Wailea Vacation Packages 2025 from $564

Wailea flight + hotel vacation packages

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

Kahana Villa

Save 100% on your flight

per person

May 14 - May 18

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 and barbecue grills are also provided.

Hono Koa Vacation Club

Save 100% on your flight

per person

May 1 - May 6

found 1 day ago

Roundtrip flight included

Detroit (DTW) 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 at the Maui Banyan

Save 100% on your flight

per person

May 6 - May 13

found 1 day ago

Roundtrip flight included

Los Angeles (LAX) to Kahului (OGG)

This hotel features an outdoor pool and an outdoor tennis court. Enjoy the hot tub and perks like free self parking and free WiFi. A picnic area, luggage storage, and barbecue grills are also on offer.

Kahana Beach Vacation Club

Save 100% on your flight

per person

May 1 - May 6

found 1 day ago

Roundtrip flight included

Detroit (DTW) 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.

Guava Suite

per person

Apr 2 - Apr 5

found 1 day ago

Roundtrip flight included

Los Angeles (LAX) to Kahului (OGG)

This bed & breakfast features free WiFi in public areas, laundry facilities, and free self parking. Enjoy the free continental breakfast each morning. A garden, luggage storage, and barbecue grills are also on offer.

Top Wailea hotels deals

Four Seasons Resort Maui at Wailea

3900 Wailea Alanui Drive, Kihei, HI

$1,056

includes taxes & fees

$895 per night

Mar 7 - Mar 8

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

Grand Wailea Maui, A Waldorf Astoria Resort

3850 Wailea Alanui Drive, Kihei, HI

$1,115

includes taxes & fees

$946 per night

Feb 27 - Feb 28

A full-service spa, 5 restaurants, and 9 outdoor pools are all featured at this luxury resort. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. 2 poolside bars and 2 bars/lounges are featured at this resort, along with a gym.

Pool

Hot Tub

Andaz Maui at Wailea Resort - a concept by Hyatt

3550 Wailea Alanui Dr, Kihei, HI

$1,120

includes taxes & fees

$950 per night

Feb 27 - Feb 28

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

Fairmont Kea Lani Maui

4100 Wailea Alanui Dr, Kihei, HI

$960

includes taxes & fees

$814 per night

Mar 13 - Mar 14

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

3700 Wailea Alanui Dr, Kihei, HI

$764

includes taxes & fees

$647 per night

Feb 28 - Mar 1

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

Wailea Ekahi - CoralTree Residence Collection

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

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.

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.

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.

Frequently asked questions

How much are vacation packages to Wailea?

Vacation packages, which include flights and hotels in Wailea, start from just $564. 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.