
Wailea-Makena Mountain Vacations
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Top Mountain vacation packages in Wailea-Makena
Price found within the past 48 hours. Click for updated prices.

The Whaler Resort Kaanapali Beach
Save 100% on your flight
Price was ¥231,513, price is now ¥153,084 per person
¥153,084
per person
May 30 - Jun 2
found 1 day ago
Roundtrip flight included
Honolulu (HNL) to Kahului (OGG)
9.6/10 Exceptional! (367 reviews)
The room was nice the staff was very friendly and helpful. Wifi was good and the view was great!!! Plenty of places to shop within walking distance and some of the finest food you will find right there. Would love to go back!
Reviewed on Mar 23, 2026

OUTRIGGER Honua Kai Resort & Spa
Save 100% on your flight
Price was ¥247,954, price is now ¥156,872 per person
¥156,872
per person
May 30 - Jun 2
found 1 day ago
Roundtrip flight included
Honolulu (HNL) to Kahului (OGG)
8.8/10 Excellent! (2,929 reviews)
Overall, a nice place to stay. Room was nice. Pools were nice. Right on a good section of beach. Free valet services, but the valets were hard to find at the desk and a little slow. It also does seems a little odd that they’re still not cleaning rooms as if we are still worried about Covid. Not even an offer to clean the room or replace towels, soap, toilet paper, etc in the week we were there. Also, a little odd that you keep the “spa” in your name when it is shut down and not opening again.
Reviewed on Mar 16, 2026

Hotel Wailea, Relais & Chateaux - Adults Only
Wailea
Save 100% on your flight
Price was ¥1,404,700, price is now ¥972,936 per person
¥972,936
per person
Apr 29 - May 6
found 13 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Kahului (OGG)
9.4/10 Exceptional! (1,001 reviews)
Literally the best hotel experience I’ve had.
Reviewed on Mar 21, 2026

Fairmont Kea Lani Maui
Wailea
Save 100% on your flight
Price was ¥921,139, price is now ¥670,626 per person
¥670,626
per person
Jun 1 - Jun 8
found 2 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Kahului (OGG)
9.4/10 Exceptional! (1,012 reviews)
Staff was incredibly welcoming and helpful. Bar/restaurant staff were amazing. Pools were clean and poolside servers were very friendly. Overall an amazing property with wonderful staff
Reviewed on Mar 16, 2026

Signature Residences at Maui Banyan
South Kihei
Price was ¥405,716, price is now ¥295,726 per person
¥295,726
per person
Jun 1 - Jun 8
found 2 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Kahului (OGG)
8.8/10 Excellent! (11 reviews)
Beautiful property. Close to the beach-Kamaole beaches just across the street. Good location. Room had beach accessories such as chairs, umbrellas, toys, goggles, ice bags for picnics. Overall clean. We will use this property again when we return!
Reviewed on Mar 13, 2026
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See all available trips from Honolulu to Wailea-Makena
View all trips5* Mountain vacations in Wailea-Makena
Price found within the past 48 hours. Click for updated prices.

Fairmont Kea Lani Maui
Wailea
Save 100% on your flight
Price was ¥921,139, price is now ¥670,626 per person
¥670,626
per person
Jun 1 - Jun 8
found 2 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Kahului (OGG)
9.4/10 Exceptional! (1,012 reviews)
Staff was incredibly welcoming and helpful. Bar/restaurant staff were amazing. Pools were clean and poolside servers were very friendly. Overall an amazing property with wonderful staff
Reviewed on Mar 16, 2026

Hotel Wailea, Relais & Chateaux - Adults Only
Wailea
Save 100% on your flight
Price was ¥1,404,700, price is now ¥972,936 per person
¥972,936
per person
Apr 29 - May 6
found 13 hours ago
Roundtrip non-stop flight included
Tokyo (TYO) to Kahului (OGG)
9.4/10 Exceptional! (1,001 reviews)
Literally the best hotel experience I’ve had.
Reviewed on Mar 21, 2026
3 Night Mountain vacations in Wailea-Makena
Price found within the past 48 hours. Click for updated prices.

The Whaler Resort Kaanapali Beach
Save 100% on your flight
Price was ¥231,513, price is now ¥153,084 per person
¥153,084
per person
May 30 - Jun 2
found 1 day ago
Roundtrip flight included
Honolulu (HNL) to Kahului (OGG)
9.6/10 Exceptional! (367 reviews)
The room was nice the staff was very friendly and helpful. Wifi was good and the view was great!!! Plenty of places to shop within walking distance and some of the finest food you will find right there. Would love to go back!
Reviewed on Mar 23, 2026

OUTRIGGER Honua Kai Resort & Spa
Save 100% on your flight
Price was ¥247,954, price is now ¥156,872 per person
¥156,872
per person
May 30 - Jun 2
found 1 day ago
Roundtrip flight included
Honolulu (HNL) to Kahului (OGG)
8.8/10 Excellent! (2,929 reviews)
Overall, a nice place to stay. Room was nice. Pools were nice. Right on a good section of beach. Free valet services, but the valets were hard to find at the desk and a little slow. It also does seems a little odd that they’re still not cleaning rooms as if we are still worried about Covid. Not even an offer to clean the room or replace towels, soap, toilet paper, etc in the week we were there. Also, a little odd that you keep the “spa” in your name when it is shut down and not opening again.
Reviewed on Mar 16, 2026

The Ritz-Carlton Maui, Kapalua
Save 100% on your flight
Price was ¥317,236, price is now ¥235,970 per person
¥235,970
per person
May 30 - Jun 2
found 1 day ago
Roundtrip flight included
Honolulu (HNL) to Kahului (OGG)
9.2/10 Wonderful! (1,007 reviews)
Beach access and pool area was clean
Reviewed on Mar 24, 2026
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See all available trips from Honolulu to Wailea-Makena
View all trips4 Night Mountain vacations in Wailea-Makena
Price found within the past 48 hours. Click for updated prices.

Sands of Kahana
Price was ¥486,122, price is now ¥341,261 per person
¥341,261
per person
Apr 24 - Apr 28
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Kahului (OGG)
8.2/10 Very Good! (503 reviews)
Everything about this property was nice and some cases better than expected. The only negative is that on the day we were leaving, at 8:30 in the morning, well before the 11 AM checkout time, while my husband was half dressed in the bathroom and I was half dressed in the kitchen, new guests entered our room with their pass key. They have been given access to the room without the front deck changing the digital card key and without being told check in time is at 4 PM. what a shock to have strangers walking into our room while we’re still there! That’s bad management. The key should’ve been changed. Also the guest should’ve been notified room won’t be ready until four. When we did check out and I told the front desk about this, they said oh I’m sorry. I’ll tell the management.
Reviewed on Mar 20, 2026

OUTRIGGER Honua Kai Resort & Spa
Price was ¥516,714, price is now ¥373,622 per person
¥373,622
per person
Apr 24 - Apr 28
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Kahului (OGG)
8.8/10 Excellent! (2,929 reviews)
Overall, a nice place to stay. Room was nice. Pools were nice. Right on a good section of beach. Free valet services, but the valets were hard to find at the desk and a little slow. It also does seems a little odd that they’re still not cleaning rooms as if we are still worried about Covid. Not even an offer to clean the room or replace towels, soap, toilet paper, etc in the week we were there. Also, a little odd that you keep the “spa” in your name when it is shut down and not opening again.
Reviewed on Mar 16, 2026

Palms at Wailea Maui
Wailea
Price was ¥478,532, price is now ¥350,256 per person
¥350,256
per person
Apr 24 - Apr 28
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Kahului (OGG)
8.4/10 Very Good! (527 reviews)
Very clean and modern condo. Very well maintained. Check in was a breeze and we loved the patio. Great location on the property.
Reviewed on Mar 12, 2026
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
