Upcountry Maui 5 Stars Hotels

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Check availability on Upcountry Maui 5 Star Hotels

Tonight
Oct 7 - Oct 8
Tomorrow
Oct 8 - Oct 9
This weekend
Oct 10 - Oct 12
Next weekend
Oct 17 - Oct 19

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

Fairmont Kea Lani Maui
View from room

Fairmont Kea Lani Maui

5.0 star property
9.4 out of 10, Exceptional, (1004)
"Loved the resort very well kept & beautiful spa was the best too"
The price is ₩1,324,948
₩1,646,167 total
includes taxes & fees
Nov 1 - Nov 2
Fairmont Kea Lani Maui
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, (1006)
"Stunning resort!"
The price is ₩846,598
₩1,090,211 total
includes taxes & fees
Oct 21 - Oct 22
Grand Wailea Maui, A Waldorf Astoria Resort
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)
"This hotel is "
The price is ₩1,197,956
₩1,504,679 total
includes taxes & fees
Oct 29 - Oct 30
The Ritz-Carlton Maui, Kapalua
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)
"Beautiful resort. Everything was absolutely perfect. Room was impeccable. Staff were very friendly and accommodating. Pool and beach area were really nice. Will stay here again. "
The price is ₩1,065,320
₩1,256,673 total
includes taxes & fees
Oct 14 - Oct 15
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 ₩1,332,271
₩1,654,802 total
includes taxes & fees
Nov 4 - Nov 5
Hotel Wailea, Relais & Chateaux - Adults Only
Montage Kapalua Bay
On the beach, beach towels, snorkeling, surfing

Montage Kapalua Bay

5.0 star property
9.6 out of 10, Exceptional, (203)
"Super nice "
The price is ₩1,411,020
₩1,814,269 total
includes taxes & fees
Oct 27 - Oct 28
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, (43)
"Perfect for Families. Quite spacious and great for a relaxing Family vacation."
The price is ₩2,874,474
₩3,482,327 total
includes taxes & fees
Oct 21 - Oct 22
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
9.8 out of 10, Exceptional, (6)
"It’s a decent hotel to stay for the family."
The price is ₩4,090,547
₩4,908,132 total
includes taxes & fees
Oct 13 - Oct 14
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
Upscale Luxurious Ocean Resort Vistas
BBQ/picnic area

Upscale Luxurious Ocean Resort Vistas

5.0 star property
Upscale Luxurious Ocean Resort Vistas
Montage Kapalua Bay Collection by KBM - 2 Units (2204/2206)
Condo (6 Bedrooms) | Property entrance

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

5.0 star property
Montage Kapalua Bay Collection by KBM - 2 Units (2204/2206)
Montage Kapalua Bay Collection by KBM - 2 Units (6301/6401)
Condo (6 Bedrooms) | Pool

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

5.0 star property
Montage Kapalua Bay Collection by KBM - 2 Units (6301/6401)
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)
KBM Resorts Luxury Oceanfront Villa at Montage Kapalua Bay Private Lanai and BBQ Free Rental Car Malia-at-montage-kapalua-bay
Condo (3 Bedrooms) | Front of property

KBM Resorts Luxury Oceanfront Villa at Montage Kapalua Bay Private Lanai and BBQ Free Rental Car Malia-at-montage-kapalua-bay

5.0 star property
KBM Resorts Luxury Oceanfront Villa at Montage Kapalua Bay Private Lanai and BBQ Free Rental Car Malia-at-montage-kapalua-bay
Honua Kai Hokulani Collection by KBM - 2 Units on same floor (201/203)
Condo (6 Bedrooms) | Pool | Outdoor pool

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

5.0 star property
Honua Kai Hokulani Collection by KBM - 2 Units on same floor (201/203)
NEW KBM Resorts Free CAR Kaanapali Shores 6th Floor Ocean View Suite Steps to Pool and Beach! Ks-616
Condo (2 Bedrooms) | Pool | Outdoor pool

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

5.0 star property
NEW KBM Resorts Free CAR Kaanapali Shores 6th Floor Ocean View Suite Steps to Pool and Beach! Ks-616
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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 ₩1,078,019 per night from Nov 4 to Nov 5
₩1,078,019
₩1,354,495 total
Nov 4 - Nov 5
includes taxes & fees
9.2/10 Wonderful! (997 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
Maui Island featuring landscape views

Top Upcountry Maui Hotel Reviews

Four Seasons Resort Maui at Wailea

Four Seasons Resort Maui at Wailea

10/10 Excellent
"Wonderful!"
Xianjun 2-night trip
Posted 2 days ago
Four Seasons Resort Maui at Wailea

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 ₩420,025

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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Explore a world of travel with Expedia