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Featured 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
The price is CA $1,088 per night from Jan 13 to Jan 14
CA $1,088
CA $1,292 total
Jan 13 - Jan 14, 2026
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! (999 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
The price is CA $938 per night from Jan 13 to Jan 14
CA $938
CA $1,202 total
Jan 13 - Jan 14, 2026
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! (1,004 reviews)
Very nice resort for a family vacation!

Reviewed on Dec 23, 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
The price is CA $1,290 per night from Jan 8 to Jan 9
CA $1,290
CA $1,613 total
Jan 8 - Jan 9, 2026
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! (999 reviews)
Good cleaning staff

Reviewed on Dec 26, 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
The price is CA $1,436 per night from Jan 4 to Jan 5
CA $1,436
CA $1,786 total
Jan 4 - Jan 5, 2026
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 ...
9.2/10 Wonderful! (1,001 reviews)
This resort with private villas is spectacular. The rooms are beautifully appointed and perfectly clean with every amenity you need. We stayed in #52 that overlooked a lagoon and it couldn't have been nicer or more peaceful. Even though there are also ocean views, this was my favorite. The staff ...

Reviewed on Dec 26, 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
The price is CA $2,723 per night from Jan 23 to Jan 24
CA $2,723
CA $3,322 total
Jan 23 - Jan 24, 2026
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 Shops at Wailea ...
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
The price is CA $3,955 per night from Jan 8 to Jan 9
CA $3,955
CA $4,746 total
Jan 8 - Jan 9, 2026
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 ...
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
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 ...
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 days ago
Travelocity Verified Review
"Room a bit generic but spacious and just what we needed "
A verified traveller stayed at Residence Inn by Marriott Maui Wailea
Residence Inn by Marriott Maui Wailea

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