Five Star Hotels in Upcountry Maui

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Top 5 Stars Hotels in Upcountry Maui

Four Seasons Resort Maui at Wailea

5.0 star property
9.6 out of 10, Exceptional, (1000)
"Amazing stay and service. Four Seasons always exceeded our expectations. Beautiful resort with nice beaches and pools. Family loved it."
The price is S$1,119
includes taxes & fees
7 Jul - 8 Jul
Four Seasons Resort Maui at Wailea

Grand Wailea Maui, A Waldorf Astoria Resort

5.0 star property
9.0 out of 10, Wonderful, (1002)
"We had the best time! The property is absolutely gorgeous and the weather was perfect. "
The price is S$1,510
includes taxes & fees
14 Jul - 15 Jul
Grand Wailea Maui, A Waldorf Astoria Resort

The Ritz-Carlton Maui, Kapalua

5.0 star property
9.0 out of 10, Wonderful, (1001)
"Excellent hotel and staff. "
The price is S$1,500
includes taxes & fees
4 Jul - 5 Jul
The Ritz-Carlton Maui, Kapalua

Fairmont Kea Lani Maui

5.0 star property
9.4 out of 10, Exceptional, (1006)
"Great place for family."
The price is S$1,286
includes taxes & fees
16 Jul - 17 Jul
Fairmont Kea Lani Maui

Hotel Wailea, Relais & Chateaux - Adults Only

5.0 star property
9.4 out of 10, Exceptional, (1002)
"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 S$1,204
includes taxes & fees
6 Jul - 7 Jul
Hotel Wailea, Relais & Chateaux - Adults Only

Montage Kapalua Bay

5.0 star property
9.8 out of 10, Exceptional, (201)
"Super nice "
The price is S$1,802
includes taxes & fees
1 Aug - 2 Aug
Montage Kapalua Bay

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 S$4,390
includes taxes & fees
11 Jul - 12 Jul
Ho‘olei Villas at Grand Wailea

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 S$3,953
includes taxes & fees
27 Jul - 28 Jul
Fairmont Kea Lani Maui Villa Experience

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

2 2 Oceanview Modern Resort Vistas

5.0 star property
10.0 out of 10, Exceptional, (2)
"This condo was great! Great ocean views, and the beach was beautiful! The condo owners thought of everything!"
2 2 Oceanview Modern Resort Vistas

Oceanfront Kihei Paradise Vistas

5.0 star property
10.0 out of 10, Exceptional, (1)
Oceanfront Kihei Paradise Vistas

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

5.0 star property
Upscale Luxurious Ocean Resort Vistas
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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.

Maui Island which includes landscape views

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 S$457

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.