Book Exclusive Wailea Vacation Packages

Choose one or more items to build your trip:

Wailea flight + hotel packages

Price found within the past 48 hours. Click for updated prices.
Kahana Beach Vacation Club

Kahana Beach Vacation Club

3 out of 5
Price was CA $2,237, price is now CA $914 per person
CA $914
per person
Jan 17 - Jan 22
found 1 day ago
Roundtrip flight included
Vancouver (YVR) to Kahului (OGG)
Stay at this 3-star beach condo in Kahana. Enjoy free WiFi, free parking, and a beach locale. Our guests praise the helpful staff in our reviews. Popular attractions Kaanapali Beach and Napili Bay are located nearby.
Sands of Kahana

Sands of Kahana

3 out of 5
Price was CA $5,796, price is now CA $2,334 per person
CA $2,334
per person
Jan 19 - Jan 25
found 1 day ago
Roundtrip flight included
Vancouver (YVR) to Kahului (OGG)
Book a stay at this beach aparthotel in Kahana. Enjoy free parking, a beach locale, and a fitness center. Our guests praise the helpful staff in our reviews. Popular attractions Kaanapali Beach and Napili Bay are located nearby.
The Gardens at West Maui

The Gardens at West Maui

3 out of 5
Price was CA $2,045, price is now CA $1,022 per person
CA $1,022
per person
Jan 15 - Jan 20
found 1 day ago
Roundtrip flight included
Vancouver (YVR) to Kahului (OGG)
Stay at this condo in Napili. Enjoy free WiFi, free parking, and a garden. Our guests praise the helpful staff in our reviews. Popular attractions Kaanapali Beach and Napili Bay are located nearby.
Kahana Villa

Kahana Villa

3 out of 5
Price was CA $2,685, price is now CA $1,384 per person
CA $1,384
per person
Mar 1 - Mar 8
found 1 day ago
Roundtrip non-stop flight included
Kelowna (YLW) to Kahului (OGG)
Stay at this condo in Kahana. Enjoy free WiFi, free parking, and laundry facilities. Popular attractions Kaanapali Beach and Napili Bay are located nearby.
Maui Banyan Vacation Club

Maui Banyan Vacation Club

3 out of 5
South Kihei
Price was CA $3,322, price is now CA $1,768 per person
CA $1,768
per person
Feb 18 - Feb 25
found 12 hours ago
Roundtrip flight included
Kelowna (YLW) to Kahului (OGG)
Stay at this condo in Kihei. Enjoy free WiFi, free parking, and a garden. Popular attractions Wailea Beach and Kamaole Beach Park 2 are located nearby.

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 $890 per night
CA $890
CA $1,139 total
Dec 12 - Dec 13
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 reviews. Popular attractions Wailea Beach and Shops at Wailea are located nearby.
Pool
Hot tub
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 $1,041 per night
CA $1,041
CA $1,228 total
Dec 19 - Dec 20
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 attractions Wailea Beach and Polo Beach are located nearby.
Pool
Hot tub
Fairmont Kea Lani Maui

Fairmont Kea Lani Maui

5 out of 5
4100 Wailea Alanui Dr Kihei HI
The price is CA $1,082 per night
CA $1,082
CA $1,358 total
Dec 13 - Dec 14
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 condition in our reviews. Popular attractions Wailea Beach and Wailea Blue Golf Course are located nearby.
Pool
Hot tub
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 $764 per night
CA $764
CA $995 total
Dec 17 - Dec 18
includes taxes & fees
Book a stay at this luxury resort in Kihei. Enjoy 4 outdoor pools, a full-service spa, and 4 restaurants. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Wailea Beach and Shops at Wailea are located nearby.
Pool
Hot tub
AC Hotel by Marriott Maui Wailea

AC Hotel by Marriott Maui Wailea

4 out of 5
88 WAILEA IKE PLACE Kihei HI
Free cancellation
Reserve now, pay when you stay
The price is CA $503 per night
CA $503
CA $628 total
Dec 13 - Dec 14
includes taxes & fees
Stay at this hotel in Kihei. Enjoy free WiFi, 2 restaurants, and breakfast (surcharge). Our guests praise the helpful staff and the property condition in our reviews. Popular attractions Wailea Beach and Shops at Wailea are located nearby.
Pool
Pet-friendly
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 $1,143 per night
CA $1,143
CA $1,430 total
Dec 14 - Dec 15
includes taxes & fees
Book a stay at this luxury resort in Kihei. Enjoy free WiFi, 5 outdoor pools, and a full-service spa. Our guests praise the helpful staff in our reviews. Popular attractions Wailea Beach and Ulua Beach Park are located nearby.
Pool
Hot tub
Don't see what you're looking for?
See all available properties in Wailea
View all properties
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 which includes swimming, tropical scenes and a 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
Maluaka Beach featuring mountains, landscape views and rugged coastline

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 Kihei. Discover the beautiful sunsets in this relaxing area, or enjoy its snorkeling spots.

Maluaka Beach
Makena Beaches

Makena Beaches

Why not spend a lazy afternoon at Makena Beaches during your trip to Kihei? Stroll along the beautiful beaches or discover the beautiful sunsets in this relaxing area.

Makena Beaches

Frequently asked questions

How much are vacation packages to Wailea?
Vacation packages, which include flights and hotels in Wailea, start from just CA $914. Make your travel fantasies come to life and secure your vacation with Travelocity today.
How long should my Wailea vacation be?
If you're looking for some guidance, most visitors spend roughly 6 nights vacationing in Wailea. But to discover the true essence of this place, stay a few extra days. You'll be able to tick off more attractions and really soak up the local vibe.
Where can I get the best vacation package deals for Wailea?
No matter your style, Travelocity can help you score an unbeatable Wailea package deal. The only thing you have to do is select a combination from our 400 air carriers and 1,000,000 worldwide properties.
Why should I book my Wailea vacation package via Travelocity?
The three S's — savings, support and a stress-free booking — are just the tip of the iceberg. Enjoy a fulfilling travel experience knowing you have access to our expert team of customer support professionals 24/7. With the Travelocity Price Match Guarantee, you know you're getting the best deal available.
Can I save on my Wailea car rental if I bundle it with hotels and flights?
With a Wailea vacation package, you can bundle your car, hotel and flight bookings and save loads. If you'd love to see the best of this impressive area, why not make a beeline for Diamond Head? This well-known sight is 153 kilometers from Wailea. With your own set of wheels, you'll be there in no time.
Which airport is best for Wailea?
Many people choose to fly into Kahului Airport (OGG), 23 kilometers north of downtown Wailea. Others prefer Molokai Airport (MKK) (88 kilometers away from central Wailea) or Lanai Airport (LNY) (56 kilometers away from central Wailea).
What is there to do in Wailea?
Wailea is brimming with things to see and do, like Wailea Beach and Makena State Park Beach. These two impressive attractions top most tourists' travel schedules.
Where should I stay when visiting Wailea?
The Palms At Wailea Maui is popular with many travelers. Book soon to avoid missing out.

Photos of local treasures

Browse Wailea vacation photos for more inspiration

Maluaka Beach showing landscape views, a beach and tropical scenes
Wailea
Wailea Beach featuring a park and tropical scenes as well as a couple
Wailea Beach which includes tropical scenes, a beach and swimming
Wailea