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Check availability on Upcountry Maui 5 Star Hotels

Tonight
28 Apr - 29 Apr
Tomorrow
29 Apr - 30 Apr
This weekend
1 May - 3 May
Next weekend
8 May - 10 May

Our top choices for Upcountry Maui 5-star hotels

Property grounds

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)
"Wonderful Hotel Great restaurants staffed by true professionals "
United States
John
The price is £742
includes taxes & fees
30 Apr - 1 May
Four Seasons Resort Maui at Wailea
9 outdoor pools, pool cabanas (surcharge), pool loungers

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, (1,004 reviews)
"Perfect location for day drinking "
United States
William
The price is £746
includes taxes & fees
12 May - 13 May
Grand Wailea Maui, A Waldorf Astoria Resort
3 outdoor pools, pool cabanas (surcharge), pool loungers

The Ritz-Carlton Maui, Kapalua

The Ritz-Carlton Maui, Kapalua
5.0 star property
Kapalua
9.2 out of 10, Wonderful, (1,004 reviews)
"Awesome resort!!!"
United States
Clifford
The price is £840
includes taxes & fees
20 May - 21 May
The Ritz-Carlton Maui, Kapalua
Exterior detail

Fairmont Kea Lani Maui

Fairmont Kea Lani Maui
5.0 star property
Wailea
9.4 out of 10, Exceptional, (1,003 reviews)
"Beautiful place"
United States
Laci
The price is £1,026
includes taxes & fees
12 May - 13 May
Fairmont Kea Lani Maui
Outdoor spa tub

Hotel Wailea, Relais & Chateaux - Adults Only

Hotel Wailea, Relais & Chateaux - Adults Only
5.0 star property
Wailea
9.4 out of 10, Exceptional, (1,000 reviews)
"We had a good time. Comfortable hotel. "
United States
andrea
The price is £730
includes taxes & fees
10 May - 11 May
Hotel Wailea, Relais & Chateaux - Adults Only
Aerial view

Royal Lahaina Bungalows & Spa

Royal Lahaina Bungalows & Spa
5.0 star property
Lahaina
8.6 out of 10, Excellent, (14 reviews)
"Clean room and staff is super friendly. Would stay here again "
United States
Rene
The price is £340
includes taxes & fees
30 Apr - 1 May
Royal Lahaina Bungalows & Spa
Restaurant

Ho‘olei Villas at Grand Wailea

Ho‘olei Villas at Grand Wailea
5.0 star property
Wailea
9.6 out of 10, Exceptional, (46 reviews)
"This was a beautiful villa across the street from the grand wailea. Booking included full use of the resort, which was excellent. Included was a shuttle service with uber-like app that we could use to go anywhere within a 1 mile radius. This was a great stay"
United States
Daniel
The price is £1,538
includes taxes & fees
7 May - 8 May
Ho‘olei Villas at Grand Wailea
Luxury Apartment | Beach/ocean view

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
Ohia Lehua 4-Bedroom, Residence, Ocean View | Living room | LCD TV, DVD player, iPod dock

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)
"Even though we booked under the montage name, the hotel met all standards even with new ownership. The property itself is one of the most magical places we have been. We are very excited to come back in the future with our family. "
United States
Olivia
The price is £1,284
includes taxes & fees
19 May - 20 May
The Resort at Kapalua Bay, Maui
View from property

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 £3,209
includes taxes & fees
10 May - 11 May
Fairmont Kea Lani Maui Villa Experience
Balcony

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
Condo (1 Bedroom) | 1 bedroom, laptop workspace, iron/ironing board, free cots/infant beds

Kapalua Bay Villas Resort by KBM

Kapalua Bay Villas Resort by KBM
5.0 star property
Kapalua
The price is £1,613
includes taxes & fees
10 May - 11 May
Kapalua Bay Villas Resort by KBM
Luxury Apartment, Ocean View | Living area | Hulu, streaming services

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
Luxury Condo | Living area | 90-inch Smart TV with digital channels, Hulu, streaming services

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
Condo (1 Bedroom) | Pool | Outdoor pool

Hale Ona Loa HOL-102 by KBM

Hale Ona Loa HOL-102 by KBM
5.0 star property
Kaanapali
The price is £675
includes taxes & fees
11 May - 12 May
Hale Ona Loa HOL-102 by KBM
Luxury Apartment, 2 Bedrooms, Kitchen, Ocean View | Living area | 700-inch Smart TV with cable channels, pay films

Upscale Luxurious Ocean Resort Vistas

Upscale Luxurious Ocean Resort Vistas
5.0 star property
South Kihei
Upscale Luxurious Ocean Resort 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.
The Westin Maui Resort & Spa, Ka'anapali

The Westin Maui Resort & Spa, Ka'anapali

2365 Kaanapali Pkwy Lahaina HI
The price is £619 per night from 8 May to 9 May
£619
8 May - 9 May
includes taxes & fees
9.2/10 Wonderful! (1,019 reviews)
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Learn more about Upcountry Maui

Venture to top sights like Haleakala National Park as you discover Upcountry Maui—a relaxing city also notable for its island views.

See all hotels in Upcountry Maui
Photo by Project Forever
Open Photo by Project Forever

Top Upcountry Maui Hotel Reviews

Grand Wailea Maui, A Waldorf Astoria Resort

Grand Wailea Maui, A Waldorf Astoria Resort

6/10 Okay
"Hotel grounds and rooms are outdated and in need of refurbishing "
Edward 4-night trip
Posted 8 hours ago
Grand Wailea Maui, A Waldorf Astoria Resort

Find out more about Upcountry Maui

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 based on when you prefer to travel and how long you plan to be away, among a range of factors. Take advantage of our price per night filter and other search tools to land the best deal on a luxurious stay.

  • Search for the lowest price per night from £289

What makes a hotel 5 stars in Upcountry Maui?
Exemplary guest service is integral to every 5-star hotel in Upcountry Maui. From the moment you enter the lobby, staff cater to your every need, whether offering luggage assistance and storage or providing a nightly turn-down service. On top of that, hotels must offer top-rate amenities to obtain a 5-star rating. These can include luxury bathrooms, on-site spa facilities, swimming pools, gastronomic restaurants and knowledgeable concierge.
Are there any 5-star all-inclusive resorts in Upcountry Maui?
Find an indulgent retreat that includes your room, meals, drinks and entertainment in Upcountry Maui with our filter tool. Search for hotels rated 5 stars and select the "All inclusive" filter. Have a look at what's included in the upfront price. This way, you're ready to take advantage of the premium perks on offer from the moment you arrive.

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