Upcountry Maui 5 Stars Hotels

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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.

Club Ocean Front One Bedroom Suite | Egyptian cotton sheets, premium bedding, down comforters, pillowtop beds
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 ₩1,107,759
₩1,306,735 total
includes taxes & fees
Dec 1 - Dec 2
Four Seasons Resort Maui at Wailea
7 restaurants, breakfast served
Grand Wailea Maui, A Waldorf Astoria Resort

Grand Wailea Maui, A Waldorf Astoria Resort

5.0 star property
Wailea
9.0 out of 10, Wonderful, (1001)
"Great hotel "
United States
Suzi
The price is ₩868,571
₩1,119,778 total
includes taxes & fees
Dec 4 - Dec 5
Grand Wailea Maui, A Waldorf Astoria Resort
View from room
Fairmont Kea Lani Maui

Fairmont Kea Lani Maui

5.0 star property
Wailea
9.4 out of 10, Exceptional, (1004)
"Beautiful hotel, amazing place, really relaxing. "
United States
Iulian
The price is ₩1,183,541
₩1,482,666 total
includes taxes & fees
Nov 29 - Nov 30
Fairmont Kea Lani Maui
3 outdoor pools, cabanas (surcharge), sun loungers
The Ritz-Carlton Maui, Kapalua

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 ₩1,025,594
₩1,305,006 total
includes taxes & fees
Dec 13 - Dec 14
The Ritz-Carlton Maui, Kapalua
Outdoor spa tub
Hotel Wailea, Relais & Chateaux - Adults Only

Hotel Wailea, Relais & Chateaux - Adults Only

5.0 star property
Wailea
9.4 out of 10, Exceptional, (1001)
"Great resort with great amenities! Very convenient to downtown wailea and the beaches and the staff are super friendly and attentive! "
United States
Margaret
The price is ₩1,250,475
₩1,561,944 total
includes taxes & fees
Dec 16 - Dec 17
Hotel Wailea, Relais & Chateaux - Adults Only
On the beach, beach towels, snorkeling, surfing
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 ₩1,467,230
₩1,886,543 total
includes taxes & fees
Dec 11 - Dec 12
Montage Kapalua Bay
Outdoor pool, sun loungers
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 ₩2,666,649
₩3,241,194 total
includes taxes & fees
Dec 17 - Dec 18
Ho‘olei Villas at Grand Wailea
Exterior
Royal Lahaina Bungalows & Spa

Royal Lahaina Bungalows & Spa

5.0 star property
Lahaina
The price is ₩399,600
₩549,258 total
includes taxes & fees
Dec 7 - Dec 8
Royal Lahaina Bungalows & Spa
View from property
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 ₩4,505,761
₩5,401,559 total
includes taxes & fees
Nov 26 - Nov 27
Fairmont Kea Lani Maui Villa Experience
Outdoor pool, pool umbrellas, sun loungers
2 2 Oceanview Modern Resort Vistas

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
Luxury Apartment | Private kitchen | Full-size fridge, microwave, oven, stovetop
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
Outdoor pool, open 10:00 AM to 7:00 PM, pool umbrellas, sun loungers
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
Luxury Condo | Balcony
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
Condo (3 Bedrooms) | Front of property
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
Condo (6 Bedrooms) | Pool
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)
Condo (3 Bedrooms) | Property entrance
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
Condo (6 Bedrooms) | Pool
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)
Condo (Multiple Bedrooms) | View from room
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)
Condo (6 Bedrooms) | Pool | Outdoor pool
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)
Condo (3 Bedrooms) | Pool | Outdoor pool
Honua Kai 2 Free Rental Cars KBM Resorts Family Friendly 2 Units, 3 Bedrooms HK Ml-1436

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

5.0 star property
Kaanapali
Honua Kai 2 Free Rental Cars KBM Resorts Family Friendly 2 Units, 3 Bedrooms HK Ml-1436
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Explore similar 4-star hotels

Many 4-star hotels have the same amenities as 5-star hotels. See all 4-star hotels in Upcountry Maui.
The Westin Maui Resort & Spa, Ka'anapali

The Westin Maui Resort & Spa, Ka'anapali

2365 Kaanapali Pkwy Lahaina HI
The price is ₩645,581 per night from Dec 3 to Dec 4
₩645,581
₩846,346 total
Dec 3 - Dec 4
includes taxes & fees
9/10 Wonderful! (1,005 reviews)
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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.

See all hotels in Upcountry Maui
Haleakala National Park showing desert views

Top Upcountry Maui Hotel Reviews

The Ritz-Carlton Maui, Kapalua

The Ritz-Carlton Maui, Kapalua

10/10 Excellent
"yes"
Karine 5-night trip
Posted 2 days ago
The Ritz-Carlton Maui, Kapalua

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 ₩491,802

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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