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Kaupo Vacation Packages

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Kaupo Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Royal Lahaina Bungalows & Spa

Royal Lahaina Bungalows & Spa

5 out of 5
Save 100% on your flight
Price was $1,782, price is now $1,297 per person
$1,297
per person
Dec 2 - Dec 9
found 17 hours ago
Roundtrip flight included
Los Angeles (LAX) 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.

Maui Beach Vacation Club

Maui Beach Vacation Club

2.5 out of 5
Save 100% on your flight
Price was $2,543, price is now $1,521 per person
$1,521
per person
Nov 10 - Nov 17
found 13 hours ago
Roundtrip non-stop flight included
Houston (IAH) 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.
Have stayed at this property a few times and have always enjoyed it.. staff is very accommodating, professional and sweet.. the rooms and pool area are nice and the facility is close by to restaurants, stores, beaches Etc. ... definitely recommend for anyone looking for a nice place to enjoy their time and stay.

Reviewed on Sep 30, 2026

Hotel Wailea Maui

Hotel Wailea Maui

5 out of 5
Save 100% on your flight
Price was $3,836, price is now $2,424 per person
$2,424
per person
Dec 8 - Dec 13
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) 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.
Everything was excellent, form the location to the incredible food!

Reviewed on Sep 22, 2026

Maui Banyan Vacation Club

Maui Banyan Vacation Club

3 out of 5
Price was $2,084, price is now $1,342 per person
$1,342
per person
Nov 23 - Nov 30
found 1 day ago
Roundtrip non-stop flight included
Houston (IAH) to Kahului (OGG)
Stay at this condo in Kihei. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Wailea Beach and Kamaole Beach Park 2 are located nearby.

Wailea Grand Champions - Maui Condo & Home

Wailea Grand Champions - Maui Condo & Home

3 out of 5
Save 100% on your flight
Price was $2,357, price is now $1,658 per person
$1,658
per person
Dec 11 - Dec 18
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Kahului (OGG)
Book a stay at this golf condo in Kihei. Enjoy free WiFi, 5 outdoor tennis courts, and cable TV channels. Popular attractions Wailea Beach and Shops at Wailea are located nearby.

Fairmont Kea Lani Maui

Fairmont Kea Lani Maui

5 out of 5
Save 100% on your flight
Price was $2,513, price is now $1,771 per person
$1,771
per person
Dec 1 - Dec 4
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Kahului (OGG)
Book a stay at this luxury resort in Kihei. Enjoy 3 outdoor pools, a full-service spa, and 6 restaurants. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Wailea Beach and Wailea Blue Golf Course are located nearby.

Maui Parkshore - Maui Condo & Home

Maui Parkshore - Maui Condo & Home

2 out of 5
Save 100% on your flight
Price was $1,912, price is now $1,396 per person
$1,396
per person
Dec 11 - Dec 18
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Kahului (OGG)
Book a stay at this beach condo in Kihei. Enjoy free WiFi, a garden, and laundry facilities. Our guests praise the property condition in our reviews. Popular attractions Wailea Beach and Kamaole Beach Park 3 are located nearby.

Palms at Wailea Maui

Palms at Wailea Maui

3.5 out of 5
Save 100% on your flight
Price was $2,004, price is now $1,498 per person
$1,498
per person
Dec 8 - Dec 13
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Kahului (OGG)
Book a stay at this golf aparthotel in Kihei. Enjoy free WiFi, free parking, and a garden. Our guests praise the property condition in our reviews. Popular attractions Wailea Beach and Keawakapu Beach South are located nearby.
Great stay!

Reviewed on Sep 19, 2026

Kaupo Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Maui Beach Vacation Club

Maui Beach Vacation Club

2.5 out of 5
North Kihei
Save 100% on your flight
Price was $1,404, price is now $929 per person
$929
per person
Nov 23 - Nov 26
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Kahului (OGG)
Fairmont Kea Lani Maui

Fairmont Kea Lani Maui

5 out of 5
Wailea
Save 100% on your flight
Price was $2,513, price is now $1,771 per person
$1,771
per person
Dec 1 - Dec 4
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Kahului (OGG)
Hotel Wailea Maui

Hotel Wailea Maui

5 out of 5
Wailea
Save 100% on your flight
Price was $3,769, price is now $2,663 per person
$2,663
per person
Dec 24 - Dec 27
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Kahului (OGG)
Hana-Maui Resort, a Destination by Hyatt Residence

Hana-Maui Resort, a Destination by Hyatt Residence

4 out of 5
Hana Town Center
Price was $1,316, price is now $999 per person
$999
per person
Dec 1 - Dec 4
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Kahului (OGG)

Kaupo Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
Maui Banyan Vacation Club

Maui Banyan Vacation Club

3 out of 5
South Kihei
Price was $2,084, price is now $1,342 per person
$1,342
per person
Nov 23 - Nov 30
found 1 day ago
Roundtrip non-stop flight included
Houston (IAH) to Kahului (OGG)
Maui Beach Vacation Club

Maui Beach Vacation Club

2.5 out of 5
North Kihei
Save 100% on your flight
Price was $2,543, price is now $1,521 per person
$1,521
per person
Nov 10 - Nov 17
found 13 hours ago
Roundtrip non-stop flight included
Houston (IAH) to Kahului (OGG)
Hotel Wailea Maui

Hotel Wailea Maui

5 out of 5
Wailea
Save 100% on your flight
Price was $3,836, price is now $2,424 per person
$2,424
per person
Dec 8 - Dec 13
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Kahului (OGG)
Wailea Grand Champions - Maui Condo & Home

Wailea Grand Champions - Maui Condo & Home

3 out of 5
Wailea
Save 100% on your flight
Price was $2,357, price is now $1,658 per person
$1,658
per person
Dec 11 - Dec 18
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Kahului (OGG)

Top Flight Deals

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

Alaska Airlines
Thu, Nov 5 - Thu, Nov 5
HNL
Daniel K. Inouye Intl.
OGG
Kahului
$135 Roundtrip, found 4 hours ago
$135
Roundtrip
found 4 hours ago
Select Alaska Airlines flight, departing Thu, Nov 5 from Daniel K. Inouye Intl. to Kahului, returning Thu, Nov 5, priced at $135 found 4 hours ago
United
Tue, Nov 3 - Tue, Nov 17
SFO
San Francisco Intl.
OGG
Kahului
$315 Roundtrip, found 14 hours ago
$315
Roundtrip
found 14 hours ago
Select United flight, departing Tue, Nov 3 from San Francisco Intl. to Kahului, returning Tue, Nov 17, priced at $315 found 14 hours ago
Bargain Flight
Tue, Dec 1 - Mon, Dec 14
LAX
Los Angeles Intl.
OGG
Kahului
$345 Roundtrip, found 4 hours ago
$345
Roundtrip
found 4 hours ago
Select Bargain Flight flight, departing Tue, Dec 1 from Los Angeles Intl. to Kahului, returning Mon, Dec 14, priced at $345 found 4 hours ago
Southwest Airlines
Mon, Nov 9 - Fri, Nov 13
OAK
Oakland Intl.
OGG
Kahului
$360 Roundtrip, found 3 days ago
$360
Roundtrip
found 3 days ago
Select Southwest Airlines flight, departing Mon, Nov 9 from Oakland Intl. to Kahului, returning Fri, Nov 13, priced at $360 found 3 days ago