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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
Southwest Rapid Rewards® Priority Credit Card – Earn 50,000 bonus points
- Through 3/19 alternate link: earn Companion Pass® good through 2/28/24 plus 30,000 points after you spend $4,000 on purchases in the first 3 months from account opening.
- $149 annual fee
- $75 annual statement credit for Southwest purchases
- 4 upgraded boardings per year
- 7500 points per year on your card member anniversary
- 3x earning on Southwest flights; 2x on local transit, internet, cable, phone services, and select streaming
- 1,500 Tier Qualifying Points for every $10,000 spent
- Check your Companion Pass strategy before applying
Chase Sapphire Preferred® Card – Learn how to apply
- Earn 60,000 bonus points after you spend $4,000 on purchases in the first 3 months from account opening. That’s $750 when you redeem through Chase Ultimate Rewards®.
- $95 annual fee
- Ultimate Rewards points can be transferred to a variety of partners like Southwest, Hyatt, United, and more!
- You can also redeem points through the Chase Travel Portal. 60,000 points = $750 of travel
- Great option for booking all-inclusive resorts or hotels in Hawaii.
1 night at the Residence Inn Wailea: 63,000 Marriott Bonvoy Points
Chase Marriott Bonvoy Boundless® Credit Card
- $95 annual fee
- Earn 100,000 bonus points after you spend $3,000 on purchases in your first 3 months from your account opening
- 1 Free Night Award annually after your Card account anniversary (up to 35k)
- Earns 6 points per $1 at Bonvoy (Starwood / Marriott) properties and 2 points per $1 on everything else.
- 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.
Marriott Bonvoy Business® American Express® Card – 125,000 bonus points
- $125 annual fee (Terms Apply | Rates and Fees)
- Earn 125,000 bonus Marriott Bonvoy points after you use your new Card to make $5,000 in purchases within the first 3 months of Card Membership.
- Provides 1 free night certificate every year on account anniversary (at a hotel up to 35k points)
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Editorial Disclosure – Opinions expressed here are author’s alone, not those of any bank, credit card issuer, hotel, airline, or other entity. This content has not been reviewed, approved or otherwise endorsed by any of the entities included within the post.