Family Holiday in Hawaii Using Points & Miles – Flights + Luxury Hotel Reviews

Hawaii Family Holiday with Points & Miles: Flights + Luxury Hotel Reviews

Trip Dates: 15 April – 24 April 2025

Get inspiration and pointers on flights and hotels for your next dream holiday to Hawaii!

Here's how we used points and miles to fly to Hawaii in Business Class and stayed at some of the most luxurious resorts across the islands. In this full review, we break down what we booked, how many points we used, and whether it was worth it.

Our Flights – Sydney to Honolulu Return with Hawaiian Airlines

Route: Sydney (SYD) to Honolulu (HNL) return, plus inter-island domestic flights

Class: Business for international flights and first and economy for domestic flights

Airline: Hawaiian Airlines

Points/Miles Used: 260,000 Hawaiian Miles per person for Sydney (SYD) to Honolulu (HNL) return and cash for the inter-island domestic flights. (Note: Miles required is variable and can be as low as 130,000 Hawaiian Miles per person return.)

How We Earnt These Miles: These miles were earnt by transferring 520,000 American Express Membership Rewards Points (AU) to 260,000 Hawaiian Airlines Hawaiian Miles.

Our Flight Ratings (International Only)

• Seats: 3

• Facilities: 3

• Food & Drink: 3.5

• Service: 3.5

• Value for Miles: 2

Overall: 3/5

The Good, The Bad And The Ugly (International Flights)

The Good

• Easy to find seats using Hawaiian Miles (unlike many other airline loyalty programs)

• Excellent (free!) onboard Wi-Fi

The Bad

• Cheap business class fit out

• 2:2:2 seating configuration (normally 1:2:1)

• Seats offer no privacy whatsoever

• No entertainment except through use of an iPad

The Ugly

• Very high miles required for a very poor international business class experience

Overall Impression (International Flights) 

Dated business class offering in desperate need of an upgrade, at an expensive miles price.

Want to Book Flights to Hawaii Using Fewer Points?

We flew Business Class from Sydney to Honolulu with Hawaiian Airlines, but there are many other options—some for fewer points or significantly lower out-of-pocket costs.

Here’s a snapshot of just a few Pointrs that show you how to book flights to Hawaii using fewer miles, or how to turn your airline points into serious cash savings.

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Request a Personal Pointr and we'll show you the best way to fly using your points – from the lowest rates to hidden airline routes most people miss.

Our Hotels in Hawaii – Luxury Resorts Across Three Islands

Kona Village, A Rosewood Resort (Big Island)

Kailua-Kona, Hawaii, USA

Dates: 15–18 April 2025

Hotel Chain: Rosewood

Room: Tree Top King Hale

Price: USD 1,447 per night (incl. taxes/fees)

Loyalty Program: None

Our Hotel Ratings

• Rooms: 5

• Facilities: 5

• Food and Drink: 4.5

• Service: 4

• Value for Money: 4

Overall: 4.5/5

The Good, The Bad And The Ugly

The Good

• Beautiful, modern villa room

• Room drinks on arrival

• Push-bikes to get around

• Beautiful beach that offered great snorkelling

• Excellent pool that never felt crowded, had ample lounges for all guests and was never noisy

• Plenty of onsite facilities including spa, gym, pickleball and tennis

  

• Choice of good restaurants along with Four Seasons’ hotel restaurants within easy walking distance

• Very friendly and helpful staff

The Bad

• A few missteps with housekeeping

• Restaurant served one main meal cold (quickly rectified and taken off the bill)

• Unfriendly service one morning at Kahuwai Market

• At one of the restaurants, staff used the public areas to do their paperwork at the end of the night

• Footpaths easily dirty your shoes

The Ugly

• USD 88.47 nightly resort fee

Overall Impression of Kona Village, A Rosewood Resort

A laid-back retreat offering outstanding accommodation, service and facilities in a beautiful expansive prime location.

🔗Find the Best Rates on Pointrs Travel: Book Kona Village, A Rosewood Resort Here

🔗Check out Kona Village, A Rosewood Resort Hotel Website.

1 Hotel Hanalei Bay (Kauai)

Princeville, Kauai, Hawaii, USA

Dates: 18–20 April 2025

Hotel Chain: 1 Hotels

Room: Garden View (upgraded to Ocean View)

Price: USD 1,425 per night (including any taxes and fees) Booked via American Express Fine Hotels And Resorts

Benefits: Free upgrade, breakfast for two, 4pm late checkout, $250 resort credit

Loyalty Program: Mission by 1 Hotels

Our Hotel Ratings

• Location: 4

• Rooms: 4

• Facilities: 3.5

• Food and Drink: 3.5

• Service: 3.5

• Value for Money: 3

Overall: 3.5/5

The Good, The Bad And The Ugly

The Good

• Beautiful room with great views of the pool, beach and bay

• Wrist bands for room keys

• Good service

• Great sushi

• Great drinks

• Free shaded cabanas (although extra charge for fancier cabanas)

The Bad

• Long check-in with many details taken for no apparent reason

• Contacting guest services is supposedly via text messages but didn’t receive their mobile number

• Rooms were put in the wrong names causing occasional confusion at restaurants and bars

• Noisy and crowded family pool

• Not enough chairs for everyone at the adult pool

• Some facilities are a distance from the hotel including pickleball and tennis

• Multiple elevators often required

• Patchy Wi-Fi

• Charge for snorkelling gear despite paying a resort fee

• Rooms keys didn’t work on late check-out

• Resort Fee

The Ugly

• Room being entered by a staff member without any warning, whilst in the room

• Crowing roosters around the pool area, ruining any resort ambiance

Overall Impression

A busy hotel in a lovely location, offering a myriad of activities and food options, but hampered by its cliffside location.

🔗Find the Best Rates on Pointrs Travel: Book 1 Hotel Hanalei Bay (Kauai) Here

🔗Check Out 1 Hotel Hanalei Bay (Kauai) Website

Halekulani (Honolulu, Oahu)

Honolulu, Oahu, Hawaii, USA

Dates: 20–23 April 2025

Hotel Chain: Leading Hotels of the World (LHW)

Room: Garden View (upgraded to Ocean View)

Price: USD 750 per night (including any taxes and fees) Booked through LHW Basic Membership

Benefits: Free upgrade, breakfast for two

Loyalty Program: Leaders Club

Our Hotel Ratings

• Location: 4

• Rooms: 3.5

• Facilities: 4

• Food and Drink: 4.5

• Service: 5

• Value for Money: 4

Overall: 4/5

The Good, The Bad And The Ugly

The Good

• Efficient and friendly check-in

• Good room with excellent Waikiki Beach views

• Lovely pool area

• Ample poolside chairs for all guests

• Beach area in front of the hotel

• Access to the main areas of Waikiki Beach along the foreshore

• Serene atmosphere

• Great food and drinks

• Excellent and friendly service

• No resort fee

The Bad

• Dated bathroom

• Inconsistent shower temperature

• Beach area in front of the hotel is small

The Ugly

• Nothing!

Overall Impression

A refined hotel amongst the hustle and bustle of Waikiki offering outstanding dining, service and facilities in a beautiful beachfront location.

🔗Find the Best Rates on Pointrs Travel: Book Halekulani Hotel Here

🔗Check out Halekulani Hotel Website

Final Thoughts: Is Booking Hawaii with Points Worth It?

• Flights: Yes, if you find low-mile redemptions. Otherwise, consider other programs for better value.
  Hotels: Absolutely—Hawaii is home to top-tier properties that deliver memorable stays.

• Using a combination of points, cash, loyalty perks, and booking platforms like Amex Fine Hotels & Resorts is the smartest way to balance value and luxury.

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