Explore top 2026 5 Star Hotels in Wailea

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Top Wailea 5 Star hotels

Four Seasons Resort Maui at Wailea

3900 Wailea Alanui Drive Kihei HI

$850 nightly

$1,009 total

Jan 19 - Jan 20

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! (999 reviews)

Service was good

Reviewed on Jan 8, 2026

Grand Wailea Maui, A Waldorf Astoria Resort

3850 Wailea Alanui Drive Kihei HI

$763 nightly

$905 total

Feb 6 - Feb 7

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! (1,005 reviews)

Beautiful Resort

Reviewed on Jan 12, 2026

Fairmont Kea Lani Maui

4100 Wailea Alanui Dr Kihei HI

$993 nightly

$1,178 total

Feb 2 - Feb 3

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)

Fantastic experience all around.

Reviewed on Jan 7, 2026

Hotel Wailea, Relais & Chateaux - Adults Only

555 Kaukahi Street Kihei HI

Fully refundableReserve now, pay when you stay

$904 nightly

$1,074 total

Jan 21 - Jan 22

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 ...

9.2/10 Wonderful! (1,000 reviews)

Rooms are beautiful

Reviewed on Jan 13, 2026

Ho‘olei Villas at Grand Wailea

146 Ho'olei Circle Kihei HI

$2,110 nightly

$2,505 total

Jan 30 - Jan 31

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! (43 reviews)

Perfect for Families. Quite spacious and great for a relaxing Family vacation.

Reviewed on Jun 15, 2025

Fairmont Kea Lani Maui Villa Experience

4100 Wailea Alanui Dr-Building A Kihei HI

$3,659 nightly

$4,316 total

Jan 30 - Jan 31

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 ...

9.6/10 Exceptional! (6 reviews)

It’s a decent hotel to stay for the family.

Reviewed on Aug 22, 2024

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.

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.