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
The price is $1,009 total per night from Jan 19 to Jan 20
$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
The price is $905 total per night from Feb 6 to Feb 7
$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
The price is $1,178 total per night from Feb 2 to Feb 3
$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
The price is $1,074 total per night from Jan 21 to Jan 22
$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
The price is $2,505 total per night from Jan 30 to Jan 31
$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
The price is $4,316 total per night from Jan 30 to Jan 31
$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
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 Ekahi - CoralTree Residence Collection
5 out of 5
Posted 4 days ago
Travelocity Verified Review
"Clean, great space and awesome location. "
A verified traveler stayed at Wailea Ekahi - CoralTree Residence Collection
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