Upcountry Maui 5 Stars Hotels

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Check availability on Upcountry Maui 5 Star Hotels

Tonight
Aug 30 - Aug 31
Tomorrow
Aug 31 - Sep 1
Next weekend
Sep 5 - Sep 7
In two weeks
Sep 12 - Sep 14

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

Our top choices for Upcountry Maui 5-star hotels

The Ritz-Carlton Maui, Kapalua
3 outdoor pools, cabanas (surcharge), sun loungers

The Ritz-Carlton Maui, Kapalua

5.0 star property
9.0 out of 10, Wonderful, (1007)
"Staff was helpful and very friendly! We got a great welcome! Would definitely stay here again. "
The price is NT$24,121
NT$30,436 total
includes taxes & fees
Sep 26 - Sep 27
The Ritz-Carlton Maui, Kapalua
Grand Wailea Maui, A Waldorf Astoria Resort
9 outdoor pools, cabanas (surcharge), sun loungers

Grand Wailea Maui, A Waldorf Astoria Resort

5.0 star property
8.8 out of 10, Excellent, (1007)
"Good food great area "
The price is NT$21,278
NT$27,084 total
includes taxes & fees
Sep 6 - Sep 7
Grand Wailea Maui, A Waldorf Astoria Resort
Fairmont Kea Lani Maui
View from room

Fairmont Kea Lani Maui

5.0 star property
9.4 out of 10, Exceptional, (1006)
"excellent resort and very clean "
The price is NT$25,440
NT$31,812 total
includes taxes & fees
Sep 7 - Sep 8
Fairmont Kea Lani Maui
Four Seasons Resort Maui at Wailea
Club Ocean Front One Bedroom Suite | Egyptian cotton sheets, premium bedding, down comforters, pillowtop beds

Four Seasons Resort Maui at Wailea

5.0 star property
9.6 out of 10, Exceptional, (1003)
"This was an exceptional property and we literally had the most amazing stay. Staff were attentive and all car journies were complkmentary. "
The price is NT$23,081
NT$27,227 total
includes taxes & fees
Sep 27 - Sep 28
Four Seasons Resort Maui at Wailea
Hotel Wailea, Relais & Chateaux - Adults Only
Outdoor spa tub

Hotel Wailea, Relais & Chateaux - Adults Only

5.0 star property
9.4 out of 10, Exceptional, (1002)
"Great resort with great amenities! Very convenient to downtown wailea and the beaches and the staff are super friendly and attentive! "
The price is NT$27,265
NT$33,965 total
includes taxes & fees
Sep 14 - Sep 15
Hotel Wailea, Relais & Chateaux - Adults Only
Montage Kapalua Bay
On the beach, beach towels, snorkeling, surfing

Montage Kapalua Bay

5.0 star property
9.8 out of 10, Exceptional, (201)
"Super nice "
The price is NT$30,571
NT$39,308 total
includes taxes & fees
Sep 20 - Sep 21
Montage Kapalua Bay
Ho‘olei Villas at Grand Wailea
Outdoor pool, sun loungers

Ho‘olei Villas at Grand Wailea

5.0 star property
9.6 out of 10, Exceptional, (42)
"Perfect for Families. Quite spacious and great for a relaxing Family vacation."
The price is NT$61,933
NT$75,041 total
includes taxes & fees
Sep 24 - Sep 25
Ho‘olei Villas at Grand Wailea
Fairmont Kea Lani Maui Villa Experience
View from property

Fairmont Kea Lani Maui Villa Experience

5.0 star property
9.6 out of 10, Exceptional, (5)
"It’s a decent hotel to stay for the family."
The price is NT$60,000
NT$72,572 total
includes taxes & fees
Sep 7 - Sep 8
Fairmont Kea Lani Maui Villa Experience
2 2 Oceanview Modern Resort Vistas
Outdoor pool, pool umbrellas, sun loungers

2 2 Oceanview Modern Resort Vistas

5.0 star property
10.0 out of 10, Exceptional, (4)
"This condo was great! Great ocean views, and the beach was beautiful! The condo owners thought of everything!"
2 2 Oceanview Modern Resort Vistas
Wailea Luxury Hilltop Resort Vistas
Luxury Apartment | Private kitchen | Full-size fridge, microwave, oven, stovetop

Wailea Luxury Hilltop Resort Vistas

5.0 star property
10.0 out of 10, Exceptional, (2)
"very nice place and location 🤗"
Wailea Luxury Hilltop Resort Vistas
Centrally Located Elegant Vistas
Luxury Condo | Balcony

Centrally Located Elegant Vistas

5.0 star property
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!"
Centrally Located Elegant Vistas
Oceanfront Kihei Paradise Vistas
Outdoor pool, open 10:00 AM to 7:00 PM, pool umbrellas, sun loungers

Oceanfront Kihei Paradise Vistas

5.0 star property
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. "
Oceanfront Kihei Paradise Vistas
Montage Kapalua Bay Collection by KBM - 3 Units (1205/1303/1304)
Condo (Multiple Bedrooms) | View from room

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

5.0 star property
Montage Kapalua Bay Collection by KBM - 3 Units (1205/1303/1304)
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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.
Andaz Maui at Wailea Resort - a concept by Hyatt

Andaz Maui at Wailea Resort - a concept by Hyatt

3550 Wailea Alanui Dr, Kihei, HI
The price is NT$23,448 per night from Oct 1 to Oct 2
NT$23,448
NT$29,454 total
Oct 1 - Oct 2
includes taxes & fees
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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.

See all hotels in Upcountry Maui
Maui Island featuring landscape views

Top Upcountry Maui Hotel Reviews

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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 NT$6,527

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.