Find 5 Star Hotels in Upcountry Maui, HI from ¥41,138

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Check availability on Upcountry Maui 5 Star Hotels

Compare Upcountry Maui 5 Star Hotels with updated room rates, reviews, and availability. Most hotels are fully refundable.

Four Seasons Resort Maui at Wailea

5.0 star property
Wailea
9.6 out of 10, Exceptional, (1000)
"Wonderful!"
United States
Xianjun
The price is ¥116,315
¥137,207 total
includes taxes & fees
Dec 6 - Dec 7
Four Seasons Resort Maui at Wailea

The Ritz-Carlton Maui, Kapalua

5.0 star property
Kapalua
9.0 out of 10, Wonderful, (1005)
"Great amenities and staff. Great location"
Canada
Jeongwon
The price is ¥107,688
¥137,026 total
includes taxes & fees
Dec 12 - Dec 13
The Ritz-Carlton Maui, Kapalua

Grand Wailea Maui, A Waldorf Astoria Resort

5.0 star property
Wailea
9.0 out of 10, Wonderful, (1007)
"Great hotel "
United States
Suzi
The price is ¥91,254
¥117,646 total
includes taxes & fees
Nov 30 - Dec 1
Grand Wailea Maui, A Waldorf Astoria Resort

Fairmont Kea Lani Maui

5.0 star property
Wailea
9.4 out of 10, Exceptional, (1007)
"Beautiful hotel, amazing place, really relaxing. "
United States
Iulian
The price is ¥117,725
¥147,955 total
includes taxes & fees
Nov 29 - Nov 30
Fairmont Kea Lani Maui

Hotel Wailea, Relais & Chateaux - Adults Only

5.0 star property
Wailea
9.4 out of 10, Exceptional, (1002)
"This place is truly amazing! The service is impeccable, the resort is beautiful, and the views are breathtaking. I can’t wait to return again."
United States
Alon
The price is ¥138,581
¥172,565 total
includes taxes & fees
Nov 30 - Dec 1
Hotel Wailea, Relais & Chateaux - Adults Only

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 ¥154,060
¥198,087 total
includes taxes & fees
Dec 13 - Dec 14
Montage Kapalua Bay

Ho‘olei Villas at Grand Wailea

5.0 star property
Wailea
9.6 out of 10, Exceptional, (44)
"This is an amazing place to stay with a family. Views. Facilities. Local entertainment, dining, shopping, and activities."
United States
David
The price is ¥278,433
¥338,446 total
includes taxes & fees
Dec 2 - Dec 3
Ho‘olei Villas at Grand Wailea

Royal Lahaina Bungalows & Spa

5.0 star property
Lahaina
The price is ¥41,983
¥57,708 total
includes taxes & fees
Dec 7 - Dec 8
Royal Lahaina Bungalows & Spa

Fairmont Kea Lani Maui Villa Experience

5.0 star property
Wailea
9.8 out of 10, Exceptional, (6)
"Good property "
United States
Itzamnan
The price is ¥462,026
¥554,060 total
includes taxes & fees
Dec 13 - Dec 14
Fairmont Kea Lani Maui Villa Experience

2 2 Oceanview Modern Resort Vistas

5.0 star property
Central Kihei
10.0 out of 10, Exceptional, (5)
"This condo was great! Great ocean views, and the beach was beautiful! The condo owners thought of everything!"
United States
Jarrod
2 2 Oceanview Modern Resort Vistas

Wailea Luxury Hilltop Resort Vistas

5.0 star property
Wailea
10.0 out of 10, Exceptional, (2)
"We loved staying here! The property is lovely and the lanai was perfect for sunsets. It has everything you need and you can walk anywhere you need to go. Will be back! "
United States
Heather
Wailea Luxury Hilltop Resort 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

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

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)

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)

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 - 3 Units (1205/1303/1304)

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

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

Honua Kai Hokulani Collection by KBM - 3 Units on same floor (332/338/344)

5.0 star property
Kaanapali
Honua Kai Hokulani Collection by KBM - 3 Units on same floor (332/338/344)

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)
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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.

Haleakala National Park showing desert views

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 ¥41,138

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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