
Kaupo Vacation Packages
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Top Kaupo vacation package deals
Price found within the past 48 hours. Click for updated prices.

3.5-star property
Kihei Kai Nani
South Kihei
10/10 Exceptional! (1 review)
Sep 9 - Sep 15
6 night stay
Los Angeles (LAX) to Kahului (OGG)
American Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $1,228, price is now $843 per person
$843
per person
found 1 day ago
Great communication with owner. The bedroom has a queen bed and there is a queen size sofa bed. Air conditioner unit in the living room only. The plenty of dish and cook wear. Washer and dryer in unit. Beach is literally across the street and 2 others on both sides. Kamaole I beach has best water clarity for snorkeling. Building 10 is super quiet.
Reviewed on May 16, 2026

3.0-star property
Maui Banyan Vacation Club
South Kihei
8/10 Very Good! (374 reviews)
Aug 27 - Sep 3
7 night stay
Chicago (CHI) to Kahului (OGG)
Alaska Airlines • Non-stop roundtrip • Coach
Price was $1,661, price is now $1,112 per person
$1,112
per person
found 14 hours ago
Great location right on Kīhei. Great walk to the beach, plenty of restaurants coffeeshops etc within walking distance
Reviewed on Jun 29, 2026

5.0-star property
Hotel Wailea, Relais & Chateaux - Adults Only
Wailea
9.4/10 Exceptional! (1,000 reviews)
Sep 20 - Sep 24
4 night stay
Chicago (CHI) to Kahului (OGG)
Alaska Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $3,404, price is now $2,332 per person
$2,332
per person
found 15 hours ago
The property was beautiful and well maintained. Lush garden spaces. Pool area and loungers being available along with poolside service was great. Room was large and felt very private. Overall quiet property and relaxing stay. Beach picnic excursion was great as well!
Reviewed on Jul 8, 2026

2.5-star property
Kihei Surfside - Maui Condo & Home
South Kihei
8.6/10 Excellent! (69 reviews)
Sep 12 - Sep 19
7 night stay
Los Angeles (LAX) to Kahului (OGG)
Delta • Coach
Kahului (OGG) to Los Angeles (LAX)
Alaska Airlines • Coach
Price was $2,012, price is now $1,422 per person
$1,422
per person
found 1 day ago
Very nice location
Reviewed on Jan 7, 2026

2.0-star property
Maui Parkshore - Maui Condo & Home
South Kihei
8/10 Very Good! (108 reviews)
Sep 12 - Sep 19
7 night stay
Los Angeles (LAX) to Kahului (OGG)
Delta • Coach
Kahului (OGG) to Los Angeles (LAX)
Alaska Airlines • Coach
Price was $1,901, price is now $1,366 per person
$1,366
per person
found 1 day ago
Things we liked about this property: beach view, manager on site, safe, designated parking spot, nice location/ area, beach items ( chairs, umbrella, toys)available in unit
Didn’t like: outdated, so it has an older smell to it and so are towels and linens in the linen cabinet. Inner coating in cabinets is chipping everywhere. Unit is well beat up. No central AC, just two floor units in bedrooms,so it gets hot and humid in the main area
Reviewed on Apr 27, 2026
Top rated hotels for your Kaupo vacation package

Hana-Maui Resort, a Destination by Hyatt Residence
5031 Hana Hwy Hana HI
Free Cancellation
Reserve now, pay when you stay
11.98 mi from city center
$479 nightly
The price is $568 total per night
$568 total
Aug 9 - Aug 10
Total with taxes and fees
Guests of Hana-Maui Resort, a Destination by Hyatt Residence have access to a full-service spa, 2 outdoor pools, and a gym. If you drive, self parking is USD 15 per night, and there's also a free beach shuttle. The front desk is staffed 24/7 to help with concierge services, luggage storage, and securing valuables. Other amenities at this spa resort include a sauna, free WiFi in public areas, and conference space.
Pool
Spa

Fisher’s Hana Bay Hale - In Hana Town across from the Bay STHA-2017 0002
Hana HI
12.17 mi from city center
$341 nightly
The price is $399 total per night
$399 total
Aug 3 - Aug 4
Total with taxes and fees
Guests staying at this vacation home have access to laundry facilities, a garden, and barbecue grills.
Kitchen
Washer

Paradise: Ocean View Cottage Solar Power Tropical Flower Gardens - 10% off JULY!
Hana HI
11.99 mi from city center
$336 nightly
The price is $393 total per night
$393 total
Jul 12 - Jul 13
Total with taxes and fees
At this cottage, guests have access to a gym, laundry facilities, and barbecue grills. This smoke-free cottage also has a garden.
Kitchen
Washer
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Things to do

Road to Hana Maui Tour: Self-Guided Audio Drive
$17
per traveler
84% of travellers recommend

Haleakala Downhill Bike Tour Self-Guided Ride with Maui Sunriders
$139
per adult
86% of travellers recommend
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