If you’ve booked your Southwest flight to Hawaii or are planning to in the coming months, your next step will be to figure out where you will stay.
My family saves more than $8,000 every year flying free using travel rewards, and I can show your family how to make flying free a LIFESTYLE too! Join my Families Fly Free program -- where flying free is GUARANTEED -- to learn my simple Fly Free Process, so you can start making more priceless travel memories with your family. Learn more below…
If you’re traveling with a family or friends and want to save money on food costs, you might want to book a gorgeous Vrbo vacation rental, or save money by using points to book Hawaii hotels and splurge a little on your meals.
Our team has compiled some great options to consider on Maui, Oahu and Kauai if you’re looking to book a hotel using points.
We’ve got options from the Hilton, Marriott, Hyatt and IHG portfolios.
To review or apply for any of the cards in this post, please use the links within this post or the CREDIT CARDS links in the main menu above (shown in the image below). This allows us to earn a commission—at no cost to you—to support our small business. Thanks so much for taking that step!
6 Outstanding Hawaii Hotels to Book Using Points
1. Grand Wailea Maui, a Waldorf Astoria Resort by Hilton
Maui is one of the most beautiful of the Hawaiian Islands, and both Cami and Stephanie have stayed at this resort, so it comes highly recommended.
In its former days it was known as the Hyatt Regency Maui Resort and Spa (which is the name of a resort in Lahaina, currently), but is now the Grand Wailea Maui, a Waldorf Astoria Resort.
Sitting oceanside, this resort is located on 40 meticulously landscaped acres in the Wailea area of Maui (south shore).
Replete with waterfalls, ponds, flowers and plants galore, you’ll want to take a picture at every turn.
It’s like a veritable fairy tale!
On the grounds, you’ll also find seven bars and restaurants, including the fine-dining HUMUHUMU.
If you can score an oceanside table, you’ll be privy to a magnificent Maui sunset.
Don’t forget to order their Humu pie, as it’s quite delicious and enough for two!
At the Grand Wailea, you’ll enjoy your day to the full with nine pools, numerous water slides, a lazy river, Tarzan rope swing and the world’s only water elevator.
Built for the former owner’s handicapped son at a cost of $1.2 million, you’ll never see or experience anything like it!
Oh, wait, we forgot to mention the 800 clean, well-equipped and spacious rooms, each with its own private lanai (a Hawaiian word for “balcony” ;-)). It’s truly paradise…
A room here goes for a minimum of 95,000 Hilton Honors points (room rates from $736), but is TOTALLY worth it for at least one night.
If you are staying a total of five nights or more booked with points, you’ll get the fifth night free!!
Gold members and higher receive two water bottles, no resort fees, a late check-out and a continental breakfast plate for everyone in their room.
Cami arrived at 10 a.m. in her swimsuit, checked her luggage and was able to get a wristband to enjoy a whole day of fun in the sun.
Even after checking out, you can keep your wristband for the entire day!
Check out their fun waterslide!
2. Sheraton Maui Resort & Spa, a Marriott hotel
Another great hotel in Maui is the Sheraton Maui Resort & Spa.
This is a Marriott Bonvoy Category 6 property, which means it costs 50,000 points per night (room rates from $566) to book.
However, if you can save 200,000 points for four nights, you get the 5th night FREE.
This is a reasonable mid-range hotel for Maui and has more than 500 rooms, each with its own lanai.
Note: Marriott doesn’t waive resort fees for rooms booked with points. This hotel charges a resort fee of $30 plus tax per night.
The hotel features a torch-lighting ceremony complete with conch shell blowing and cliff-diving sunset ceremony.
If you’re brave, you can also cliff dive or jump right from the rocks!
The beach here is the perfect place to walk right into the water on a sandy bottom and snorkel to your heart’s content.
Cami saw a turtle, a school of thousands of fish, an eel and various tropical fish just from the beach out to the end of Black Rock.
In addition to the Marriott cards, Chase Ultimate Rewards points (mentioned above) ALSO transfer to Marriott Bonvoy at a 1:1 ratio if you need more points to book your stay and a card like Chase Sapphire Preferred, Lyn’s FAVORITE travel credit card (read her full review), is a great way to earn a 60,000-point bonus that you can use to book a room here.
Check out a view of a room in the video below…
3. Grand Hyatt Kauai Resort & Spa
The Grand Hyatt Kauai Resort & Spa is a beachfront resort on the island of Kauai with classic Hawaiian guest rooms each with its own balcony or lanai (this definitely seems standard in Hawaii).
The property has an award-winning restaurant, spa and pools with waterfalls, lazy river, water slide and seating nooks.
If you’d rather be in the ocean, Keoneloa Bay/Shipwreck Beach’s white sand is close by.
Nancy says her family uses the World of Hyatt rewards program frequently to book free hotel rooms.
HOT TIP: The daily Resort Fee of $35, which can add up quickly, is waived when you book with World of Hyatt award points (but not the points + cash options)!
4. Sheraton Princess Kaiulani, Part of the Marriott family
The Sheraton Princess Kaiulani hotel on Oahu sits only one block from Waikiki Beach, as well as shopping and dining in the heart of Honolulu.
The hotel has a freshwater pool, poolside bar and cabanas, a Hawaiian-inspired restaurant and an evening Polynesian Dinner Show, which is definitely something you should experience when in Hawaii!
This is another property that would allow you to use Marriott Bonvoy points for a stay.
A free night at the Sheraton Princess Kaiulani is 35,000 Marriott Bonvoy points (room rates from $245), though depending on peak or off-peak seasons, points can be lower and higher.
Again, take advantage of the great perk with Marriott Bonvoy to redeem four nights and get the fifth night FREE!
So for a total of 140,00 points, you could spend five nights at the Sheraton Princess Kaiulani.
There is also a daily resort fee of $33 plus tax, which you will have to pay.
You can also book and pay for your room by combining cash and points, if you don’t have enough points, to help save on your Hawaiian vacation.
5. Holiday Inn Express Waikiki, an IHG hotel
Another affordable points option on Oahu is the Holiday Inn Express Waikiki, which is actually the largest Holiday Inn Express in the Americas with almost 600 rooms and standing at 44 stories.
The property opened in 2017 and has a more modern design with a communal work space, more charging options.
On the fifth floor, there is an amazing Sky Deck with games like giant chess, mini golf, a video game room, shuffleboard, foosball and ping pong, and the hotel also has an outdoor pool and fitness center.
The hotel is only three blocks from Waikiki Beach, two blocks from Luxury Row shopping and four blocks from the Hawaii Convention Center, and it comes with free breakfast, which is one of Cami’s suggestions in her 10 Hacks to Save BIG Money on Your Hawaii Vacation post.
Hawaii can be expensive, so having a free full breakfast every morning is a great savings!
You can book the Holiday Inn Express Waikiki for 35,000 points per night (room rates from $223).
Rooms come with one or two beds, but unfortunately when booking with points, you don’t get to choose (though you can make a request); you sort of get what you get, which is not ideal.
To book the property you can transfer Chase Ultimate Rewards points to IHG Rewards (the loyalty program for Holiday Inn Express) or open an IHG credit card like the IHG Rewards Club Premier card. [Read about BOTH IHG credit card options]
Cardholders of the Premier card also get a FREE fourth night when you book three award nights, and you also get a free night to use each year after your account’s yearly anniversary.
Note: This card also counts toward the Chase 5/24 rule.
6. Ritz Carlton Kapalua, a Marriott resort
If you want a truly isolated destination, consider the five-star luxury Ritz Carlton Kapalua?
This hotel sits in the far northwest part of Maui nestled on 54 private acres. With six restaurants and bars, you won’t even have to leave the resort.
Don’t miss their Burger Shack, famous for their shakes and with views to the beach!
Indulge yourself at the spa, enjoy the many pools, tee off at the two golf courses, head down to the secluded beach, or play bocce ball, tennis or pickleball.
If that’s not enough, walk the Kapalua trail along the coast where you might happen upon a sea turtle, a rainbow, cliff divers or Dragon’s Teeth.
This jagged coastline was formed when one of Maui’s last volcanic eruptions hit the wind and waves at the coastline and is almost on Ritz Carlton property.
Be respectful of the ancient Hawaiian burial ground here, known as Honokahua, discovered when the hotel began developing the property.
You can book the Ritz Carlton for 85,000 Marriott Rewards points per night (room rates start at $965 per night), remembering that your resort fee will not be waived but you can take advantage of the great perk with Marriott Bonvoy to redeem four nights and get the fifth night FREE!
Will you choose any of these Hawaii hotels to book with points for your Hawaiian vacation?
- 10 Hacks to Save BIG Money in Hawaii
- How My Family is Planning a Trip to Hawaii on Southwest
- 11 Things You Need to Know About Southwest Hawaii Flights
- 19 Incredible Not-to-Miss Things to do in Hawaii
- What’s It Like to Fly to Hawaii on Southwest Airlines
Thanks again for using the TRAVEL CREDIT CARDS links or the links within this post for your credit card applications!