Wailea Holiday Deals

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Top Wailea holiday deals

Price found within the past 48 hours. Click for updated prices.
Kaanapali Maui at the Eldorado by OUTRIGGER

Kaanapali Maui at the Eldorado by OUTRIGGER

3 out of 5
Save 100% on your flight
Price was AU$3,769, price is now AU$1,769 per person
AU$1,769
per person
6 Feb - 13 Feb
found 15 hours ago
Return direct flight included
Sydney (SYD) to Kahului (OGG)
When you stay at Kaanapali Maui at the Eldorado by OUTRIGGER in Kaanapali, you'll be next to a golf course, within a 15-minute walk of Kaanapali Beach and Black Rock.
The Gardens at West Maui

The Gardens at West Maui

3 out of 5
Save 100% on your flight
Price was AU$4,349, price is now AU$2,377 per person
AU$2,377
per person
6 Feb - 13 Feb
found 15 hours ago
Return direct flight included
Sydney (SYD) to Kahului (OGG)
When you stay at The Gardens at West Maui in Napili, you'll be near the beach, within a 15-minute drive of Kaanapali Beach and Napili Bay.
Hyatt Vacation Club at Ka'anapali Beach, Maui

Hyatt Vacation Club at Ka'anapali Beach, Maui

3.5 out of 5
Save 100% on your flight
Price was AU$9,539, price is now AU$5,666 per person
AU$5,666
per person
6 Feb - 13 Feb
found 15 hours ago
Return direct flight included
Sydney (SYD) to Kahului (OGG)
When you stay at Hyatt Vacation Club at Ka'anapali Beach, Maui in Kaanapali, you'll be on the beach, just steps from Kaanapali Beach and 13 minutes by foot from Whalers Village.
The Whaler Resort Kaanapali Beach

The Whaler Resort Kaanapali Beach

4 out of 5
Save 100% on your flight
Price was AU$5,798, price is now AU$3,486 per person
AU$3,486
per person
6 Feb - 13 Feb
found 15 hours ago
Return direct flight included
Sydney (SYD) to Kahului (OGG)
A stay at this condo places you in the heart of Kaanapali, within a 10-minute walk of Kaanapali Beach and Whalers Village.
OUTRIGGER Kaanapali Beach Resort

OUTRIGGER Kaanapali Beach Resort

3.5 out of 5
Save 100% on your flight
Price was AU$4,930, price is now AU$2,971 per person
AU$2,971
per person
6 Feb - 13 Feb
found 15 hours ago
Return direct flight included
Sydney (SYD) to Kahului (OGG)
With a stay at OUTRIGGER Kaanapali Beach Resort in Kaanapali, you'll be on the beach, within a 10-minute walk of Kaanapali Beach and Black Rock.

Top hotels for your Wailea holiday

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 AU$1,405 per night from 8 Jan to 9 Jan
AU$1,405
per night
8 Jan - 9 Jan
With a stay at Four Seasons Resort Maui at Wailea in Kihei (Wailea), you'll be within a 15-minute walk of Wailea Beach and Polo Beach.
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 2 Dec 2025

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
The price is AU$1,604 per night from 8 Jan to 9 Jan
AU$1,604
per night
8 Jan - 9 Jan
With a stay at Fairmont Kea Lani Maui in Kihei (Wailea), you'll be within a 15-minute walk of Wailea Beach and Wailea Blue Golf Course.
Room setup was great, pools and beach were excellent. Everyone had a great time

Reviewed on 22 Dec 2025

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
The price is AU$1,307 per night from 9 Jan to 10 Jan
AU$1,307
per night
9 Jan - 10 Jan
With a stay at Grand Wailea Maui, A Waldorf Astoria Resort in Kihei (Wailea), you'll be within a 10-minute walk of Wailea Beach and Shops at Wailea.
Very nice resort for a family vacation!

Reviewed on 23 Dec 2025

Opens in a new windowGrand Wailea Maui, A Waldorf Astoria Resort
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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.

Popular places to visit

Wailea Beach showing a sandy beach, tropical scenes and swimming

Wailea Beach

Nothing says holiday like spending a lazy day at Wailea Beach, a popular beach in Kihei. Wander the seaside or discover the beautiful sunsets in this romantic area.

Wailea Beach
Maluaka Beach which includes rocky coastline, mountains and a pebble beach

Maluaka Beach

If a restful holiday is part of your travel plans, Maluaka Beach might be the perfect place to visit during your trip to Kihei. Discover the beautiful sunsets in this relaxing area or enjoy its snorkelling spots.

Maluaka Beach
Makena Beach State Park showing a beach

Makena State Park Beach

If a restful holiday is part of your travel plans, Makena State Park Beach might be the perfect place to visit during your trip to Kihei. Stroll along the seaside in this romantic area or seek out the snorkelling spots.

Makena State Park Beach