Wailea Vacations from CA $2,265

Wailea flight + hotel packages

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

OUTRIGGER Kaanapali Beach Resort

Save 100% on your flight

per person

Jul. 21 - Jul. 28

Roundtrip non-stop flight included

Montreal (YUL) 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

Save 100% on your flight

per person

Jul. 20 - Jul. 27

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 Kaanapali Shores

Save 100% on your flight

per person

Jul. 20 - Jul. 27

Roundtrip flight included

Vancouver (YVR) to Kahului (OGG)

Stay at this beach aparthotel in Kaanapali. Enjoy 2 outdoor pools, a beach locale, and a full-service spa. 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 Kaanapali Shores along with the latest prices and availability – book now.

Aston Mahana at Kaanapali

Save 100% on your flight

per person

Jul. 20 - Jul. 27

Roundtrip flight included

Vancouver (YVR) to Kahului (OGG)

Stay at this beach aparthotel in Kaanapali. Enjoy free WiFi, free parking, and a beach locale. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Kaanapali Beach and Black Rock are located nearby. Discover genuine guest reviews for Aston Mahana at Kaanapali along with the latest prices and availability – book now.

Aston at Papakea Resort

Save 100% on your flight

per person

Jul. 20 - Jul. 27

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.

Top Wailea hotels deals

Grand Wailea Maui, A Waldorf Astoria Resort

3850 Wailea Alanui Drive, Kihei, HI

CA $1,037

per night

May 8 - May 9

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

4100 Wailea Alanui Dr, Kihei, HI

CA $1,413

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.

Hot tub

Pet-friendly

Four Seasons Resort Maui at Wailea

3900 Wailea Alanui Drive, Kihei, HI

CA $1,366

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.

Hot tub

Pool

Wailea Beach Resort - Marriott, Maui

3700 Wailea Alanui Dr, Kihei, HI

CA $991

per night

May 23 - May 24

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

3550 Wailea Alanui Dr, Kihei, HI

CA $1,228

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

555 Kaukahi Street, Kihei, HI

CA $1,234

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.

Pool

Spa

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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

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.

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.

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.