Upcountry Maui 5 Stars Hotels

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Check availability on Upcountry Maui 5 Star Hotels

Compare Upcountry Maui 5 Star Hotels with updated room rates, reviews, and availability. Most hotels are fully refundable.

The Ritz-Carlton Maui, Kapalua
3 outdoor pools, cabanas (surcharge), sun 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 ₩1,118,033
₩1,409,640 total
includes taxes & fees
Sep 5 - Sep 6
The Ritz-Carlton Maui, Kapalua
Grand Wailea Maui, A Waldorf Astoria Resort
9 outdoor pools, cabanas (surcharge), sun 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 ₩961,354
₩1,224,819 total
includes taxes & fees
Aug 28 - Aug 29
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, (1000)
"Beautiful resort "
The price is ₩1,164,419
₩1,456,103 total
includes taxes & fees
Aug 31 - Sep 1
Fairmont Kea Lani Maui
Four Seasons Resort Maui at Wailea
Club Ocean Front One Bedroom Suite | Egyptian cotton sheets, premium bedding, down comforters, pillowtop beds

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 ₩986,499
₩1,163,695 total
includes taxes & fees
Aug 23 - Aug 24
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, (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 ₩1,247,957
₩1,554,653 total
includes taxes & fees
Sep 14 - Sep 15
Hotel Wailea, Relais & Chateaux - Adults Only
Montage Kapalua Bay
On the beach, beach towels, snorkeling, surfing

Montage Kapalua Bay

5.0 star property
9.8 out of 10, Exceptional, (201)
"Super nice "
The price is ₩1,399,290
₩1,799,189 total
includes taxes & fees
Sep 13 - Sep 14
Montage Kapalua Bay
Ho‘olei Villas at Grand Wailea
Outdoor pool, sun 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 ₩2,937,110
₩3,555,459 total
includes taxes & fees
Sep 18 - Sep 19
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 ₩2,639,271
₩3,195,490 total
includes taxes & fees
Aug 28 - Aug 29
Fairmont Kea Lani Maui Villa Experience
2 2 Oceanview Modern Resort Vistas
Outdoor pool, pool umbrellas, sun 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 | Full-size fridge, microwave, oven, stovetop

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, sun 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 ₩1,085,849 per night from Sep 22 to Sep 23
₩1,085,849
₩1,363,042 total
Sep 22 - Sep 23
includes taxes & fees
9.2/10 Wonderful! (997 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

Head to sights like Haleakalā Visitor Center and Haleakala Crater as you discover Upcountry Maui—a relaxing area also known for its island views.

See all hotels in Upcountry Maui
Maui Island featuring landscape views

Top Upcountry Maui Hotel Reviews

Fairmont Kea Lani Maui

Fairmont Kea Lani Maui

10/10 Excellent
"Everyone was so kind and willing to make your stay that much more beautiful!! The grounds are breathtaking!! Just sitting on the lawn and enjoying the view was priceless. Very family friendly, something for everyone here! "
Lumnije 7-night trip
Posted 2 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 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 ₩287,134

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.