Spending ten days in Maui on points and miles is the ultimate travel dream come true—especially for a multigenerational trip! From a luxury beachfront resort on Ka’anapali Beach to the luxury of the Wailea area, our family, spanning grandparents, parents, and four rambunctious boys, experienced paradise together without draining our bank accounts. Using a mix of airline miles, hotel loyalty points, a timeshare presentation, and some cash, we turned what could have been an expensive group vacation into a nearly free, memory-filled adventure. 

It all started with Alex receiving a mailer for a timeshare presentation offer to The Westin Nanea Ocean Villas, Ka’anapali. They offered her a two-bedroom villa for five days for $1,999. Of course, that involved enduring a timeshare presentation. 🥴 More on that later. You can also book that property with points for approximately 128,000 Marriott Bonvoy® points per night.

 

Flights to Maui

Alex’s family of six flew to Maui for 46K points round-trip per person. Because she has two Southwest® Companion Passes, she only paid for four people. Unfortunately, Alex’s route was not ideal as it was a two-connection flight—which is not what she is usually able to find to get to Hawaii. 

We paid cash for our flights from Denver on United. Because I have elite status with United, I buy an economy seat but am able to book an Economy Plus seat. Because I need to fly a lot of segments and spend a substantial amount on United flights each year so I can maintain my platinum status, I always pay for my United domestic flights. But I could have used United MileagePlus miles for them at about 25,000 miles each way. 

 

Car Rentals

I booked a small SUV through Costco for $579, which came out to about $57/day, which I thought was great. However, Alex did even better working through a local company, Makoa Rental Car Maui, and rented a van at $371 for 7 nights. That was $53 a day and included two chairs.

 

First Stop: Westin Nanea Ocean Villas, Ka’anapali

We spent five days at The Westin Nanea Ocean Villas in Ka’anapali. This resort provided a great stay, featuring a large pool area, ample seating, a children’s area with a slide, a small water park, and numerous barbecue grills for grilling dinner.

We had a two-bedroom villa, so the adults had their own bedrooms and large bathrooms. Three of the boys slept comfortably on the large sofa, and Noah, surprisingly, chose to sleep every night in a portable crib that was left in our room. We were shocked that he chose this experience, but it worked out great!

 

 

 

There was even a washer and dryer in the unit, which was really nice since my husband and I were going over to Kauai after this trip. We could pack lighter, knowing that we could wash clothes. The rooms were also serviced every other day, so we enjoyed the clean towels and clean rooms. 

 

 

 

The Kitchen Area

Having a kitchen area (and a grill outside) made the trip so affordable. We could cook breakfast, lunch, and dinner as often as we wanted without always having to choose a restaurant meal. There was a large table in the center of the kitchen area, as well as another table on the patio, so we had plenty of room. A small pantry allowed us to store our food, and we enjoyed eating homemade meals for the first five days, knowing that the last few nights would be spent eating out, which would be more expensive. 

We all enjoyed the resort and wouldn’t hesitate to return. However, 128K Marriott Bonvoy® points per night is a hefty spend.

 

 

 

Timeshare Presentation

Alex and Mitch met in the lobby of the resort for their 90-minute timeshare presentation. They were shuttled over to the Westin Ocean Villas for their presentation. Remember, they saved $3,000 to attend this presentation. How torturous was it, though? (I know how bad they can be; I’ve gone through some bad ones!)

Their presentation wasn’t too bad, and they were done in two hours. After going through three people, the reps finally realized that Alex knew travel deals and wasn’t buying in. One person even took down the information for TMS so she could learn more about points and miles!😜

At the end of the presentation, they offered her the chance to stay in a one-bedroom Westin at another location for approximately $2,000. She took them up on it with plans to try the Westin Princeville in Kauai. This means another timeshare presentation, but she’s up for it. I guess if we want to go on that trip, we need to find a similar deal!

 

Next Stop: Andaz Maui

The Andaz Maui is a hotel that our readers love, but Alex and I hadn’t stayed at it yet. We chose to stay there two nights after our visit in the Ka’anapali area.  Jess has stayed there before and loved it. It is a Category 8 hotel, and we used 40,000 points per night to stay there, with the cash rate being around $800 per night. 

 

 

Alex and family were there with us for two nights, and we stayed an additional night before moving for two nights to the Marriott Wailea Beach Resort. Both of these hotels were booked with points or free-night certificates.

Unfortunately, we did not get an upgrade at this hotel. Our garden-view standard rooms featured two queen beds and were quite spacious, complete with a good-sized bathroom. Because it was an Andaz, we found daily treats in our free minibar area. This hotel had Hawaiian cookies, Maui chips, and a couple of drinks in the mini-fridge. 

 

 

 

 

As a welcome gift, we had some gummy candy, dark chocolate, and chocolate chip cookies waiting in the room.  They also provided refillable aluminum water bottles and a small tote.

 

 

 

 

Globalist Amenities

As Globalists, the breakfast buffet at the Andaz in the Ka’ana Kitchen was complimentary. The normal cost is $49 per person and $24.50 for children. We saved a ton as Globalists. It was extensive and included made-to-order eggs and omelettes.

Valet parking was also included as a Globalist benefit, and it usually costs $59. Our group of eight saved $588 on breakfasts (which were overpriced) and more than $200 on parking with those Globalist benefits over the two days we were there.

 

Last Stop: Marriott Wailea Beach Resort

I used two 85K free-night certificates for the Marriott Wailea Beach Resort. One came from my Marriott Bonvoy Brilliant® American Express® Card and one from my Ritz-Carlton™ card (which is available only as through a product change). This hotel would cost about $800 per night to book as a cash stay. As a Marriott Bonvoy® Platinum Elite member, I receive a bonus of five Nightly Upgrade Awards every year. I applied one to each of these nights in hopes of getting a suite. 

We were lucky and did get upgraded to a suite! There was ample space, including a full bathroom and a half-bathroom. Yes, we had to pay a $57 resort fee and $45 for parking, but it was totally worth it.  This is the perfect spot for a chill vibe, peace, and relaxation—ideal for couples, although there is also a family pool. No crazy music by the adults’ pool, just serene Hawaiian melodies!

 

 

 

 

 

 

 

Activities in Maui

• Twin Falls Hike – suitable for families. Noah went and loved it! $10 per car for parking.
• Ho’okipa Beach – Head to the far left for the most amazing view of huge sea turtles sunning in the sand!
• D.T. Fleming Beach – Boogie boarding and body surfing!
• Dinner at food trucks in Kihei – try the shave ice at Da Sweet Stuff and thank me later!
• Snorkeling – We love the good snorkeling from Ka’anapali beach.
• Pool and beach days everywhere, along with açai bowls and shave ice!

 

 

Bottom Line

Our ten days in Maui on points and miles were more than just a vacation—they were filled with laughter, relaxation, and plenty of beach time. And it was made even sweeter by the fact that we were able to save so much money using points and miles for flights and lodging. From watching sunsets together on the beach to digging in the sand with little Noah, we created lasting memories without the financial stress that often comes with group travel. With a bit of planning, the right credit card strategy, and some flexibility, we proved that a dream trip to paradise can be both luxurious and affordable for the whole family.

 

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