Lesser Antilles Kid friendly Vacations

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Flight and Kid friendly hotel deals in Lesser Antilles

Price found within the past 48 hours. Click for updated prices.
Simpson Bay Resort, Marina & Spa

Simpson Bay Resort, Marina & Spa

Pelican Key
Save 100% on your flight
CA $1,448
per person
Nov 1 - Nov 6
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Philipsburg (SXM)
9/10 Wonderful! (2,074 reviews)
Ocean view was not quite true

Reviewed on Oct 2, 2026

The Verandah Antigua - All Inclusive - Adults Only

The Verandah Antigua - All Inclusive - Adults Only

Save 100% on your flight
CA $2,102
per person
Dec 2 - Dec 6
found 5 hours 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

St. James's Club Antigua - All Inclusive

Save 100% on your flight
CA $2,004
per person
Dec 2 - Dec 6
found 5 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to St. John's (ANU)
8.2/10 Very good! (834 reviews)
The Villas at Simpson Bay Resort

The Villas at Simpson Bay Resort

Pelican Key
Save 100% on your flight
CA $1,541
per person
Nov 1 - Nov 6
found 7 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Philipsburg (SXM)
9.2/10 Wonderful! (1,560 reviews)
Sonesta Maho Beach All Inclusive Resort Casino & Spa

Sonesta Maho Beach All Inclusive Resort Casino & Spa

CA $2,160
per person
Nov 1 - Nov 6
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Philipsburg (SXM)
8/10 Very good! (3,244 reviews)
I had some concerns once we arrived since it was right on the strip. I was concerned about safety. That concern was quickly removed. Security was enforced. The check-in process was somewhat chaotic with long lines of people checking in and those who had checked in waiting on their rooms. We were served warm champagne, but didn't receive the cool towel as advertised. The food was good for resort food and the servers in all the restaurants were great. The man on the hamburger grill was the best and those burgers were seasoned to perfection. The parking garage is very small and narrow to maneuver which made it hard to get in and out. The room was great except for the sink slow drainage and not a lot of hot water. I took cold showers the first two days. Overall, I would recommend the resort.

Reviewed on Oct 2, 2026

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5* Kid friendly holidays in Lesser Antilles

Price found within the past 48 hours. Click for updated prices.
The Ritz-Carlton, St. Thomas

The Ritz-Carlton, St. Thomas

CA $4,514
per person
Dec 2 - Dec 8
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to St. Thomas (STT)
8.4/10 Very good! (499 reviews)
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3 Night Kid friendly holidays in Lesser Antilles

Price found within the past 48 hours. Click for updated prices.
The Villas at Simpson Bay Resort

The Villas at Simpson Bay Resort

Pelican Key
CA $1,035
per person
Nov 3 - Nov 6
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Philipsburg (SXM)
9.2/10 Wonderful! (1,560 reviews)
St. James's Club Antigua - All Inclusive

St. James's Club Antigua - All Inclusive

Save 100% on your flight
CA $1,611
per person
Nov 1 - Nov 4
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to St. John's (ANU)
8.2/10 Very good! (834 reviews)
Simpson Bay Resort, Marina & Spa

Simpson Bay Resort, Marina & Spa

Pelican Key
CA $1,418
per person
Nov 12 - Nov 15
found 20 hours ago
Roundtrip flight included
Toronto (YYZ) to Philipsburg (SXM)
9/10 Wonderful! (2,074 reviews)
Ocean view was not quite true

Reviewed on Oct 2, 2026

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4 Night Kid friendly holidays in Lesser Antilles

Price found within the past 48 hours. Click for updated prices.
Simpson Bay Resort, Marina & Spa

Simpson Bay Resort, Marina & Spa

Pelican Key
Save 100% on your flight
CA $1,389
per person
Dec 14 - Dec 18
found 1 day ago
Roundtrip non-stop flight included
Ottawa (YOW) to Philipsburg (SXM)
9/10 Wonderful! (2,074 reviews)
Ocean view was not quite true

Reviewed on Oct 2, 2026

The Verandah Antigua - All Inclusive - Adults Only

The Verandah Antigua - All Inclusive - Adults Only

Save 100% on your flight
CA $2,102
per person
Dec 2 - Dec 6
found 5 hours 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

St. James's Club Antigua - All Inclusive

Save 100% on your flight
CA $2,004
per person
Dec 2 - Dec 6
found 5 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to St. John's (ANU)
8.2/10 Very good! (834 reviews)
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Plan the perfect family-friendly vacation in Lesser Antilles with Expedia

What are some benefits of booking a family-friendly vacation?

Whether it's luxurious or cheap, family vacations in Lesser Antilles are among the most memorable experiences you'll ever have with your family. It can be a great way to bond and explore new destinations with the people you love most. Plus, it's easy to keep an eye on your little ones without having to worry about how they are with a sitter back home. You may even meet some other families and establish long-lasting friendships.

How can I find the best family-friendly vacations?

Using search filters makes finding the perfect family-friendly vacation easy. You can implement the search filter for family-friendly accommodations specifically, but that's just the beginning. You'll also find search filters for price range along with the desired number of bedrooms, so you can ensure you have enough space for everyone you want to bring to Lesser Antilles.

Are there cheap family vacations to Lesser Antilles?

Price varies quite a bit, ranging from to . The price you'll be paying depends on a variety of factors, and you can filter for them all. You can implement a filter for your budget limitations and also remove any 4- and 5-star stays from your search. You can even filter by accommodation type, which can present you with cheap alternatives to what is typically considered standard.

When should I book family-friendly vacation packages?

The right time to book family-friendly vacation packages in Lesser Antilles depends on what you're looking for. If you're looking to save, booking during least popular month tends to be cheaper compared to the rest of the year, though that's not always a guarantee. Keep in mind that the off-season and the busy season differ from place to place, with family-friendly vacations in Canada being very different compared to options in France and Spain, for example.

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

Yes, you'll find plenty of all-inclusive family vacation packages for Lesser Antilles. To see what's available, just select the all-inclusive filter on your search.

How can I book the best family activity vacation?

If you're looking to make the most out of the available activities in Lesser Antilles, you'll need to consider what your family likes to do. Cater your itinerary to your family's interests, and you'll create memories that you and your kids will hold on to for the rest of your lives whether it's family ski vacations in Lesser Antilles or something a bit more relaxed.

Can I find luxury family vacations in Lesser Antilles?

If you're looking for a luxury family vacation to Lesser Antilles, you can use search filters to find the best options available. Activate the filter for 5-star packages to only see the best of the best. Plus, you'll find a range of first-class flights available to make even the journey there top-of-the-line.

How can I search for family vacation deals?

Finding deals is easy when you take advantage of the array of available search filters. You can set budget limitations and remove 4- and 5-star options from your search. If you don't want to miss out on your favourite amenities, however, you can consider travelling during , which often have lower prices because of the off-season in Lesser Antilles.

Can I book a family vacation package that is fully refundable?

If you're looking for a fully refundable reservation, you won't have to look far on Expedia. Quite a few properties in Lesser Antilles are fully refundable. You can search for this feature, but always make sure to check the specific property's policies and requirements before booking.

Why should I book my family trip with Expedia?

When you book with Expedia, you can book your accommodation and your flight together, with some discounts available for doing both at once. Additionally, you may be able to enjoy special discounts with Expedia Rewards that will earn you points you can then put toward discounts for subsequent bookings.

Kid friendly Hotels in Lesser Antilles

The Westin St. Thomas Beach Resort & Spa

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 ...
8.6/10 Excellent! (1,519 reviews)
"Staff members very friendly"

Reviewed on Oct 1, 2026

The Westin St. Thomas Beach Resort & Spa
Hilton Vacation Club Royal Palm St. Maarten

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! (1,310 reviews)
"The staff was very friendly"

Reviewed on Sep 29, 2026

Hilton Vacation Club Royal Palm St. Maarten
Simpson Bay Resort, Marina & Spa

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! (2,086 reviews)
"Ocean view was not quite true"

Reviewed on Oct 2, 2026

Simpson Bay Resort, Marina & Spa
See all 15,315 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.

More vacations you might like

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