Upcountry Maui 5 Stars Hotels

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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, (1005)
"Had a wonderful stay for our anniversary and we definitely will be back! The service was impeccable and everyone was SO friendly wherever we went in the hotel, even the housekeeping when passing in the halls. It's so rare these days, even in top hotels. Breakfast was a little overpriced for the ala carte menu, but the food in every restaurant was very good. Had the best massage of my life at the spa (Holly is AMAZING) and wished we had planned to spend more time there. Have stayed at other...
The price is NT$23,402
NT$29,396 total
includes taxes & fees
Dec 7 - Dec 8
The Ritz-Carlton Maui, Kapalua
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, (1001)
"Excellent customer service "
The price is NT$25,876
NT$30,524 total
includes taxes & fees
Dec 17 - Dec 18
Four Seasons Resort Maui at Wailea
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, (1001)
"Beautiful, well maintained, best pool on island."
The price is NT$25,680
NT$32,083 total
includes taxes & fees
Dec 12 - Dec 13
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, (981)
"Great place to rest and enjoy the island. Very quiet and relaxed place. The only down side would be very limited dining option in the resort. Restaurants are very, very expensive but they do not offer many options for dining. Not a great kind of restaurant for a hotel resort. You can go once maybe twice and eat, and you already tried everything on the menu. Two person dinner at least $450 and breakfast at least $150-$200 which is just too crazy. "
The price is NT$34,143
NT$42,195 total
includes taxes & fees
Dec 3 - Dec 4
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, (193)
"Our stay was amazing! I can’t say enough great things about the accommodations and the staff. The only thing I had a hard time with was the valet parking. The constant in and out every time you just want to stop by for an hour to change for dinner or something is a hassle with dropping the car off and requesting it again. Other than that it was fabulous!"
The price is NT$34,472
NT$42,957 total
includes taxes & fees
Dec 13 - Dec 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, (37)
"Best property in Maui "
The price is NT$51,269
NT$62,590 total
includes taxes & fees
Dec 11 - Dec 12
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, (4)
"It’s a decent hotel to stay for the family."
The price is NT$75,479
NT$90,947 total
includes taxes & fees
Nov 24 - Nov 25
Fairmont Kea Lani Maui Villa Experience
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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.
Fairmont Kea Lani Maui

Fairmont Kea Lani Maui

4100 Wailea Alanui Dr, Kihei, HI
The price is NT$18,510 per night from Dec 1 to Dec 2
NT$18,510
NT$23,755 total
includes taxes & fees
Dec 1 - Dec 2
9.2/10 Wonderful! (999 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.

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 NT$12,038

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.