Upcountry Maui 5 Stars Hotels

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Our top choices for Upcountry Maui 5-star hotels

Four Seasons Resort Maui at Wailea

Four Seasons Resort Maui at Wailea
5.0 star property
Wailea
9.6 out of 10, Exceptional, (1,000 reviews)
"10/10 service, amazing room with gorgeous view! "
United States
Timothy
The price is ₩1,155,800
₩1,372,074 total
includes taxes & fees
Apr 30 - May 1
Four Seasons Resort Maui at Wailea

Fairmont Kea Lani Maui

Fairmont Kea Lani Maui
5.0 star property
Wailea
9.4 out of 10, Exceptional, (1,001 reviews)
"Great location. Clean hotel, friendly staff. Beautiful surroundings. "
Canada
Jamie
The price is ₩1,660,424
₩2,060,805 total
includes taxes & fees
May 3 - May 4
Fairmont Kea Lani Maui

Grand Wailea Maui, A Waldorf Astoria Resort

Grand Wailea Maui, A Waldorf Astoria Resort
5.0 star property
Wailea
8.8 out of 10, Excellent, (1,002 reviews)
"Excellent and beautiful place to visit."
United States
DAVID
The price is ₩1,297,820
₩1,638,698 total
includes taxes & fees
May 6 - May 7
Grand Wailea Maui, A Waldorf Astoria Resort

The Ritz-Carlton Maui, Kapalua

The Ritz-Carlton Maui, Kapalua
5.0 star property
Kapalua
9.2 out of 10, Wonderful, (1,006 reviews)
"Awesome resort!!!"
United States
Clifford
The price is ₩1,267,603
₩1,610,616 total
includes taxes & fees
Apr 21 - Apr 22
The Ritz-Carlton Maui, Kapalua

Hotel Wailea, Relais & Chateaux - Adults Only

Hotel Wailea, Relais & Chateaux - Adults Only
5.0 star property
Wailea
9.4 out of 10, Exceptional, (1,001 reviews)
"Literally the best hotel experience I’ve had. "
United States
Isabel
The price is ₩1,509,339
₩1,881,446 total
includes taxes & fees
Apr 21 - Apr 22
Hotel Wailea, Relais & Chateaux - Adults Only

The Resort at Kapalua Bay, Maui

The Resort at Kapalua Bay, Maui
5.0 star property
Lahaina
9.6 out of 10, Exceptional, (211 reviews)
"The views are next level. We enjoyed the pools, spa, restaurant and more. It was our second stay there and definitely going back. "
United States
Mandy D
The price is ₩2,415,849
₩3,199,715 total
includes taxes & fees
Apr 18 - Apr 19
The Resort at Kapalua Bay, Maui

Ho‘olei Villas at Grand Wailea

Ho‘olei Villas at Grand Wailea
5.0 star property
Wailea
9.6 out of 10, Exceptional, (45 reviews)
"Womderful home, terrific service, access to hotel amenities was key."
United States
ALAN
The price is ₩3,047,324
₩3,715,573 total
includes taxes & fees
Apr 23 - Apr 24
Ho‘olei Villas at Grand Wailea

Royal Lahaina Bungalows & Spa

Royal Lahaina Bungalows & Spa
5.0 star property
Lahaina
9.4 out of 10, Exceptional, (9 reviews)
"Clean room and staff is super friendly. Would stay here again "
United States
Rene
The price is ₩522,149
₩700,050 total
includes taxes & fees
Apr 20 - Apr 21
Royal Lahaina Bungalows & Spa

2 2 Oceanview Modern Resort Vistas

2 2 Oceanview Modern Resort Vistas
5.0 star property
Central Kihei
9.8 out of 10, Exceptional, (8 reviews)
"The condo was very clean, loved all of the decor, was very beautiful. Had everything you could possibly need in kitchen and bathrooms. Would definitely stay again! Everyone we talked to was very nice and helpful! "
United States
Paulina
2 2 Oceanview Modern Resort Vistas

Wailea Luxury Hilltop Resort Vistas

Wailea Luxury Hilltop Resort Vistas
5.0 star property
Wailea
10.0 out of 10, Exceptional, (2 reviews)
"very nice place and location 🤗"
United States
Maryna
Wailea Luxury Hilltop Resort Vistas

Fairmont Kea Lani Maui Villa Experience

Fairmont Kea Lani Maui Villa Experience
5.0 star property
Wailea
9.8 out of 10, Exceptional, (6 reviews)
"It’s a decent hotel to stay for the family."
United States
Sze Wai
The price is ₩5,180,705
₩6,238,821 total
includes taxes & fees
May 6 - May 7
Fairmont Kea Lani Maui Villa Experience

Centrally Located Elegant Vistas

Centrally Located Elegant Vistas
5.0 star property
South Kihei
10.0 out of 10, Exceptional, (1 review)
"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!"
United States
Edwin
Centrally Located Elegant Vistas

Oceanfront Kihei Paradise Vistas

Oceanfront Kihei Paradise Vistas
5.0 star property
Central Kihei
10.0 out of 10, Exceptional, (2 reviews)
"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. "
United States
Mae
Oceanfront Kihei Paradise Vistas

Hale Ona Loa HOL-102 by KBM

Hale Ona Loa HOL-102 by KBM
5.0 star property
Kaanapali
The price is ₩691,821
₩1,497,447 total
includes taxes & fees
Apr 12 - Apr 13
Hale Ona Loa HOL-102 by KBM

Kapalua Bay Villas Resort by KBM

Kapalua Bay Villas Resort by KBM
5.0 star property
Kapalua
The price is ₩3,747,286
₩5,178,456 total
includes taxes & fees
Apr 15 - Apr 16
Kapalua Bay Villas Resort by KBM

Kapalua Ridge Villas KBM Resorts 2 Units, 2 Bedrooms KRV Ml-3535

Kapalua Ridge Villas KBM Resorts 2 Units, 2 Bedrooms KRV Ml-3535
5.0 star property
Kapalua
Kapalua Ridge Villas KBM Resorts 2 Units, 2 Bedrooms KRV Ml-3535
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Venture to top sights like Haleakala National Park as you discover Upcountry Maui—a relaxing area also known for its island views.

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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 ₩700,050

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.