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Top Wailea 5 Star hotels

Four Seasons Resort Maui at Wailea

Four Seasons Resort Maui at Wailea

5 out of 5
3900 Wailea Alanui Drive Kihei HI
$945 nightly
The price is $1,122 total per night from Jun 30 to Jul 1
$1,122 total
Jun 30 - Jul 1
Total with taxes and fees
A full-service spa, 3 restaurants, and 3 outdoor pools are all featured at this luxury resort. Spend a day at the beach surfing, or relax with sun loungers and ...
9.6/10 Exceptional! (1,004 reviews)
"Stay somewhere else!!!!!! For $1400/night, I expected a lot better. I stayed here in 2019 and it was much better then. I let the hotel know beforehand that I would be coming with a baby. They let us know at check-in that there was some work going around the hotel so some things would be closed/temporary ..."

Reviewed on Jun 28, 2026

Opens in a new windowFour Seasons Resort Maui at Wailea
Grand Wailea Maui, A Waldorf Astoria Resort

Grand Wailea Maui, A Waldorf Astoria Resort

5 out of 5
3850 Wailea Alanui Drive Kihei HI
$863 nightly
The price is $1,024 total per night from Jul 11 to Jul 12
$1,024 total
Jul 11 - Jul 12
Total with taxes and fees
A full-service spa, 7 restaurants, and 9 outdoor pools are all featured at this luxury resort. Spend a day at the beach snorkeling, or relax with sun loungers ...
8.8/10 Excellent! (1,002 reviews)
"Love the Grand Wailea but things are starting to show wear and tear. They need updating on the cobblestone pathways around the pools. There are broken ones that you can trip on and they become so slippery I saw several people fall while we’re there. They also get so hot during the day people are ..."

Reviewed on Jun 26, 2026

Opens in a new windowGrand Wailea Maui, A Waldorf Astoria Resort
Fairmont Kea Lani Maui

Fairmont Kea Lani Maui

5 out of 5
4100 Wailea Alanui Dr Kihei HI
$1,139 nightly
The price is $1,352 total per night from Jul 3 to Jul 4
$1,352 total
Jul 3 - Jul 4
Total with taxes and fees
A full-service spa, 6 restaurants, and 3 outdoor pools are all featured at this luxury resort. Relax with beach cabanas, sun loungers, and beach umbrellas. There's ...
9.4/10 Exceptional! (1,000 reviews)
"Very clean. Staff were very personable."

Reviewed on Jun 25, 2026

Opens in a new windowFairmont Kea Lani Maui
Hotel Wailea, Relais & Chateaux - Adults Only

Hotel Wailea, Relais & Chateaux - Adults Only

5 out of 5
555 Kaukahi Street Kihei HI
Fully refundableReserve now, pay when you stay
$713 nightly
The price is $847 total per night from Jul 11 to Jul 12
$847 total
Jul 11 - Jul 12
Total with taxes and fees
This luxury resort includes 3 restaurants, an outdoor pool, and a gym. Traveling on business? Take advantage of the business center, laundry service, and valet ...
9.4/10 Exceptional! (1,000 reviews)
"If there isn’t a wedding going on watch the sunset from the front lawn area by the old ice cream truck. Better view than from the birdcage. More open and less blockage. Great high end vibe."

Reviewed on Jun 22, 2026

Opens in a new windowHotel Wailea, Relais & Chateaux - Adults Only
Ho‘olei Villas at Grand Wailea

Ho‘olei Villas at Grand Wailea

5 out of 5
146 Ho'olei Circle Kihei HI
$2,186 nightly
The price is $2,595 total per night from Jul 24 to Jul 25
$2,595 total
Jul 24 - Jul 25
Total with taxes and fees
A full-service spa, an outdoor pool, and a restaurant are all featured at this luxury resort. Bring the family and enjoy the children's club, children's pool, ...
9.6/10 Exceptional! (48 reviews)
"Pools are great, the villa is perfect for families, service was good, and the F&B options are outstanding"

Reviewed on Jun 14, 2026

Opens in a new windowHo‘olei Villas at Grand Wailea
Fairmont Kea Lani Maui Villa Experience

Fairmont Kea Lani Maui Villa Experience

5 out of 5
4100 Wailea Alanui Dr-Building A Kihei HI
$4,548 nightly
The price is $5,400 total per night from Jul 28 to Jul 29
$5,400 total
Jul 28 - Jul 29
Total with taxes and fees
A full-service spa, 4 restaurants, and 3 outdoor pools are all featured at this luxury resort. Spend a day at the beach snorkeling, or relax with beach cabanas ...
Opens in a new windowFairmont Kea Lani Maui Villa Experience
NEW Palms at Wailea Updated 2 Bedroom Villa With Garden Views + Complimentary Rental Car With 6+ Nights! Paw-1706 by KBM Resorts

NEW Palms at Wailea Updated 2 Bedroom Villa With Garden Views + Complimentary Rental Car With 6+ Nights! Paw-1706 by KBM Resorts

5 out of 5
3200 Wailea Alanui Dr Kihei HI
This condo features a restaurant, an outdoor pool, and a bar/lounge. Enjoy the hot tub and perks like free self parking and free WiFi. A coffee shop, a terrace, ...
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Opens in a new windowNEW Palms at Wailea Updated 2 Bedroom Villa With Garden Views + Complimentary Rental Car With 6+ Nights! Paw-1706 by KBM Resorts
Wailea Luxury Hilltop Resort Vistas

Wailea Luxury Hilltop Resort Vistas

5 out of 5
10 Wailea Ekolu Pl Kihei HI
This apartment features a terrace, barbecue grills, and free self parking. A garden and a picnic area are also provided.
10/10 Exceptional! (2 reviews)
"We loved staying here! The property is lovely and the lanai was perfect for sunsets. It has everything you need and you can walk anywhere you need to go. Will be back!"

Reviewed on Nov 28, 2024

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Opens in a new windowWailea Luxury Hilltop Resort Vistas
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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.

Recent Wailea hotel reviews by fellow wanderers

Wailea Beach Resort - Marriott, Maui

Wailea Beach Resort - Marriott, Maui

5 out of 5
Posted 1 day ago
Travelocity Verified Review
"Wonderful waterfront resort for families with multiple pool and beach options"
A verified traveler stayed at Wailea Beach Resort - Marriott, Maui
Wailea Beach Resort - Marriott, Maui

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