Top Kid friendly vacation packages in Lesser Antilles

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

Hilton Vacation Club Flamingo Beach St. Maarten

Pelican Key

$751

per person

Mar 25 - Mar 28

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Philipsburg (SXM)

9/10 Wonderful! (1,339 reviews)

The room was SO CLEAN!! I have OCD and I Lysol wiped all the shelves before putting any of my things down and not a speck of dirt was seen on the bright white wipe. 90% of the staff were so pleasant, only a few older men were grumpy and obviously not happy. Other than that, we were treated wonderfully. The neighboring resort we spent a lot of time at as well and they were fabulous. Only slight concern is my husband’s sweater went mysteriously missing from our room. We never had anything laundered and he never wore it (it’s a sweater) because of how warm it was daily. I would 100000% stay at this resort again though. It was a great overall experience.

Reviewed on Jan 20, 2026

Simpson Bay Resort, Marina & Spa

Pelican Key

Save 100% on your flight

$852

per person

Mar 25 - Mar 28

found 11 hours ago

Roundtrip non-stop flight included

Boston (BOS) to Philipsburg (SXM)

9/10 Wonderful! (1,463 reviews)

We never did the breakfast, but we did order a room service pizza couple times which was more affordable than eating at the restaurants nearby. It would be nice if there was music around the pool room service was great. Our rooms were clean zero complaints on that. The roads around the property definitely need work, but overall, we definitely enjoyed our stay.

Reviewed on Jan 19, 2026

The Villas at Simpson Bay Resort

Pelican Key

Save 100% on your flight

$1,020

per person

Mar 25 - Mar 28

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Philipsburg (SXM)

9.2/10 Wonderful! (1,309 reviews)

Staff and facilities, including dining options all excellent

Reviewed on Jan 18, 2026

The Verandah Antigua - All Inclusive - Adults Only

Save 100% on your flight

$2,504

per person

Mar 25 - Mar 30

found 1 day ago

Roundtrip non-stop flight included

Charlotte (CLT) to St. John's (ANU)

8.6/10 Excellent! (552 reviews)

Rooms were big overall pretty clean. Need more bar staff.

Reviewed on Jan 22, 2026

St. James's Club Antigua - All Inclusive

Save 100% on your flight

$1,987

per person

Mar 25 - Mar 30

found 1 day ago

Roundtrip non-stop flight included

Charlotte (CLT) to St. John's (ANU)

8.4/10 Very Good! (766 reviews)

Staff was courteous and helpful. Food was good. The rooms were clean but a little dated. More mosquitos than expected but not enough to spoil the trip.

Reviewed on Jan 18, 2026

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5* Kid friendly vacations in Lesser Antilles

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

The Ritz-Carlton, St. Thomas

$1,775

per person

Feb 22 - Feb 24

found 1 day ago

Roundtrip non-stop flight included

Newark Liberty Intl. Airport (EWR) to St. Thomas (STT)

8.4/10 Very Good! (434 reviews)

We came home one afternoon after being on the Lady Lynsey for the day to find our hotel room ajar. No belongings were disturbed & I'm guessing maybe housekeeping didn't pull the door hard enough to latch it but I would expect less carelessness.

Reviewed on Jan 19, 2026

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3 Night Kid friendly vacations 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

$852

per person

Mar 25 - Mar 28

found 11 hours ago

Roundtrip non-stop flight included

Boston (BOS) to Philipsburg (SXM)

9/10 Wonderful! (1,463 reviews)

We never did the breakfast, but we did order a room service pizza couple times which was more affordable than eating at the restaurants nearby. It would be nice if there was music around the pool room service was great. Our rooms were clean zero complaints on that. The roads around the property definitely need work, but overall, we definitely enjoyed our stay.

Reviewed on Jan 19, 2026

The Villas at Simpson Bay Resort

Pelican Key

$926

per person

Feb 28 - Mar 3

just found

Roundtrip flight included

Atlanta (ATL) to Philipsburg (SXM)

9.2/10 Wonderful! (1,309 reviews)

Staff and facilities, including dining options all excellent

Reviewed on Jan 18, 2026

St. James's Club Antigua - All Inclusive

Save 100% on your flight

$1,028

per person

Apr 11 - Apr 14

found 1 day ago

Roundtrip flight included

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

8.4/10 Very Good! (766 reviews)

Staff was courteous and helpful. Food was good. The rooms were clean but a little dated. More mosquitos than expected but not enough to spoil the trip.

Reviewed on Jan 18, 2026

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4 Night Kid friendly vacations in Lesser Antilles

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Princess Heights Luxury Boutique Condo Hotel

Oyster Pond

Save 100% on your flight

$903

per person

Feb 23 - Feb 27

found 6 hours ago

Roundtrip non-stop flight included

Columbus (CMH) to Philipsburg (SXM)

9.2/10 Wonderful! (973 reviews)

The Breakfast was great and fresh but nothing compared to the service that we received from the front desk clerk. A+ From all the hotels i stayed im pleased.

Reviewed on Jan 19, 2026

Simpson Bay Resort, Marina & Spa

Pelican Key

$1,019

per person

Mar 25 - Mar 29

found 19 hours ago

Roundtrip non-stop flight included

Boston (BOS) to Philipsburg (SXM)

9/10 Wonderful! (1,463 reviews)

We never did the breakfast, but we did order a room service pizza couple times which was more affordable than eating at the restaurants nearby. It would be nice if there was music around the pool room service was great. Our rooms were clean zero complaints on that. The roads around the property definitely need work, but overall, we definitely enjoyed our stay.

Reviewed on Jan 19, 2026

The Villas at Simpson Bay Resort

Pelican Key

Save 100% on your flight

$1,499

per person

Feb 28 - Mar 4

found 22 hours ago

Roundtrip flight included

Atlanta (ATL) to Philipsburg (SXM)

9.2/10 Wonderful! (1,309 reviews)

Staff and facilities, including dining options all excellent

Reviewed on Jan 18, 2026

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How can I find the best family vacation packages in Lesser Antilles?

For fam-tastic vacation packages in Lesser Antilles, check the family-friendly filter and add child-charming amenities, like water parks and pools. Read reviews written by other broods to be sure your chosen stay packs plenty of rest and play.

How can I book family-friendly vacations in Lesser Antilles on a budget?

For family- and wallet-friendly trips, filter your search results by budget. You can also sort by price. When bringing the whole brigade on a budget, consider staying in low season or outside the city or. To save more coin, accommodation with a kitchen can be your friend—a bowl of pasta at home is always cheaper than feeding the team at a restaurant.

What does a family trip to Lesser Antilles cost?

You could book your amazing family trip to Lesser Antilles just $751. But with so many brilliant breaks on offer, there’s something for every wallet. Prices and availability are subject to change. Additional terms may apply.

Can I book an all-inclusive Lesser Antilles family vacation package?

Check the all-inclusive filter for an all-you-could-ever-wish-for family vacay. Click more of your favorite filters for even more extravagance. Perhaps an ocean view, spa, or hot tub. Maybe a water park, epic kids club, or activities galore.

How can I plan a fun family vacation in Lesser Antilles?

Search for stays with kid-satisfying extras, like water parks, and teenage-friendly free Wi-Fi, so they can post about all their vacation adventures for all their buddies back home. Book up local attractions, excursions, and experiences—and they might even put their phone down for a few minutes.

How can I find Lesser Antilles family vacation deals?

Delightful deals often dwell outside high season, so move your travel dates around for top deals. You can also book up a little away from the major Lesser Antilles landmarks to save cash. Whenever you wish to travel, sort your search results by deals for the most brilliant bargains.

Can I book a Lesser Antilles family vacation package with free cancellation and/or flexible dates?

Free cancellation makes for a hassle-free family vacation. Filter by payment option to find fully flexible trips, including buy now, pay later options.

Why should I book my Lesser Antilles family trip with Expedia?

You can easily find fun for all the family with the super-handy filters. It’s easy to build your dream kid-friendly vacation in just a few clicks. And you can bundle your accommodation, airfare, and car rental in just a few more.

Top Kid friendly Lesser Antilles Hotels

The Westin St. Thomas Beach Resort & Spa

5 Estate Bakkeroe St. Thomas St. Thomas

4 hours drive from Oyster Bay Marina

Book a stay at this luxury resort in St. Thomas. Enjoy free WiFi, 3 outdoor pools, and a full-service spa. Our guests praise the helpful staff and the clean ...

8.2/10 Very Good! (1,041 reviews)

The atmosphere and amenities, the location and the views are breathtaking. It is a wonderful place to visit for a getaway.

Reviewed on Jan 18, 2026

Hilton Vacation Club Royal Palm St. Maarten

115 Welfare Road Simpson Bay

10 min drive from Oyster Bay Marina

Book a stay at this beach aparthotel in Simpson Bay. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the helpful staff and the property ...

9/10 Wonderful! (1,171 reviews)

We had an end unit that offered a lovely sunset view. The room was so comfortable and clean. Enjoyed having the kitchen to cook our own breakfast. Location was excellent with many dining options nearby

Reviewed on Jan 17, 2026

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 ...

8.8/10 Excellent! (1,578 reviews)

Families like: Outdoor pools, kitchen, playground, babysitting

Travelers say...

We never did the breakfast, but we did order a room service pizza couple times which was more affordable than eating at the restaurants nearby. It would be nice if there was music around the pool room service was great. Our rooms were clean zero complaints on that. The roads around the property definitely ...

Reviewed on Jan 19, 2026

See all 14,519 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.