
Wailea-Makena Romantic Vacations
Book a Romantic Hotel + Flight or Car together to unlock savings
- 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 Romantic 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 ¥365,043, price is now ¥226,158 per person
¥226,158
per person
Apr 23 - Apr 28
found 1 day ago
Roundtrip flight included
Tokyo (TYO) to Kahului (OGG)
9.6/10 Exceptional! (292 reviews)
Location is absolutely perfect…lots of space and nice kitchen amenities
Reviewed on Feb 6, 2026

Grand Wailea Maui, A Waldorf Astoria Resort
Wailea
Save 100% on your flight
Price was ¥1,236,317, price is now ¥964,176 per person
¥964,176
per person
Mar 17 - Mar 24
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Kahului (OGG)
9/10 Wonderful! (1,000 reviews)
The room was always clean. Susie at the front desk was so helpful and kind.
I’ll be coming back
Reviewed on Feb 2, 2026

The Ritz-Carlton Maui, Kapalua
Save 100% on your flight
Price was ¥790,604, price is now ¥622,329 per person
¥622,329
per person
Mar 17 - Mar 24
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Kahului (OGG)
9/10 Wonderful! (1,001 reviews)
Yes it's secluded. Yes it is a large property that requires a lot of walking. The rooms are slightly dated.
It's all made up by the attention and care from the staff at the Ritz. My wife and I were celebrating our honeymoon. We were treated with the utmost care from the kind folks there. The property is well manicured and clean. The pools were fun and the golf cart ride for the long walk to the beach is a must.
Unfortunately we left with a slight sour note at the end of the trip. I left my Nike Dri-Fit hoodie in the armoire the entire time during my stay... Never took it out, and only had it there for the weather back home.
Although it was my mistake, I left my sweater behind. I contacted the hotel an hour after I checked out. And somehow, the staff "did not locate" the sweater. It was frustrating to have to keep asking for updates for a sweater. Until lost and found finally admitted they didn't find a sweater.
Reviewed on Jan 3, 2026

Signature Residences at Maui Banyan
South Kihei
Price was ¥433,222, price is now ¥343,084 per person
¥343,084
per person
Mar 17 - Mar 24
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Kahului (OGG)
No reviews
Clean and convenient accommodation in a quiet and friendly environment
Reviewed on Feb 8, 2026

5* Romantic vacations in Wailea-Makena
Price found within the past 48 hours. Click for updated prices.


Grand Wailea Maui, A Waldorf Astoria Resort
Wailea
Save 100% on your flight
Price was ¥1,236,317, price is now ¥964,176 per person
¥964,176
per person
Mar 17 - Mar 24
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Kahului (OGG)
9/10 Wonderful! (1,000 reviews)
The room was always clean. Susie at the front desk was so helpful and kind.
I’ll be coming back
Reviewed on Feb 2, 2026

The Ritz-Carlton Maui, Kapalua
Save 100% on your flight
Price was ¥790,604, price is now ¥622,329 per person
¥622,329
per person
Mar 17 - Mar 24
found 1 day ago
Roundtrip non-stop flight included
Tokyo (TYO) to Kahului (OGG)
9/10 Wonderful! (1,001 reviews)
Yes it's secluded. Yes it is a large property that requires a lot of walking. The rooms are slightly dated.
It's all made up by the attention and care from the staff at the Ritz. My wife and I were celebrating our honeymoon. We were treated with the utmost care from the kind folks there. The property is well manicured and clean. The pools were fun and the golf cart ride for the long walk to the beach is a must.
Unfortunately we left with a slight sour note at the end of the trip. I left my Nike Dri-Fit hoodie in the armoire the entire time during my stay... Never took it out, and only had it there for the weather back home.
Although it was my mistake, I left my sweater behind. I contacted the hotel an hour after I checked out. And somehow, the staff "did not locate" the sweater. It was frustrating to have to keep asking for updates for a sweater. Until lost and found finally admitted they didn't find a sweater.
Reviewed on Jan 3, 2026
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
