Upcountry Maui 5 Stars Hotels

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Check availability on Upcountry Maui 5 Star Hotels

Our top choices for Upcountry Maui 5-star hotels

Property grounds

Four Seasons Resort Maui at Wailea

Four Seasons Resort Maui at Wailea
5.0 star property
Wailea
9.6 out of 10, Exceptional, (1,003 reviews)
"Service was good"
Canada
kathy
The price is ₩1,155,374
₩1,466,454 total
includes taxes & fees
Feb 21 - Feb 22
Four Seasons Resort Maui at Wailea
9 outdoor pools, cabanas (surcharge), sun loungers

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, (1,003 reviews)
"Beautiful room and view. Amazing pool area. So much fun for the entire family! "
United States
Laura
The price is ₩959,038
₩1,232,626 total
includes taxes & fees
Mar 5 - Mar 6
Grand Wailea Maui, A Waldorf Astoria Resort
Exterior detail

Fairmont Kea Lani Maui

Fairmont Kea Lani Maui
5.0 star property
Wailea
9.4 out of 10, Exceptional, (1,003 reviews)
"Wonderful staff and facility"
United States
Sheila
The price is ₩1,306,019
₩1,636,526 total
includes taxes & fees
Mar 8 - Mar 9
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, (1,002 reviews)
"Top notch property with amazing service and staff"
Canada
Delaine
The price is ₩1,405,912
₩1,763,121 total
includes taxes & fees
Mar 21 - Mar 22
The Ritz-Carlton Maui, Kapalua
Bar (on property)

Hotel Wailea, Relais & Chateaux - Adults Only

Hotel Wailea, Relais & Chateaux - Adults Only
5.0 star property
Wailea
9.4 out of 10, Exceptional, (1,001 reviews)
"Everything was exceptional! Great property, quiet and peaceful "
United States
Abdulla
The price is ₩1,539,045
₩1,913,299 total
includes taxes & fees
Mar 1 - Mar 2
Hotel Wailea, Relais & Chateaux - Adults Only
Outdoor pool, pool umbrellas, sun loungers

Montage Kapalua Bay

Montage Kapalua Bay
5.0 star property
Lahaina
9.6 out of 10, Exceptional, (207 reviews)
"The views are next level. We enjoyed the pools, spa, restaurant and more. It was our second stay there and definitely going back. "
United States
Mandy D
The price is ₩1,929,684
₩2,496,935 total
includes taxes & fees
Mar 1 - Mar 2
Montage Kapalua Bay
Restaurant

Ho‘olei Villas at Grand Wailea

Ho‘olei Villas at Grand Wailea
5.0 star property
Wailea
9.6 out of 10, Exceptional, (44 reviews)
"Perfect for Families. Quite spacious and great for a relaxing Family vacation."
United States
Leslie
The price is ₩3,043,851
₩3,707,550 total
includes taxes & fees
Mar 1 - Mar 2
Ho‘olei Villas at Grand Wailea
Aerial view

Royal Lahaina Bungalows & Spa

Royal Lahaina Bungalows & Spa
5.0 star property
Lahaina
9.6 out of 10, Exceptional, (4 reviews)
"Clean room and staff is super friendly. Would stay here again "
United States
Rene
The price is ₩632,186
₩827,626 total
includes taxes & fees
Mar 1 - Mar 2
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 reviews)
"It’s a decent hotel to stay for the family."
United States
Sze Wai
The price is ₩4,931,575
₩5,939,553 total
includes taxes & fees
Mar 8 - Mar 9
Fairmont Kea Lani Maui Villa Experience
Balcony

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 reviews)
"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
Luxury Apartment | Beach/ocean view

Wailea Luxury Hilltop Resort Vistas

Wailea Luxury Hilltop Resort Vistas
5.0 star property
Wailea
10.0 out of 10, Exceptional, (2 reviews)
"very nice place and location 🤗"
United States
Maryna
Wailea Luxury Hilltop Resort Vistas
Luxury Apartment, Ocean View | Living area | Hulu, streaming services

Oceanfront Kihei Paradise Vistas

Oceanfront Kihei Paradise Vistas
5.0 star property
Central Kihei
10.0 out of 10, Exceptional, (2 reviews)
"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 | Living area | 90-inch Smart TV with digital channels, Hulu, streaming services

Centrally Located Elegant Vistas

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

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) | Property entrance

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
The price is ₩58,080,897
₩69,310,695 total
includes taxes & fees
Mar 11 - Mar 12
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) | Property entrance

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) | Property entrance

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
The price is ₩96,998,241
₩115,692,003 total
includes taxes & fees
Feb 22 - Feb 23
Montage Kapalua Bay Collection by KBM - 3 Units (1205/1303/1304)
Outdoor pool, a waterfall pool, pool umbrellas, sun loungers

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)
4.5 star property
Kaanapali
Honua Kai Hokulani Collection by KBM - 2 Units on same floor (201/203)
Condo (3 Bedrooms) | Pool | Outdoor pool, a waterfall pool, pool umbrellas, sun loungers

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
4.0 star property
Kaanapali
Honua Kai Konea 2 Free Rental Cars KBM Resorts Family Friendly 2 Units, 3 Bedrooms Ml-1436
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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 ₩680,144 per night from Mar 1 to Mar 2
₩680,144
₩891,414 total
Mar 1 - Mar 2
includes taxes & fees
9.2/10 Wonderful! (1,004 reviews)
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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

Venture to top sights like Haleakala National Park as you discover Upcountry Maui—a relaxing area also known for its island views.

See all hotels in Upcountry Maui
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

Grand Wailea Maui, A Waldorf Astoria Resort

Grand Wailea Maui, A Waldorf Astoria Resort

10/10 Excellent
"Beautiful room and view. Amazing pool area. So much fun for the entire family! "
Laura 1-night trip
Posted 2 days ago
Grand Wailea Maui, A Waldorf Astoria Resort

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 ₩622,723

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.