5 Star Hotels in Upcountry Maui, Hawaii

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Top Upcountry Maui 5 Star Hotels

The Ritz-Carlton Maui, Kapalua
Relax by the oceanfront pool surrounded by palm trees and lounge chairs.

The Ritz-Carlton Maui, Kapalua

5.0 star property
9.0 out of 10, Wonderful, (1003)
"A great place to relax."
The price is €967
includes taxes & fees
15 Aug - 16 Aug
The Ritz-Carlton Maui, Kapalua
Four Seasons Resort Maui at Wailea
Enjoy breathtaking ocean views from this beachfront resort, surrounded by palm trees and a sandy beach area.

Four Seasons Resort Maui at Wailea

5.0 star property
9.6 out of 10, Exceptional, (1000)
"Fantastic staff! "
The price is €714
includes taxes & fees
5 Sept - 6 Sept
Four Seasons Resort Maui at Wailea
Grand Wailea Maui, A Waldorf Astoria Resort
9 outdoor pools, pool cabanas (surcharge), pool loungers

Grand Wailea Maui, A Waldorf Astoria Resort

5.0 star property
8.8 out of 10, Excellent, (1002)
"This place was AMAZING!!!"
The price is €752
includes taxes & fees
17 Aug - 18 Aug
Grand Wailea Maui, A Waldorf Astoria Resort
Fairmont Kea Lani Maui
Relax by the wavy pool surrounded by palm trees and lounge areas, with ocean views from the adjacent beachfront.

Fairmont Kea Lani Maui

5.0 star property
9.4 out of 10, Exceptional, (1001)
"Beautiful resort "
The price is €859
includes taxes & fees
28 Aug - 29 Aug
Fairmont Kea Lani Maui
Hotel Wailea, Relais & Chateaux - Adults Only
Relax by the fire pit in our outdoor lounge, surrounded by comfortable seating and a serene pool.

Hotel Wailea, Relais & Chateaux - Adults Only

5.0 star property
9.4 out of 10, Exceptional, (1001)
"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."
Hotel Wailea, Relais & Chateaux - Adults Only
Montage Kapalua Bay
Relax by the serene infinity pool surrounded by lush palm trees and a well-maintained garden.

Montage Kapalua Bay

5.0 star property
9.8 out of 10, Exceptional, (201)
"Super nice "
The price is €1,105
includes taxes & fees
29 Aug - 30 Aug
Montage Kapalua Bay
Ho‘olei Villas at Grand Wailea
Relax by the serene pool surrounded by palm trees and lounge chairs.

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 €2,128
includes taxes & fees
25 Aug - 26 Aug
Ho‘olei Villas at Grand Wailea
2 2 Oceanview Modern Resort Vistas
Enjoy ocean views from the pool area surrounded by lush greenery and palm trees.

2 2 Oceanview Modern Resort Vistas

5.0 star property
10.0 out of 10, Exceptional, (3)
"This condo was great! Great ocean views, and the beach was beautiful! The condo owners thought of everything!"
2 2 Oceanview Modern Resort Vistas
Fairmont Kea Lani Maui Villa Experience
Relax by the infinity pool overlooking the ocean and mountains.

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 €2,065
includes taxes & fees
30 Aug - 31 Aug
Fairmont Kea Lani Maui Villa Experience
Wailea Luxury Hilltop Resort Vistas
Enjoy cooking in this well-lit kitchen with ample storage and a spacious layout.

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
Relax on the balcony with a glass door leading to an outdoor seating area, perfect for enjoying the view.

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
Guests can enjoy ocean views from their balcony, surrounded by lush greenery and a golf course.

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
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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 €517 per night from 23 Aug to 24 Aug
€517
23 Aug - 24 Aug
includes taxes & fees
9/10 Wonderful! (909 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 sights like Haleakalā Visitor Center and Haleakala Crater as you discover Upcountry Maui—a relaxing area also notable for its island views.

See all hotels in Upcountry Maui
Maui Island showing landscape views

Top Upcountry Maui Hotel Reviews

Grand Wailea Maui, A Waldorf Astoria Resort

Grand Wailea Maui, A Waldorf Astoria Resort

10/10 Excellent
"Top of our list for sure. We will be coming back. "
Reynold 5-night trip
Posted 5 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 €286

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.