Lesser Antilles Beach Vacations 2026

Top Beach vacation packages in Lesser Antilles

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

Simpson Bay Resort, Marina & Spa

Pelican Key

$573

per person

Nov 17 - Nov 20

found 1 day ago

Roundtrip non-stop flight included

Orlando (MCO) to Philipsburg (SXM)

9/10 Wonderful! (1,987 reviews)

The property is older/dated, however, it is clean. The staff were friendly and helpful.

Reviewed on Sep 15, 2026

The Villas at Simpson Bay Resort

Pelican Key

$615

per person

Nov 17 - Nov 20

found 1 day ago

Roundtrip non-stop flight included

New York (JFK) to Philipsburg (SXM)

9.2/10 Wonderful! (1,525 reviews)

Excellent and friendly staff. Clean room and property

Reviewed on Sep 16, 2026

The Verandah Antigua - All Inclusive - Adults Only

Save 100% on your flight

$1,102

per person

Nov 17 - Nov 20

found 3 hours ago

Roundtrip flight included

New York (JFK) to St. John's (ANU)

8.6/10 Excellent! (640 reviews)

St. James's Club Antigua - All Inclusive

Save 100% on your flight

$948

per person

Nov 17 - Nov 20

found 1 day ago

Roundtrip flight included

New York (JFK) to St. John's (ANU)

8.2/10 Very Good! (829 reviews)

Cocobay Resort Antigua - All Inclusive - Adults Only

Save 100% on your flight

$1,258

per person

Oct 17 - Oct 20

found 1 day ago

Roundtrip non-stop flight included

Newark Liberty Intl. Airport (EWR) to St. John's (ANU)

9.4/10 Exceptional! (1,001 reviews)

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5* Beach vacations 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

$1,348

per person

Nov 17 - Nov 20

found 1 day ago

Roundtrip non-stop flight included

New York (JFK) to Philipsburg (SXM)

8.8/10 Excellent! (1,005 reviews)

10/10

Reviewed on Sep 15, 2026

Zemi Beach House, LXR Hotels & Resorts

$3,730

per person

Nov 17 - Nov 22

found 1 day ago

Roundtrip flight included

New York (JFK) to The Valley (AXA)

9.8/10 Exceptional! (287 reviews)

The Ritz-Carlton, St. Thomas

$1,580

per person

Oct 17 - Oct 19

found 1 day ago

Roundtrip flight included

Charlotte (CLT) to St. Thomas (STT)

8.4/10 Very Good! (492 reviews)

The whole experience was amazing. There are so many amenities that come with your stay that it takes a few days, yes days to understand everything that is available. The staff is amazing. You can ask anyone a question about the property and they either give you the answer or know who to get you too for the answer. My favorite was the pool is open 24 hours. The night swimming was alot of fun.

Reviewed on Sep 10, 2026

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3 Night Beach vacations in Lesser Antilles

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

Simpson Bay Resort, Marina & Spa

Pelican Key

$573

per person

Nov 17 - Nov 20

found 1 day ago

Roundtrip non-stop flight included

Orlando (MCO) to Philipsburg (SXM)

9/10 Wonderful! (1,987 reviews)

The property is older/dated, however, it is clean. The staff were friendly and helpful.

Reviewed on Sep 15, 2026

The Villas at Simpson Bay Resort

Pelican Key

$615

per person

Nov 17 - Nov 20

found 1 day ago

Roundtrip non-stop flight included

New York (JFK) to Philipsburg (SXM)

9.2/10 Wonderful! (1,525 reviews)

Excellent and friendly staff. Clean room and property

Reviewed on Sep 16, 2026

The Verandah Antigua - All Inclusive - Adults Only

Save 100% on your flight

$1,102

per person

Nov 17 - Nov 20

found 3 hours ago

Roundtrip flight included

New York (JFK) to St. John's (ANU)

8.6/10 Excellent! (640 reviews)

Don't see what you're looking for?

See all available trips from Columbus to Lesser Antilles

View all trips

4 Night Beach vacations in Lesser Antilles

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

The Villas at Simpson Bay Resort

Pelican Key

$691

per person

Nov 17 - Nov 21

found 1 day ago

Roundtrip non-stop flight included

New York (JFK) to Philipsburg (SXM)

9.2/10 Wonderful! (1,525 reviews)

Excellent and friendly staff. Clean room and property

Reviewed on Sep 16, 2026

The Verandah Antigua - All Inclusive - Adults Only

Save 100% on your flight

$1,484

per person

Oct 17 - Oct 21

found 1 day ago

Roundtrip non-stop flight included

Newark Liberty Intl. Airport (EWR) to St. John's (ANU)

8.6/10 Excellent! (640 reviews)

St. James's Club Antigua - All Inclusive

Save 100% on your flight

$1,454

per person

Nov 17 - Nov 21

found 1 day ago

Roundtrip non-stop flight included

Georgetown (GEO) to St. John's (ANU)

8.2/10 Very Good! (829 reviews)

Don't see what you're looking for?

See all available trips from Columbus to Lesser Antilles

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How do I book the best Lesser Antilles beach vacation packages?

Life’s a beach when you dive into our brilliant Lesser Antilles beach vacation deals. Chuck a check in the filter boxes to find ocean views, pools, and resorts just a short saunter from the sizzling sands.

How can I find cheap beach vacations in Lesser Antilles?

A rental steps from the shore creates an amazingly affordable Lesser Antilles beach vacation. Seaside sojourns during low season start from $573. Prices and availability are subject to change. Additional terms may apply.

When should I book a Lesser Antilles beach holiday?

For a bustling beach break, book in . For a less crowded coast, is the time to turn up.

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

With a flick of a finger, the family-friendly filter brings you the best breaks on offer for the whole brood. Look out for kids’ clubs, waterparks, and other incredible extras for a vacay the little ones will love.

How do I find a Lesser Antilles beachfront vacation?

Check the beachfront filter and, bam, the best available oceanside resorts will appear before your eyes. Along with the incredible view, when you book a beachfront resort, you can get from the lapping waves to your patio lounger in a matter of moments.

Can I book a package including a Lesser Antilles vacation beach house rental?

Hit up the vacation rental filter to book your dream beach house. Once you’ve selected the most alluring abode, add your flights and car rental for the perfect package deal.

Can I find Lesser Antilles beach vacation deals?

Sort your search results by deals to delight in amazing Lesser Antilles beach vacation offers. If you want more pizzazz for your pennies, travel outside the high season or stay a little further from the shoreline.

Can I book a Lesser Antilles beach trip with free cancellation and/or flexible dates?

Just like the Lesser Antilles tides, plans change. Filter by payment option to find trips with free cancellation. Buy now, pay later options are also available for full-on flexibility.

Why should I book my Lesser Antilles beach vacation with Expedia?

Relax long before you see the shore with simple search, fantastic filters, and more great deals than there are grains of sand in Lesser Antilles. (OK, maybe not that last part.)

Top Beach Lesser Antilles Hotels

Margaritaville Vacation Club - St. Thomas

6080 Estate Smith Bay St. Thomas

4 hours drive from Oyster Bay Marina

This hotel is a few steps from Pineapple Beach, where you can watch the sunset on your beach trip. Amenities at Margaritaville Vacation Club - St. Thomas include ...

8/10 Very Good! (2,512 reviews)

"Overall it was a good experience. I didn't know that there wasn't daily room service which is important to me. The property could be better maintained. For example the stairs going down to the front parking lot was always covered in leaves,flowers, and chicken poop. The seaweed was terrible but they ..."

Reviewed on Sep 17, 2026

Sonesta Maho Beach All Inclusive Resort Casino & Spa

1 Rhine Road Lowlands

12 min drive from Oyster Bay Marina

At this spa all-inclusive property, get ready to stroll along the shore in Lowlands, as you'll be a short walk from Maho Beach. Amenities at Sonesta Maho Beach ...

The Morgan Resort Spa Village

2 Beacon Hill Road Simpson Bay

12 min drive from Oyster Bay Marina

At this spa resort, get ready to lounge by the shoreline in Simpson Bay, as you'll be near Maho Beach. Amenities at The Morgan Resort Spa Village include a full-service ...

9/10 Wonderful! (2,397 reviews)

"Room was great! Pool even better!!"

Reviewed on Sep 17, 2026

See all 15,310 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.