Upcountry Maui 5 Stars Hotels

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Check availability on Upcountry Maui 5 Star Hotels

Tonight
Mar 30 - Mar 31
Tomorrow
Mar 31 - Apr 1
Next weekend
Apr 4 - Apr 6
In two weeks
Apr 11 - Apr 13

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

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, (1049)
"Excellent service, clean and beautiful property"
The price is ₩1,095,515
₩1,292,291 total
includes taxes & fees
Apr 1 - Apr 2
Four Seasons Resort Maui at Wailea
The Ritz-Carlton Maui, Kapalua
3 outdoor pools, cabanas (surcharge), sun loungers

The Ritz-Carlton Maui, Kapalua

5.0 star property
9.2 out of 10, Wonderful, (1083)
"Everything you needed is there on the property. The only thing I wish they had was a shuttle bus. Unless you have transportation, you have to take a taxi. Other than that the concierge the staff were great. I did miss having Poi at the luau. "
The price is ₩1,321,971
₩1,640,299 total
includes taxes & fees
Apr 1 - Apr 2
The Ritz-Carlton Maui, Kapalua
Grand Wailea Maui, A Waldorf Astoria Resort
2 bars/lounges, 2 poolside bars, swim-up bar

Grand Wailea Maui, A Waldorf Astoria Resort

5.0 star property
9.0 out of 10, Wonderful, (1204)
" There was limited vegetarian food options. Otherwise a fantastic trip."
The price is ₩1,248,446
₩1,553,558 total
includes taxes & fees
May 1 - May 2
Grand Wailea Maui, A Waldorf Astoria Resort
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, (1008)
"Hotel Wailea was a beautiful property with excellent amenities and a friendly staff. Highlight was using the pool, cabanas, and poolside dining every day. The walk to the beach was hilly which made the hotel less walkable than Wailea Beach but the views from our ocean view room were gorgeous. Excellent amenities provided throughout our stay. "
The price is ₩1,542,544
₩1,906,347 total
includes taxes & fees
Apr 5 - Apr 6
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, (197)
"I liked everything except the dining service. The staff was unfriendly and rude. They should not work there.- they kept us in the bar in excess of 15 minutes even after 4 tables had been open We had to walk over to tell them that tables had been open. "
The price is ₩1,611,657
₩2,004,739 total
includes taxes & fees
May 1 - May 2
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, (40)
"Best property in Maui "
The price is ₩2,918,923
₩3,538,624 total
includes taxes & fees
Apr 27 - Apr 28
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 ₩4,035,980
₩4,847,254 total
includes taxes & fees
Apr 23 - Apr 24
Fairmont Kea Lani Maui Villa Experience
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, (1)
"We loved staying here! The property is lovely and the lanai was perfect for sunsets. It has everything you need and you can walk anywhere you need to go. Will be back! "
Wailea Luxury Hilltop Resort 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, (1)
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.
Hilton Vacation Club Ka'anapali Beach Maui

Hilton Vacation Club Ka'anapali Beach Maui

104 Ka'anapali Shores Place, Kaanapali, HI
The price is ₩375,269 per night from Apr 24 to Apr 25
₩375,269
₩494,716 total
includes taxes & fees
Apr 24 - Apr 25
8.8/10 Excellent! (1,005 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

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 ₩369,534

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.
Are there any 5-star vacation rentals in Upcountry Maui?
Although you won’t find any 5-star vacation rentals in Upcountry Maui on our site, we have a range of retreats that promise an unforgettable getaway. Discover one that suits your needs by checking out our vacation rentals in Upcountry Maui.