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.
Esmeralda Resort

Esmeralda Resort

4 out of 5
Price was CA $1,989, price is now CA $1,306 per person
CA $1,306
per person
Jun 15 - Jun 21
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Philipsburg (SXM)
8.6/10 Excellent! (528 reviews)
I suggest they add a loveseat and coffee table to add a level of comfort. The rooms are large and could handle the additional furniture.

Reviewed on May 9, 2026

The Villas at Simpson Bay Resort

The Villas at Simpson Bay Resort

4 out of 5
Pelican Key
Price was CA $4,036, price is now CA $1,923 per person
CA $1,923
per person
Jun 18 - Jun 23
found 2 days ago
Roundtrip non-stop flight included
Montreal (YMQ) to Philipsburg (SXM)
9.2/10 Wonderful! (1,388 reviews)
We absolutely loved our stay at Simpson Bay Resort, Marina & Spa! The location was perfect, the views were beautiful, and the staff made us feel so welcome from the moment we arrived. We enjoyed relaxing by the beach and pool, and everything we needed was close by. The atmosphere was fun, peaceful, and exactly what we needed for a vacation. We’re already talking about coming back again. Highly recommend for anyone visiting St. Martin!

Reviewed on May 7, 2026

Simpson Bay Resort, Marina & Spa

Simpson Bay Resort, Marina & Spa

4 out of 5
Pelican Key
Price was CA $2,455, price is now CA $1,327 per person
CA $1,327
per person
Jul 4 - Jul 8
found 2 days ago
Roundtrip non-stop flight included
Montreal (YMQ) to Philipsburg (SXM)
8.8/10 Excellent! (1,682 reviews)
Everyone on the resort was so welcoming and helpful. Would highly recommend

Reviewed on May 10, 2026

La Playa Orient Bay

La Playa Orient Bay

4 out of 5
Price was CA $2,503, price is now CA $1,483 per person
CA $1,483
per person
Jun 15 - Jun 21
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Philipsburg (SXM)
9.4/10 Exceptional! (701 reviews)
The breakfast has so many delicious options! It’s not your usual continental breakfast. They go above and beyond. The staff are all friendly and very accommodating. We have stayed there 3 times and always look forward to seeing the staff. They must be doing something right to keep the staff. Love having the chairs and umbrellas. Would definitely recommend.

Reviewed on May 10, 2026

Princess Heights Luxury Boutique Condo Hotel

Princess Heights Luxury Boutique Condo Hotel

3.5 out of 5
Oyster Pond
Price was CA $2,776, price is now CA $1,923 per person
CA $1,923
per person
Jun 18 - Jun 23
found 2 days ago
Roundtrip non-stop flight included
Montreal (YMQ) to Philipsburg (SXM)
9.2/10 Wonderful! (1,002 reviews)
Yes, everything was there. The continental breakfast was good.

Reviewed on May 7, 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
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

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Lesser Antilles Hotel Deals

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 $415 per night from Jun 7 to Jun 8
CA $415
CA $526 total
Jun 7 - Jun 8
includes taxes & fees
9/10 Wonderful! (2,136 reviews)
Highly recommend staying at The Morgan. The staff are always happy to help, the views will exceed your expectations. Would absolutely come back.

Reviewed on May 10, 2026

The Morgan Resort Spa Village
Bluebeard's Castle Resort

Bluebeard's Castle Resort

4 out of 5
1331 Estate Taarneberg Charlotte Amalie Saint Thomas
The price is CA $312 per night from May 25 to May 26
CA $312
CA $420 total
May 25 - May 26
includes taxes & fees
8.8/10 Excellent! (373 reviews)
We prefer the rooms overlooking the West; town side...

Reviewed on May 9, 2026

Bluebeard's Castle Resort
Margaritaville Vacation Club - St. Thomas

Margaritaville Vacation Club - St. Thomas

4 out of 5
6080 Estate Smith Bay St. Thomas
8/10 Very Good! (2,444 reviews)
The staff was very friendly and helpful. Our room was clean and comfortable. Shuttles were readily available as we had a room that required a good uphill walk — great view!!

Reviewed on May 8, 2026

Get rates
Margaritaville Vacation Club - St. Thomas
See all 14,904 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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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.