Wailea-Makena Luxury Vacations
Book a Luxury Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
Better together
Save up to ￥45,448 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 Luxury vacation packages in Wailea-Makena
Price found within the past 48 hours. Click for updated prices.
Royal Lahaina Resort & Bungalows
Price was ￥195,315, price is now ￥85,545 per person
￥85,545
per person
Oct 26 - Nov 1
found 1 day ago
Roundtrip flight included
Honolulu (HNL) to Kahului (OGG)
8.4/10 Very Good! (1,425 reviews)
Property is good overall. The bathroom fixtures, especially the shower fixtures, were not clean because we could see signs of mildew.
Reviewed on Sep 7, 2025
OUTRIGGER Honua Kai Resort & Spa
Save 100% on your flight
Price was ￥275,058, price is now ￥172,927 per person
￥172,927
per person
Oct 26 - Nov 1
found 1 day ago
Roundtrip flight included
Honolulu (HNL) to Kahului (OGG)
8.8/10 Excellent! (2,829 reviews)
Very clean and convenient, great location and great beaches
Reviewed on Sep 3, 2025
Aston at The Whaler on Kaanapali Beach
Save 100% on your flight
Price was ￥188,972, price is now ￥120,383 per person
￥120,383
per person
Oct 26 - Nov 1
found 1 day ago
Roundtrip flight included
Honolulu (HNL) to Kahului (OGG)
9.2/10 Wonderful! (1,484 reviews)
The staff was great, but our room was awesome. It had a full kitchen. The room was updated. It had everything we needed. We are already planning our next trip.
Reviewed on Sep 5, 2025
The Whaler Resort Kaanapali Beach
Save 100% on your flight
Price was ￥389,443, price is now ￥256,790 per person
￥256,790
per person
Nov 10 - Nov 17
found 4 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Kahului (OGG)
9.6/10 Exceptional! (226 reviews)
Great property and views
Reviewed on Sep 5, 2025
Hotel Wailea, Relais & Chateaux - Adults Only
Wailea
Save 100% on your flight
Price was ￥949,226, price is now ￥644,182 per person
￥644,182
per person
Oct 26 - Nov 1
found 1 day ago
Roundtrip flight included
Honolulu (HNL) to Kahului (OGG)
9.4/10 Exceptional! (1,002 reviews)
Great resort with great amenities! Very convenient to downtown wailea and the beaches and the staff are super friendly and attentive!
Reviewed on Aug 27, 2025
Don't see what you're looking for?
See all available trips from Honolulu to Wailea-Makena
View all trips5* Luxury vacations in Wailea-Makena
Price found within the past 48 hours. Click for updated prices.
Ho‘olei Villas at Grand Wailea
Wailea
Save 100% on your flight
Price was ￥808,248, price is now ￥565,552 per person
￥565,552
per person
Nov 15 - Nov 19
found 15 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Kahului (OGG)
9.6/10 Exceptional! (42 reviews)
Perfect for Families. Quite spacious and great for a relaxing Family vacation.
Reviewed on Jun 15, 2025
Hotel Wailea, Relais & Chateaux - Adults Only
Wailea
Save 100% on your flight
Price was ￥949,226, price is now ￥644,182 per person
￥644,182
per person
Oct 26 - Nov 1
found 1 day ago
Roundtrip flight included
Honolulu (HNL) to Kahului (OGG)
9.4/10 Exceptional! (1,002 reviews)
Great resort with great amenities! Very convenient to downtown wailea and the beaches and the staff are super friendly and attentive!
Reviewed on Aug 27, 2025
Fairmont Kea Lani Maui Villa Experience
Wailea
Save 100% on your flight
Price was ￥1,232,048, price is now ￥890,424 per person
￥890,424
per person
Nov 15 - Nov 19
found 15 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Kahului (OGG)
9.6/10 Exceptional! (5 reviews)
It’s a decent hotel to stay for the family.
Reviewed on Aug 22, 2024
4 Night Luxury vacations in Wailea-Makena
Price found within the past 48 hours. Click for updated prices.
Royal Lahaina Resort & Bungalows
Price was ￥233,794, price is now ￥154,252 per person
￥154,252
per person
Nov 15 - Nov 19
found 15 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Kahului (OGG)
8.4/10 Very Good! (1,425 reviews)
Property is good overall. The bathroom fixtures, especially the shower fixtures, were not clean because we could see signs of mildew.
Reviewed on Sep 7, 2025
Mana Kai Maui- Official Onsite Rental
Save 100% on your flight
Price was ￥342,673, price is now ￥165,722 per person
￥165,722
per person
Nov 15 - Nov 19
found 15 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Kahului (OGG)
8.8/10 Excellent! (1,011 reviews)
The access to the beach close vicinity to the condo was excellent. Very happy.
Reviewed on Sep 6, 2025
Napili Kai Beach Resort
Save 100% on your flight
Price was ￥363,708, price is now ￥208,698 per person
￥208,698
per person
Nov 15 - Nov 19
found 15 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Kahului (OGG)
9.4/10 Exceptional! (1,006 reviews)
Excellent 5 stars! I am so happy we chose Napili Kai for our big trip. We stayed in Puna 2 and the views, the room, the staff and amenities were top notch. We felt like royalty. Sheryl who serviced our room was a dream. Thank you!!!
We are at OGG right now and looking to book again. Thank you for making our vacation so memorable.
Reviewed on Sep 7, 2025
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
