A beach with clear turquoise water, people sunbathing and swimming, and a mountain in the background.

Find 5 Star Hotels in Wailea, HI from SAR 2,113

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on Wailea 5 Star Hotels

Our top choices for Wailea 5-star hotels

9 outdoor pools, cabanas (surcharge), sun loungers

1. Grand Wailea Maui, A Waldorf Astoria Resort

Grand Wailea Maui, A Waldorf Astoria Resort
5.0 star property
Wailea
8.6 out of 10, Excellent, (1,023 reviews)
"Amazing Resort!"
United States
Charli
The price is SAR 2,747
SAR 3,504 total
includes taxes & fees
23 Sep - 24 Sep
Grand Wailea Maui, A Waldorf Astoria Resort
4 outdoor pools, pool umbrellas, sun loungers

2. Wailea Beach Resort - Marriott, Maui

Wailea Beach Resort - Marriott, Maui
5.0 star property
Wailea
9.2 out of 10, Wonderful, (1,001 reviews)
"Place is amazing perfect for vacation with kids"
United States
Michal
The price is SAR 2,422
SAR 3,138 total
includes taxes & fees
5 Oct - 6 Oct
Wailea Beach Resort - Marriott, Maui
Property grounds

3. 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)
"Loved every moment we spent there! Best decision to stay at Four Seasons for our honeymoon trip :)"
United States
You Jin
The price is SAR 3,098
SAR 3,923 total
includes taxes & fees
13 Sep - 14 Sep
Four Seasons Resort Maui at Wailea
Exterior detail

4. Fairmont Kea Lani Maui

Fairmont Kea Lani Maui
5.0 star property
Wailea
9.6 out of 10, Exceptional, (1,006 reviews)
"Our 5th time staying here. Love the resort, clean, wonderful staff, beautiful setting, incredible food on the resort at their restaurants."
United States
Brian
The price is SAR 3,752
SAR 4,717 total
includes taxes & fees
14 Sep - 15 Sep
Fairmont Kea Lani Maui
Outdoor spa tub

5. 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)
"Great atmosphere relaxing,.quiet & beautiful!"
United States
Rashonner
The price is SAR 3,001
SAR 3,785 total
includes taxes & fees
26 Sep - 27 Sep
Hotel Wailea, Relais & Chateaux - Adults Only
Restaurant

6. Ho‘olei Villas at Grand Wailea

Ho‘olei Villas at Grand Wailea
5.0 star property
Wailea
9.6 out of 10, Exceptional, (54 reviews)
"Amazing property with an incredible staff. A+++ all the way around!"
United States
Justin Robert
The price is SAR 6,463
SAR 7,916 total
includes taxes & fees
23 Sep - 24 Sep
Ho‘olei Villas at Grand Wailea
View from property

7. Fairmont Kea Lani Maui Villa Experience

Fairmont Kea Lani Maui Villa Experience
5.0 star property
Wailea
9.8 out of 10, Exceptional, (7 reviews)
"It’s a decent hotel to stay for the family."
United States
Sze Wai
The price is SAR 11,262
SAR 13,632 total
includes taxes & fees
18 Sep - 19 Sep
Fairmont Kea Lani Maui Villa Experience
Outdoor pool, open 8:00 AM to 10:00 PM, free cabanas, pool umbrellas

8. Villa, Garden View, 2-bedroom

Villa, Garden View, 2-bedroom
5.0 star property
Wailea
Villa, Garden View, 2-bedroom
Luxury Apartment | Beach/ocean view

9. Wailea Luxury Hilltop Resort Vistas

Wailea Luxury Hilltop Resort Vistas
5.0 star property
Wailea
10.0 out of 10, Exceptional, (3 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 Wailea.
Andaz Maui at Wailea Resort - a concept by Hyatt

Andaz Maui at Wailea Resort - a concept by Hyatt

3550 Wailea Alanui Dr Kihei HI
The price is SAR 2,918 per night from Oct 10 to Oct 11
SAR 2,918
SAR 3,685 total
10 Oct - 11 Oct
includes taxes & fees
9.2/10 Wonderful! (1,000 reviews)
Still don't see what you're looking for?
See all properties in Wailea.
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.

Top Wailea Hotel Reviews

Grand Wailea Maui, A Waldorf Astoria Resort

Grand Wailea Maui, A Waldorf Astoria Resort

10/10 Excellent
"!"
Dmitriy 9-night trip
Posted 12 hours ago
Grand Wailea Maui, A Waldorf Astoria Resort

Frequently asked questions

What are the best 5-star hotels in Wailea?
According to Expedia customer reviews, Grand Wailea Maui, A Waldorf Astoria Resort, Ho'olei Villas at Grand Wailea and Four Seasons Resort Maui at Wailea are some of the top 5-star hotels in Wailea. Featuring top-of-the-line amenities and unmatchable service, you'll enjoy an indulgent and memorable stay.
How much does it cost to stay in a 5-star hotel in Wailea?
How much you pay for a 5-star hotel in Wailea depends on things like when you plan to travel and the length of your escape. Our top tip for landing the best deal? Use our pricing filters to check out all of the available accommodations for your preferred dates.

  • Search for the lowest price per night from SAR 2,113

What makes a hotel 5 stars in Wailea?
From gourmet dining venues and 24/7 fitness centers to swimming pools and luxury bedding, the 5-star experience in Wailea is all about comfort and luxury. But it calls for more than just top-notch amenities to earn a 5-star rating. Stays also have to provide outstanding services like in-room massages, on-site laundry and 24-hour concierge services.