
Wailea-Makena Cheap Holidays
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
Top flight + Cheap hotel deals in Wailea-Makena
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 4 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 4 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 4 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

Ho‘olei Villas at Grand Wailea
Wailea
Save 100% on your flight
Price was NZ$19,124, price is now NZ$16,060 per person
NZ$16,060
per person
14 Nov - 21 Nov
found 4 hours ago
Return direct flight included
Auckland (AKL) to Kahului (OGG)
9.6/10 Exceptional! (42 reviews)
Perfect for Families. Quite spacious and great for a relaxing Family vacation.
Reviewed on 15 June 2025

Don't see what you're looking for?
See all available trips from Columbus to Wailea-Makena
View all trips5* Cheap holidays in Wailea-Makena
Price found within the past 48 hours. Click for updated prices.

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 4 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

Ho‘olei Villas at Grand Wailea
Wailea
Save 100% on your flight
Price was NZ$19,124, price is now NZ$16,060 per person
NZ$16,060
per person
14 Nov - 21 Nov
found 4 hours ago
Return direct flight included
Auckland (AKL) to Kahului (OGG)
9.6/10 Exceptional! (42 reviews)
Perfect for Families. Quite spacious and great for a relaxing Family vacation.
Reviewed on 15 June 2025

Grand Wailea Maui, A Waldorf Astoria Resort
Wailea
Price was NZ$8,465, price is now NZ$7,250 per person
NZ$7,250
per person
14 Nov - 21 Nov
found 4 hours ago
Return direct flight included
Auckland (AKL) to Kahului (OGG)
8.8/10 Excellent! (1,008 reviews)
Excellent property, beautiful rooms, very clean rooms and property, the beach is excellent with nice clear water year round, staff is very attentive, food is first class, very safe, property is kept in excellent shape, pools are nice and clean, the gardens are always clean and nicely manicured, loved the fish ponds around the rooms, excellent experience, highly recommended property.
Reviewed on 6 Oct 2025
Don't see what you're looking for?
See all available trips from Columbus to Wailea-Makena
View all trips* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.