Kailua Holidays from NZ$2,452
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
Better together
Save up to NZ$616 when you book a flight and hotel together*
Find the right fit
With over 300,000 hotels worldwide, it's easy to create a perfect package
Rest easy
Plan, book, and manage your trip all in one place
The Latest Kailua Holiday Deals
Price found within the past 48 hours. Click for updated prices.
Royal Lahaina Resort & Bungalows
Save 100% on your flight
Price was NZ$4,231, price is now NZ$2,529 per person
NZ$2,529
per person
14 Nov - 21 Nov
found 17 hours ago
Return direct flight included
Auckland (AKL) to Kahului (OGG)
8.4/10 Very Good! (1,448 reviews)
Everything about this resort was beautiful. My husband and I had the pleasure of staying in one of the ocean front bungalows for our honeymoon in September 2025. From the time we arrived we knew this would be an experience we could remember forever. The beach and pools were steps away from our room and we even saw dolphins from the shore. An unforgettable experience. Cleanliness was top tier and the staff was beyond friendly and accommodating. We didn’t care for the restaurant, it was expensive and the food wasn’t the greatest, but Whalers Village is a short distance via resort-provided trolley and we ended up going there most nights. Overall, we would highly recommend this resort, you won’t be disappointed!
Reviewed on 5 Oct 2025
The Whaler Resort Kaanapali Beach
Save 100% on your flight
Price was NZ$4,846, price is now NZ$3,010 per person
NZ$3,010
per person
14 Nov - 21 Nov
found 17 hours ago
Return direct flight included
Auckland (AKL) to Kahului (OGG)
9.6/10 Exceptional! (237 reviews)
It's right on the main tourist area of kaanapali beach with lots of shopping and dining right outside and great access to the beach and great views of the sunset from the oceanview rooms. I appreciated having a full kitchen and not needing to pay resort fees for extras that I would not use.
Reviewed on 6 Oct 2025
Hotel Wailea, Relais & Chateaux - Adults Only
Wailea
Save 100% on your flight
Price was NZ$9,598, price is now NZ$6,716 per person
NZ$6,716
per person
14 Nov - 21 Nov
found 17 hours ago
Return direct flight included
Auckland (AKL) to Kahului (OGG)
9.4/10 Exceptional! (1,001 reviews)
Great resort with great amenities! Very convenient to downtown wailea and the beaches and the staff are super friendly and attentive!
Reviewed on 27 Aug 2025
Kailua Holiday
Our pick of the best Kailua Hotel Deals
Maui Seaside Hotel
100 W Kaahumanu Ave, Kahului, HI
Fully refundableReserve now, pay when you stay
The price is NZ$469 per night from 20 Oct to 21 Oct
NZ$469
20 Oct - 21 Oct
includes taxes & fees
8.8/10 Excellent! (1,179 reviews)
"They are in the process of renovating and initially I was placed in a king bed pool side room which had not been renovated. It was terrible and reminded me of a tiny cheap nasty motel room which had numerous issues. As a result they upgraded me free of charge to a renovated room which was like night ..."
Reviewed on 1 Oct 2025
Hilton Grand Vacations Club Maui Bay Villas
575 S Kihei Road, Kihei, HI
The price is NZ$706 per night from 8 Oct to 9 Oct
NZ$706
8 Oct - 9 Oct
includes taxes & fees
9/10 Wonderful! (199 reviews)
"Oven front views and I would highly recommend it to families with kids or just adults trying to have time alone"
Reviewed on 29 Sept 2025
Maui Beach Hotel
170 W Kaahumanu Avenue, Kahului, HI
Fully refundableReserve now, pay when you stay
The price is NZ$417 per night from 12 Oct to 13 Oct
NZ$417
12 Oct - 13 Oct
includes taxes & fees
7.2/10 Good! (1,090 reviews)
"I liked the location of the property. The staff was friendly"
Reviewed on 30 Sept 2025
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Discover the most popular places to visit in Kailua
Twin Falls
Commune with nature and explore the great outdoors at Twin Falls during your travels in Haiku. While you're in the area, stroll along the beautiful beaches.
Haiku Park
Explore the great outdoors at Haiku Park, a lovely green space in Pauwela. Wander the area's beautiful beaches or simply enjoy one of its top-notch restaurants.
What to do in Kailua
Maui Zipline Eco Adventure: 8 Lines through the Jungle
NZ$280
per adult
100% of travellers recommend
Orchid Airport Lei Greeting (Maui, Kahului Airport, OGG)
NZ$81
per adult
100% of travellers recommend
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
