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

The Whaler Resort Kaanapali Beach
Price was ¥339,373, price is now ¥260,228 per person
¥260,228
per person
Apr 26 - Apr 29
found 12 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Kahului (OGG)
9.6/10 Exceptional! (292 reviews)
The staff was great. The location was perfect. Everything was in walking distance. The only issue was it said ocean view when it should have said partial ocean view. I was a little disappointed.
Reviewed on Feb 19, 2026

OUTRIGGER Honua Kai Resort & Spa
Save 100% on your flight
Price was ¥575,004, price is now ¥388,399 per person
¥388,399
per person
Apr 12 - Apr 17
found 1 day ago
Roundtrip flight included
Tokyo (NRT) to Kahului (OGG)
8.8/10 Excellent! (2,864 reviews)
2 weeks before we arrived I got an email from Expedia to call the resort. It did. They said the room we reserved was not available and that they needed to move us. I reserved a 3 bedroom unit w/ an ocean view. Mia kept trying to tell us what an upgrade it was. Our room ended up being at the back of the property w/ no ocean view, no housekeeping services and the pool near us had no pool service. Definitely not an upgrade! Upon check in, the woman who checked us in said they’ve known since November about the maintenance on our room. We were contacted the end of January. Had we known sooner, we could have tried to find somewhere else to stay. By waiting until 2 weeks before, they took that opportunity away. We had someone w/ us who had never been to Hawaii before. Having an ocean view was important to us. Sad we didn’t get one!
Reviewed on Feb 18, 2026


Montage Kapalua Bay
Save 100% on your flight
Price was ¥1,139,934, price is now ¥864,610 per person
¥864,610
per person
Apr 24 - May 1
found 17 hours ago
Roundtrip non-stop flight included
Tokyo (NRT) to Kahului (OGG)
9.6/10 Exceptional! (204 reviews)
Staff was great. Some maintenance issues, leaking water dispenser on fridge leading to pooling and warping of floor. Same on large lanai. Otherwise, great
Reviewed on Feb 14, 2026

Fairmont Kea Lani Maui
Wailea
Price was ¥647,860, price is now ¥515,225 per person
¥515,225
per person
Apr 12 - Apr 17
found 1 day ago
Roundtrip flight included
Tokyo (NRT) to Kahului (OGG)
9.4/10 Exceptional! (1,001 reviews)
Incredible sunset views
Great beach
Friendly staff that were good at turning over unused sunbeds on the beach and cocktail staff at the restaurants were particularly good
Resort was very clean and beautifully designed
Liked the water refill in the lovely fairmont bottles
Minor quibbles
Limited non cabana seating near the adult pool (not a problem for us as we prefer the beach)
Breakfast buffet was busy - again not a problem as we ordered room service for breakfast which was extraordinary given the views and lots of choice
Would have been lovely to have some kind of small welcome or leaving gift which is becoming common in hotels of this price category
A bit more variety in food choices especially in the marketplace of an evening would be great
FYI we bought the top two floors room and would do so again. While the views are spectacular from the bar so I’m sure all rooms are lovely, we adored the view at sunset from our room
Re weather we visited in feb. Great to see whales which you can see from the hotel! We got lucky it only rained briefly once in over a week thought it rained before we arrived. Much better and warmer than the uk! This part of the island is drier so not all parts of Maui are like this!
Reviewed on Feb 21, 2026
5* Cheap vacations in Wailea-Makena
Price found within the past 48 hours. Click for updated prices.


Montage Kapalua Bay
Save 100% on your flight
Price was ¥1,139,934, price is now ¥864,610 per person
¥864,610
per person
Apr 24 - May 1
found 17 hours ago
Roundtrip non-stop flight included
Tokyo (NRT) to Kahului (OGG)
9.6/10 Exceptional! (204 reviews)
Staff was great. Some maintenance issues, leaking water dispenser on fridge leading to pooling and warping of floor. Same on large lanai. Otherwise, great
Reviewed on Feb 14, 2026

Fairmont Kea Lani Maui
Wailea
Price was ¥647,860, price is now ¥515,225 per person
¥515,225
per person
Apr 12 - Apr 17
found 1 day ago
Roundtrip flight included
Tokyo (NRT) to Kahului (OGG)
9.4/10 Exceptional! (1,001 reviews)
Incredible sunset views
Great beach
Friendly staff that were good at turning over unused sunbeds on the beach and cocktail staff at the restaurants were particularly good
Resort was very clean and beautifully designed
Liked the water refill in the lovely fairmont bottles
Minor quibbles
Limited non cabana seating near the adult pool (not a problem for us as we prefer the beach)
Breakfast buffet was busy - again not a problem as we ordered room service for breakfast which was extraordinary given the views and lots of choice
Would have been lovely to have some kind of small welcome or leaving gift which is becoming common in hotels of this price category
A bit more variety in food choices especially in the marketplace of an evening would be great
FYI we bought the top two floors room and would do so again. While the views are spectacular from the bar so I’m sure all rooms are lovely, we adored the view at sunset from our room
Re weather we visited in feb. Great to see whales which you can see from the hotel! We got lucky it only rained briefly once in over a week thought it rained before we arrived. Much better and warmer than the uk! This part of the island is drier so not all parts of Maui are like this!
Reviewed on Feb 21, 2026
3 Night Cheap vacations in Wailea-Makena
Price found within the past 48 hours. Click for updated prices.

The Whaler Resort Kaanapali Beach
Price was ¥339,373, price is now ¥260,228 per person
¥260,228
per person
Apr 26 - Apr 29
found 12 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Kahului (OGG)
9.6/10 Exceptional! (292 reviews)
The staff was great. The location was perfect. Everything was in walking distance. The only issue was it said ocean view when it should have said partial ocean view. I was a little disappointed.
Reviewed on Feb 19, 2026

OUTRIGGER Honua Kai Resort & Spa
Price was ¥368,675, price is now ¥283,640 per person
¥283,640
per person
Apr 26 - Apr 29
found 12 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Kahului (OGG)
8.8/10 Excellent! (2,864 reviews)
2 weeks before we arrived I got an email from Expedia to call the resort. It did. They said the room we reserved was not available and that they needed to move us. I reserved a 3 bedroom unit w/ an ocean view. Mia kept trying to tell us what an upgrade it was. Our room ended up being at the back of the property w/ no ocean view, no housekeeping services and the pool near us had no pool service. Definitely not an upgrade! Upon check in, the woman who checked us in said they’ve known since November about the maintenance on our room. We were contacted the end of January. Had we known sooner, we could have tried to find somewhere else to stay. By waiting until 2 weeks before, they took that opportunity away. We had someone w/ us who had never been to Hawaii before. Having an ocean view was important to us. Sad we didn’t get one!
Reviewed on Feb 18, 2026

Ho‘olei Villas at Grand Wailea
Wailea
Price was ¥722,071, price is now ¥609,678 per person
¥609,678
per person
Apr 26 - Apr 29
found 12 hours ago
Roundtrip non-stop flight included
Tokyo (HND) to Kahului (OGG)
9.6/10 Exceptional! (44 reviews)
We stayed in Villa 99-5. . To sum it up quickly, the price to experience was in our opinion way too high. Also as a member an elite member, I did not get the discounts on the Cabana rentals and beach chair. The restaurant staff and food was very good. For the price we believe that there should be more comps than provided. Also on checking out the elevator was not working to allow the upstairs to bring their luggage down conveniently. The other complaint which was an ongoing complaint was the TVs not that you need to watch him when you're on such a beautiful island but if kids were staying they would need some entertainment at the evening I would believe. Again the cost to the experience was too expensive. For what you got. I would look at other opportunities or options for lodging where there was more bang for the buck.
Reviewed on Oct 22, 2025
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
