Find and compare 5 Star hotels in Wailea

Name: Wailea Luxury Hilltop Resort Vistas
Rating: 10

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Featured Wailea 5 Star hotels

Four Seasons Resort Maui at Wailea

3900 Wailea Alanui Drive Kihei HI

CA $1,341

CA $1,592 total

Jun 30 - Jul 1

includes taxes & fees

Book a stay at this luxury resort in Kihei. Enjoy free WiFi, 3 outdoor pools, and a full-service spa. Our guests praise the helpful staff in our reviews. Popular ...

9.6/10 Exceptional! (1,004 reviews)

"Stay somewhere else!!!!!! For $1400/night, I expected a lot better. I stayed here in 2019 and it was much better then. I let the hotel know beforehand that I would be coming with a baby. They let us know at check-in that there was some work going around the hotel so some things would be closed/temporary ..."

Reviewed on Jun 28, 2026

Grand Wailea Maui, A Waldorf Astoria Resort

3850 Wailea Alanui Drive Kihei HI

CA $1,150

CA $1,457 total

Jul 12 - Jul 13

includes taxes & fees

Book a stay at this luxury resort in Kihei. Enjoy free WiFi, 9 outdoor pools, and a full-service spa. Our guests praise the pool and the helpful staff in our ...

8.8/10 Excellent! (1,002 reviews)

Reviewed on Jun 26, 2026

Fairmont Kea Lani Maui

4100 Wailea Alanui Dr Kihei HI

CA $1,546

CA $1,919 total

Jul 3 - Jul 4

includes taxes & fees

Book a stay at this luxury resort in Kihei. Enjoy 3 outdoor pools, a full-service spa, and 6 restaurants. Our guests praise the helpful staff and the property ...

9.4/10 Exceptional! (1,000 reviews)

"Very clean. Staff were very personable."

Reviewed on Jun 25, 2026

Hotel Wailea, Relais & Chateaux - Adults Only

555 Kaukahi Street Kihei HI

Fully refundableReserve now, pay when you stay

CA $941

CA $1,202 total

Jul 12 - Jul 13

includes taxes & fees

Book a stay at this luxury resort in Kihei. Enjoy 3 restaurants, breakfast (surcharge), and a free beach shuttle. Our guests praise the helpful staff in our ...

9.4/10 Exceptional! (1,000 reviews)

"If there isn’t a wedding going on watch the sunset from the front lawn area by the old ice cream truck. Better view than from the birdcage. More open and less blockage. Great high end vibe."

Reviewed on Jun 22, 2026

Ho‘olei Villas at Grand Wailea

146 Ho'olei Circle Kihei HI

CA $3,025

CA $3,683 total

Jul 24 - Jul 25

includes taxes & fees

Book a stay at this luxury resort in Kihei. Enjoy free WiFi, a full-service spa, and breakfast (surcharge). Popular attractions Wailea Beach and Grand Wailea ...

9.6/10 Exceptional! (48 reviews)

"Pools are great, the villa is perfect for families, service was good, and the F&B options are outstanding"

Reviewed on Jun 14, 2026

Fairmont Kea Lani Maui Villa Experience

4100 Wailea Alanui Dr-Building A Kihei HI

CA $6,386

CA $7,665 total

Jul 28 - Jul 29

includes taxes & fees

Book a stay at this luxury resort in Kihei. Enjoy free breakfast, free valet parking, and 3 outdoor pools. Popular attractions Wailea Beach and Polo Beach are ...

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

3200 Wailea Alanui Dr Kihei HI

Book a stay at this luxury condo in Kihei. Enjoy free parking, a beach locale, and free grocery shopping service. Popular attractions Wailea Beach and Keawakapu ...

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Wailea Luxury Hilltop Resort Vistas

10 Wailea Ekolu Pl Kihei HI

Book a stay at this luxury apartment in Kihei. Enjoy free WiFi, free parking, and 2 outdoor pools. Popular attractions Wailea Beach and Shops at Wailea are located ...

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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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 Beach Resort - Marriott, Maui

5 out of 5

Posted 1 day ago

Travelocity Verified Review

"Wonderful waterfront resort for families with multiple pool and beach options"

A verified traveller stayed at Wailea Beach Resort - Marriott, Maui

Grand Wailea Maui, A Waldorf Astoria Resort

5 out of 5

Posted 3 days ago

Travelocity Verified Review

"Love the Grand Wailea but things are starting to show wear and tear. They need updating on the cobblestone pathways around the pools. There are broken ones that you can trip on and they become so slippery I saw several people fall while we’re there. They also get so hot during the day people are always complaining and rushing to get off them. There has to be some sort of non-slip/anti heat coating they can put on them or they should find a new material to use. It’s dangerous. Bathrooms in the rooms could also use a deep clean but everything else about the property is absolutely beautiful!"

A verified traveller stayed at Grand Wailea Maui, A Waldorf Astoria Resort