Upcountry Maui Vacation Packages for 2025

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Upcountry Maui Flight + Hotel packages

Price found within the past 48 hours. Click for updated prices.
AEI at Kaanapali Shores

AEI at Kaanapali Shores

4 out of 5
Save 100% on your flight
per person
Sep 1 - Sep 6
found 8 hours ago
Roundtrip non-stop flight included
Ontario (ONT) to Kahului (OGG)
Stay at this 4-star beach aparthotel in Kaanapali. Enjoy free WiFi, a full-service spa, and a beach locale. Popular attractions Whalers Village and Kaanapali Beach are located nearby.

Royal Lahaina Resort & Bungalows

Royal Lahaina Resort & Bungalows

4 out of 5
per person
Jul 29 - Aug 5
found 7 hours ago
Roundtrip flight included
Atlanta (ATL) to Kahului (OGG)
Stay at this 4-star beach hotel in Kaanapali. Enjoy free WiFi, 2 outdoor pools, and a full-service spa. Our guests praise the bar and the helpful staff in our reviews. Popular attractions Whalers Village and Kaanapali Beach are located nearby.

AEI at The Mahana Kaanapali Resort

AEI at The Mahana Kaanapali Resort

4 out of 5
Save 100% on your flight
per person
Sep 1 - Sep 6
found 8 hours ago
Roundtrip non-stop flight included
Ontario (ONT) to Kahului (OGG)
Stay at this 4-star beach aparthotel in Kaanapali. Enjoy free WiFi, free parking, and a beach locale. Our guests praise the helpful staff in our reviews. Popular attractions Whalers Village and Kaanapali Beach are located nearby.

AEI at Maui Kaanapali Villas Resort

AEI at Maui Kaanapali Villas Resort

3.5 out of 5
Save 100% on your flight
per person
Jul 29 - Aug 5
found 7 hours ago
Roundtrip flight included
Atlanta (ATL) to Kahului (OGG)
Stay at this 3.5-star beach hotel in Kaanapali. Enjoy free WiFi, free parking, and 2 outdoor pools. Popular attractions Whalers Village and Kaanapali Beach are located nearby.

Aston Kaanapali Shores

Aston Kaanapali Shores

3.5 out of 5
Save 100% on your flight
per person
Sep 1 - Sep 6
found 8 hours ago
Roundtrip non-stop flight included
Ontario (ONT) to Kahului (OGG)
Book a stay at this beach aparthotel in Kaanapali. Enjoy 2 outdoor pools, a full-service spa, and a beach locale. Our guests praise the pool and the restaurant in our reviews. Popular attractions Whalers Village and Kaanapali Beach are located nearby.

Kahana Beach Vacation Club

Kahana Beach Vacation Club

3 out of 5
Save 100% on your flight
per person
Jul 29 - Aug 5
found 7 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 Whalers Village and Kaanapali Beach are located nearby.

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Top Hotel Deals

Gods Peace Of Maui

Gods Peace Of Maui

2 out of 5
1290 Haliimaile Rd, Makawao, HI
15.88 km from city center
Book a stay at this spa B&B in Makawao. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Hali imaile Farmer's Market and Hui Noʻeau Visual ...
Maui Coast Hotel

Maui Coast Hotel

3.5 out of 5
2259 S Kihei Rd, Kihei, HI
21.75 km from city center
Stay at this 3.5-star hotel in Kihei. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the breakfast and the pool in our reviews. Popular ...
The Westin Maui Resort & Spa, Ka'anapali

The Westin Maui Resort & Spa, Ka'anapali

4.5 out of 5
2365 Kaanapali Pkwy, Lahaina, HI
50.61 km from city center
Stay at this 4.5-star luxury hotel in Kaanapali. Enjoy 3 outdoor pools, a full-service spa, and 2 restaurants. Our guests praise the helpful staff and the property ...
Four Seasons Resort Maui at Wailea

Four Seasons Resort Maui at Wailea

5 out of 5
3900 Wailea Alanui Drive, Kihei, HI
22.43 km from city center
Stay at this 5-star luxury resort in Kihei. Enjoy free WiFi, 3 outdoor pools, and a full-service spa. Our guests praise the helpful staff and the property condition ...
Grand Wailea Maui, A Waldorf Astoria Resort

Grand Wailea Maui, A Waldorf Astoria Resort

5 out of 5
3850 Wailea Alanui Drive, Kihei, HI
22.07 km from city center
Stay at this 5-star 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 ...
Royal Lahaina Resort & Bungalows

Royal Lahaina Resort & Bungalows

4 out of 5
2780 Kekaa Dr, Lahaina, HI
50.81 km from city center
Stay at this 4-star beach hotel in Kaanapali. Enjoy free WiFi, 2 outdoor pools, and a full-service spa. Our guests praise the bar and the helpful staff in our ...
OUTRIGGER Kaanapali Beach Resort

OUTRIGGER Kaanapali Beach Resort

3.5 out of 5
2525 Kaanapali Parkway, Lahaina, HI
50.66 km from city center
Stay at this 3.5-star beach resort in Kaanapali. Enjoy free WiFi, a beach locale, and breakfast (surcharge). Our guests praise the helpful staff and the clean ...
Hilton Vacation Club Ka'anapali Beach Maui

Hilton Vacation Club Ka'anapali Beach Maui

4 out of 5
104 Ka'anapali Shores Place, Kaanapali, HI
51.39 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 ...
The Ritz-Carlton Maui, Kapalua

The Ritz-Carlton Maui, Kapalua

5 out of 5
1 Ritz-Carlton Drive, Kapalua, HI
50.89 km from city center
Stay at this 5-star luxury resort in Kapalua. Enjoy 3 outdoor pools, a full-service spa, and 6 restaurants. Our guests praise the helpful staff and the property ...
Hyatt Regency Maui Resort & Spa

Hyatt Regency Maui Resort & Spa

4 out of 5
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 ...
Andaz Maui at Wailea Resort - a concept by Hyatt

Andaz Maui at Wailea Resort - a concept by Hyatt

4.5 out of 5
3550 Wailea Alanui Dr, Kihei, HI
21.89 km from city center
Stay at this 4.5-star luxury resort in Kihei. Enjoy free WiFi, 5 outdoor pools, and a full-service spa. Our guests praise the helpful staff in our reviews. Popular ...
Maui Seaside Hotel

Maui Seaside Hotel

3 out of 5
100 W Kaahumanu Ave, Kahului, HI
28.2 km from city center
Stay at this 3-star beach hotel in Kahului. Enjoy free WiFi, a beach locale, and breakfast (surcharge). Our guests praise the pool and the restaurant in our ...
Maui Beach Hotel

Maui Beach Hotel

3 out of 5
170 W Kaahumanu Avenue, Kahului, HI
28.29 km from city center
Book a stay at this beach hotel in Kahului. Enjoy a beach locale, breakfast (surcharge), and a 24-hour fitness center. Our guests praise the helpful staff and ...
Fairmont Kea Lani Maui

Fairmont Kea Lani Maui

5 out of 5
4100 Wailea Alanui Dr, Kihei, HI
22.47 km from city center
Stay at this 5-star luxury resort in Kihei. 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

Wailea Beach Resort - Marriott, Maui

4.5 out of 5
3700 Wailea Alanui Dr, Kihei, HI
21.93 km from city center
Stay at this 4.5-star luxury resort in Kihei. Enjoy 4 outdoor pools, a full-service spa, and 4 restaurants. Our guests praise the pool and the helpful staff ...
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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.

Alaska Airlines
Tue, Jul 8 - Tue, Jul 15
HNL
Daniel K. Inouye Intl.
OGG
Kahului
$98 Roundtrip, found 9 hours ago
$98
Roundtrip
found 9 hours ago
Select Alaska Airlines flight, departing Tue, Jul 8 from Daniel K. Inouye Intl. to Kahului, returning Tue, Jul 15, priced at $98 found 9 hours ago
Hawaiian Airlines
Sun, Aug 17 - Tue, Aug 26
OAK
Oakland Intl.
OGG
Kahului
$328 Roundtrip, found 3 days ago
$328
Roundtrip
found 3 days ago
Select Hawaiian Airlines flight, departing Sun, Aug 17 from Oakland Intl. to Kahului, returning Tue, Aug 26, priced at $328 found 3 days ago
Hawaiian Airlines
Thu, Sep 18 - Thu, Oct 2
SFO
San Francisco Intl.
OGG
Kahului
$328 Roundtrip, found 6 days ago
$328
Roundtrip
found 6 days ago
Select Hawaiian Airlines flight, departing Thu, Sep 18 from San Francisco Intl. to Kahului, returning Thu, Oct 2, priced at $328 found 6 days ago
American Airlines
Mon, Oct 20 - Mon, Oct 20
LAX
Los Angeles Intl.
OGG
Kahului
$332 Roundtrip, found 5 days ago
$332
Roundtrip
found 5 days ago
Select American Airlines flight, departing Mon, Oct 20 from Los Angeles Intl. to Kahului, returning Mon, Oct 20, priced at $332 found 5 days ago