Explore top 2026 5 Star Hotels in Wailea

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Top Wailea 5 Star hotels

Grand Wailea Maui, A Waldorf Astoria Resort

Grand Wailea Maui, A Waldorf Astoria Resort

5 out of 5
3850 Wailea Alanui Drive Kihei HI
$997 nightly
The price is $1,183 total per night from Apr 4 to Apr 5
$1,183 total
Apr 4 - Apr 5
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! (1,004 reviews)
Enjoyed everything about this property. Great service and amenities!

Reviewed on Mar 5, 2026

Opens in a new windowGrand Wailea Maui, A Waldorf Astoria Resort
Four Seasons Resort Maui at Wailea

Four Seasons Resort Maui at Wailea

5 out of 5
3900 Wailea Alanui Drive Kihei HI
$1,005 nightly
The price is $1,193 total per night from Mar 9 to Mar 10
$1,193 total
Mar 9 - Mar 10
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! (1,005 reviews)
Staff

Reviewed on Feb 28, 2026

Opens in a new windowFour Seasons Resort Maui at Wailea
Fairmont Kea Lani Maui

Fairmont Kea Lani Maui

5 out of 5
4100 Wailea Alanui Dr Kihei HI
$1,010 nightly
The price is $1,199 total per night from Mar 7 to Mar 8
$1,199 total
Mar 7 - Mar 8
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! (1,005 reviews)
Lovely

Reviewed on Mar 5, 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
$1,099 nightly
The price is $1,305 total per night from Apr 5 to Apr 6
$1,305 total
Apr 5 - Apr 6
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! (1,001 reviews)
abslout great

Reviewed on Feb 26, 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
$2,216 nightly
The price is $2,630 total per night from Mar 6 to Mar 7
$2,630 total
Mar 6 - Mar 7
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! (45 reviews)
Womderful home, terrific service, access to hotel amenities was key.

Reviewed on Feb 28, 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
$3,398 nightly
The price is $4,034 total per night from Mar 12 to Mar 13
$4,034 total
Mar 12 - Mar 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 ...
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.
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
Grand Champions 2 Free Rental Cars KBM Resorts Extra Large Corner Suite 2 Units, 3 Bedrooms Ml-1499

Grand Champions 2 Free Rental Cars KBM Resorts Extra Large Corner Suite 2 Units, 3 Bedrooms Ml-1499

5 out of 5
155 Wailea Ike Pl Kihei HI
This condo features a restaurant, an outdoor pool, and a bar/lounge. Guests will appreciate free perks like free self parking and WiFi in public areas. A coffee ...
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Opens in a new windowGrand Champions 2 Free Rental Cars KBM Resorts Extra Large Corner Suite 2 Units, 3 Bedrooms Ml-1499
Wailea Elua Collection by KBM - 2 Units (2009/2103)

Wailea Elua Collection by KBM - 2 Units (2009/2103)

5 out of 5
3600 Wailea Alanui Drive Kihei HI
A restaurant and an outdoor pool are featured at this condo. WiFi in public areas is free. A coffee shop, a terrace, and a garden are also on offer.
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Opens in a new windowWailea Elua Collection by KBM - 2 Units (2009/2103)
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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

Grand Wailea Maui, A Waldorf Astoria Resort

Grand Wailea Maui, A Waldorf Astoria Resort

5 out of 5
Posted 3 days ago
Travelocity Verified Review
"Having multiple pool options available just steps away from the beach was amazing! The outdoor lobby is the epitome of island paradise and the overall setting is just gorgeous!"
A verified traveler stayed at Grand Wailea Maui, A Waldorf Astoria Resort
Grand Wailea Maui, A Waldorf Astoria Resort

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