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

$690

per person

Jul 12 - Jul 15

found 1 day ago

Roundtrip non-stop flight included

Atlanta (ATL) to Philipsburg (SXM)

9.2/10 Wonderful! (1,528 reviews)

Excellent stay Staff the best Weber bbq great Peli market 1 minute walk great market with everything you want Bucaneer beach bar 10 mins along ocean Kayak rentals , paddle boats Will return

Reviewed on May 11, 2026

The Verandah Antigua - All Inclusive - Adults Only

Save 100% on your flight

$1,464

per person

Jul 12 - Jul 17

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to St. John's (ANU)

8.6/10 Excellent! (595 reviews)

Me and my partner had a wonderful time celebrating my 45th birthday at the Verandah. I met some of the best people. I have to give an honorable mention to Jensen in watersports at lovers beach, as he made our day everyday and also (Elvis or OlivisI believe that’s how you say it, the best bartender ever who made me feel special everyday and had the best positive attitude. Always greeted with a smile! Everyone was very warm and welcoming. I will definitely be returning. So many people to mention/ the guys who drive the golf carts very pleasant and welcoming. Front desk crew/ very helpful. I love you had everything you needed right there! We enjoyed our stay

Reviewed on May 11, 2026

Simpson Bay Resort, Marina & Spa

Pelican Key

Save 100% on your flight

$727

per person

Jul 12 - Jul 16

found 16 hours ago

Roundtrip non-stop flight included

New York (NYC) to Philipsburg (SXM)

8.8/10 Excellent! (1,682 reviews)

The beach was excellent. The property was old and outdated and could use a better shuttle system. The A/C units in the rooms weren't cooling good enough so the rooms were warm

Reviewed on May 11, 2026

The Villas at Simpson Bay Resort

Pelican Key

Save 100% on your flight

$796

per person

Jul 12 - Jul 15

found 1 day ago

Roundtrip non-stop flight included

Atlanta (ATL) to Philipsburg (SXM)

9.2/10 Wonderful! (1,388 reviews)

Staff very friendly.

Reviewed on May 12, 2026

Hilton Vacation Club Royal Palm St. Maarten

$1,106

per person

Jul 12 - Jul 16

found 1 day ago

Roundtrip non-stop flight included

New York (NYC) to Philipsburg (SXM)

9/10 Wonderful! (1,215 reviews)

The property was clean, staff are friendly and our room had a beautiful ocean view. The only negative feedback is that the bed was hard and uncomfortable. I would love to go back if that is updated.

Reviewed on May 4, 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

$1,309

per person

Jul 12 - Jul 15

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to St. Thomas (STT)

8.4/10 Very Good! (465 reviews)

Everything here was excellent, including the staff, the facilities, the room, the view from the room, the food in the restaurants, the pool, the available water toys (kayak, hobbies, ) and the very attention to details that convey that sense of luxury (ie the shampoo, the towel, the soap, the amazing bedding, etc). They are trying to keep the sargassum away with a barrier and partially succeeding at keeping it under control. The beach is relatively small and facing east.

Reviewed on May 10, 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

$612

per person

Jul 13 - Jul 16

found 11 hours ago

Roundtrip flight included

Fort Lauderdale (FLL) to Philipsburg (SXM)

8.8/10 Excellent! (1,682 reviews)

The beach was excellent. The property was old and outdated and could use a better shuttle system. The A/C units in the rooms weren't cooling good enough so the rooms were warm

Reviewed on May 11, 2026

The Villas at Simpson Bay Resort

Pelican Key

Save 100% on your flight

$796

per person

Jul 12 - Jul 15

found 1 day ago

Roundtrip non-stop flight included

Atlanta (ATL) to Philipsburg (SXM)

9.2/10 Wonderful! (1,388 reviews)

Staff very friendly.

Reviewed on May 12, 2026

St. James's Club Antigua - All Inclusive

Save 100% on your flight

$1,261

per person

Jun 11 - Jun 14

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to St. John's (ANU)

8.4/10 Very Good! (804 reviews)

Staff was extremely helpful. Food was nice

Reviewed on May 12, 2026

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4 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

$727

per person

Jul 12 - Jul 16

found 16 hours ago

Roundtrip non-stop flight included

New York (NYC) to Philipsburg (SXM)

8.8/10 Excellent! (1,682 reviews)

The beach was excellent. The property was old and outdated and could use a better shuttle system. The A/C units in the rooms weren't cooling good enough so the rooms were warm

Reviewed on May 11, 2026

The Villas at Simpson Bay Resort

Pelican Key

$793

per person

Jul 12 - Jul 16

found 7 hours ago

Roundtrip non-stop flight included

Dallas (DFW) to Philipsburg (SXM)

9.2/10 Wonderful! (1,388 reviews)

Staff very friendly.

Reviewed on May 12, 2026

The Verandah Antigua - All Inclusive - Adults Only

$1,798

per person

Jun 18 - Jun 22

found 15 hours ago

Roundtrip non-stop flight included

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

8.6/10 Excellent! (595 reviews)

Me and my partner had a wonderful time celebrating my 45th birthday at the Verandah. I met some of the best people. I have to give an honorable mention to Jensen in watersports at lovers beach, as he made our day everyday and also (Elvis or OlivisI believe that’s how you say it, the best bartender ever who made me feel special everyday and had the best positive attitude. Always greeted with a smile! Everyone was very warm and welcoming. I will definitely be returning. So many people to mention/ the guys who drive the golf carts very pleasant and welcoming. Front desk crew/ very helpful. I love you had everything you needed right there! We enjoyed our stay

Reviewed on May 11, 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 $612. 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 ...

8.4/10 Very Good! (1,218 reviews)

Services are terrible at this hotel. It may be discriminated specfic type of perple. To some, it is extremely friendly with talking and explaining for 20 min. or longer while we were line up to check out for rushing to the airport at the time there were only two customers service representatives ...

Reviewed on May 11, 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! (1,223 reviews)

Staff is wonderful. Rooms are very spacious with gorgeous views. Plenty of places to walk around nearby. 10/10 recommended stay.

Reviewed on May 4, 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 ...

9/10 Wonderful! (1,725 reviews)

Families like: Outdoor pools, kitchen, playground, babysitting

Travelers say...

The beach was excellent. The property was old and outdated and could use a better shuttle system. The A/C units in the rooms weren't cooling good enough so the rooms were warm

Reviewed on May 11, 2026

See all 14,877 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.