Deals on vacations and trips to Wailea

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Wailea flight + hotel vacation packages

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

Kahana Beach Vacation Club

3 out of 5
Save 100% on your flight
per person
May 3 - May 7
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Kahului (OGG)
This condo features an outdoor pool and a hot tub. Guests will appreciate free perks like free self parking and WiFi in public areas. Laundry facilities, concierge services, and barbecue grills are also on offer.
Hono Koa Vacation Club

Hono Koa Vacation Club

3 out of 5
per person
May 28 - Jun 3
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Kahului (OGG)
An outdoor pool, free self parking, and barbecue grills are featured at this condo. WiFi in public areas is free. A garden is also provided.
Aston Maui Kaanapali Villas

Aston Maui Kaanapali Villas

3 out of 5
Save 100% on your flight
per person
May 3 - May 7
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Kahului (OGG)
This aparthotel features a full-service spa, 2 outdoor pools, and 2 hot tubs. There's a restaurant and a bar/lounge for dining and drinks, and also a 24-hour gym on site.
Aston Kaanapali Shores

Aston Kaanapali Shores

3.5 out of 5
Save 100% on your flight
per person
May 1 - May 6
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Kahului (OGG)
This aparthotel's full-service spa, 2 outdoor pools, and 2 outdoor tennis courts are some of the highlights. Enjoy the 2 hot tubs and gym, and unwind with a drink at the bar/lounge.
OUTRIGGER Kaanapali Beach Resort

OUTRIGGER Kaanapali Beach Resort

3.5 out of 5
Save 100% on your flight
per person
Jun 2 - Jun 8
found 1 day ago
Roundtrip flight included
Los Angeles (LAX) to Kahului (OGG)
This resort features a restaurant, an outdoor pool, and a bar/lounge. Enjoy beachfront dining and relax with beach cabanas and sun loungers. Guests will appreciate perks like free WiFi and a free area shuttle.

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 $1,115 per night
$1,115
includes taxes & fees
$946 per night
Apr 1 - Apr 2
A full-service spa, 7 restaurants, and 9 outdoor pools are all featured at this luxury resort. Spend a day at the beach snorkeling, or relax with sun loungers and beach umbrellas. Bring the family and enjoy the lazy river, children's pool, and waterslide.
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 $879 per night
$879
includes taxes & fees
$745 per night
Apr 1 - Apr 2
A full-service spa, 3 restaurants, and 3 outdoor pools are all featured at this luxury resort. Spend a day at the beach surfing, or relax with sun loungers and beach umbrellas. There's fun for all ages with a free kid's club and a children's pool, and free supervised childcare is an added bonus.
Pool
Hot Tub
Fairmont Kea Lani Maui

Fairmont Kea Lani Maui

4.5 out of 5
4100 Wailea Alanui Dr, Kihei, HI
The price is $1,301 per night
$1,301
includes taxes & fees
$1,103 per night
Apr 19 - Apr 20
A full-service spa, 6 restaurants, and 3 outdoor pools are all featured at this luxury resort. Relax with beach cabanas, sun loungers, and beach umbrellas. There's fun for all ages with a children's pool and a waterslide, and families will appreciate the onsite laundry facilities.
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 $887 per night
$887
includes taxes & fees
$752 per night
Mar 30 - Mar 31
A full-service spa, 4 restaurants, and 4 outdoor pools are all featured at this smoke-free resort. There's fun for all ages with a children's pool and a waterslide, and supervised childcare is an added bonus. Enjoy the 2 hot tubs and perks like free WiFi.
Pool
Hot Tub
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 $1,237 per night
$1,237
includes taxes & fees
$1,049 per night
Apr 22 - Apr 23
A full-service spa, 4 restaurants, and 5 outdoor pools are all featured at this luxury resort. Spend a day at the beach kayaking, or relax with sun loungers and beach umbrellas. Relax with a drink at one of the 2 poolside bars and get perks like free WiFi.
Pool
Hot Tub
AC Hotel by Marriott Maui Wailea

AC Hotel by Marriott Maui Wailea

3.5 out of 5
88 WAILEA IKE PLACE, Kihei, HI
Free Cancellation
Reserve now, pay when you stay
The price is $651 per night
$651
includes taxes & fees
$552 per night
Apr 18 - Apr 19
This smoke-free hotel includes 2 restaurants, an outdoor pool, and a gym. Relax with a drink at the bar/lounge and enjoy perks like free WiFi. Self parking, a grocery/convenience store, and dry cleaning are also offered.
Pool
Free WiFi
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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 tropical scenes, swimming and a sandy beach

Wailea Beach

4.5/5(1,614 reviews)

This stretch of powdery sand is part of an upscale resort community and is an ideal place to sunbathe, snorkel, and dive with Hawaiian green turtles and manta rays.

Wailea Beach
Makena Beach State Park showing a beach

Makena State Park Beach

4.5/5(438 reviews)

Three distinct, undeveloped beaches and a dormant volcano crater form this scenic southern region of Maui.

Makena State Park Beach
Maluaka Beach featuring rocky coastline, mountains and landscape views

Maluaka Beach

4.5/5(101 reviews)

This is part of Maui’s so-called “Turtle Town,” a prime spot for sighting the inquisitive Hawaiian green turtles that are very common here.

Maluaka Beach

Frequently asked questions

How much are vacation packages to Wailea?
Vacation packages, which include flights and hotels in Wailea, start from just $795. 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 95 mi 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), 14 mi north of downtown Wailea. Others prefer Molokai Airport (MKK) (55 mi away from central Wailea) or Lanai Airport (LNY) (35 mi 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 featuring landscape views, tropical scenes and a beach
Molokini featuring coral and marine life
Wailea Beach featuring tropical scenes and a park as well as a couple
Wailea Beach which includes a sandy beach, a pebble beach and a coastal town
Maluaka Beach featuring general coastal views and landscape views