5 Stars Hotels in Wailea, Kihei from CA $892

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Check availability on Wailea 5 Star Hotels

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Sep 1 - Sep 2
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Sep 2 - Sep 3
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Sep 5 - Sep 7
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Sep 12 - Sep 14

Top Wailea 5 Star Hotels

Our top choices for Wailea 5-star hotels

Grand Wailea Maui, A Waldorf Astoria Resort
9 outdoor pools, cabanas (surcharge), sun loungers

Grand Wailea Maui, A Waldorf Astoria Resort

5.0 star property
8.8 out of 10, Excellent, (1008)
"Good food great area "
The price is CA $956
CA $1,217 total
includes taxes & fees
Sep 7 - Sep 8
Grand Wailea Maui, A Waldorf Astoria Resort
Fairmont Kea Lani Maui
View from room

Fairmont Kea Lani Maui

5.0 star property
9.4 out of 10, Exceptional, (1008)
"excellent resort and very clean "
The price is CA $1,167
CA $1,457 total
includes taxes & fees
Sep 4 - Sep 5
Fairmont Kea Lani Maui
Four Seasons Resort Maui at Wailea
Club Ocean Front One Bedroom Suite

Four Seasons Resort Maui at Wailea

5.0 star property
9.6 out of 10, Exceptional, (1004)
"This was an exceptional property and we literally had the most amazing stay. Staff were attentive and all car journies were complkmentary. "
The price is CA $1,037
CA $1,224 total
includes taxes & fees
Sep 27 - Sep 28
Four Seasons Resort Maui at Wailea
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)
"Great resort with great amenities! Very convenient to downtown wailea and the beaches and the staff are super friendly and attentive! "
The price is CA $1,225
CA $1,527 total
includes taxes & fees
Sep 14 - Sep 15
Hotel Wailea, Relais & Chateaux - Adults Only
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, (42)
"Perfect for Families. Quite spacious and great for a relaxing Family vacation."
The price is CA $2,784
CA $3,373 total
includes taxes & fees
Sep 24 - Sep 25
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 CA $2,697
CA $3,262 total
includes taxes & fees
Sep 7 - Sep 8
Fairmont Kea Lani Maui Villa Experience
Wailea Luxury Hilltop Resort Vistas
Luxury Apartment | Private kitchen

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
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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 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 CA $1,054 per night from Oct 1 to Oct 2
CA $1,054
CA $1,324 total
Oct 1 - Oct 2
includes taxes & fees
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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 Wailea

Indulge in Hawai’i’s high life with a stay in this beautiful coastal area known for its luxury accommodation and secluded beaches.

See all hotels in Wailea
Maluaka Beach showing landscape views, a beach and tropical scenes

Top Wailea Hotel Reviews

Find out more about Wailea

Find out more about Wailea

Five Star Hotels in Wailea

There's nothing wrong with enjoying the finer things in life. Indulge yourself on your next leisure time. After all, this is one of the Top 10 locations in Expedia's portfolio. You'll join the multitudes of vacationers who have made Wailea so fashionable in the last year. We should also mention, the hotels in this area receive outstanding marks for guest services, so you know you'll be looked after during your getaway. You deserve the great vacation you're dreaming about. Book one of Expedia's luxurious 5-star hotels in Wailea and get ready to be pampered like never before.

Get a Great Deal on 5-Star Hotels in Wailea

Don't be afraid to live the high life while you're on vacation, along with pristine rooms. Excellent customer care, spacious rooms, and fabulous spa offerings are all on offer. We have a huge number of hotels in the region, and all of them offer outstanding amenities. Besides that, you'll find that these hotels are kept in fantastic condition and provide a fine place to kick back after your daily adventures. What kind of amenities will make your stay a wonderful one? A concierge to help you plan every detail of your day? A Swedish massage to help your cares fall away? Fluffy down pillows, piping hot coffees, and even space for your family pet in some cases...these hotels have it all. Want to see for yourself? Then explore the 31,943 reviews various guests have left on Expedia and get to know these places.

Can't wait to get outside? We've got you covered. You'll find lots of attractions to see in a sprawling city like this one, like visiting art galleries and taking in live performances. Say hi to the locals—they're sure to have advice on what kind of excitement you can find in town.

Make Your Escape to Wailea

The results are in, and Wailea 5-star hotels are the place to be when you book your next vacation. Many visitors recommend a trip to this location, so don't wait any longer. This is a great time to find 5-star hotel deals in Wailea! Don't put off your dream vacation any longer. Choose one of the 5-star hotels in Wailea today and settle down in the lap of luxury tomorrow.

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Explore a world of travel with Expedia

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 among the best 5-star hotels in Wailea. Providing first-rate amenities and unparalleled service, you'll enjoy an opulent 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 such as when you plan to travel and the length of your stay. An insider tip for landing the best deal? Use our pricing filters to check out the available accommodations for your selected dates.

  • Search for the lowest price per night from CA $892

What makes a hotel 5 stars in Wailea?
In Wailea, a hotel must offer a specific level of high-end conveniences to earn 5 stars. These can include on-site gyms, gourmet restaurants, saunas and spas, premium bedding, luxury bathroom products and more. What also sets 5-star hotels apart is their exceptional standard of service. You'll enjoy things like concierge services, nightly turn-down services and in-room massage. Some may even offer extra touches like welcome gifts.