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

Categories: Trip ReportsBy Last Updated: July 21, 2026

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

Elevated Offer - Ending Soon
Marriott Bonvoy Boundless® Credit Card
Learn How to Apply

Marriott Bonvoy Boundless® Credit Card

Earns Marriott Bonvoy Counts Toward 5/24 Keeper Card
Annual Fee $95
Welcome Offer
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bonus_miles_full

Highlights

The key benefits and earning rates at a glance.

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  • Annual Free Night Award 1 Free Night Award each year after your card account anniversary, valid at properties costing up to 35,000 points per night. Can be 'topped up' with up to 25,000 additional points from your Bonvoy account, allowing redemptions at properties costing up to 60,000 points per night.
  • Automatic Marriott Bonvoy® Silver Elite Status Automatic Silver Elite status as long as the account is open. Benefits include 10% bonus on base points (1x extra at Marriott), late checkout (subject to availability), and exclusive Member Rates.
  • 15 Elite Night Credits Annually + 1 Elite Night Credit Per $5K Spent 15 Elite Night Credits each calendar year automatically toward next status tier. Plus 1 Elite Night Credit per $5,000 spent.
  • Up to $100 Airline Statement Credits ($50 Biannually) Earn up to $100 in airline statement credits each year through 6/30/2027 — a $50 credit after spending $250 on eligible airline purchases in the first half of the year, and another $50 after spending $250 in the second half. Eligible spending includes base fares, seat selection, checked bags, and in-flight purchases charged directly by the airline. No enrollment required.

Offer History

See past welcome bonuses to gauge whether the current offer is elevated.

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Offer Spend Req. Date
125,000 Bonus Points + 1 Free Night AwardElevated $3,000 in 3 months Current as of June 2026
Up to 4 Free Nights (3 + 1 additional after $4K) + $100 Airline CreditElevated $3,000 in 3 mo + $4,000 total in 4 mo Launched March 12, 2026
5 Free Night Awards (Up to 50K Points Each)Elevated $3,000 in 3 mo Best-ever; ENDED March 11, 2026
125,000 Bonus Points + 1 Free Night AwardElevated Standard spend ENDED November 2025
3 Free Night Awards (Up to 50K Each) $3,000 in 3 mo Previous standard offer
75,000 Bonus Points Standard spend Standard baseline offer
Marriott Bonvoy Business® American Express Card
Learn How to Apply

Marriott Bonvoy Business® American Express® Card

Earns Marriott Bonvoy Keeper Card
Annual Fee $125
Welcome Offer
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bonus_miles_full

Highlights

The key benefits and earning rates at a glance.

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  • Automatic Marriott Bonvoy® Gold Elite Status Automatic Marriott Bonvoy® Gold Elite status with your Card. Earn 25% more points on every eligible hotel purchase.
  • Annual Free Night Award 1 Free Night Award annually after your Card account anniversary, with a redemption level at or under 35,000 Marriott Bonvoy® points. Plus you could top off with up to 25k more points. Certain hotels have resort fees.
  • 7% Marriott Booking Discount 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.

Offer History

See past welcome bonuses to gauge whether the current offer is elevated.

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Offer Spend Req. Date
150,000 Points + $125 Statement CreditElevated $8,000 in 6 months Ended 07/15/2026
175,000 PointsElevated $5,000 in 6 months Ended second quarter 2026
5 Free Night Awards (up to 50K each)Elevated $6K + $3K in 6 mo Ended second quarter 2026
5 Free Night Awards (up to 50K each)Elevated Ended July 2024
5 Free Night Awards (up to 50K each)Elevated Ended March 2024
3 Free Night Certificates (up to 50K each) Recurring
75,000 - 125,000 Points Typical fluctuation range

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