Upcountry Maui Vacation Packages for 2026
Build a Flight + Hotel Bundle & Save up to $536 On Your Vacation*
Upcountry Maui Flight + Hotel packages
Price found within the past 48 hours. Click for updated prices.
Maui Beach Vacation Club
North Kihei
Price was $1,459, price is now $1,084 per person
$1,084
per person
Jun 15 - Jun 21
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) 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 Hawaiian Islands Humpback Whale National Marine Sanctuary Headquarters are located nearby.
Hotel Wailea, Relais & Chateaux - Adults Only
Wailea
Save 100% on your flight
Price was $4,937, price is now $3,000 per person
$3,000
per person
Jun 15 - Jun 21
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, breakfast (surcharge), and a free beach shuttle. Our guests praise the helpful staff in our reviews. Popular attractions Wailea Beach and Wailea Blue Golf Course are located nearby.
Maui Banyan Vacation Club
South Kihei
Price was $1,566, price is now $1,101 per person
$1,101
per person
Jun 15 - Jun 21
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) 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.
Signature Residences at Maui Banyan
South Kihei
Save 100% on your flight
Price was $2,477, price is now $1,779 per person
$1,779
per person
Jun 3 - Jun 10
found 1 day ago
Roundtrip non-stop flight included
Sacramento (SMF) to Kahului (OGG)
Book a stay at this business-friendly condo in Kihei. Enjoy free WiFi, free parking, and 2 outdoor pools. Popular attractions Wailea Beach and Kamaole Beach Park 2 are located nearby.
Mana Kai Maui- Official Onsite Rental
South Kihei
Save 100% on your flight
Price was $2,843, price is now $2,044 per person
$2,044
per person
Jun 15 - Jun 21
found 16 hours ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Kahului (OGG)
Book a stay at this beach hotel in Kihei. Enjoy free WiFi, free parking, and a beach locale. Our guests praise the property condition in our reviews. Popular attractions Wailea Beach and Keawakapu Beach North are located nearby.
Grand Wailea Maui, A Waldorf Astoria Resort
Wailea
Save 100% on your flight
Price was $4,142, price is now $3,135 per person
$3,135
per person
Jun 15 - Jun 21
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Kahului (OGG)
Book a stay at this luxury resort in Kihei. Enjoy free WiFi, 9 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Wailea Beach and Shops at Wailea are located nearby.
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Gods Peace Of Maui
1290 Haliimaile Rd Makawao HI
15.94 km from city center
Book a stay at this spa B&B in Makawao. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Haliʻimaile Farmer's Market and Hui Noʻeau Visual ...
Grand Wailea Maui, A Waldorf Astoria Resort
3850 Wailea Alanui Drive Kihei HI
22.07 km from city center
Book a stay at this luxury resort in Kihei. Enjoy free WiFi, 9 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff in our ...
The Westin Maui Resort & Spa, Ka'anapali
2365 Kaanapali Pkwy Lahaina HI
50.61 km from city center
Book a stay at this luxury hotel in Kaanapali. Enjoy 3 outdoor pools, a full-service spa, and 2 restaurants. Our guests praise the helpful staff and the property ...
Maui Coast Hotel
2259 S Kihei Rd Kihei HI
21.58 km from city center
Stay at this hotel in Kihei. Enjoy free WiFi, 2 outdoor pools, and 2 restaurants. Our guests praise the breakfast and the pool in our reviews. Popular attractions ...
Royal Lahaina Resort & Bungalows
2780 Kekaa Dr Lahaina HI
50.81 km from city center
Book a stay at this beach hotel in Kaanapali. Enjoy free WiFi, 2 outdoor pools, and a full-service spa. Our guests praise the helpful staff and the clean rooms ...
Hyatt Regency Maui Resort & Spa
200 Nohea Kai Dr Lahaina HI
50.51 km from city center
Book a stay at this beach resort in Kaanapali. Enjoy free WiFi, 6 outdoor pools, and a full-service spa. Our guests praise the helpful staff and the property ...
Fairmont Kea Lani Maui
4100 Wailea Alanui Dr Kihei HI
22.47 km from city center
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 ...
Hilton Vacation Club Ka'anapali Beach Maui
104 Ka'anapali Shores Place Kaanapali HI
51.44 km from city center
Book a stay at this beach hotel in Kaanapali. Enjoy a beach locale, breakfast (surcharge), and a fitness center. Our guests praise the helpful staff and the ...
Four Seasons Resort Maui at Wailea
3900 Wailea Alanui Drive Kihei HI
22.43 km from city center
Book a stay at this luxury resort in Kihei. Enjoy free WiFi, 3 outdoor pools, and a full-service spa. Our guests praise the helpful staff in our reviews. Popular ...
OUTRIGGER Kaanapali Beach Resort
2525 Kaanapali Parkway Lahaina HI
50.66 km from city center
Book a stay at this beach resort in Kaanapali. Enjoy free WiFi, a beach locale, and breakfast (surcharge). Our guests praise the helpful staff and the clean ...
Maui Seaside Hotel
100 W Kaahumanu Ave Kahului HI
28.23 km from city center
Book a stay at this beach hotel in Kahului. Enjoy free WiFi, a beach locale, and breakfast (surcharge). Our guests praise the pool and the restaurant in our ...
The Ritz-Carlton Maui, Kapalua
1 Ritz-Carlton Drive Kapalua HI
50.89 km from city center
Book a stay at this luxury resort in Kapalua. Enjoy 3 outdoor pools, a full-service spa, and 6 restaurants. Our guests praise the helpful staff and the property ...
Wailea Beach Resort - Marriott, Maui
3700 Wailea Alanui Dr Kihei HI
21.93 km from city center
Book a stay at this luxury resort in Kihei. Enjoy 4 outdoor pools, a full-service spa, and 4 restaurants. Our guests praise the pool and the helpful staff in ...
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.
Top Flight Deals
These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.
Tue, Sep 29 - Wed, Sep 30
HNL
Daniel K. Inouye Intl.
OGG
Kahului
$185 Roundtrip, found 1 day ago
$185
Roundtrip
found 1 day ago
Tue, Sep 29 - Wed, Sep 30
HNL
Daniel K. Inouye Intl.
OGG
Kahului
$185 Roundtrip, found 1 day ago
$185
Roundtrip
found 1 day ago
Tue, Sep 29 - Wed, Sep 30
HNL
Daniel K. Inouye Intl.
OGG
Kahului
$256 Roundtrip, found 1 day ago
$256
Roundtrip
found 1 day ago
Tue, Jun 2 - Tue, Jun 9
LAX
Los Angeles Intl.
OGG
Kahului
$377 Roundtrip, found 5 days ago
$377
Roundtrip
found 5 days ago
Tue, Jun 2 - Tue, Jun 9
LAX
Los Angeles Intl.
OGG
Kahului
$407 Roundtrip, found 5 days ago
$407
Roundtrip
found 5 days ago