Reader Success Story: Oahu and Maui as a Family of 6

Categories: Trip ReportsBy Last Updated: October 29, 2023

Thanks to Lindsay (@vandytravel) for sharing her miles and points story with us! For this trip, Lindsay flew her family of 6 to Hawaii for $67 (taxes) and stayed on Maui (on points) and Oahu. Read how she used her points and leveraged a timeshare presentation to make this trip more affordable. She estimates savings of $2500+ using miles and points on this trip!

We recently returned from a trip to Hawaii in January 2023.

We used Southwest Points (transferred from Chase) to book 6 economy flights from Las Vegas to Honolulu for 120k points total roundtrip.

We decided to go on an inter-island flight (also on Southwest) to Maui for 1 night and used 25k points total for 6 people.

We stayed in the Residence Inn Wailea in Maui and it was gorgeous! We paid with Marriott points  (63K) and got upgraded to a 2-bedroom suite with my husband’s Marriott status.

The hotel offers free breakfast but we went whale-watching early in the morning so we did not take advantage of that. We came back and swam and took advantage of all the amenities of the hotel and explored the island while we waited for our flight back to HNL that night.

We stayed at the beautiful Marriott Ko’Olina Resort in Honolulu at a timeshare vacation rental for the remaining six nights of our stay.

We saved on a rental car by continuously checking Costco Travel and from monitoring it, we were able to save $200 off the initial quoted price.

We paid for rental car, food, and activities out of pocket but made this vacation very affordable for our family of 6!

Timeshare deal

We had stayed at the Marriott Ko’Olina before in 2020 and were asked while we were there if we wanted to do a timeshare presentation in exchange for an incentive. We opted to do that, got the incentive (but did not buy the timeshare) and opted to purchase their bounce-back opportunity at $1,000 for a 6 night stay in the next few years.

When it got closer to booking, we called and upgraded to a one-bedroom unit which comfortably sleeps my family of 6 (even though the rooms sleep 4). Since my kids are still little, they did not seem worried about that idea. The cost was $400 more to upgrade.

We did the timeshare presentation while we were there in January, and again, did not purchase the timeshare, and this time their offerings were way more expensive than I knew we could stay elsewhere so we declined. However, a few weeks later I did get an offer in my email for more affordable options to other Marriott properties which we are considering.

Marriott timeshares have always been respectful and nice and even if we decline we are still treated with kindness. Plus, the quality of Marriott Vacation Clubs is always stellar and consistent so even if you decide to buy in, you won’t be disappointed with the level of service and facilities.

Miles and points Lindsay used for her trip

Roundtrip flights Las Vegas to Honolulu, Honolulu to Kahului: 145,000 Rapid Rewards

1 night at the Residence Inn Wailea: 63,000 Marriott Bonvoy Points

Current Bonus:

Earn 3 free night awards

Earn 3 Free Night Awards (each night valued up to 50,000 points) after you spend $3,000 on purchases in your first 3 months from your account opening.

Annual Fee:

$95

(Terms Apply)

  • Earn up to 17X total points per $1 spent at thousands of hotels participating in Marriott Bonvoy® with the Marriott Bonvoy Boundless® Card.
  • Earn 3X Bonvoy points per $1 on the first $6,000 spent in combined purchases each year on grocery stores, gas stations, and dining.
  • 1 Free Night Award annually after your Card account anniversary (up to 35k)
  • After holding this card for 1 year, you can upgrade to the Ritz Carlton card, which is one option for families to get airport lounge access.

If you like Marriott, this is a solid card to get and then hold on to — we find that the annual free night is easy to redeem at hotels that cost $250+ per night. That’s a half price hotel! Some people prefer the welcome bonus that includes certificates for up to 50k per night, but keep in mind these expire within a year of earning so you need to have a redemption in mind. Check out my map of family friendly Marriotts for inspiration.

Bonus fluctuates from 75,000 bonus points and up. Sometimes the bonus is 3 or 5 free night certificates for up to 50k per night. Note that personal referral offers often don’t match the best available offer.

welcome offer:

3 free night awards (up to 50k each)

Go > Limited Time Offer: Earn three Free Night Awards after you use your new Card to make $6,000 in eligible purchases within the first 6 months of Card Membership. Redemption level up to 50,000 Marriott Bonvoy® points for each bonus Free Night Award, at hotels participating in Marriott Bonvoy®. Certain hotels have resort fees. Offer

Annual Fee:

$125

(Terms Apply | Rates and Fees)

  • 6x Marriott Bonvoy points on each dollar of eligible purchases at hotels participating in the Marriott Bonvoy® program.
  • 4x points for purchases made at restaurants worldwide, at U.S. gas stations, on wireless telephone services purchased directly from U.S. service providers and on U.S. purchases for shipping.
  • Receive 1 Free Night Award every year after your Card renewal month. Plus, earn an additional Free Night Award after you spend $60K in purchases on your Card in a calendar year. Award can be used for one night (redemption level at or under 35,000 Marriott Bonvoy® points) at hotels participating in Marriott Bonvoy®. Certain hotels have resort fees.
  • Enjoy Complimentary Marriott Bonvoy Gold Elite Status with your Card
  • Receive a 7% discount on eligible bookings as a benefit of being both a Marriott Bonvoy® member & a Marriott Bonvoy Business® American Express® Card Member when you book directly with Marriott through an eligible channel for a participating property under the Amex Business Card Rate.

If you like Marriott, this is a solid card to get and then hold on to — we find that the annual free night is easy to redeem at hotels that cost $250+ per night. That’s a half price hotel! Some people prefer the welcome bonus that includes certificates for up to 50k per night, but keep in mind these expire within a year of earning so you need to have a redemption in mind. Check out my map of family friendly Marriotts for inspiration.

Bonus fluctuates from 75,000 bonus points to 125,000 points. Sometimes the bonus is 3 free night certificates for up to 50k per night – highest ever was 5 free nights (up to 50k and ended 3/21/24). Note that personal referral offers often don’t match the best available offer.

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