Search Deals on
Kaupakulua Vacation Packages

Build your package with 2 more options

Kaupakulua Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Aston at the Maui Banyan

Aston at the Maui Banyan

3 out of 5
Price was $1,484, price is now $1,122 per person
$1,122
per person
Nov 18 - Nov 22
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Kahului (OGG)
Book a stay at this beach hotel in Kihei. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Wailea Beach and Kamaole Beach Park 2 are located nearby.
The main bedroom AC was not enough for the room was hot

Reviewed on Aug 30, 2026

Maui Beach Vacation Club

Maui Beach Vacation Club

2.5 out of 5
Price was $2,905, price is now $1,942 per person
$1,942
per person
Nov 22 - Nov 29
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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.

Fairmont Kea Lani Maui

Fairmont Kea Lani Maui

5 out of 5
Save 100% on your flight
Price was $5,394, price is now $3,806 per person
$3,806
per person
Oct 13 - Oct 20
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) 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.

Lumeria Maui Educational Retreat Center

Lumeria Maui Educational Retreat Center

3.5 out of 5
Price was $1,820, price is now $1,332 per person
$1,332
per person
Nov 11 - Nov 15
found 1 day ago
Roundtrip non-stop flight included
Dallas (DAL) to Kahului (OGG)
Book a stay at this boutique hotel in Makawao. Enjoy free breakfast, onsite spa services, and a garden. Popular attractions Haliʻimaile Farmer's Market and Maui Gold Pineapple Farm are located nearby.

Maui Banyan - Maui Condo & Home

Maui Banyan - Maui Condo & Home

3 out of 5
Save 100% on your flight
Price was $1,932, price is now $1,416 per person
$1,416
per person
Nov 1 - Nov 7
found 24 hours ago
Roundtrip flight included
Los Angeles (LAX) 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.

Maui Banyan Vacation Club

Maui Banyan Vacation Club

3 out of 5
Price was $2,037, price is now $1,504 per person
$1,504
per person
Nov 22 - Nov 29
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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.
Na

Reviewed on Aug 30, 2026

Maui Parkshore - Maui Condo & Home

Maui Parkshore - Maui Condo & Home

2 out of 5
Save 100% on your flight
Price was $1,666, price is now $1,244 per person
$1,244
per person
Nov 1 - Nov 7
found 24 hours 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.
This place is so totally worth all the money. For its amazing price you get a a good size place with a lot of amenities included. Shampoo, condit

Reviewed on Aug 27, 2026

The Kalama Residence

The Kalama Residence

3 out of 5
Save 100% on your flight
Price was $4,671, price is now $3,508 per person
$3,508
per person
Nov 8 - Nov 12
found 2 hours 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

Kaupakulua Vacation Packages 3-4 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 $1,207, price is now $877 per person
$877
per person
Nov 18 - Nov 22
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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 $1,606, price is now $1,011 per person
$1,011
per person
Nov 18 - Nov 22
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Kahului (OGG)
Hotel Wailea, Relais & Chateaux - Adults Only

Hotel Wailea, Relais & Chateaux - Adults Only

5 out of 5
Wailea
Save 100% on your flight
Price was $3,035, price is now $1,991 per person
$1,991
per person
Nov 7 - Nov 10
found 8 hours ago
Roundtrip flight included
Dallas (DFW) to Kahului (OGG)
Lumeria Maui Educational Retreat Center

Lumeria Maui Educational Retreat Center

3.5 out of 5
Price was $1,820, price is now $1,332 per person
$1,332
per person
Nov 11 - Nov 15
found 1 day ago
Roundtrip non-stop flight included
Dallas (DAL) to Kahului (OGG)

Kaupakulua Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
Maui Schooner Resort

Maui Schooner Resort

3.5 out of 5
Central Kihei
Save 100% on your flight
Price was $1,553, price is now $1,097 per person
$1,097
per person
Nov 1 - Nov 7
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Kahului (OGG)
Maui Beach Vacation Club

Maui Beach Vacation Club

2.5 out of 5
North Kihei
Price was $2,905, price is now $1,942 per person
$1,942
per person
Nov 22 - Nov 29
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Kahului (OGG)
Fairmont Kea Lani Maui

Fairmont Kea Lani Maui

5 out of 5
Wailea
Save 100% on your flight
Price was $5,394, price is now $3,806 per person
$3,806
per person
Oct 13 - Oct 20
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to Kahului (OGG)
Maui Banyan - Maui Condo & Home

Maui Banyan - Maui Condo & Home

3 out of 5
South Kihei
Save 100% on your flight
Price was $1,932, price is now $1,416 per person
$1,416
per person
Nov 1 - Nov 7
found 24 hours 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
Tue, Oct 6 - Tue, Oct 6
HNL
Daniel K. Inouye Intl.
OGG
Kahului
$133 Roundtrip, found 1 hour ago
$133
Roundtrip
found 1 hour ago
Select Alaska Airlines flight, departing Tue, Oct 6 from Daniel K. Inouye Intl. to Kahului, returning Tue, Oct 6, priced at $133 found 1 hour ago
Southern Airways Express
Sun, Sep 27 - Wed, Oct 7
HNL
Daniel K. Inouye Intl.
JHM
West Maui
$201 Roundtrip, found 14 hours ago
$201
Roundtrip
found 14 hours ago
Select Southern Airways Express flight, departing Sun, Sep 27 from Daniel K. Inouye Intl. to West Maui, returning Wed, Oct 7, priced at $201 found 14 hours ago
Bargain Flight
Tue, Nov 3 - Tue, Nov 17
SEA
Seattle - Tacoma Intl.
OGG
Kahului
$240 Roundtrip, found 10 hours ago
$240
Roundtrip
found 10 hours ago
Select Bargain Flight flight, departing Tue, Nov 3 from Seattle - Tacoma Intl. to Kahului, returning Tue, Nov 17, priced at $240 found 10 hours ago
Bargain Flight
Mon, Nov 9 - Fri, Nov 13
OAK
Oakland Intl.
OGG
Kahului
$280 Roundtrip, found 1 hour ago
$280
Roundtrip
found 1 hour ago
Select Bargain Flight flight, departing Mon, Nov 9 from Oakland Intl. to Kahului, returning Fri, Nov 13, priced at $280 found 1 hour ago