Search Deals onKaupakulua Vacation Packages
Kaupakulua Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.

Maui Beach Vacation Club
Price was $1,849, price is now $1,305 per person
$1,305
per person
Dec 3 - Dec 10
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Kahului (OGG)
Book a stay at this beach aparthotel in Kihei. Enjoy free WiFi, free parking, and a garden. Our guests praise the helpful staff in our reviews. Popular attractions Wailea Beach and Hawaiian Islands Humpback Whale National Marine Sanctuary Headquarters are located nearby.

Hotel Wailea Maui
Price was $8,449, price is now $5,199 per person
$5,199
per person
Nov 20 - Nov 27
found 19 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Kahului (OGG)
Book a stay at this luxury resort in Kihei. Enjoy 3 restaurants, 3 bars/lounges, and breakfast (surcharge). Our guests praise the helpful staff in our reviews. Popular attractions Wailea Beach and Wailea Blue Golf Course are located nearby.

Maui Banyan - Maui Condo & Home
Price was $2,822, price is now $2,067 per person
$2,067
per person
Dec 30 - Jan 4
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Kahului (OGG)
Stay at this condo in Kihei. Enjoy free WiFi, 2 outdoor pools, and a picnic area. Popular attractions Wailea Beach and Kamaole Beach Park 2 are located nearby.

Kihei Surfside - Maui Condo & Home
Save 100% on your flight
Price was $3,253, price is now $2,384 per person
$2,384
per person
Dec 20 - Dec 27
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Kahului (OGG)
Stay at this condo in Kihei. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Wailea Beach and Keawakapu Beach North are located nearby.
We booked this room because we had planned a family trip for my mother's 60th birthday and traveled with 3 other families that also booked rooms in the same building.
As soon as we walked in we noticed the disgusting carpet that is stained, worn, wrinkled and just felt disgusting to step on. Then the pullout couch was old and broken. Just touching the cushions felt like we needed to wash our hands. Then the bedroom comforter and bed was disgusting and old. Looked orginal from 1980's same with all the furniture in the room was just old and grungy. My allergies which are not bad we're completely triggered every night with the musty nasty mix of humid carpet and old furniture and bed sheet smell. It was terrible. Then they do not provide any beach towels and only provided 5 shower towels for a 5 night 6 day stay. We had to email for more shower towels which they brought 3. Even the coffee machine was old and gross. The drapes are old and gross and had to call maintenance because the cord to pull them up and down broke. Just over all terrible place to stay!
On the flip side, the other family rooms were completely updated, beautiful, smelt clean, and comfortable.
This owner clearly doesn't care to upkeep or care about customer experience. We paid really good money for this unit and the only reason I gave two stars is because of the view.
I would not recommend to anyone. Save your money and poor experience.
Reviewed on Jul 29, 2026

Maui Kamaole - Maui Condo & Home
Save 100% on your flight
Price was $3,370, price is now $2,479 per person
$2,479
per person
Dec 20 - Dec 27
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Kahului (OGG)
Stay at this condo in Kihei. Enjoy free WiFi, 2 outdoor pools, and a garden. Popular attractions Wailea Beach and Kihei Boat Ramp are located nearby.

The Kalama Residence
Price was $6,063, price is now $4,496 per person
$4,496
per person
Dec 27 - Dec 31
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Kahului (OGG)
Book a stay at this beach apartment in Kihei. Enjoy free WiFi, free parking, and a beach locale. Popular attractions Wailea Beach and Cove Park are located nearby.
The property was clean and nice. It did need some maintenance, but it was in good condition for its age. We liked how it was stocked to make our stay more comfortable.
Reviewed on Jan 4, 2026

Maui Schooner Resort
Price was $2,075, price is now $1,565 per person
$1,565
per person
Dec 18 - Dec 22
found 1 day ago
Roundtrip flight included
Boston (BOS) to Kahului (OGG)
Book a stay at this beach aparthotel in Kihei. Enjoy free WiFi, free parking, and a beach locale. Our guests praise the helpful staff in our reviews. Popular attractions Wailea Beach and Waipuilani Park are located nearby.
the unit was clean and the staff were polite
Reviewed on Oct 12, 2026

Royal Lahaina Bungalows & Spa
Price was $3,425, price is now $2,621 per person
$2,621
per person
Nov 20 - Nov 27
found 19 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Kahului (OGG)
Book a stay at this luxury aparthotel in Lahaina. Enjoy free WiFi, 2 outdoor pools, and a full-service spa. Popular attractions Kaanapali Beach and Whalers Village are located nearby.
Kaupakulua Vacation Packages 3-4 Night Stays
Price found within the past 48 hours. Click for updated prices.



Kaupakulua Vacation Packages 5-7 Night Stays
Price found within the past 48 hours. Click for updated prices.



Top Flight Deals
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Thu, Nov 5 - Thu, Nov 5
HNL
Daniel K. Inouye Intl.
OGG
Kahului
$133 Roundtrip, found 15 hours ago
$133
Roundtrip
found 15 hours ago

Tue, Nov 10 - Tue, Nov 10
OAK
Oakland Intl.
OGG
Kahului
$310 Roundtrip, found 2 hours ago
$310
Roundtrip
found 2 hours ago

Tue, Jan 5 - Tue, Jan 12
SFO
San Francisco Intl.
OGG
Kahului
$312 Roundtrip, found 17 hours ago
$312
Roundtrip
found 17 hours ago

Mon, May 10 - Wed, May 19
LAX
Los Angeles Intl.
OGG
Kahului
$366 Roundtrip, found 16 hours ago
$366
Roundtrip
found 16 hours ago
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