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.
Oyster Bay Beach Resort

Oyster Bay Beach Resort

4 out of 5
Oyster Pond
Price was CA $1,466, price is now CA $875 per person
CA $875
per person
Oct 26 - Oct 31
found 1 day ago
Roundtrip non-stop flight included
Montreal (YMQ) to Philipsburg (SXM)
8.6/10 Excellent! (927 reviews)
The staff was great and the food was delicious!!

Reviewed on Sep 3, 2025

The Villas at Simpson Bay Resort

The Villas at Simpson Bay Resort

4 out of 5
Price was CA $3,063, price is now CA $1,539 per person
CA $1,539
per person
Nov 27 - Dec 4
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Philipsburg (SXM)
9.2/10 Wonderful! (1,244 reviews)
Friendly respectable staff accessible to places off the resort

Reviewed on Sep 9, 2025

Simpson Bay Resort, Marina & Spa

Simpson Bay Resort, Marina & Spa

4 out of 5
Pelican Key
Price was CA $1,628, price is now CA $934 per person
CA $934
per person
Nov 16 - Nov 21
found 1 day ago
Roundtrip non-stop flight included
Ottawa (YOW) to Philipsburg (SXM)
9/10 Wonderful! (1,321 reviews)
Great staff amenities were out of date. Rooms were clean beach was perfect.

Reviewed on Sep 9, 2025

Princess Heights Luxury Boutique Condo Hotel

Princess Heights Luxury Boutique Condo Hotel

3.5 out of 5
Oyster Pond
Price was CA $2,050, price is now CA $1,238 per person
CA $1,238
per person
Nov 27 - Dec 4
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Philipsburg (SXM)
9.2/10 Wonderful! (963 reviews)
Its a beautiful property and the customer service experience is wonderful

Reviewed on Aug 30, 2025

Holland House Beach Hotel

Holland House Beach Hotel

4 out of 5
Downtown Philipsburg
Price was CA $2,978, price is now CA $1,905 per person
CA $1,905
per person
Nov 27 - Dec 4
found 1 day ago
Roundtrip flight included
Montreal (YMQ) to Philipsburg (SXM)
9.2/10 Wonderful! (1,002 reviews)
I enjoyed my stay at Holland House! I stayed 4 nights. The staff is friendly and accommodating. The front desk check in process was easy and they were helpful with providing excursion information and arranging cabs when needed. I most enjoyed the bar staff & on-site beachfront restaurant. The room was clean and standard but not with the best view. There is a boardwalk with food & drink options just steps from the beach but EVERYTHING closes daily no later than 5pm. I spent a lot of time paying for cabs to visit other areas of the island. Holland House is located in a semi-quiet part of the Dutch side and great for couples or solo travelers!

Reviewed on Sep 9, 2025

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
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Maho

4.5/5(2 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

Sonesta Maho Beach All Inclusive Resort Casino & Spa

Sonesta Maho Beach All Inclusive Resort Casino & Spa

4 out of 5
1 Rhine Road, Maho Bay, Lowlands
The price is CA $257 per night from Sep 11 to Sep 12
CA $257
CA $311 total
Sep 11 - Sep 12
includes taxes & fees
Sonesta Maho Beach All Inclusive Resort Casino & Spa
Margaritaville Vacation Club - St. Thomas

Margaritaville Vacation Club - St. Thomas

4 out of 5
6080 Estate Smith Bay, St. Thomas
The price is CA $371 per night from Sep 14 to Sep 15
CA $371
CA $418 total
Sep 14 - Sep 15
includes taxes & fees
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
Fully refundableReserve now, pay when you stay
The price is CA $114 per night from Sep 25 to Sep 26
CA $114
CA $137 total
Sep 25 - Sep 26
includes taxes & fees
Simpson Bay Resort, Marina & Spa
See all 14,579 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 Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

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
Magens Bay featuring a sandy beach

Magens Bay Beach

Appreciate the excellent views of hilly forests as you meander along a scenic trail on your way to this haven of white sand and inviting water.

Magens Bay Beach
Orient Bay Beach

Orient Bay Beach

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

Orient Bay Beach

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.

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