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.
Maui Banyan Vacation Club

Maui Banyan Vacation Club

3 out of 5
South Kihei
Price was $1,325, price is now $856 per person
$856
per person
Jan 7 - Jan 11
found 1 day ago
Roundtrip flight included
Dallas (DFW) 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.
Maui Beach Vacation Club

Maui Beach Vacation Club

2.5 out of 5
North Kihei
Save 100% on your flight
Price was $1,906, price is now $1,073 per person
$1,073
per person
Jan 7 - Jan 11
found 1 day ago
Roundtrip flight included
Dallas (DFW) 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.
Hotel Wailea Maui

Hotel Wailea Maui

5 out of 5
Wailea
Save 100% on your flight
Price was $3,099, price is now $1,872 per person
$1,872
per person
Jan 7 - Jan 11
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Kahului (OGG)
This luxury resort includes 3 restaurants, an outdoor pool, and a hot tub. Traveling on business? Take advantage of the free WiFi in public areas, laundry service, and valet parking. Unwind with a drink at one of the 3 bars/lounges and enjoy perks like a free beach shuttle.
Lahaina Shores Beach Resort By Castle

Lahaina Shores Beach Resort By Castle

3.5 out of 5
Price was $1,574, price is now $1,089 per person
$1,089
per person
Jan 7 - Jan 11
found 1 day ago
Roundtrip flight included
Dallas (DFW) to Kahului (OGG)
An outdoor pool, self parking, and laundry facilities are featured at this apartment. The front desk is staffed around-the-clock and barbecue grills are on offer.
Grand Champions

Grand Champions

2.5 out of 5
Wailea
Save 100% on your flight
Price was $2,943, price is now $2,066 per person
$2,066
per person
Jan 7 - Jan 11
just found
Roundtrip flight included
Dallas (DFW) to Kahului (OGG)
This resort features an outdoor pool and a hot tub. Free self parking, a terrace, and a garden are also offered.

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
$813 nightly
The price is $965 total per night
$965 total
Oct 29 - Oct 30
Total with taxes and fees
A full-service spa, 7 restaurants, and 9 outdoor pools are all featured at this luxury resort. There's fun for all ages with a lazy river and a children's pool, and in-room childcare is an added bonus. Enjoy the 3 hot tubs and perks like free WiFi.
Pool
Hot Tub
Fairmont Kea Lani Maui

Fairmont Kea Lani Maui

5 out of 5
4100 Wailea Alanui Dr Kihei HI
$1,128 nightly
The price is $1,339 total per night
$1,339 total
Oct 25 - Oct 26
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
Wailea Beach Resort - Marriott, Maui

Wailea Beach Resort - Marriott, Maui

5 out of 5
3700 Wailea Alanui Dr Kihei HI
$629 nightly
The price is $747 total per night
$747 total
Nov 15 - Nov 16
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
Four Seasons Resort Maui at Wailea

Four Seasons Resort Maui at Wailea

5 out of 5
3900 Wailea Alanui Drive Kihei HI
$1,080 nightly
The price is $1,282 total per night
$1,282 total
Oct 21 - Oct 22
Total with taxes and fees
A full-service spa, 3 restaurants, and 3 outdoor pools are all featured at this luxury resort. There's fun for all ages with a free kid's club and a children's pool, and families will appreciate the onsite laundry facilities. Unwind with a drink at one of the 2 poolside bars and enjoy perks like a free shopping center shuttle.
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
$879 nightly
The price is $1,043 total per night
$1,043 total
Nov 15 - Nov 16
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
AC Hotel by Marriott Maui Wailea

AC Hotel by Marriott Maui Wailea

4 out of 5
88 WAILEA IKE PLACE Kihei HI
Free Cancellation
Reserve now, pay when you stay
$474 nightly
The price is $563 total per night
$563 total
Oct 21 - Oct 22
Total with taxes and fees
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
Pet friendly
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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.

Stay near popular Wailea attractions

A beach with palm trees, a row of beach umbrellas, and a green boat on the grass.

Wailea Beach

9.4/10 (4,138 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.
See properties

Frequently asked questions

How much are vacation packages to Wailea?
Vacation packages, which include flights and hotels in Wailea, start from just $856. 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

A beach with clear turquoise water, people sunbathing and swimming, and a mountain in the background.
A vibrant coral reef with diverse marine life, including a yellow and black fish and a red sea anemone.
A pathway flanked by lush greenery and palm trees, leading to a building with a red roof.
A beach with rocky foreground, palm trees, and a golf course in the background.
A golf course with sand bunkers, green grass, two trees, a mountain, and a body of water.

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