Compare and book 5 Star hotels in Upcountry Maui, Hawaii

    price find illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Save instantly and earn perks with One Key
    Learn about One Key
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check availability on Upcountry Maui 5 Star Hotels

Top Upcountry Maui 5 Star Hotels

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, (1000)
"Great hotel! Loved our stay."
The price is £753
includes taxes & fees
11 Aug - 12 Aug
Fairmont Kea Lani Maui
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, (1001)
"Amazing stay and service. Four Seasons always exceeded our expectations. Beautiful resort with nice beaches and pools. Family loved it."
The price is £655
includes taxes & fees
24 Jul - 25 Jul
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, (1000)
"We had the best time! The property is absolutely gorgeous and the weather was perfect. "
The price is £831
includes taxes & fees
1 Aug - 2 Aug
Grand Wailea Maui, A Waldorf Astoria Resort
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, (1004)
"Excellent hotel and staff. "
The price is £751
includes taxes & fees
8 Aug - 9 Aug
The Ritz-Carlton Maui, Kapalua
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."
The price is £707
includes taxes & fees
19 Jul - 20 Jul
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 £1,054
includes taxes & fees
7 Aug - 8 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 £1,984
includes taxes & fees
18 Aug - 19 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 £1,992
includes taxes & fees
15 Aug - 16 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
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
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
Upscale Luxurious Ocean Resort Vistas
Enjoy al fresco dining and relaxation by the pool amidst lush greenery and palm trees.

Upscale Luxurious Ocean Resort Vistas

5.0 star property
Upscale Luxurious Ocean Resort Vistas
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

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

Fairmont Kea Lani Maui

Fairmont Kea Lani Maui

10/10 Excellent
"We lives the Fairmont "
Julie 5-night trip
Posted 6 days ago
Fairmont Kea Lani Maui

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 based on when you prefer to travel and how long you plan to be away, among a range of factors. Take advantage of our price per night filter and other search tools to land the best deal on a luxurious stay.

  • Search for the lowest price per night

What makes a hotel 5 stars in Upcountry Maui?
Exemplary guest service is integral to every 5-star hotel in Upcountry Maui. From the moment you enter the lobby, staff cater to your every need, whether offering luggage assistance and storage or providing a nightly turn-down service. On top of that, hotels must offer top-rate amenities to obtain a 5-star rating. These can include luxury bathrooms, on-site spa facilities, swimming pools, gastronomic restaurants and knowledgeable concierge.
Are there any 5-star all-inclusive resorts in Upcountry Maui?
Find an indulgent retreat that includes your room, meals, drinks and entertainment in Upcountry Maui with our filter tool. Search for hotels rated 5 stars and select the "All inclusive" filter. Have a look at what's included in the upfront price. This way, you're ready to take advantage of the premium perks on offer from the moment you arrive.