Explore top 2026 5 Star Hotels in Wailea

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Aug 21 - Aug 23
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Aug 28 - Aug 30

Top Wailea 5 Star hotels

Fairmont Kea Lani Maui

Fairmont Kea Lani Maui

5 out of 5
4100 Wailea Alanui Dr Kihei HI
$1,028 nightly
The price is $1,220 total per night from Aug 17 to Aug 18
$1,220 total
Aug 17 - Aug 18
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 ...
Opens in a new windowFairmont Kea Lani Maui
Grand Wailea Maui, A Waldorf Astoria Resort

Grand Wailea Maui, A Waldorf Astoria Resort

5 out of 5
3850 Wailea Alanui Drive Kihei HI
$786 nightly
The price is $933 total per night from Aug 28 to Aug 29
$933 total
Aug 28 - Aug 29
Total with taxes and fees
A full-service spa, 7 restaurants, and 9 outdoor pools are all featured at this luxury resort. There's fun for all ages with a lazy river and a children's pool, ...
8.6/10 Excellent! (1,001 reviews)
"This was a lovely stay. We ended up in the Napua wing and it truly was great. The staff was very kind and remembered our names instantly. A lazy river should come with every hotel hahaha!"

Reviewed on Aug 14, 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
$880 nightly
The price is $1,045 total per night from Aug 24 to Aug 25
$1,045 total
Aug 24 - Aug 25
Total with taxes and fees
A full-service spa, 3 restaurants, and 3 outdoor pools are all featured at this luxury resort. There's fun for all ages with a free kid's club and a children's ...
Opens in a new windowFour Seasons Resort Maui at Wailea
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
$771 nightly
The price is $916 total per night from Sep 14 to Sep 15
$916 total
Sep 14 - Sep 15
Total with taxes and fees
This luxury resort includes 3 restaurants, an outdoor pool, and a gym. Traveling on business? Take advantage of the laundry service, conference center, and valet ...
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
$1,776 nightly
The price is $2,108 total per night from Aug 30 to Aug 31
$2,108 total
Aug 30 - Aug 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, ...
Opens in a new windowHo‘olei Villas at Grand Wailea
NEW Palms at Wailea Updated 2 Bedroom Villa With Garden Views + Complimentary Rental Car With 6+ Nights! Paw-1706 by KBM Resorts

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

5 out of 5
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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Opens in a new windowNEW Palms at Wailea Updated 2 Bedroom Villa With Garden Views + Complimentary Rental Car With 6+ Nights! Paw-1706 by KBM Resorts
Fairmont Kea Lani Maui Villa Experience

Fairmont Kea Lani Maui Villa Experience

5 out of 5
4100 Wailea Alanui Dr-Building A Kihei HI
$2,978 nightly
The price is $3,535 total per night from Aug 26 to Aug 27
$3,535 total
Aug 26 - Aug 27
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! (3 reviews)
"The best place while we in Hawaii. The first time we had a place with cool Ac . Nice view . Gotta to stay here guys. Big kitchen and clean everywhere. Awesome bathroom, the mirror with light and the view from kitchen.. Amazing❤️"

Reviewed on Aug 11, 2026

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Opens in a new windowWailea Luxury Hilltop Resort Vistas
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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

Wailea Ekahi - CoralTree Residence Collection

Wailea Ekahi - CoralTree Residence Collection

5 out of 5
Posted 5 hours ago
Travelocity Verified Review
"Very nice condo and conveniently located to beach and dining options."
A verified traveler stayed at Wailea Ekahi - CoralTree Residence Collection
Wailea Ekahi - CoralTree Residence Collection

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