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 8 - Sep 15
found 9 hours ago
Roundtrip non-stop flight included
Los Angeles (LAX) 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
Save 100% on your flight
per person
Sep 8 - Sep 15
found 9 hours ago
Roundtrip non-stop flight included
Los Angeles (LAX) 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.

Napili Kai Beach Resort

Napili Kai Beach Resort

3.5 out of 5
Save 100% on your flight
per person
Sep 30 - Oct 7
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to Kahului (OGG)
Stay at this 3.5-star beach hotel in Kapalua. Enjoy free WiFi, free parking, and 4 outdoor pools. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Whalers Village and Kaanapali Beach are located nearby.

The Gardens at West Maui

The Gardens at West Maui

3 out of 5
per person
Sep 30 - Oct 7
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to Kahului (OGG)
Stay at this 3-star condo in Kapalua. Enjoy free WiFi, free parking, and a garden. Our guests praise the helpful staff and the property condition 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
Sep 8 - Sep 15
found 9 hours ago
Roundtrip non-stop flight included
Los Angeles (LAX) 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.

OUTRIGGER Kaanapali Beach Resort

OUTRIGGER Kaanapali Beach Resort

3.5 out of 5
Save 100% on your flight
per person
Sep 8 - Sep 15
found 9 hours ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Kahului (OGG)
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 rooms 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 ...
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 ...
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 ...
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 ...
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 ...
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 ...
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 ...
Aston Maui Kaanapali Villas

Aston Maui Kaanapali Villas

3 out of 5
45 Kai Ala Dr, Lahaina, HI
50.87 km from city center
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 helpful staff and the ...
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 ...
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 ...
Aston Kaanapali Shores

Aston Kaanapali Shores

3.5 out of 5
3445 Lower Honoapiilani Hwy, Lahaina, HI
51.36 km from city center
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 ...
AEI at Maui Kaanapali Villas Resort

AEI at Maui Kaanapali Villas Resort

3.5 out of 5
45 Kai Ala Drive, Lahaina, HI
50.85 km from city center
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 ...
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, Nov 4 - Wed, Nov 12
HNL
Daniel K. Inouye Intl.
OGG
Kahului
$99 Roundtrip, found 5 days ago
$99
Roundtrip
found 5 days ago
Select Alaska Airlines flight, departing Tue, Nov 4 from Daniel K. Inouye Intl. to Kahului, returning Wed, Nov 12, priced at $99 found 5 days ago
Hawaiian Airlines
Tue, Nov 4 - Wed, Nov 12
HNL
Daniel K. Inouye Intl.
OGG
Kahului
$99 Roundtrip, found 5 days ago
$99
Roundtrip
found 5 days ago
Select Hawaiian Airlines flight, departing Tue, Nov 4 from Daniel K. Inouye Intl. to Kahului, returning Wed, Nov 12, priced at $99 found 5 days ago
United
Tue, Sep 16 - Wed, Sep 24
SEA
Seattle - Tacoma Intl.
OGG
Kahului
$297 Roundtrip, found 5 days ago
$297
Roundtrip
found 5 days ago
Select United flight, departing Tue, Sep 16 from Seattle - Tacoma Intl. to Kahului, returning Wed, Sep 24, priced at $297 found 5 days ago
Delta
Tue, Sep 16 - Wed, Sep 24
SEA
Seattle - Tacoma Intl.
OGG
Kahului
$298 Roundtrip, found 5 days ago
$298
Roundtrip
found 5 days ago
Select Delta flight, departing Tue, Sep 16 from Seattle - Tacoma Intl. to Kahului, returning Wed, Sep 24, priced at $298 found 5 days ago
Southern Airways Express
Fri, Aug 1 - Sun, Aug 3
HNL
Daniel K. Inouye Intl.
OGG
Kahului
$361 Roundtrip, found 1 day ago
$361
Roundtrip
found 1 day ago
Select Southern Airways Express flight, departing Fri, Aug 1 from Daniel K. Inouye Intl. to Kahului, returning Sun, Aug 3, priced at $361 found 1 day ago