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When I first envisioned taking my family to Hawaii, I thought of palm trees, shave ice, beautiful beaches. It seemed like a dream. I quickly woke up when I looked at hotel prices.
Hawaii hotels are expensive. And not every hotel is created equal.
This is one of the BEST trips to use points for.
I’m going to walk you through the best family resorts on each island, and exactly how you can actually stay at them for way less (or close to free) with transferable points and travel portals.
There’s also a way to fly for free! Read Best Ways to Fly Your Family to Hawaii and the 5 Best Points Programs for Domestic Flights.
If you’re brand new to this, start with my free beginner’s guide. It will give you all the info you need to get started.
Maui: The Best All-Around Island for Families
Image of Grand Wailea from Hilton
Image from Hyatt Regency Maui Resort and Spa
Maui is one of those places that just feels like Hawaii the moment you land. It has the perfect mix of everything: beautiful, swimmable beaches, lush tropical scenery, and enough adventure to keep everyone happy. You can spend the morning snorkeling or exploring waterfalls, then be back at your resort by the afternoon for pool time and sunset dinners. It’s one of the best places for whale watching in the winter, and has plenty of amenities without feeling too touristy.
Maui Resorts
Grand Wailea, A Waldorf Astoria Resort
This is the resort kids talk about long after the trip is over.
There’s a swimmable beach, tons of on-site dining, and enough going on that you can easily spend full days at the resort without needing to plan much else. If you want that “everything in one place” Hawaii experience, this is one of the best options.
How to book this with points:
Part of the Hilton Honors loyalty program. Read all about that program HERE.
- Book directly through Hilton Honors and toggle “Use Points” when searching
- Look specifically for standard room rewards (this is key; premium rooms cost dramatically more points)
- Standard award availability can be limited, so booking early (or checking frequently) makes a big difference
- Use the 5th night free perk on award stays if you have Hilton status to stretch your points further
- Use free night certificates if you have them—this can be one of the best ways to book this property
Typical points per night:
95,000–150,000 Hilton points. Free night certificates work too!
Cash rates here can easily hit $1,200+ per night.
Hyatt Regency Maui Resort and Spa
Kids can see penguins and flamingos right on property, explore the grounds, and stay busy without you needing to plan every second of the day. At the same time, it still feels relaxing for parents, with a beautiful beachfront location and plenty of space to unwind. It strikes that perfect balance where your kids are entertained and you actually get to enjoy the vacation too.
How to book this with points:
Part of World of Hyatt loyalty program
- Earn via flexible points cards
- Transfer points
- Stay at Hyatt properties
Typical points per night:
20,000–29,000 Hyatt points
One of the BEST value redemptions in Hawaii.
Wailea Beach Resort – Marriott
Don’t get it confused. This is resort is different than Grand Wailea. Grand Wailea is Hilton, and this is a Marriott property that sits on a beautiful stretch of coastline between two beaches. You’ve got easy access to snorkeling, sand, and sunsets right outside your room. It’s got multiple pools spread across the property, including a dedicated adventure pool with waterslides. The resort does feel more spread out and calm than some of the bigger properties, so it never feels overwhelming.
How to book this with points:
- Book directly through Marriott Bonvoy using points (select “Use Points” when searching)
- Look for standard room availability for the best redemption rates
- Use the “stay 5 nights, pay for 4” perk on award bookings to stretch your points further
- Use cash + points if you’re short on points
Typical points per night:
50,000–80,000 Marriott points
Four Seasons Resort Maui at Wailea
From the moment you arrive, you can tell they’ve thought of every detail. It’s luxury, but in a way that still feels completely comfortable with kids. There are multiple pools (including a great family pool with a small slide), a complimentary kids club, and tons of activities right on property. The service really sets it apart, and they go out of their way to make your stay effortless . It’s the kind of place where you get that true luxury experience, but still feel totally at ease traveling as a family.
How to book this with points:
No traditional points program, BUT,
- Book through Capital One Travel
- Use points to erase the purchase
Typical cash price:
$900–$1,500+ per night
Oahu: The Easiest Island with the Most to Do
Image from Sheraton Waikiki Beach Resort
Image from Sheraton Waikiki Beach Resort
Oahu is special because it gives you a little bit of everything. You can spend the morning on a quiet beach, grab lunch from a food truck, hike to a waterfall or overlook, and still be back in time for dinner in a lively area with and excellent foodie scene. It has that classic Hawaii beauty, but with more convenience, more activities, and more variety than the other islands. From the history found at Pearl Harbor and the Polynesian Cultural Center, to true Hawaiian life watching surfers on the North Shore, you will never be bored on Oahu!
Oahu Resorts
Aulani, A Disney Resort & Spa
Aulani brings Disney-level attention to detail to a beach setting, with a lazy river, splash zones, and just enough magic to keep kids engaged without feeling like a theme park. It’s fun, immersive, and takes a lot of the planning off your plate, which is exactly what most parents want on a Hawaii vacation.
How to book this with points
- Book through Getaway Today
- Use one of the strategies in How to Save on All Things Disney to cover it!
Typical cash price:
$600–$1,200+ per night
Hilton Hawaiian Village
This is the closest thing you’ll find on Oahu to a true “family resort” experience without using a travel eraser for a luxury stay. Hilton Hawaiian Village Waikiki Beach Resort is a massive beachfront property with multiple pools, a saltwater lagoon that’s perfect for kids, and enough on-site dining and activities that you don’t feel like you have to leave.
There’s a weekly fireworks show, easy beach access, and plenty of space for families to spread out. It’s not as polished as Aulani, but it’s fun, flexible, and much easier to book with points.
How to book this with points:
Part of the Hilton Honors loyalty program. Read all about that program HERE.
- Transfer from American Express Membership Rewards
- Earn through hotel stays or welcome offers
Typical cash price:
$400–$700+ per night (can be higher during peak seasons)
The Ritz-Carlton Oahu, Turtle Bay
This hotel feels very different than any you would find on Waikiki. It’s set on the North Shore, so everything is more open, peaceful, and connected to nature. Instead of crowds and busy beaches, you get wide ocean views, walking trails, and space for kids to explore. It’s a great option if you want a more laid-back, outdoorsy Hawaii experience while still staying at a beautiful resort.
How to book this with points:
- Book directly through Marriott Bonvoy using points (select “Use Points” when searching)
- Look for standard room availability (premium rooms cost significantly more points)
- Use the “stay 5 nights, pay for 4” perk on award bookings to stretch your points further
- Use free night certificates (up to 85k) and top them off with extra points if needed
Typical points per night:
70,000–130,000 points
Sheraton Waikiki
Location and convenience are some of the best you can get with this hotel. You’re right in the heart of Waikiki, which means you can walk to restaurants, shops, and activities without needing a car. It still has a great beachfront and family-friendly pool area, but what really sets it apart is how easy it makes your entire trip with its location.
How to book this with points:
- Book directly through Marriott Bonvoy and toggle “Use Points/Awards” when searching
- Use flexible date searches: pricing can swing quite a bit based on demand
- Use the “stay 5 nights, pay for 4” perk on award bookings to stretch your points further
- Use free night certificates and top them off with points if needed (Marriott allows top-offs up to 25k points)
Typical points per night:
53,000–76,000 points
Kauai: The Most Beautiful, Slow-Paced Option
Image from Grand Hyatt Kauai
Image from 1 Hotel Hanalei Bay
Kauai feels like stepping into a completely different version of Hawaii; one that’s slower, quieter, and even more breathtaking. It’s known as the “Garden Isle”, with lush green mountains, dramatic cliffs, and some of the most beautiful scenery you’ll ever see. There’s less hustle and fewer big resorts, which means your days naturally slow down. Instead of trying to do everything, Kauai is where you settle in, explore a little, and actually relax.
Kauai Resorts
Grand Hyatt Kauai Resort & Spa
This is one of those resorts where you could easily spend your entire trip without ever leaving. The grounds are lush and spread out, the lazy river and saltwater lagoon are perfect for kids, and there’s so much space to explore that it never feels crowded. It has that laid-back Kauai vibe and enough built-in activities to keep the whole family happy.
How to book this with points:
- Book directly through World of Hyatt and toggle “Use Points” when searching
- Look specifically for standard room availability (this unlocks the lowest point pricing)
- Use the points calendar to scan flexible dates and find lower pricing
- Use Points + Cash if you’re short on points (mix points and cash for the same stay)
- Resort fees are waived when booking with points (a big hidden savings)
Typical points per night:
35,000-45,000 points
1 Hotel Hanalei Bay
This hotel has one of the most stunning views in all of Hawaii, overlooking Hanalei Bay with mountains in the background. The vibe is more peaceful and elevated than high-energy, which makes it a better fit for families with older kids or teens. It feels less like a busy resort and more like a place to slow down, take it all in, and really appreciate how beautiful Kauai is.
How to book this with points:
This is not part of Marriott, Hilton, or Hyatt, so you can’t book it with traditional hotel points
- Book through a travel portal and use points to erase the purchase
- Book through programs like Fine Hotels + Resorts or similar luxury portals to get perks like breakfast, upgrades, and resort credits
- Use a mix of points + cash if needed (this is often the most realistic way to book it)
- Join their Mission Membership program for small perks, but it’s not a traditional points redemption system
Typical cash price:
$900–$1,800+ per night
Big Island: Best for Adventure and Unique Experiences
Image from Hilton Waikoloa Village
The Big Island feels like the most adventurous version of Hawaii. It’s bigger than all the other islands combined, which means everything feels more spread out and a little more wild. You’ve got active volcanoes, black sand beaches, lava rock landscapes, and some of the most unique experiences you won’t find anywhere else. It’s not quite as polished or resort-focused as Maui, but that’s part of what makes it special. This is the island for families who want to explore, try new things, and see a completely different side of Hawaii all in one trip.
Big Island Resorts
Hilton Waikoloa Village
The Hilton Waikoloa Village is one of the most fun and unique resorts in Hawaii for families. It’s huge. So much so that you’ll take a boat or a tram just to get around. Between the lagoons, pools, and built-in activities, it feels more like a resort and an adventure all in one, which makes it easy to keep everyone entertained without leaving the property.
How to book this with points:
Part of the Hilton Honors loyalty program. Read all about that program HERE.
- Book directly through Hilton Honors and toggle “Use Points” when searching
- Look for standard room rewards for the best value (premium rooms cost significantly more points)
- Use flexible date searches to find lower point pricing (this makes a big difference)
- Use the 5th night free on award stays if you have Hilton status
- Use free night certificates if you have them (these can work really well here)
Typical points per night:
50,000–90,000 points
Four Seasons Resort Hualalai
This property is spread out along the coastline, with beautiful pools and even a natural-feeling snorkeling lagoon where kids can see fish without leaving the resort. It’s incredibly peaceful and polished, but still welcoming for families, which makes it a perfect blend of relaxation and experience.
How to book this with points:
- Four Seasons does not have a loyalty program, so you can’t book it with hotel points like Marriott, Hilton, or Hyatt
- Book through a travel portal and use points to cover or erase the purchase
- Use “Pay with Points” through Amex Travel or similar programs to offset part or all of the stay
- Book through luxury programs like Fine Hotels + Resorts or Preferred Partner programs to get perks like breakfast, upgrades, and resort credits
- Use a mix of points + cash if needed; this is often the most realistic way to book
Typical cash price:
$1,200–$2,000+ per night
Mauna Lani, Auberge Resorts Collection
The Mauna Lani, Auberge Resorts Collection has a quieter, more relaxed feel compared to some of the larger resorts, which makes it really appealing for families who don’t want the crowds. The beach is one of the best on the Big Island for swimming, and the whole property feels easy to navigate. It’s still beautiful and upscale, but in a way that feels laid-back and approachable rather than busy or overwhelming.
How to book this with points:
This is not part of Marriott, Hilton, or Hyatt, so you can’t book it with traditional hotel points
- Book through a travel portal and use points to cover or erase the purchase
- Use “Pay with Points” options through Amex Travel or similar programs to offset part or all of your stay
- Book through luxury programs like Fine Hotels + Resorts to get perks like breakfast, upgrades, and resort credits
- Look for promos like “4th night free” or package deals when booking direct to stretch your value
- It’s often more realistic to use points plus cash with these types of resorts
Typical cash price:
$700–$1,200+ per night
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