Wailea Vacation Packages 2026 from $1,513

Wailea flight + hotel vacation packages

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

Maui Banyan Vacation Club

South Kihei

$1,513

per person

Jul 13 - Jul 20

found 11 hours ago

Roundtrip flight included

Mesa (AZA) 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, concierge services, and barbecue grills are also on offer.

Hotel Wailea, Relais & Chateaux - Adults Only

Wailea

Save 100% on your flight

$2,160

per person

Jul 30 - Aug 4

found 1 day ago

Roundtrip non-stop flight included

Dallas (DFW) to Kahului (OGG)

This luxury resort includes 3 restaurants, an outdoor pool, and a gym. Traveling on business? Take advantage of the business center, laundry service, and valet parking. Unwind with a drink at the poolside bar and enjoy perks like a free beach shuttle.

Maui Beach Vacation Club

North Kihei

Save 100% on your flight

$1,956

per person

Jul 13 - Jul 20

found 11 hours ago

Roundtrip flight included

Mesa (AZA) to Kahului (OGG)

This aparthotel features a restaurant, an outdoor pool, and a bar/lounge. Enjoy the hot tub and perks like free self parking and free WiFi. A garden and barbecue grills are also provided.

Hampton Inn & Suites Maui North Shore

Save 100% on your flight

$1,701

per person

Jul 13 - Jul 20

found 11 hours ago

Roundtrip flight included

Mesa (AZA) to Kahului (OGG)

This hotel features an outdoor pool, a 24-hour gym, and a restaurant. Unwind with a drink at the bar/lounge and enjoy perks like free buffet breakfast and free WiFi. Self parking, a business center, and a coffee shop are also offered.

Palms at Wailea Maui

Wailea

$1,869

per person

Jun 25 - Jun 30

found 1 day ago

Roundtrip flight included

Dallas (DFW) 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 terrace, a garden, and luggage storage are also on offer.

Top Wailea hotels deals

Grand Wailea Maui, A Waldorf Astoria Resort

3850 Wailea Alanui Drive Kihei HI

$1,030 nightly

$1,222 total

May 29 - May 30

Total with taxes and fees

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

Fairmont Kea Lani Maui

4100 Wailea Alanui Dr Kihei HI

$1,159 nightly

$1,376 total

Jun 1 - Jun 2

Total with taxes and fees

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

Four Seasons Resort Maui at Wailea

3900 Wailea Alanui Drive Kihei HI

$845 nightly

$1,003 total

May 25 - May 26

Total with taxes and fees

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

Wailea Beach Resort - Marriott, Maui

3700 Wailea Alanui Dr Kihei HI

$802 nightly

$952 total

Jun 12 - Jun 13

Total with taxes and fees

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

3550 Wailea Alanui Dr Kihei HI

$890 nightly

$1,056 total

Jun 18 - Jun 19

Total with taxes and fees

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

Hotel Wailea, Relais & Chateaux - Adults Only

555 Kaukahi Street Kihei HI

Free Cancellation

Reserve now, pay when you stay

$849 nightly

$1,008 total

Jun 15 - Jun 16

Total with taxes and fees

Pool

Spa

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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

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

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.

Shops at Wailea

You can find the perfect gifts to bring home at Shops at Wailea during your stay in Kihei. Wander the beautiful beaches or discover the beautiful sunsets in this romantic area.

Frequently asked questions

How much are vacation packages to Wailea?

Vacation packages, which include flights and hotels in Wailea, start from just $1,513. 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.