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Find 5 Star Hotels in Upcountry Maui, HI from ¥73,429

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Our top choices for Upcountry Maui 5-star hotels

Four Seasons Resort Maui at Wailea

Four Seasons Resort Maui at Wailea
5.0 star property
Wailea
9.6 out of 10, Exceptional, (1000)
"Beautiful property, efficient staff, truly a wonderful stay "
Canada
Angela
The price is ¥124,131
¥147,359 total
includes taxes & fees
Jan 26 - Jan 27, 2026
Four Seasons Resort Maui at Wailea

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, (1005)
"Very nice resort for a family vacation!"
United States
Ashwini
The price is ¥107,246
¥137,472 total
includes taxes & fees
Jan 9 - Jan 10, 2026
Grand Wailea Maui, A Waldorf Astoria Resort

Fairmont Kea Lani Maui

Fairmont Kea Lani Maui
5.0 star property
Wailea
9.4 out of 10, Exceptional, (1000)
"Wonderful staff and facility"
United States
Sheila
The price is ¥133,913
¥168,238 total
includes taxes & fees
Jan 25 - Jan 26, 2026
Fairmont Kea Lani Maui

The Ritz-Carlton Maui, Kapalua

The Ritz-Carlton Maui, Kapalua
5.0 star property
Kapalua
9.2 out of 10, Wonderful, (1001)
"Top notch property with amazing service and staff"
Canada
Delaine
The price is ¥124,756
¥158,229 total
includes taxes & fees
Jan 17 - Jan 18, 2026
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, (1002)
"Staff was great and the property was stunning. It was everything we wanted for our honeymoon. Other couples mentioned "
United States
Jacob
The price is ¥164,242
¥204,269 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Hotel Wailea, Relais & Chateaux - Adults Only

Montage Kapalua Bay

Montage Kapalua Bay
5.0 star property
Lahaina
9.6 out of 10, Exceptional, (204)
"We used Spa, expedia mentioned there is 20% discount and we didn't get it"
United States
Ronak
The price is ¥217,632
¥281,607 total
includes taxes & fees
Jan 24 - Jan 25, 2026
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, (44)
"Perfect for Families. Quite spacious and great for a relaxing Family vacation."
United States
Leslie
The price is ¥313,347
¥382,138 total
includes taxes & fees
Jan 8 - Jan 9, 2026
Ho‘olei Villas at Grand Wailea

Royal Lahaina Bungalows & Spa

Royal Lahaina Bungalows & Spa
5.0 star property
Lahaina
9.0 out of 10, Wonderful, (2)
"Clean room and staff is super friendly. Would stay here again "
United States
Rene
The price is ¥54,854
¥73,429 total
includes taxes & fees
Jan 9 - Jan 10, 2026
Royal Lahaina Bungalows & Spa

Fairmont Kea Lani Maui Villa Experience

Fairmont Kea Lani Maui Villa Experience
5.0 star property
Wailea
9.8 out of 10, Exceptional, (6)
"It’s a decent hotel to stay for the family."
United States
Sze Wai
The price is ¥451,112
¥541,307 total
includes taxes & fees
Jan 17 - Jan 18, 2026
Fairmont Kea Lani Maui Villa Experience

2 2 Oceanview Modern Resort Vistas

2 2 Oceanview Modern Resort Vistas
5.0 star property
Central Kihei
9.8 out of 10, Exceptional, (7)
"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

Wailea Luxury Hilltop Resort Vistas

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

Oceanfront Kihei Paradise Vistas

Oceanfront Kihei Paradise Vistas
5.0 star property
Central Kihei
10.0 out of 10, Exceptional, (2)
"This property was clean, quiet, and had excellent security. The barbecue grill was easy to use. They had sandless beach towels, which worked so well. The view was beautiful! I want to go again next year. "
United States
Mae
Oceanfront Kihei Paradise Vistas

Centrally Located Elegant Vistas

Centrally Located Elegant Vistas
5.0 star property
South Kihei
10.0 out of 10, Exceptional, (1)
"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

KBM Resorts Free CAR Luxury Oceanfront Villa at Montage Kapalua Bay Private Lanai and BBQ Mon-5203

KBM Resorts Free CAR Luxury Oceanfront Villa at Montage Kapalua Bay Private Lanai and BBQ Mon-5203
5.0 star property
Kapalua
KBM Resorts Free CAR Luxury Oceanfront Villa at Montage Kapalua Bay Private Lanai and BBQ Mon-5203

Montage Kapalua Bay Collection by KBM - 2 Units (2204/2206)

Montage Kapalua Bay Collection by KBM - 2 Units (2204/2206)
5.0 star property
Kapalua
Montage Kapalua Bay Collection by KBM - 2 Units (2204/2206)

NEW KBM Resorts Free CAR Hale Nalu At Montage Kapalua Bay, Sleeps 10! Oceanfront 3-bedroom Condo With Daily Housekeeping, Spa! Mon-6302

NEW KBM Resorts Free CAR Hale Nalu At Montage Kapalua Bay, Sleeps 10! Oceanfront 3-bedroom Condo With Daily Housekeeping, Spa! Mon-6302
5.0 star property
Kapalua
NEW KBM Resorts Free CAR Hale Nalu At Montage Kapalua Bay, Sleeps 10! Oceanfront 3-bedroom Condo With Daily Housekeeping, Spa! Mon-6302

Montage Kapalua Bay Collection by KBM - 2 Units (6301/6401)

Montage Kapalua Bay Collection by KBM - 2 Units (6301/6401)
5.0 star property
Kapalua
Montage Kapalua Bay Collection by KBM - 2 Units (6301/6401)

Montage Kapalua Bay Collection by KBM - 3 Units (1205/1303/1304)

Montage Kapalua Bay Collection by KBM - 3 Units (1205/1303/1304)
5.0 star property
Kapalua
Montage Kapalua Bay Collection by KBM - 3 Units (1205/1303/1304)

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

Honua Kai Konea 2 Free Rental Cars KBM Resorts Family Friendly 2 Units, 3 Bedrooms Ml-1436

Honua Kai Konea 2 Free Rental Cars KBM Resorts Family Friendly 2 Units, 3 Bedrooms Ml-1436
5.0 star property
Kaanapali
Honua Kai Konea 2 Free Rental Cars KBM Resorts Family Friendly 2 Units, 3 Bedrooms Ml-1436
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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

Head to sights like Haleakalā Visitor Center and Haleakala Crater 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 ¥74,229

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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