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

5 Stars Hotels in Wailea, Kihei from CA $802

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Check availability on Wailea 5 Star Hotels

Next weekend
Oct 9 - Oct 11
In two weeks
Oct 16 - Oct 18

Our top choices for Wailea 5-star hotels

A pool with a waterfall feature, surrounded by palm trees and a stone structure.

1. 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)
"Great walking and beautiful grounds."
United States
Jason
The price is CA $1,081
CA $1,375 total
includes taxes & fees
Oct 25 - Oct 26
Grand Wailea Maui, A Waldorf Astoria Resort
A resort pool area with a central fountain, surrounded by lounge chairs and palm trees, leading to the ocean.

2. 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)
"Loved every moment we spent there! Best decision to stay at Four Seasons for our honeymoon trip :)"
United States
You Jin
The price is CA $1,461
CA $1,827 total
includes taxes & fees
Oct 19 - Oct 20
Four Seasons Resort Maui at Wailea
A water park with multiple slides and a pool area surrounded by lush greenery and palm trees.

3. Wailea Beach Resort - Marriott, Maui

Wailea Beach Resort - Marriott, Maui
5.0 star property
Wailea
9.0 out of 10, Wonderful, (1,002 reviews)
"Location was fantastic and the staff was great."
United States
Christina
The price is CA $837
CA $1,093 total
includes taxes & fees
Oct 25 - Oct 26
Wailea Beach Resort - Marriott, Maui
A staircase with a view of a garden, palm trees, and a bridge.

4. Fairmont Kea Lani Maui

Fairmont Kea Lani Maui
5.0 star property
Wailea
9.6 out of 10, Exceptional, (1,001 reviews)
"Really nice resort, 100% would recommend staying at Fairmont Kea Lani"
United States
Blanca Veronica
The price is CA $1,509
CA $1,891 total
includes taxes & fees
Oct 23 - Oct 24
Fairmont Kea Lani Maui
A poolside area with a fire pit, lounge chairs, and umbrellas.

5. Hotel Wailea Maui

Hotel Wailea Maui
5.0 star property
Wailea
9.4 out of 10, Exceptional, (1,000 reviews)
"Great atmosphere relaxing,.quiet & beautiful!"
United States
Rashonner
The price is CA $1,149
CA $1,449 total
includes taxes & fees
Oct 31 - Nov 1
Hotel Wailea Maui
A resort with thatched-roof structures, a pool with a waterfall, and wooden railings.

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 CA $2,455
CA $3,007 total
includes taxes & fees
Oct 17 - Oct 18
Ho‘olei Villas at Grand Wailea
A staircase with a view of a garden, palm trees, and a bridge.

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 CA $3,761
CA $4,564 total
includes taxes & fees
Oct 24 - Oct 25
Fairmont Kea Lani Maui Villa Experience
A resort pool area with a hot tub, lounge chairs, and palm trees.

8. Villa, Garden View, 2-bedroom

Villa, Garden View, 2-bedroom
5.0 star property
Wailea
The price is CA $1,200
CA $2,231 total
includes taxes & fees
Oct 19 - Oct 20
Villa, Garden View, 2-bedroom
A modern kitchen with white cabinets, stainless steel appliances, and a large island.

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
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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 $1,153 per night from Nov 3 to Nov 4
CA $1,153
CA $1,453 total
Nov 3 - Nov 4
includes taxes & fees
9.2/10 Wonderful! (1,001 reviews)
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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
A sailboat on calm blue waters with a clear sky and distant mountains.

Top Wailea Hotel Reviews

Four Seasons Resort Maui at Wailea

Four Seasons Resort Maui at Wailea

10/10 Excellent
"We were here with our adult children for a family trip and really enjoyed the pools, spa, Spago, the complementary car service and every employee we came in contact with! A great trip!"
Quinn 5-night trip
Posted 2 hours ago
Four Seasons Resort Maui at 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.

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 $802

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.

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