! (2,033 reviews)
We had a great stay on this incredible property. A few things that stood out were the kind staff, ideal location, and amazing facility.

Reviewed on Mar 24, 2026

The Atrium Beach Resort and Spa, an Ascend Collection Resort

The Atrium Beach Resort and Spa, an Ascend Collection Resort

3 out of 5
Price was CA $2,620, price is now CA $1,790 per person
CA $1,790
per person
Apr 24 - Apr 30
found 23 hours ago
Roundtrip flight included
Hamilton (YHM) to Philipsburg (SXM)
8.6/10 Excellent! (1,012 reviews)
A little older property but very clean, conveniently located on a beach, next to strip of restaurants, bars, supermarket. Nice kitchenette with full-size fridge. Pool area very small but beach is very nice.

Reviewed on Mar 21, 2026

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
Mullet Bay Beach which includes a beach, tropical scenes and general coastal views

Maho

4.5/5(3 area reviews)

While visiting Maho, you might make a stop by sights like Mullet Bay Beach and Mullet Bay.

Find hotels in Maho

Ready to book your vacation to Lesser Antilles?

 

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Lesser Antilles Hotel Deals

Bluebeard's Castle Resort

Bluebeard's Castle Resort

4 out of 5
1331 Estate Taarneberg Charlotte Amalie Saint Thomas
The price is CA $355 per night from Apr 22 to Apr 23
CA $355
CA $478 total
Apr 22 - Apr 23
includes taxes & fees
8.8/10 Excellent! (170 reviews)
Very clean resort with delicious food. Front desk was very rude upon checking in and out and the waiters at the pool area were beyond rude . The lady with short blonde hair ignored us on multiple occasions and the man with blonde hair kept talking about how horrible of a day it was . Their whole ...

Reviewed on Mar 24, 2026

Bluebeard's Castle Resort
The Morgan Resort Spa Village

The Morgan Resort Spa Village

4 out of 5
2 Beacon Hill Road Simpson Bay
Fully refundableReserve now, pay when you stay
The price is CA $571 per night from Apr 5 to Apr 6
CA $571
CA $701 total
Apr 5 - Apr 6
includes taxes & fees
9/10 Wonderful! (2,046 reviews)
We had a great stay on this incredible property. A few things that stood out were the kind staff, ideal location, and amazing facility.

Reviewed on Mar 24, 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 CA $814 per night from Mar 27 to Mar 28
CA $814
CA $916 total
Mar 27 - Mar 28
includes taxes & fees
8/10 Very Good! (2,391 reviews)
It's ok. Convenient location, nice sized rooms. Be able to walk and climb many stairs to get to your room. Only 1 good option that is meh, staff is unresponsive, slow, and will just lie to make you go away and not deal with you on anything - even trivial things like getting a cab in the morning.

Reviewed on Mar 24, 2026

Margaritaville Vacation Club - St. Thomas
See all 14,631 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.
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Discover the most popular places to visit in Lesser Antilles

Sapphire Beach which includes a sandy beach and tropical scenes

Sapphire Beach

4.5/5(5 reviews)

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

Sapphire Beach
Maho beach

Maho Beach

4/5(62 reviews)

Nothing says vacation like spending a lazy day at Maho Beach, a popular beach in Maho Reef. Check out the top-notch restaurants or lively bars in this romantic area.

Maho Beach
Trunk Bay which includes island views

Trunk Bay

5/5(5 reviews)

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 travelers 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.