Book Exclusive Wailea Vacation Packages

Wailea flight + hotel packages

Price found within the past 48 hours. Click for updated prices.
OUTRIGGER Kaanapali Beach Resort

OUTRIGGER Kaanapali Beach Resort

3 out of 5
Save 100% on your flight
per person
Jul. 18 - Jul. 24
Roundtrip flight included
Vancouver (YVR) to Kahului (OGG)
Stay at this beach hotel in Kaanapali. Enjoy free WiFi, a beach locale, and breakfast. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Kaanapali Beach and Whalers Village are located nearby. Discover genuine guest reviews for OUTRIGGER Kaanapali Beach Resort along with the latest prices and availability – book now.
Aston Maui Hill

Aston Maui Hill

3 out of 5
Save 100% on your flight
per person
Jul. 14 - Jul. 21
Roundtrip flight included
Vancouver (YVR) to Kahului (OGG)
Stay at this aparthotel in Kihei. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Wailea Beach and Kamaole Beach Park are located nearby. Discover genuine guest reviews for Aston Maui Hill along with the latest prices and availability – book now.
Aston at Papakea Resort

Aston at Papakea Resort

3 out of 5
Save 100% on your flight
per person
Jul. 14 - Jul. 21
Roundtrip flight included
Vancouver (YVR) to Kahului (OGG)
Stay at this beach aparthotel in Kaanapali. Enjoy free parking, a garden, and a library. Popular attractions Kaanapali Beach and Black Rock are located nearby. Discover genuine guest reviews for Aston at Papakea Resort along with the latest prices and availability – book now.
Aston at the Maui Banyan

Aston at the Maui Banyan

3 out of 5
Save 100% on your flight
per person
Jul. 14 - Jul. 21
Roundtrip flight included
Vancouver (YVR) to Kahului (OGG)
Stay at this beach hotel in Kihei. Enjoy free WiFi, free parking, and dry cleaning or laundry services. Popular attractions Wailea Beach and Kamaole Beach Park are located nearby. Discover genuine guest reviews for Aston at the Maui Banyan along with the latest prices and availability – book now.
Aston Maui Kaanapali Villas

Aston Maui Kaanapali Villas

3 out of 5
Save 100% on your flight
per person
Jul. 14 - Jul. 21
Roundtrip flight included
Vancouver (YVR) to Kahului (OGG)
Stay at this beach aparthotel in Kaanapali. Enjoy free parking, 2 outdoor pools, and a beach locale. Our guests praise the pool and the restaurant in our reviews. Popular attractions Kaanapali Beach and Black Rock are located nearby. Discover genuine guest reviews for Aston Maui Kaanapali Villas along with the latest prices and availability – book now.

Top Wailea hotels deals

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 $1,041 per night
CA $1,041
per night
May 7 - May 8
Stay at this beach resort in Kihei. Enjoy free WiFi, 9 outdoor pools, and 5 restaurants. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Wailea Beach and Kamaole Beach Park are located nearby. Discover genuine guest reviews for Grand Wailea Maui, A Waldorf Astoria Resort, in Wailea neighborhood, along with the latest prices and availability – book now.
Fairmont Kea Lani Maui

Fairmont Kea Lani Maui

4.5 out of 5
4100 Wailea Alanui Dr, Kihei, HI
The price is CA $1,418 per night
CA $1,418
per night
May 6 - May 7
Stay at this beach resort in Kihei. Enjoy 3 outdoor pools, 4 restaurants, and a beach locale. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Wailea Beach and Kamaole Beach Park are located nearby. Discover genuine guest reviews for Fairmont Kea Lani Maui, in Wailea neighborhood, along with the latest prices and availability – book now.
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 $1,371 per night
CA $1,371
per night
May 18 - May 19
Stay at this beach resort in Kihei. Enjoy free WiFi, 3 outdoor pools, and 3 restaurants. Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Wailea Beach and Kamaole Beach Park are located nearby. Discover genuine guest reviews for Four Seasons Resort Maui at Wailea, in Wailea neighborhood, along with the latest prices and availability – book now.
Wailea Beach Resort - Marriott, Maui

Wailea Beach Resort - Marriott, Maui

4.5 out of 5
3700 Wailea Alanui Dr, Kihei, HI
The price is CA $991 per night
CA $991
per night
May 20 - May 21
Stay at this luxury resort in Kihei. Enjoy 4 outdoor pools, 4 restaurants, and 2 poolside bars. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Wailea Beach and Kamaole Beach Park are located nearby. Discover genuine guest reviews for Wailea Beach Resort - Marriott, Maui, in Wailea neighborhood, along with the latest prices and availability – book now.
Hot tub
Pool
Andaz Maui at Wailea Resort - a concept by Hyatt

Andaz Maui at Wailea Resort - a concept by Hyatt

4.5 out of 5
3550 Wailea Alanui Dr, Kihei, HI
The price is CA $1,233 per night
CA $1,233
per night
May 14 - May 15
Stay at this beach resort in Kihei. Enjoy free WiFi, 5 outdoor pools, and 4 restaurants. Our guests praise the helpful staff in our reviews. Popular attractions Wailea Beach and Kamaole Beach Park are located nearby. Discover genuine guest reviews for Andaz Maui at Wailea Resort - a concept by Hyatt, in Wailea neighborhood, along with the latest prices and availability – book now.
Hot tub
Pet-friendly
Hotel Wailea, Relais & Chateaux - Adults Only

Hotel Wailea, Relais & Chateaux - Adults Only

5 out of 5
555 Kaukahi Street, Kihei, HI
The price is CA $1,239 per night
CA $1,239
per night
May 4 - May 5
Stay at this 5-star luxury resort in Kihei. Enjoy 3 restaurants, a full-service spa, and breakfast. Popular attractions Wailea Beach and Kamaole Beach Park are located nearby. Discover genuine guest reviews for Hotel Wailea, Relais & Chateaux - Adults Only, in Wailea neighborhood, along with the latest prices and availability – book now.
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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

Image for Wailea Beach

Wailea Beach

4.5/5(295 reviews)

Nothing says vacation 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
Image for Makena State Park Beach

Makena State Park Beach

4.5/5(105 reviews)

Explore the great outdoors at Makena State Park Beach, a lovely green space in Makena. Wander the beautiful beaches and seaside in this romantic area.

Makena State Park Beach
Image for Maluaka Beach

Maluaka Beach

4/5(25 reviews)

If a restful vacation is part of your travel plans, Maluaka Beach might be the perfect place to seek out during your trip to Makena. Discover the beautiful sunsets in this relaxing area, or enjoy its snorkeling spots.

Maluaka Beach