Find 5 Star Hotels in Upcountry Maui, HI from SAR 995

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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.

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, (1000)
"One of the best resorts in Hawaii "
The price is SAR 2,644
SAR 3,119 total
includes taxes & fees
21 May - 22 May
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, (1006)
"Will stay here again. "
The price is SAR 2,996
SAR 3,741 total
includes taxes & fees
26 May - 27 May
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, (1001)
"Great place to stay in Wailea!"
The price is SAR 3,184
SAR 3,962 total
includes taxes & fees
9 May - 10 May
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, (1002)
"I can’t recommend Hotel Wailea enough! I’ve been fortunate to stay at most of the resorts in Wailea and none compare to the hospitality and service that you receive at Hotel Wailea. "
The price is SAR 2,996
SAR 3,756 total
includes taxes & fees
5 May - 6 May
Hotel Wailea, Relais & Chateaux - Adults Only
Montage Kapalua Bay
On the beach, beach towels, snorkeling, surfing

Montage Kapalua Bay

5.0 star property
9.6 out of 10, Exceptional, (199)
"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 SAR 4,920
SAR 6,068 total
includes taxes & fees
2 Jun - 3 Jun
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, (41)
"Best property in Maui "
The price is SAR 6,938
SAR 8,428 total
includes taxes & fees
18 May - 19 May
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 SAR 11,772
SAR 14,107 total
includes taxes & fees
3 Jun - 4 Jun
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, (2)
"very nice place and location 🤗"
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 SAR 1,077 per night from May 14 to May 15
SAR 1,077
SAR 1,403 total
includes taxes & fees
14 May - 15 May
8.8/10 Excellent! (994 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