Compare and book 5 Star hotels in Upcountry Maui, Hawaii

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Top Upcountry Maui 5 Star Hotels

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Fairmont Kea Lani Maui Villa Experience
5.0 star property
10.0 out of 10, Exceptional, (3)
"Good property "
The price is £4,229
includes taxes & fees
13 Jun - 14 Jun
Fairmont Kea Lani Maui Villa Experience
On the beach, beach towels, snorkelling, surfing
Montage Kapalua Bay
5.0 star property
9.8 out of 10, Exceptional, (190)
"Beautiful resort!"
The price is £1,241
includes taxes & fees
8 Jun - 9 Jun
Montage Kapalua Bay
Club Suite, 1 Bedroom | Egyptian cotton sheets, premium bedding, down duvets, pillow-top beds
Four Seasons Resort Maui at Wailea
5.0 star property
9.6 out of 10, Exceptional, (1000)
"Great in everything "
The price is £925
includes taxes & fees
19 May - 20 May
Four Seasons Resort Maui at Wailea
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Outdoor pool, pool loungers
Ho‘olei Villas at Grand Wailea
5.0 star property
9.6 out of 10, Exceptional, (36)
"This is an amazing place to stay with a family. Views. Facilities. Local entertainment, dining, shopping, and activities."
The price is £1,944
includes taxes & fees
22 May - 23 May
Ho‘olei Villas at Grand Wailea
3 outdoor pools, pool cabanas (surcharge), pool loungers
The Ritz-Carlton Maui, Kapalua
5.0 star property
9.2 out of 10, Wonderful, (1001)
"Amazing facility, great staff, always attentive and great for families!"
The price is £981
includes taxes & fees
27 May - 28 May
The Ritz-Carlton Maui, Kapalua
Outdoor spa tub
Hotel Wailea, Relais & Chateaux - Adults Only
5.0 star property
9.2 out of 10, Wonderful, (944)
"This hotel is a total gem. It's a rare adults-only property in Hawaii, and the amenities are everything you need, nothing you don't. The bar is perfect, the restaurant is great (especially for breakfast or a celebratory dinner), and the pool bar is first rate. Best Mai Tai we had in Maui! If you prefer boutique hotels and want a quiet experience with a lovely suite, look no further!"
The price is £873
includes taxes & fees
17 May - 18 May
Hotel Wailea, Relais & Chateaux - Adults Only
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)
"Great place "
The price is £725
includes taxes & fees
15 Jun - 16 Jun
Grand Wailea Maui, A Waldorf Astoria Resort
Outdoor pool
Hale Kai at Maui Kamaole
5.0 star property
Hale Kai at Maui Kamaole

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 Kaanapali Shores Pl, Lahaina, HI
The price is £231 per night from May 24 to May 25
£231
per night
24 May - 25 May
8.6/10 Excellent! (1,002 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.

Upcountry Maui Hotel Reviews
Expedia verified reviews

Grand Wailea Maui, A Waldorf Astoria Resort

Grand Wailea Maui, A Waldorf Astoria Resort

5/5 Excellent
"👍"
A verified traveller stayed at Grand Wailea Maui, A Waldorf Astoria Resort
Posted 7 days ago
Grand Wailea Maui, A Waldorf Astoria Resort
Four Seasons Resort Maui at Wailea

Four Seasons Resort Maui at Wailea

5/5 Excellent
"Great in everything "
A verified traveller stayed at Four Seasons Resort Maui at Wailea
Posted 2 weeks ago
Four Seasons Resort Maui at Wailea