How to Book a Hawaiian Vacation Using Hotel and Credit Card Points

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Now that we’re well into autumn, cold weather will begin blanketing much of the country. If that has you dreaming about a Hawaiian vacation, your hotel points and the rewards you earn using credit cards for everyday purchases can help you save on an island getaway just as Hawaii begins reopening to tourists.

Before you book anything, make sure you are aware of any developments. Check the Hawaii Department of Health website, be sure you can fulfill the prerequisites of Hawaii’s Pre-Travel Testing Program, and go over the rules of the individual islands you plan to visit. We already covered how to use airline miles and credit card points to book flights. Here, let’s take a look at some of the best accommodation options and how you can take advantage of points and credit card perks to book them.

Save on stays

There are dozens of resorts across the islands where rooms can be reserved using hotel points. Here are just a few of the top ones to consider and the credit cards that can save you a bundle on stays. Rather than going island by island, we’ve grouped these by hotel chain to make the points component easier to follow.

Hilton

Hilton Honors members are spoiled for choice when it comes to fun in the sun. The chain’s flagship Hawaiian property is the sprawling Grand Wailea, a Waldorf Astoria Resort, on Maui’s tranquil west coast. Guests can take advantage of plenty of kids’ activities, not to mention the expansive Wailea Canyon Activity Pool, with waterslides, rapids, and even a ropes course. You can find nights here and there from January to August starting at 95,000 points each. That’s a lot, but it beats paying rates of over $700 per night.

If you prefer the rugged Kona coast on the Island of Hawaii itself, the Hilton Waikoloa Village is a solid choice with easy access to plenty of water- and land-based activities. Throughout this winter and spring, rooms are running at around 60,000 points per night, or $250. For a more self-catering style of stay in the same area, you could also book Hilton Grand Vacations properties such as Kings’ Land by Hilton Grand Vacations and Ocean Tower by Hilton Grand Vacations for rates that are running at between 90,000–100,000 points per night for the next several months.

Stocking up on Hilton Honors points

There are currently two incredible credit card offers to help you boost your Hilton Honors points balance relatively quickly.

The Hilton Honors American Express Aspire Card: Right now, you can earn 150,000 Hilton Honors bonus points after using your new card to make $4,000 in purchases within the first three months of card membership (terms apply). The Aspire comes with automatic top-tier Hilton Honors Diamond elite status with advantages like the highest priority for upgrades, complimentary breakfast during stays at most full-service properties, and earning double the points on stays as a regular member. Here’s why else you should consider the card.

• Earn 14 points per dollar at participating Hilton hotels and resorts
• Earn seven points per dollar on flights booked directly with airlines or via Amex Travel, on car rentals booked from select rental companies, and at U.S. restaurants
• Earn three points per dollar on everything else
• Each year upon renewal, get a free weekend night certificate redeemable at almost any Hilton property around the world, which can be worth several hundred dollars depending on where you spend it
• Cardholders receive up to $250 in statement credits each year toward purchases at Hilton Resorts (like those in Hawaii) such as restaurant and spa tabs
• Get up to another $250 in statement credits toward qualifying airline incidental fees, such as lounge passes or checked bags (enrollment required)
• The annual fee is $450 (see rates and fees)

The Hilton Honors American Express Surpass® Card: If that’s too steep, this card has an annual fee of just $95 (see rates and fees). But it still packs in the perks. You can earn 130,000 Hilton Honors bonus points after spending $2,000 in purchases on the card within the first three months of card membership plus an additional 50,000 points after spending $10,000 total on purchases in the first six months (terms apply).

• Rack up 12 points per dollar on eligible Hilton charges
• Earn six points per dollar at U.S. restaurants, U.S. supermarkets, and U.S. gas stations
• Get three per dollar on everything else
• Cardholders enjoy complimentary Gold elite status with perks like space-available upgrades, late check-out priority, and even complimentary continental breakfast at most of Hilton’s higher-end properties
• They also get 10 Priority Pass lounge passes each year to make passing time at the airport more pleasant

Photo by MH Anderson Photography / Shutterstock

Hyatt

Hyatt has a handful of great properties across the islands with plenty of award availability from November onwards. If you’re craving the cosmopolitan vibe of Honolulu, the Hyatt Regency Waikiki Beach Resort and Spa has rooms for just 20,000 points per night or $248 this winter and spring. For something a bit calmer, you could opt for the Grand Hyatt Kauai Resort and Spa along the so-called Garden Island’s sunny southern coast. Room rates this winter and spring start at around $460 on average, but you can also book them for just 25,000 points apiece. Finally, the chic Andaz Maui at Wailea Resort proffers award rates that start at 30,000 points per night, while standard paid rates are a jaw-dropping $739 and up this January to August. If that sounds like a lot of money, or points, the minimalist rooms and multi-level pools overlooking the dramatic coast might make a redemption or paid stay worth it.

Stocking up on World of Hyatt points

Chase Ultimate Rewards points transfer to World of Hyatt at a 1:1 rate, so you can always top up your hotel loyalty account if you have points from the Chase Sapphire Preferred® Card or Chase Sapphire Reserve®. Otherwise, you could consider carrying Hyatt’s main cobranded credit card.

The World of Hyatt Credit Card: New applicants can currently earn up to 60,000 bonus points: 30,000 after spending $3,000 in the first three months of account opening, and up to 30,000 more bonus points with two bonus points per dollar spent on purchases that earn one bonus point up to $15,000 in the first 6 months of account opening. Here’s more information on the card:

• Earn up to nine bonus points per dollar spent at Hyatt hotels (four bonus points plus the five base points World of Hyatt members already earn)
• Earn two points per dollar spent at restaurants, on airline tickets purchased directly from airlines, on local transit and commuting, and on fitness and gym memberships
• Earn one point per dollar on everything else
• Receive one free night certificate redeemable at Category 1–4 Hyatt hotels and resorts (so it’s worth up to 15,000 points per night) after every cardholder anniversary
• Get automatic Hyatt Discoverist elite status, with benefits like premium internet during stays, upgrades and late checkout depending on availability, and bonus points-earning opportunities
• The annual fee is $95

Marriott

As you might expect, the largest hotel chain in the world fields numerous properties throughout Hawaii, but concentrate on the one or two that most intrigue you. Book a few nights at the famed Pink Palace of the Pacific, Waikiki’s historic Royal Hawaiian, a Luxury Collection Resort Waikiki. Room rates there average around $350 per night, or between 50,000–70,000 points. The lush gardens and festive luau are added bonuses.

Over on the Big Island is an icon of another era, the Mauna Kea Beach Hotel, Autograph Collection, the most expensive hotel ever built when it opened in 1965. Perched above a crescent-shaped cove along the Kona coast, rooms here also cost 50,000–70,000 points per night thanks to Marriott’s variable pricing, though there is plenty of availability from January to September 2021 at the lower end of that range. Paid rates are running around $650–$700 per night. On Kauai, the Westin Princeville Ocean Resort Villas is near some of that island’s best golf courses and the spectacular scenery of Hanalei Bay. Rates there from January onward are running upwards of $350 per night for the next several months, but you can also snag nights for 50,000–70,000 points each.

Stocking up on Marriott Bonvoy points

Both American Express Membership Rewards points and Chase Ultimate Rewards points transfer to Marriott, but you could also consider getting one of these cobranded cards, both of which are fielding incredible limited-time welcome offers.

Marriott Bonvoy Boundless® Credit Card: This card is currently offering 125,000 bonus points and a bonus award night worth up to 50,000 points after spending $5,000 on purchases within the first three months.

• Earn six points per dollar on purchases made at participating hotels
• Earn two points per dollar on everything else
• Cardholders receive 15 elite night credits per calendar year, enough to enjoy Marriott Bonvoy Silver status
• The annual fee is $95

Marriott Bonvoy Brilliant® American Express® Card: If you want a more premium product, this card’s annual fee is $450 (see rates and fees), but it confers a plethora of perks. Now through November 3, 2021, it is offering new members up to 150,000 bonus points plus a free night award worth up to 85,000 points after making $5,000 in eligible purchases in the first three months (terms apply).

The Marriott Bonvoy Brilliant American Express Card’s benefits include:

• Six points per dollar on purchases at Marriott hotels, three points per dollar at U.S. restaurants and on flights booked directly with airlines, and two points per dollar on everything else
• Up to $300 in statement credits each year of card membership for eligible purchases at hotels participating in the Marriott Bonvoy program, plus a free night award each year worth up to 50,000 points
• When you use your card to book an eligible rate for stays of two nights or more at Ritz-Carlton or St. Regis properties, you also receive up to $100 in credit for qualifying charges, like meals or activities, and you can enroll for Priority Pass Select
• Cardholders also get up to $100 in statement credits toward a Global Entry application once every 4 years, or up to $85 toward TSA PreCheck once every 4.5 years

Vacation rentals

If you’d rather skip the full-service hotels and book a condo or timeshare, you can also use your points to do so. The major hotel loyalty programs incorporate ownership properties, some of which you can redeem points for. However, you can also cash in certain credit card points directly for vacation rentals.

For instance, via the Chase travel portal, you can redeem Ultimate Rewards points for rentals at a fixed rate. If you have the Chase Sapphire Preferred, points are worth 1.25 cents apiece, and if you have the Chase Sapphire Reserve, they’re worth 1.5 cents. So if you book a stay for $300 per night, you’d only need 20,000 points per night with the Reserve. Citi’s ThankYou Rewards portal also has an option for redeeming points for vacation rentals.

If you have the Capital One® Venture® Rewards Credit Card or the Capital One® VentureOne® Rewards Credit Card, you can use your card to pay for your stay and then redeem your miles for statement credits toward the bill afterwards at a rate of one cent per mile. So a $1,000 stay would cost 100,000 miles. Otherwise, you could consider just using a cash-back card like the Blue Cash Preferred® Card from American Express (see rates and fees) to earn Rewards Dollars that you can then redeem as statement credit at a later date.

There are many hotel and vacation rental options, so the possibilities for using points and miles to book your island vacation are practically infinite. Rather than getting overwhelmed by the possibilities, though, think about the types of hotel points you have and the credit cards you carry. Then focus on the choices that you can maximize, either through sheer value, or through extra perks that will help you enjoy your getaway even more.

While the offers mentioned above are accurate at the time of publication, they are subject to change at any time, and may have changed or may no longer be available. This article was originally published on October 27, 2020, and was updated on October 29, 2020, and again on October 1, 2021.