Wailea Vacation Packages 2025 from $867

Wailea flight + hotel vacation packages

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

AEI at Kaanapali Shores

per person

Aug 14 - Aug 18

found 1 day ago

Roundtrip non-stop flight included

Dallas (DAL) to Kahului (OGG)

A full-service spa, an outdoor pool, and a restaurant are all featured at this smoke-free aparthotel. Enjoy the gym and perks like free WiFi. Enjoy the outdoor tennis court and unwind at the bar/lounge and poolside bar.

Hono Koa Vacation Club

Save 100% on your flight

per person

Aug 22 - Aug 28

found 1 day ago

Roundtrip non-stop flight included

Dallas (DFW) 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.

AEI at The Mahana Kaanapali Resort

Save 100% on your flight

per person

Aug 14 - Aug 18

found 1 day ago

Roundtrip non-stop flight included

Dallas (DAL) to Kahului (OGG)

This aparthotel features an outdoor pool and a hot tub. Guests will appreciate free perks like free self parking and WiFi in public areas. A garden, a library, and a picnic area are also on offer.

The Gardens at West Maui

per person

Jul 22 - Jul 27

found 1 day ago

Roundtrip flight included

Dallas (DAL) 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. A garden, luggage storage, and barbecue grills are also on offer.

Royal Lahaina Resort & Bungalows

per person

Jul 22 - Jul 27

found 1 day ago

Roundtrip flight included

Dallas (DAL) to Kahului (OGG)

A full-service spa, 2 outdoor pools, and 11 outdoor tennis courts are featured at this eco-certified hotel. Enjoy beachfront dining and relax with beach cabanas and sun loungers. Unwind with a drink at one of the 2 bars/lounges and enjoy freebies like WiFi in public areas and a shopping center shuttle.

Top Wailea hotels deals

Grand Wailea Maui, A Waldorf Astoria Resort

3850 Wailea Alanui Drive, Kihei, HI

Get rates

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

3900 Wailea Alanui Drive, Kihei, HI

Get rates

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

4100 Wailea Alanui Dr, Kihei, HI

Get rates

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

Get rates

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

AC Hotel by Marriott Maui Wailea

88 WAILEA IKE PLACE, Kihei, HI

Free Cancellation

Reserve now, pay when you stay

Get rates

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

Andaz Maui at Wailea Resort - a concept by Hyatt

3550 Wailea Alanui Dr, Kihei, HI

Get rates

A full-service spa, 4 restaurants, and 5 outdoor pools are all featured at this luxury resort. Spend a day at the beach surfing, or relax with sun loungers and beach umbrellas. Unwind with a drink at one of the 2 poolside bars and enjoy freebies like WiFi in public areas and an area shuttle.

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

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.

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.

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.

Frequently asked questions

How much are vacation packages to Wailea?

Vacation packages, which include flights and hotels in Wailea, start from just $867. 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.