Explore top 2026 5 Star Hotels in Wailea

Name: Wailea Luxury Hilltop Resort Vistas
Rating: 10

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Top Wailea 5 Star hotels

Four Seasons Resort Maui at Wailea

3900 Wailea Alanui Drive Kihei HI

$1,000 nightly

$1,187 total

Jul 3 - Jul 4

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! (1,000 reviews)

"This was the most amazing property we’ve ever stayed at, the staff was incredible"

Reviewed on Jun 29, 2026

Grand Wailea Maui, A Waldorf Astoria Resort

3850 Wailea Alanui Drive Kihei HI

$865 nightly

$1,027 total

Jul 14 - Jul 15

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 ...

Fairmont Kea Lani Maui

4100 Wailea Alanui Dr Kihei HI

$1,139 nightly

$1,352 total

Jul 5 - Jul 6

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! (1,003 reviews)

Reviewed on Jul 1, 2026

Hotel Wailea, Relais & Chateaux - Adults Only

555 Kaukahi Street Kihei HI

Fully refundableReserve now, pay when you stay

$737 nightly

$875 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

Ho‘olei Villas at Grand Wailea

146 Ho'olei Circle Kihei HI

$2,186 nightly

$2,595 total

Jul 25 - Jul 26

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

Fairmont Kea Lani Maui Villa Experience

4100 Wailea Alanui Dr-Building A Kihei HI

$4,078 nightly

$4,842 total

Jul 31 - Aug 1

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 ...

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

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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Wailea Luxury Hilltop Resort Vistas

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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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

Fairmont Kea Lani Maui

4 out of 5

Posted 4 hours ago

Travelocity Verified Review

"The property layout in rooms are quite beautiful however staff were rushed to leave at the end of their shift and didn’t seem happy to have non-locals on their island. Numerous times we tried to get beach supplies and were told no because the rental workers wanted to leave early. This was at 12pm one day and 2pm another day. Ridiculous with over 5-7 hours of daylight left on the beach. Super disappointing when we flew 12 hours and spent over 10k to be there"

A verified traveler stayed at Fairmont Kea Lani Maui