Family Resorts in the USA and Caribbean: Luxury for All Ages

The Best Resorts for Families in the USA and the Caribbean

April 28, 2025

As a mom of two little ones and a luxury travel blogger, I’ve come to truly appreciate the destinations that go the extra mile for families—without compromising on luxury!!! After all, when is having a luxurious resort more important than when traveling with little ones? Where you choose to stay matters more than ever – and it’s something I’m not willing to compromise on when it comes to choosing our family vacations. Whether you’re looking for a relaxing beach vacation with a baby, a resort where toddlers can run free, or a spot the whole family will remember forever, these are the best family-friendly resorts in the USA and the Caribbean.

These aren’t just any resorts. These are the BEST of the best – that I’ve been to and LOVE – for the families who want the best of both worlds: where kid-friendly meets five-star luxury.

So let’s get to it why don’t we!!!!

The Best Family Resorts in the USA

Four Seasons Resort Maui at Wailea – Maui, Hawaii

If you know me, you know FS Maui is one of my all-time favorite resorts. It’s just as dreamy for adults as it is surprisingly accommodating for kids. From a dreamy kids pool, to poolside pack n’ plays available (for free) to the beachfront setting that’s both breathtaking and safe for little ones, this is Maui family-friendly luxury at its best.

And if you want the very best rate + free breakfast for two, a $100 resort credit, and a room upgrade (if available), you can book directly through me here. I am a Four Seasons Preferred Advisor and have been a very strong relationship with the FS Maui (we even got married here!) I offer complimentary hotel bookings on any of these resorts and can secure preferred perks like daily complimentary breakfast, resort credits, and priority for room upgrades at no extra cost to you (at any of these hotels!)

Four Seasons Resort Hualalai – Big Island, Hawaii

This Big Island gem is laid-back luxury with an incredible kids’ program, plus seven pools (including a sand-bottom one for littles). FS Hualalai is the kind of place where you can snorkel with your kids in the King’s Pond in the morning, then enjoy a glass of wine on your lanai after bedtime. It’s paradise for the whole fam. PLUS they have complimentary laundry facilities on property – a huge win for traveling families with little ones.

And if you want the very best rate + free breakfast for two, a $100 resort credit, and a room upgrade (if available), you can book directly through me here. I am a Four Seasons Preferred Advisor and I offer complimentary hotel bookings on any of these resorts and can secure preferred perks like daily complimentary breakfast, resort credits, and priority for room upgrades at no extra cost to you

Four Seasons Resort Palm Beach – Palm Beach, Florida

This one’s for my East Coast families looking for a great family-friendly luxury resort that’s still close to home. Four Seasons Palm Beach is intimate, polished, and incredibly warm—from the staff to the suites. The beachfront is serene and shallow enough for toddlers to splash around, and the kids’ amenities (think tiny robes and beach toys waiting in your room) are next-level thoughtful.

How to get free perks when booking FS Palm Beach (or any of the hotels on this list!)

For free perks like complimentary breakfast, resort credit, and a room upgrade (when available), email [email protected] and my agency will reach out with more information and can help book you with all kinds of fun perks (at no extra cost to you, and we don’t charge a fee to book for Jetset readers!)

Four Seasons Orlando – Florida

We can’t talk about the very best family-friendly luxury hotels in the USA and not mention FS Orlando!!!! Four Seasons Resort Orlando at Walt Disney World is the gold standard for doing Disney in a way that still feels like a luxury vacation. It’s a true oasis from the chaos of park-hopping, with a lazy river and waterslides, kid-friendly pools, and standout family programming (including character experiences), while still giving parents an adults-only pool, a chic rooftop restaurant, a spa, and even a golf course when you need a reset. The complimentary shuttle makes getting to the parks feel seamless (think: smooth, easy, no parking headaches), and if you book through me as a Four Seasons Preferred travel advisor, you can also receive complimentary VIP perks like daily breakfast for two per bedroom, resort credit, and potential upgrades when available.

The Boca Raton Resort – Boca Raton, Florida

This historic resort has had a modern glow-up in the best way. With its private beach, lazy river, and multiple pools (including an epic kids’ pool area), The Boca Raton is a perfect family retreat in the USA. There’s also Camp Boca, the on-site kids’ club, which means parents get a little vacation too. The vibe is elevated yet playful — the kind of place where you can sip rosé by the pool while your kids are happily splashing nearby.

The Boca Raton is made up of five distinct areas, each with its own vibe. The Cloister is the iconic pink building at the heart of the resort — classic, elegant, and family-friendly. The Beach Club sits directly on the ocean and feels like a modern, sun-soaked escape. The Yacht Club is adults-only and ultra-luxurious, perfect for couples or a parents-only weekend. The Tower offers spacious, newly renovated rooms with great views – ideal for families! while the Bungalows are more residential, with full kitchens and extra space for longer stays or multigenerational trips.

Hotel del Coronado – San Diego, California

This California classic hits the sweet spot of beachy family-friendly fun and historic charm. It’s super walkable with strollers, and the beach is wide, soft, and ideal for sandcastle-building. During the holidays, the resort even has beachfront ice skating in the winter. Iconic, magical, and effortlessly family-friendly.

Thanks to a recent renovation and expansion, it now feels fresher, more elevated, and is set right on the wide, golden sands of Coronado Beach (consistently ranked one of the best beaches in California).

The Del offers a variety of room choices— from historic rooms in the original Victorian building to modern, multi-bedroom residences at Shore House and Beach Village, which are perfect for families wanting space and privacy. There are kid-focused activities like beach bonfires, surf lessons, and crafts, plus a big pool, and both casual and upscale dining options.

Cloister Sea Island and the Lodge at Sea Island – Sea Island, Georgia

My full blog post on Sea Island is here
Sea Island is one of my favorite luxury family resorts in the U.S.—hands down. It’s Southern hospitality meets five-star elegance. You’ve got everything from falconry and horseback riding to beach bonfires and babysitting services. There’s a reason families return here year after year.

Email [email protected] to book with VIP perks!

Westin Maui

If you’re headed to Maui with kids, The Westin Maui is one of the most family-friendly resorts on the island! Set on Ka’anapali Beach, this resort is a prime, happening location on Maui (think: walkable to so much shopping and cute restaurants on the beach!). But let’s talk about the real highlight for families: the pools. We’re talking multiple tiers of water fun, including waterfalls, a waterslide, a splash zone for little ones, water basketball, and even a hidden grotto. It’s basically a dream water playground for kids (and let’s be honest, parents too). It’s the kind of place where the whole family can truly unwind — with a mai tai in hand and happy kids in tow!!! I grew up going to the Westin Maui and I still have the fondest memories of our family vacations there.

The Best Family Resorts in the Caribbean

Rosewood Mayakoba – Riviera Maya, Mexico

Rosewood Mayakoba is family-friendly luxury wrapped in nature. This beautiful, jungle-meets-beach resort has incredible suites (many with private plunge pools), the BEST family-centric service we’ve experienced, and a fab kids club. They even offer little explorers’ programs and a TON of baby amenities, making it perfect for first-time international family travel. In fact, this is the hotel we chose both times as our first trip after each of our babies were born due to how easy they make it for parents. We can’t recommend highly enough! Read everything you need to know about Rosewood Mayakoba in here!

Belmond Maroma – Riviera Maya, Mexico

The brand new, breathtakingly beautiful Belmond Maroma is one of the best luxe options in the Riviera Maya. It’s ideal for families looking to unwind in a peaceful, authentic Mexican setting with impeccable service and easy beach access. Tucked into the lush jungle along one of this area of Mexico’s best stretches of beach, this resort feels like a hidden oasis that still delivers five-star service, thoughtful design, and that signature Belmond warmth (We LOVE a Belmond!)

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Email [email protected] for the best rates and to book with FREE VIP perks like Room Upgrades, $100 Resort Credit, and more.

Belmond Cap Juluca – Anguilla

This one is one of my top picks for traveling with babies. The peaceful, uncrowded beach is so baby-friendly, the rooms are spacious and serene, and the service is impeccable. Older kids may prefer other resorts in Anguilla with bigger pools and more structured activities, but for young families, Cap Juluca is pure Caribbean bliss.

Four Seasons Resort and Residences Anguilla – Anguilla

Stylish, spacious, and sophisticated, FS Anguilla is perfect for families with kids of all ages. The multi-bedroom villas with kitchens and plunge pools make traveling with little ones so much easier, and there’s tons of kid-friendly dining on-site. The beach is calm, and the resort is walkable and chic, and located on the PERFECT location on Mead’s Bay (by all of my favorite restaurants in Anguilla!)

Email [email protected] to book with the best rate + FREE VIP perks like room upgrades, late check out, $100 resort credit and more!

Malliouhana – Anguilla

Set on the iconic (and best beach in Anguilla) Meads Bay, Malliouhana blends colorful charm with Caribbean cool. Families will love the two-bedroom suites, and warm, welcoming vibe. There’s also an AMAZING kids’ club, located right on the beach above Leon’s, and my toddler LOVED the family pool here, too (and so did I, it’s gorgeous!!!!!). Highly recommend this resort! Email [email protected] to book with the best rate + FREE VIP perks like room upgrades, late check out, $100 resort credit and more!

Round Hill Hotel and Villas – Montego Bay, Jamaica

Classic and timeless, Round Hill is where understated luxury meets Jamaican hospitality. The villas here are ideal for multi-generational travel, and their on-site nanny service is a huge plus for parents looking for downtime. It’s cozy, historic, and incredibly family-minded. in Jamaica is it. This iconic resort – once the getaway of legends like JFK and Grace Kelly – has the perfect blend of old-school glamour and relaxed, family-friendly luxury. The villas are ideal for traveling with kids (many come with private pools and dedicated staff like a cook and housekeeper!), and the expansive, quiet beaches are perfect for little ones to splash and explore. There’s a FAB kids’ club for traveling families, full of fun daily activities, allowing parents to sneak away to the spa or enjoy a rum punch by the water. Everything at Round Hill feels warm, personal, and easy!

How to get free VIP perks for your stay:

For free perks like a room upgrade on arrival, subject to availability, full complimentary breakfast daily for two guests, and a $100 USD resort credit for your stay, email my travel agency here with your ideal dates, and I reach out with more information and can help book you with all these perks (at no extra cost to you, we don’t charge any fee to book your hotels!)

Shore Club Turks and Caicos

Nestled on the stunning Long Bay Beach, this resort offers the perfect balance of relaxed island vibes and five-star amenities. The suites and villas are incredibly spacious – ideal for families needing room to spread out -and many come with full kitchens, private pools, and direct beach access (hello, barefoot mornings!). There’s a beautiful kids’ club for little travelers, multiple pools to explore, and calm, shallow waters that make Long Bay perfect for toddlers and young swimmers. Plus, you’re just a short drive to Grace Bay’s restaurants and activities if you want a little adventure off-property.

How to get free VIP perks for your stay:

For free perks like a room upgrade on arrival, subject to availability, full complimentary breakfast daily for all guests, and a $100 USD resort credit for your stay, email my travel agency here with your ideal dates, and I reach out with more information and can help book you with all these perks (at no extra cost to you, we don’t charge any fee to book your hotels!)

Rosewood Little Dix Bay – Virgin Gorda, British Virgin Islands

An icon in barefoot luxury, this resort is just as magical for kids as it is for adults. There’s a beautiful beach, and you’re on the best island in the BVI! It’s peaceful, private, and perfect for families looking for a relaxing, luxurious getaway in the British Virgin Islands.

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How to get free VIP perks for your stay at Rosewood Little Dix Bay:

From Hawaii to the British Virgin Islands, these are the family-friendly resorts that combine effortless luxury with everything you need to travel well with kids in tow. Whether it’s your first trip with a baby or your fifth family vacation abroad, these spots deliver comfort, service, and memories you’ll treasure forever.

Finest Playa Mujeres – Cancun, Mexico

This is one of the best all-inclusive options for families. With splash pads, kids’ clubs, baby gear, and even family suites with swim-out pools, it’s a stress-free and budget-conscious way to do luxury. Great food, chic design, and tons for kids of all ages to do? Yes, please.