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Upcountry Maui Vacation Packages

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Upcountry Maui Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Sands of Kahana

Sands of Kahana

3 out of 5
Save 100% on your flight
Price was $1,819, price is now $838 per person
$838
per person
Jan 26 - Feb 1
just found
Roundtrip flight included
Atlanta (ATL) to Kahului (OGG)
Book a stay at this beach aparthotel in Kahana. Enjoy free parking, a beach locale, and a fitness center. Our guests praise the helpful staff in our reviews. Popular attractions Kaanapali Beach and Napili Bay are located nearby.
Valle Isle

Valle Isle

3 out of 5
Save 100% on your flight
Price was $2,686, price is now $1,659 per person
$1,659
per person
Jan 26 - Feb 1
just found
Roundtrip flight included
Atlanta (ATL) to Kahului (OGG)
Book a stay at this beach apartment in Kahana. Enjoy free WiFi, free parking, and a beach locale. Popular attractions Kaanapali Beach and Napili Bay are located nearby.
The Whaler Resort Kaanapali Beach

The Whaler Resort Kaanapali Beach

4 out of 5
Save 100% on your flight
Price was $3,512, price is now $2,195 per person
$2,195
per person
Jan 30 - Feb 7
just found
Roundtrip flight included
Atlanta (ATL) to Kahului (OGG)
Book a stay at this beach condo in Kaanapali. Enjoy free WiFi, free parking, and a beach locale. Our guests praise the helpful staff in our reviews. Popular attractions Kaanapali Beach and Whalers Village are located nearby.
Kahana Beach Vacation Club

Kahana Beach Vacation Club

3 out of 5
Price was $2,773, price is now $1,750 per person
$1,750
per person
Feb 9 - Feb 14
found 20 hours ago
Roundtrip flight included
Atlanta (ATL) to Kahului (OGG)
Stay at this 3-star beach condo in Kahana. Enjoy free WiFi, free parking, and a beach locale. Our guests praise the helpful staff in our reviews. Popular attractions Kaanapali Beach and Napili Bay are located nearby.
Hyatt Vacation Club at Ka'anapali Beach, Maui

Hyatt Vacation Club at Ka'anapali Beach, Maui

3.5 out of 5
Save 100% on your flight
Price was $3,992, price is now $2,582 per person
$2,582
per person
Jan 31 - Feb 7
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Kahului (OGG)
Book a stay at this beach hotel in Kaanapali. Enjoy free WiFi, 2 outdoor pools, and a beach locale. Popular attractions Kaanapali Beach and Whalers Village are located nearby.
Honua Kai Hokulani Collection by KBM - 2 Units on same floor (201/203)

Honua Kai Hokulani Collection by KBM - 2 Units on same floor (201/203)

5 out of 5
Save 100% on your flight
Price was $16,857, price is now $10,996 per person
$10,996
per person
Jan 13 - Jan 18
found 23 hours ago
Roundtrip non-stop flight included
Portland (PDX) to Kahului (OGG)
Stay at this 5-star luxury condo in Kaanapali. Enjoy free parking, a beach locale, and a health club. Popular attractions Kaanapali Beach and Whalers Village are located nearby.
Wailea Grand Champions - Maui Condo & Home

Wailea Grand Champions - Maui Condo & Home

3 out of 5
Price was $3,863, price is now $2,540 per person
$2,540
per person
Jan 31 - Feb 8
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) to Kahului (OGG)
Stay at this 3-star 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.
The Residences at Kamaole Sands Resort

The Residences at Kamaole Sands Resort

4.5 out of 5
Save 100% on your flight
Price was $9,745, price is now $6,525 per person
$6,525
per person
Jan 31 - Feb 8
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Kahului (OGG)
Book a stay at this luxury aparthotel in Kihei. Enjoy free WiFi, free parking, and a fitness center. Popular attractions Wailea Beach and Kamaole Beach Park 3 are located nearby.

Upcountry Maui 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
Save 100% on your flight
Price was $1,328, price is now $739 per person
$739
per person
Feb 10 - Feb 14
found 1 day ago
Roundtrip non-stop flight included
Portland (PDX) to Kahului (OGG)
Sands of Kahana

Sands of Kahana

3 out of 5
Price was $2,822, price is now $1,084 per person
$1,084
per person
Jan 21 - Jan 25
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Kahului (OGG)
Kahana Beach Vacation Club

Kahana Beach Vacation Club

3 out of 5
Save 100% on your flight
Price was $1,849, price is now $1,014 per person
$1,014
per person
Feb 13 - Feb 16
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to Kahului (OGG)
Hono Koa Vacation Club

Hono Koa Vacation Club

3 out of 5
Save 100% on your flight
Price was $1,751, price is now $1,009 per person
$1,009
per person
Jan 21 - Jan 25
found 1 day ago
Roundtrip flight included
Chicago (ORD) to Kahului (OGG)

Upcountry Maui Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
Sands of Kahana

Sands of Kahana

3 out of 5
Save 100% on your flight
Price was $1,819, price is now $838 per person
$838
per person
Jan 26 - Feb 1
just found
Roundtrip flight included
Atlanta (ATL) to Kahului (OGG)
Grand Champions

Grand Champions

2.5 out of 5
Wailea
Save 100% on your flight
Price was $3,499, price is now $2,080 per person
$2,080
per person
Feb 9 - Feb 16
found 1 day ago
Roundtrip non-stop flight included
Chicago (ORD) to Kahului (OGG)
The Kalama Residence

The Kalama Residence

3 out of 5
South Kihei
Save 100% on your flight
Price was $2,702, price is now $1,611 per person
$1,611
per person
Jan 21 - Jan 27
found 3 hours ago
Roundtrip non-stop flight included
Portland (PDX) to Kahului (OGG)
The Whaler Resort Kaanapali Beach

The Whaler Resort Kaanapali Beach

4 out of 5
Save 100% on your flight
Price was $3,891, price is now $2,373 per person
$2,373
per person
Feb 8 - Feb 15
just found
Roundtrip flight included
Atlanta (ATL) to Kahului (OGG)

Top Flight Deals

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

Alaska Airlines
Wed, Feb 18 - Wed, Feb 18
HNL
Daniel K. Inouye Intl.
OGG
Kahului
$124 Roundtrip, found 1 day ago
$124
Roundtrip
found 1 day ago
Select Alaska Airlines flight, departing Wed, Feb 18 from Daniel K. Inouye Intl. to Kahului, returning Wed, Feb 18, priced at $124 found 1 day ago
Alaska Airlines
Wed, Jan 7 - Mon, Jan 12
SEA
Seattle - Tacoma Intl.
OGG
Kahului
$218 Roundtrip, found 2 days ago
$218
Roundtrip
found 2 days ago
Select Alaska Airlines flight, departing Wed, Jan 7 from Seattle - Tacoma Intl. to Kahului, returning Mon, Jan 12, priced at $218 found 2 days ago
Delta
Tue, Jan 27 - Tue, Feb 3
SJC
Norman Y. Mineta San Jose Intl.
OGG
Kahului
$243 Roundtrip, found 1 hour ago
$243
Roundtrip
found 1 hour ago
Select Delta flight, departing Tue, Jan 27 from Norman Y. Mineta San Jose Intl. to Kahului, returning Tue, Feb 3, priced at $243 found 1 hour ago
Hawaiian Airlines
Tue, Dec 9 - Tue, Dec 9
OAK
Oakland Intl.
OGG
Kahului
$252 Roundtrip, found 3 days ago
$252
Roundtrip
found 3 days ago
Select Hawaiian Airlines flight, departing Tue, Dec 9 from Oakland Intl. to Kahului, returning Tue, Dec 9, priced at $252 found 3 days ago