Compare and book 5 Star hotels in Upcountry Maui, Hawaii

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Save instantly and earn perks with One Key
    Learn about One Key

  • Be picky

    Search almost a million properties worldwide

Check availability on Upcountry Maui 5 Star Hotels

Our top choices for Upcountry Maui 5-star hotels

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, (1,017 reviews)
"Great hotel. Had an awesome stay and staff was very friendly. Beautiful property and love that you could walk right onto the beach from the resort."
United States
Dustin
The price is £725
includes taxes & fees
29 Jun - 30 Jun
Grand Wailea Maui, A Waldorf Astoria Resort
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, (1,001 reviews)
"Wonderful Hotel Great restaurants staffed by true professionals "
United States
John
The price is £885
includes taxes & fees
8 Jul - 9 Jul
Four Seasons Resort Maui at Wailea
Exterior detail

Fairmont Kea Lani Maui

Fairmont Kea Lani Maui
5.0 star property
Wailea
9.4 out of 10, Exceptional, (1,005 reviews)
"The resort was excellent and made for a great trip!"
United States
Ed
The price is £1,035
includes taxes & fees
22 Jun - 23 Jun
Fairmont Kea Lani Maui
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, (1,005 reviews)
"Our stay was wonderful, "
United States
Christopher
The price is £848
includes taxes & fees
22 Jun - 23 Jun
The Ritz-Carlton Maui, Kapalua
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, (1,002 reviews)
"We had a good time. Comfortable hotel. "
United States
andrea
The price is £688
includes taxes & fees
28 Jun - 29 Jun
Hotel Wailea, Relais & Chateaux - Adults Only
Restaurant

Ho‘olei Villas at Grand Wailea

Ho‘olei Villas at Grand Wailea
5.0 star property
Wailea
9.6 out of 10, Exceptional, (48 reviews)
"Womderful home, terrific service, access to hotel amenities was key."
United States
ALAN
The price is £1,946
includes taxes & fees
13 Jul - 14 Jul
Ho‘olei Villas at Grand Wailea
Aerial view

Royal Lahaina Bungalows & Spa

Royal Lahaina Bungalows & Spa
5.0 star property
Lahaina
8.2 out of 10, Very good, (16 reviews)
"Place was beautiful and I really enjoyed the live music under the stats every night"
United States
AURA MARINA
The price is £323
includes taxes & fees
27 Jun - 28 Jun
Royal Lahaina Bungalows & Spa
Outdoor pool, pool umbrellas, pool loungers

The Resort at Kapalua Bay, Maui

The Resort at Kapalua Bay, Maui
5.0 star property
Lahaina
9.6 out of 10, Exceptional, (212 reviews)
"Beautiful setting, views, rooms and spa"
Canada
Rachel
The price is £1,296
includes taxes & fees
7 Jul - 8 Jul
The Resort at Kapalua Bay, Maui
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, (9 reviews)
"Beautifully renovated. Everything you need to enjoy the beach is there for you to use."
United States
Carrie
2 2 Oceanview Modern Resort Vistas
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 £4,028
includes taxes & fees
10 Jul - 11 Jul
Fairmont Kea Lani Maui Villa Experience
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
BBQ/picnic Area

Aloha Chic Penthouse Vistas

Aloha Chic Penthouse Vistas
5.0 star property
Central Kihei
10.0 out of 10, Exceptional, (4 reviews)
"Condo was very well stocked and very clean. Thank you for great accommodations."
United States
Shirley
Aloha Chic Penthouse Vistas
Villa, 1 Bedroom (Ocean View, Sleeps 4 (KBV-15B3)) | 1 bedroom, laptop workspace, iron/ironing board, bed sheets

Kapalua Bay Villas Resort by KBM

Kapalua Bay Villas Resort by KBM
5.0 star property
Kapalua
Kapalua Bay Villas Resort by KBM
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
Villa, 1 Bedroom (Ocean View, Sleeps 4 (HOL-102)) | 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 £1,292
includes taxes & fees
19 Jun - 20 Jun
Hale Ona Loa HOL-102 by KBM
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
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

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 £483 per night from 28 Jun to 29 Jun
£483
28 Jun - 29 Jun
includes taxes & fees
9.2/10 Wonderful! (1,064 reviews)
Still don't see what you're looking for?
See all properties in Upcountry Maui.
You can also use these popular filters to refine your search.
PoolSpaHot tubBreakfast includedWaterpark
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

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

The Ritz-Carlton Maui, Kapalua

The Ritz-Carlton Maui, Kapalua

8/10 Good
"Property is absolutely gorgeous. We stayed in one of the ocean view suites. Rooms could use a little updating. Firepit did not work, furniture was old. At one point during our stay, staff set up a huge double white tent in front of our suite for one and a half days, completely blocking our view, as well as compromising our privacy. Apparently there was a wedding event, but the tent could have been set up in a different location. I did call to complain and the manager did remove all of the hotel taxes for the week that we were there."
Shane Taylor 5-night trip
Posted 15 hours ago
The Ritz-Carlton Maui, Kapalua

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 £483

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.

Explore a world of travel with Expedia