Wailea-Makena Cheap Vacations
Book a Cheap Hotel + Flight or Car together to unlock savings
Photo by Raul Munguia
- Plan, book, travel with confidence
- Better togetherSave up to ￥45,448 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Top Cheap vacation packages 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 ￥357,850, price is now ￥216,460 per person
￥216,460
per person
Jan 21 - Jan 26
found 1 day ago
Roundtrip non-stop flight included
Osaka (KIX) to Kahului (OGG)
8.4/10 Very Good! (1,548 reviews)
The room was clean and the view was amazing. Staff was so friendly and helpful. 10/10 would stay again!
Reviewed on Dec 2, 2025
Hotel Wailea, Relais & Chateaux - Adults Only
Wailea
Save 100% on your flight
Price was ￥737,112, price is now ￥435,098 per person
￥435,098
per person
Jan 21 - Jan 26
found 1 day ago
Roundtrip non-stop flight included
Osaka (KIX) 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 Aug 27, 2025
Montage Kapalua Bay
Save 100% on your flight
Price was ￥806,754, price is now ￥530,260 per person
￥530,260
per person
Jan 21 - Jan 26
found 1 day ago
Roundtrip non-stop flight included
Osaka (KIX) to Kahului (OGG)
9.6/10 Exceptional! (204 reviews)
I liked everything except the dining service. The staff was unfriendly and rude. They should not work there.-
they kept us in the bar in excess of 15 minutes even after 4 tables had been open We had to walk over to tell them that tables had been open.
Reviewed on Mar 4, 2025
Fairmont Kea Lani Maui
Wailea
Save 100% on your flight
Price was ￥603,230, price is now ￥401,973 per person
￥401,973
per person
Jan 21 - Jan 26
found 1 day ago
Roundtrip non-stop flight included
Osaka (KIX) to Kahului (OGG)
9.4/10 Exceptional! (1,001 reviews)
very nicely rennovated hotel and rooms
very convenient shuttle service
very good food
the staff was sometimes variable in quality and experience
the concierge service can be improved - lacking concrete tips and details related to trip to hana, no supporting documentation, poor leasing staff
Reviewed on Nov 30, 2025
5* Cheap vacations 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 ￥737,112, price is now ￥435,098 per person
￥435,098
per person
Jan 21 - Jan 26
found 1 day ago
Roundtrip non-stop flight included
Osaka (KIX) 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 Aug 27, 2025
Montage Kapalua Bay
Save 100% on your flight
Price was ￥806,754, price is now ￥530,260 per person
￥530,260
per person
Jan 21 - Jan 26
found 1 day ago
Roundtrip non-stop flight included
Osaka (KIX) to Kahului (OGG)
9.6/10 Exceptional! (204 reviews)
I liked everything except the dining service. The staff was unfriendly and rude. They should not work there.-
they kept us in the bar in excess of 15 minutes even after 4 tables had been open We had to walk over to tell them that tables had been open.
Reviewed on Mar 4, 2025
3 Night Cheap vacations in Wailea-Makena
Price found within the past 48 hours. Click for updated prices.
Royal Lahaina Resort & Bungalows
Price was ￥286,876, price is now ￥202,711 per person
￥202,711
per person
Feb 17 - Feb 20
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Kahului (OGG)
8.4/10 Very Good! (1,548 reviews)
The room was clean and the view was amazing. Staff was so friendly and helpful. 10/10 would stay again!
Reviewed on Dec 2, 2025
The Whaler Resort Kaanapali Beach
Price was ￥374,488, price is now ￥269,290 per person
￥269,290
per person
Feb 17 - Feb 20
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Kahului (OGG)
9.6/10 Exceptional! (292 reviews)
The location is perfect, parking is free, check-in & out is easy, friendly service.
Reviewed on Nov 29, 2025
OUTRIGGER Honua Kai Resort & Spa
Price was ￥397,861, price is now ￥293,281 per person
￥293,281
per person
Feb 17 - Feb 20
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Kahului (OGG)
8.8/10 Excellent! (2,864 reviews)
Rooms and staff are amazing, pools are amazing, couldn’t ask for a better experience
Reviewed on Dec 1, 2025
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
