Wailea Holiday Deals

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Top Wailea holiday deals

Price found within the past 48 hours. Click for updated prices.
Maui Schooner Resort

Maui Schooner Resort

3.5 out of 5
Central Kihei
Price was NZ$4,794, price is now NZ$3,965 per person
NZ$3,965
per person
26 June - 2 July
found 17 hours ago
Return direct flight included
Auckland (AKL) to Kahului (OGG)
Stay at this beach aparthotel in Kihei. Enjoy free Wi-Fi, free parking and a beach locale. Our guests praise the helpful staff in their reviews. Popular attractions Wailea Beach and Waipuilani Park are located nearby.
Hampton Inn & Suites Maui North Shore

Hampton Inn & Suites Maui North Shore

3 out of 5
Price was NZ$5,606, price is now NZ$4,153 per person
NZ$4,153
per person
26 June - 2 July
found 17 hours ago
Return direct flight included
Auckland (AKL) to Kahului (OGG)
Stay at this beach hotel in Kahului. Enjoy free breakfast, free Wi-Fi and a beach locale. Popular attractions Ho'aloha Park and Queen Ka’ahumanu Center are located nearby.
Fairmont Kea Lani Maui

Fairmont Kea Lani Maui

5 out of 5
Wailea
Price was NZ$12,746, price is now NZ$10,017 per person
NZ$10,017
per person
25 June - 2 July
found 17 hours ago
Return direct flight included
Auckland (AKL) to Kahului (OGG)
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 condition in their reviews. Popular attractions Wailea Beach and Wailea Blue Golf Course are located nearby.
Makena Surf - CoralTree Residence Collection

Makena Surf - CoralTree Residence Collection

4 out of 5
Wailea
Price was NZ$8,381, price is now NZ$7,033 per person
NZ$7,033
per person
26 June - 2 July
found 17 hours ago
Return direct flight included
Auckland (AKL) to Kahului (OGG)
Stay at this beach condo in Kihei. Enjoy free Wi-Fi, free parking and a beach locale. Popular attractions Wailea Beach and Chang's Beach are located nearby.
Wailea Beach Villas

Wailea Beach Villas

4.5 out of 5
Wailea
Price was NZ$13,769, price is now NZ$11,884 per person
NZ$11,884
per person
25 June - 2 July
found 17 hours ago
Return direct flight included
Auckland (AKL) to Kahului (OGG)
Stay at this luxury aparthotel in Kihei. Enjoy free Wi-Fi, free parking and 2 outdoor pools. Popular attractions Wailea Beach and Shops at Wailea are located nearby.

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 NZ$1,697 per night from 25 May to 26 May
NZ$1,697
25 May - 26 May
includes taxes & fees
Stay at this luxury resort in Kihei. Enjoy free Wi-Fi, 3 outdoor pools and a full-service spa. Our guests praise the helpful staff in their reviews. Popular ...
Like always four season has the best service.

Reviewed on 15 May 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
The price is NZ$2,336 per night from 31 May to 1 June
NZ$2,336
31 May - 1 June
includes taxes & fees
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 condition ...
What a fantastic hotel! I travelled to Maui with my husband and two children aged 5 & 8. Upton arrival the valet helped with our bags, gave the children and us gorgeous necklaces and check-in was quick! I didn’t like that the room we received was such a stretch to walk to so came back and the really ...

Reviewed on 11 May 2026

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 NZ$2,225 per night from 26 May to 27 May
NZ$2,225
26 May - 27 May
includes taxes & fees
Stay at this luxury resort in Kihei. Enjoy free Wi-Fi, 9 outdoor pools and a full-service spa. Our guests praise the pool and the helpful staff in their reviews. ...
We stayed at Grand Wailea in May 2026. Here's what we thought about it: Good: ---The grounds are gorgeous ---The pool was clever and lots of fun ---The staff was helpful Bad: ---Greed, greed, greed I've never been to a place that seemed so intent on extracting my last dollar from me so ardently. ...

Reviewed on 15 May 2026

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

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

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 State Park 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 relaxing area or seek out the snorkelling spots.

Makena State Park Beach

Top Picks