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.
Castle Kama'ole Sands

Castle Kama'ole Sands

3 out of 5
per person
Jun 7 - Jun 10
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Kahului (OGG)
This condo features an outdoor pool and a gym. Enjoy the hot tub and perks like free self parking and free WiFi. A garden, a picnic area, and luggage storage are also on offer.
Hono Koa Vacation Club

Hono Koa Vacation Club

3 out of 5
per person
Jul 11 - Jul 14
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.
Papaya Suite

Papaya Suite

3 out of 5
per person
Jul 4 - Jul 6
found 18 hours ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Kahului (OGG)
This bed & breakfast features free self parking and free WiFi in public areas. Enjoy the free continental breakfast each morning.
Endless & Elegant Vistas

Endless & Elegant Vistas

4 out of 5
per person
Jun 26 - Jun 30
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Kahului (OGG)
This condo features an outdoor pool and a hot tub. Free self parking, a terrace, and a garden are also offered.
Elegant Oceanfront Vistas

Elegant Oceanfront Vistas

4.5 out of 5
per person
Jun 26 - Jun 30
found 1 day ago
Roundtrip non-stop flight included
Los Angeles (LAX) to Kahului (OGG)
This condo features an outdoor pool and a hot tub. Free self parking, a terrace, and a garden are also offered.

Top Wailea hotels deals

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 $832 per night
$832
includes taxes & fees
$705 per night
May 2 - May 3
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 $1,249 per night
$1,249
includes taxes & fees
$1,059 per night
May 7 - May 8
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
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 $1,056 per night
$1,056
includes taxes & fees
$896 per night
May 1 - May 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
Wailea Beach Resort - Marriott, Maui

Wailea Beach Resort - Marriott, Maui

4.5 out of 5
3700 Wailea Alanui Dr, Kihei, HI
The price is $858 per night
$858
includes taxes & fees
$727 per night
May 4 - May 5
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
Wailea Ekahi - CoralTree Residence Collection

Wailea Ekahi - CoralTree Residence Collection

3 out of 5
3300 Wailea Alanui, Kihei, HI
Get rates
This condo doesn't skimp on freebies - guests receive free WiFi and free self parking. A picnic area, laundry facilities, and concierge services are also on offer.
Pool
Kitchen
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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
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
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

Frequently asked questions

How much are vacation packages to Wailea?
Vacation packages, which include flights and hotels in Wailea, start from just $887. 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