5 Star Hotels in Upcountry Maui, Hawaii

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Top Upcountry Maui 5 Star Hotels

The Ritz-Carlton Maui, Kapalua
3 outdoor pools, pool cabanas (surcharge), pool loungers

The Ritz-Carlton Maui, Kapalua

5.0 star property
9.0 out of 10, Wonderful, (1001)
"The staff is very attentive and friendly."
The price is €867
includes taxes & fees
5 Sept - 6 Sept
The Ritz-Carlton Maui, Kapalua
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)
"Good food great area "
The price is €751
includes taxes & fees
2 Sept - 3 Sept
Grand Wailea Maui, A Waldorf Astoria Resort
Fairmont Kea Lani Maui
View from room

Fairmont Kea Lani Maui

5.0 star property
9.4 out of 10, Exceptional, (1003)
"Beautiful resort "
The price is €893
includes taxes & fees
31 Aug - 1 Sept
Fairmont Kea Lani Maui
Four Seasons Resort Maui at Wailea
Club Ocean Front One Bedroom Suite

Four Seasons Resort Maui at Wailea

5.0 star property
9.6 out of 10, Exceptional, (1002)
"This was an exceptional property and we literally had the most amazing stay. Staff were attentive and all car journies were complkmentary. "
The price is €714
includes taxes & fees
14 Sept - 15 Sept
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, (1004)
"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 €957
includes taxes & fees
14 Sept - 15 Sept
Hotel Wailea, Relais & Chateaux - Adults Only
Montage Kapalua Bay
On the beach, beach towels, snorkelling, surfing

Montage Kapalua Bay

5.0 star property
9.8 out of 10, Exceptional, (201)
"Super nice "
The price is €1,103
includes taxes & fees
10 Sept - 11 Sept
Montage Kapalua Bay
Ho‘olei Villas at Grand Wailea
Outdoor pool, pool loungers

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 €2,188
includes taxes & fees
18 Sept - 19 Sept
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
9.6 out of 10, Exceptional, (5)
"It’s a decent hotel to stay for the family."
The price is €1,966
includes taxes & fees
28 Aug - 29 Aug
Fairmont Kea Lani Maui Villa Experience
2 2 Oceanview Modern Resort Vistas
Outdoor pool, pool umbrellas, pool 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

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, pool 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
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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 €812 per night from 26 Aug to 27 Aug
€812
26 Aug - 27 Aug
includes taxes & fees
9.2/10 Wonderful! (997 reviews)
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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
"Amazing property "
Jennifer 5-night trip
Posted 3 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 €253

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.