Explore top 2026 5 Star Hotels in Wailea

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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
$755 nightly
The price is $891 total per night from Dec 8 to Dec 9
$891 total
Dec 8 - Dec 9
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 property has long been one of my global Four Seasons favorites, and I remain truly grateful for the warm hospitality I always receive. I was also very appreciative of the wonderful upgrade to an ocean-view room — mahalo for that thoughtful gesture. I’ve been visiting this resort regularly since ...

Reviewed on Dec 2, 2025

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
$647 nightly
The price is $763 total per night from Dec 17 to Dec 18
$763 total
Dec 17 - Dec 18
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! (1,010 reviews)
Incredible stay

Reviewed on Dec 1, 2025

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
$831 nightly
The price is $980 total per night from Dec 6 to Dec 7
$980 total
Dec 6 - Dec 7
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! (1,011 reviews)
very nicely rennovated hotel and rooms very convenient shuttle service very good food the staff was sometimes variable in quality and experience the concierge service can be improved - lacking concrete tips and details related to trip to hana, no supporting documentation, poor leasing staff

Reviewed on Nov 30, 2025

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
$899 nightly
The price is $1,060 total per night from Dec 16 to Dec 17
$1,060 total
Dec 16 - Dec 17
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! (1,001 reviews)
Great

Reviewed on Dec 3, 2025

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
$1,845 nightly
The price is $2,177 total per night from Dec 14 to Dec 15
$2,177 total
Dec 14 - Dec 15
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

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
$3,109 nightly
The price is $3,667 total per night from Dec 12 to Dec 13
$3,667 total
Dec 12 - Dec 13
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

Opens in a new windowFairmont Kea Lani Maui Villa Experience
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.
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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Recent Wailea hotel reviews by fellow wanderers

Residence Inn by Marriott Maui Wailea

Residence Inn by Marriott Maui Wailea

5 out of 5
Posted 3 hours ago
Travelocity Verified Review
"Room was clean, staffs are kind and the pool was big enough for my children."
A verified traveler stayed at Residence Inn by Marriott Maui Wailea
Residence Inn by Marriott Maui Wailea

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