Beach Vacations in Lesser Antilles 2026

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Flight and Beach hotel deals in Lesser Antilles

Price found within the past 48 hours. Click for updated prices.

The Villas at Simpson Bay Resort

Pelican Key

Save 100% on your flight

CA $999

per person

Dec 8 - Dec 11

found 13 hours ago

Roundtrip flight included

Toronto (YTO) to Philipsburg (SXM)

9.2/10 Wonderful! (1,560 reviews)

Best place to stay while visiting St. Maarten. Everything is literally right there. The room was clean and looks just like the photos.

Reviewed on Oct 7, 2026

Simpson Bay Resort, Marina & Spa

Pelican Key

Save 100% on your flight

CA $1,412

per person

Dec 8 - Dec 14

found 24 hours ago

Roundtrip non-stop flight included

Ottawa (YOW) to Philipsburg (SXM)

9/10 Wonderful! (2,074 reviews)

The Verandah Antigua - All Inclusive - Adults Only

Save 100% on your flight

CA $1,877

per person

Dec 11 - Dec 14

found 1 day ago

Roundtrip non-stop flight included

Toronto (YYZ) to St. John's (ANU)

8.6/10 Excellent! (643 reviews)

St. James's Club Antigua - All Inclusive

Save 100% on your flight

CA $1,770

per person

Dec 11 - Dec 14

found 1 day ago

Roundtrip non-stop flight included

Toronto (YYZ) to St. John's (ANU)

8.2/10 Very good! (834 reviews)

Sonesta Maho Beach All Inclusive Resort Casino & Spa

Save 100% on your flight

CA $2,850

per person

Dec 8 - Dec 14

found 24 hours ago

Roundtrip non-stop flight included

Ottawa (YOW) to Philipsburg (SXM)

8/10 Very good! (3,244 reviews)

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5* Beach holidays in Lesser Antilles

Price found within the past 48 hours. Click for updated prices.

Sonesta Ocean Point All Inclusive, Adults Only Resort

Save 100% on your flight

CA $2,771

per person

Nov 7 - Nov 11

found 1 day ago

Roundtrip non-stop flight included

Toronto (YYZ) to Philipsburg (SXM)

8.8/10 Excellent! (1,018 reviews)

The food was fresh, all restaurants offered a wide variety of food selections, and they always asked about allergies. They also asked guests to sanitize their hands prior to being seated (loved that!). The staff is friendly and accommodating. Room service had a lot of options and was delivered promptly, even during late hours of the night. The resort offers free chairs and umbrellas on a first come first serve basis so you have to be there early to take advantage of those. The entertainment could use a little revamp but other than that everything was great.

Reviewed on Oct 8, 2026

The Ritz-Carlton, St. Thomas

CA $5,275

per person

Dec 8 - Dec 15

found 14 hours ago

Roundtrip flight included

Ottawa (YOW) to St. Thomas (STT)

8.4/10 Very good! (499 reviews)

Zemi Beach House, LXR Hotels & Resorts

CA $5,401

per person

Dec 10 - Dec 17

found 1 day ago

Roundtrip non-stop flight included

Fredericton (YFC) to The Valley (AXA)

9.8/10 Exceptional! (291 reviews)

Beautiful ph

Reviewed on Sep 27, 2026

Don't see what you're looking for?

See all available trips from Columbus to Lesser Antilles

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3 Night Beach holidays in Lesser Antilles

Price found within the past 48 hours. Click for updated prices.

The Villas at Simpson Bay Resort

Pelican Key

Save 100% on your flight

CA $999

per person

Dec 8 - Dec 11

found 13 hours ago

Roundtrip flight included

Toronto (YTO) to Philipsburg (SXM)

9.2/10 Wonderful! (1,560 reviews)

Best place to stay while visiting St. Maarten. Everything is literally right there. The room was clean and looks just like the photos.

Reviewed on Oct 7, 2026

The Verandah Antigua - All Inclusive - Adults Only

Save 100% on your flight

CA $1,877

per person

Dec 11 - Dec 14

found 1 day ago

Roundtrip non-stop flight included

Toronto (YYZ) to St. John's (ANU)

8.6/10 Excellent! (643 reviews)

St. James's Club Antigua - All Inclusive

Save 100% on your flight

CA $1,770

per person

Dec 11 - Dec 14

found 1 day ago

Roundtrip non-stop flight included

Toronto (YYZ) to St. John's (ANU)

8.2/10 Very good! (834 reviews)

Don't see what you're looking for?

See all available trips from Columbus to Lesser Antilles

View all trips

4 Night Beach holidays in Lesser Antilles

Price found within the past 48 hours. Click for updated prices.

Simpson Bay Resort, Marina & Spa

Pelican Key

Save 100% on your flight

CA $1,149

per person

Dec 13 - Dec 17

found 15 hours ago

Roundtrip non-stop flight included

Ottawa (YOW) to Philipsburg (SXM)

9/10 Wonderful! (2,074 reviews)

The Villas at Simpson Bay Resort

Pelican Key

Save 100% on your flight

CA $1,259

per person

Dec 11 - Dec 15

found 1 day ago

Roundtrip flight included

Toronto (YYZ) to Philipsburg (SXM)

9.2/10 Wonderful! (1,560 reviews)

Best place to stay while visiting St. Maarten. Everything is literally right there. The room was clean and looks just like the photos.

Reviewed on Oct 7, 2026

COCOS Hotel - Adults Only - Caters to Couples - All Inclusive

Save 100% on your flight

CA $4,093

per person

Dec 18 - Dec 22

found 11 hours ago

Roundtrip non-stop flight included

Montreal (YMQ) to St. John's (ANU)

9.4/10 Exceptional! (857 reviews)

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What are some benefits when booking beach vacations in Lesser Antilles?

When you travel to the beach in Lesser Antilles, soft sands and inviting waters, warm sun and gentle breezes will help you relax. This applies to the whole family, as kids and adults can find something fun to do, so family beach vacations are the quintessential family trip.

How can I book the best beach vacations in Lesser Antilles?

To find the best beach vacation, you'll need to book the right accommodations for your family. What the best is depends on what you want from your Lesser Antilles trip. Fortunately, you can use various filters combined with the beach filter to sort for what you want. Additionally, you'll need to consider the time of year you visit.

Can I book cheap beach vacations in Lesser Antilles?

There are quite a few things you can do to get cheap beach vacations in Lesser Antilles. Prices range from CA $999, and if you want to keep yours on the lower side, you may want to consider just how close to the beach you are. If you don't mind a bit of a walk, further away is typically cheaper. Additionally booking something with a kitchen can help you save by avoiding dining out.

Can I book beach packages?

Yes, and you'll find quite a few beach packages available in Lesser Antilles. These package deals let you save by booking your accommodation and your flight together with savings of up to 41.

Why should I book family beach vacations?

When you're travelling with the family to Lesser Antilles, booking your vacation by the beach is one of the best ways to keep everyone happy. There's a reason why some of the most memorable family trips for kids are family beach vacations. You'll be just steps away from the water, and you can often enjoy stunning views of the shore from your room.

How can I find a beachfront vacation in Lesser Antilles?

It's easy to find a beachfront vacation accommodation in Lesser Antilles using the search filter. You can filter for waterfront properties specifically that will only show you results that have beautiful views of the shoreline.

How can I book last-minute beach vacations?

Travelling at the last minute doesn't mean you're out of luck to have a dream beach vacation. Last-minute beach vacations may even offer a nice discount as the owners of hotels or other accommodations try to fill their remaining vacancies. All you have to do is input your travel dates and Lesser Antilles as your destination and see what's available.

Can I find all-inclusive beach vacations ?

Yes, all you have to do to find all-inclusive beach vacations in Lesser Antilles is to use the search filter. It will automatically restrict your results to all-inclusive deals that allow you to plan the entire trip in advance.

Can I book a beach trip that's fully refundable?

Any fully refundable booking can bring peace of mind, and we're happy to offer this feature in several packages and locations throughout Caribbean. All you have to do to find them is check the policies section on each accommodation page. Of course, you can filter for fully-refundable results specifically, too.

Why should I book beach vacations with Expedia?

When you book with Expedia, you'll find a one-stop shop for all your planning needs. You can book your flight and accommodation at the same place and potentially get a discount for booking these together. You can also take advantage of the Expedia Rewards program. Becoming a member is free, and when you do, you'll earn points with every booking will add discounts on subsequent trips.

Beach Hotels in Lesser Antilles

Margaritaville Vacation Club - St. Thomas

6080 Estate Smith Bay St. Thomas

4 hours drive from Oyster Bay Marina

Stay at this hotel in St. Thomas. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the pool and the helpful staff in our reviews. Popular ...

Sonesta Maho Beach All Inclusive Resort Casino & Spa

1 Rhine Road Lowlands

12 min drive from Oyster Bay Marina

Enjoy free WiFi, 2 outdoor pools, and a full-service spa. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Maho Beach ...

Simpson Bay Resort, Marina & Spa

Billy Folly Road 37 Simpson Bay

10 min drive from Oyster Bay Marina

Book a stay at this beach resort in Simpson Bay. Enjoy free WiFi, free parking, and 6 outdoor pools. Our guests praise the pool and the helpful staff in our ...

See all 15,296 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.