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Our top choices for Upcountry Maui 5-star hotels

Grand Wailea Maui, A Waldorf Astoria Resort

Grand Wailea Maui, A Waldorf Astoria Resort
5.0 star property
Wailea
8.8 out of 10, Excellent, (1,004 reviews)
"Beautiful room and view. Amazing pool area. So much fun for the entire family! "
United States
Laura
The price is ¥148,021
¥185,903 total
includes taxes & fees
Apr 4 - Apr 5
Grand Wailea Maui, A Waldorf Astoria Resort

Four Seasons Resort Maui at Wailea

Four Seasons Resort Maui at Wailea
5.0 star property
Wailea
9.6 out of 10, Exceptional, (1,005 reviews)
"Service was good"
Canada
kathy
The price is ¥196,200
¥243,161 total
includes taxes & fees
Mar 9 - Mar 10
Four Seasons Resort Maui at Wailea

Fairmont Kea Lani Maui

Fairmont Kea Lani Maui
5.0 star property
Wailea
9.4 out of 10, Exceptional, (1,005 reviews)
"Beautiful hotel, amazing place, really relaxing. "
United States
Iulian
The price is ¥150,627
¥188,129 total
includes taxes & fees
Mar 8 - Mar 9
Fairmont Kea Lani Maui

The Ritz-Carlton Maui, Kapalua

The Ritz-Carlton Maui, Kapalua
5.0 star property
Kapalua
9.0 out of 10, Wonderful, (1,004 reviews)
"Top notch property with amazing service and staff"
Canada
Delaine
The price is ¥208,112
¥258,105 total
includes taxes & fees
Apr 2 - Apr 3
The Ritz-Carlton Maui, Kapalua

Hotel Wailea, Relais & Chateaux - Adults Only

Hotel Wailea, Relais & Chateaux - Adults Only
5.0 star property
Wailea
9.4 out of 10, Exceptional, (1,001 reviews)
"Everything was exceptional! Great property, quiet and peaceful "
United States
Abdulla
The price is ¥164,651
¥204,778 total
includes taxes & fees
Apr 5 - Apr 6
Hotel Wailea, Relais & Chateaux - Adults Only

Montage Kapalua Bay

Montage Kapalua Bay
5.0 star property
Lahaina
9.6 out of 10, Exceptional, (208 reviews)
"The views are next level. We enjoyed the pools, spa, restaurant and more. It was our second stay there and definitely going back. "
United States
Mandy D
The price is ¥345,312
¥446,818 total
includes taxes & fees
Mar 7 - Mar 8
Montage Kapalua Bay

Ho‘olei Villas at Grand Wailea

Ho‘olei Villas at Grand Wailea
5.0 star property
Wailea
9.6 out of 10, Exceptional, (45 reviews)
"Perfect for Families. Quite spacious and great for a relaxing Family vacation."
United States
Leslie
The price is ¥339,191
¥412,843 total
includes taxes & fees
Mar 6 - Mar 7
Ho‘olei Villas at Grand Wailea

2 2 Oceanview Modern Resort Vistas

2 2 Oceanview Modern Resort Vistas
5.0 star property
Central Kihei
9.4 out of 10, Exceptional, (8 reviews)
"The condo was very clean, loved all of the decor, was very beautiful. Had everything you could possibly need in kitchen and bathrooms. Would definitely stay again! Everyone we talked to was very nice and helpful! "
United States
Paulina
2 2 Oceanview Modern Resort Vistas

Fairmont Kea Lani Maui Villa Experience

Fairmont Kea Lani Maui Villa Experience
5.0 star property
Wailea
9.8 out of 10, Exceptional, (6 reviews)
"It’s a decent hotel to stay for the family."
United States
Sze Wai
The price is ¥525,659
¥633,234 total
includes taxes & fees
Mar 12 - Mar 13
Fairmont Kea Lani Maui Villa Experience

Centrally Located Elegant Vistas

Centrally Located Elegant Vistas
5.0 star property
South Kihei
10.0 out of 10, Exceptional, (1 review)
"Love this Kihei home! Centrally located! It is very clean. We love that they have beach chairs and towels on hand. Overall great experience stay!"
United States
Edwin
Centrally Located Elegant Vistas

Wailea Luxury Hilltop Resort Vistas

Wailea Luxury Hilltop Resort Vistas
5.0 star property
Wailea
10.0 out of 10, Exceptional, (2 reviews)
"very nice place and location 🤗"
United States
Maryna
Wailea Luxury Hilltop Resort Vistas

NEW KBM Resorts Free CAR Kaanapali Shores 6th Floor Ocean View Suite Steps to Pool and Beach Ks-616

NEW KBM Resorts Free CAR Kaanapali Shores 6th Floor Ocean View Suite Steps to Pool and Beach Ks-616
5.0 star property
Kaanapali
NEW KBM Resorts Free CAR Kaanapali Shores 6th Floor Ocean View Suite Steps to Pool and Beach Ks-616

Kapalua Ridge Villas KBM Resorts 2 Units, 2 Bedrooms KRV Ml-3535

Kapalua Ridge Villas KBM Resorts 2 Units, 2 Bedrooms KRV Ml-3535
5.0 star property
Kapalua
Kapalua Ridge Villas KBM Resorts 2 Units, 2 Bedrooms KRV Ml-3535
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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.

Learn more about Upcountry Maui

Venture to top sights like Haleakala National Park as you discover Upcountry Maui—a relaxing area also known for its island views.

View over Haleakala crater, at 3000 ft. Make sure that the skies are clear before heading to Haleakala, otherwise this view could be totally blocked by clouds.
#AboveItAll
Photo by Project Forever
Open Photo by Project Forever

Top Upcountry Maui Hotel Reviews

Frequently asked questions

How much does it cost to stay in a 5-star hotel in Upcountry Maui?
The amount you pay for a 5-star hotel in Upcountry Maui can vary according to when you decide to travel and how long you plan to stay, among a number of factors. Use our price per night filter and other search tools to find the best rate on a plush stay.

  • Search for the lowest price per night from ¥60,318

What makes a hotel 5 stars in Upcountry Maui?
Faultless guest service is at the heart of every 5-star hotel in Upcountry Maui. From the minute you step through the door, staff are at your beck and call, whether arranging valet parking or providing a nightly turn-down service. In addition, hotels have to feature top-rate conveniences to qualify for a 5-star rating. These can include luxury baths, spas or saunas, swimming pools, gastronomic restaurants and knowledgeable concierge.
Are there any 5-star all-inclusive resorts in Upcountry Maui?
Use Expedia's filters to find a high-end retreat in Upcountry Maui where everything you need is included. After your initial search, narrow down your results for properties that have 5 stars and are deemed "All inclusive." The main thing on the agenda at these stays? Pure relaxation and indulgence.

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