Wailea Vacation Packages

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Top Holiday Package Deals in Wailea

Price found within the past 48 hours. Click for updated prices.
Maui Banyan Vacation Club

Maui Banyan Vacation Club

South Kihei
CA $1,744
per person
Oct 18 - Oct 24
found 1 day ago
Roundtrip flight included
Edmonton (YEG) to Kahului (OGG)
8/10 Very good! (385 reviews)
Check in was smooth, Rooms were a lot smaller then when looking to book. Air conditioning did not see to work right. Room fan also did not work right, bed was not as comfortable

Reviewed on Aug 22, 2026

Hotel Wailea, Relais & Chateaux - Adults Only

Hotel Wailea, Relais & Chateaux - Adults Only

Wailea
CA $4,426
per person
Nov 9 - Nov 15
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to Kahului (OGG)
9.4/10 Exceptional! (1,004 reviews)
Maui Beach Vacation Club

Maui Beach Vacation Club

North Kihei
CA $2,617
per person
Nov 8 - Nov 14
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Kahului (OGG)
8.4/10 Very good! (933 reviews)
Lahaina Shores Beach Resort By Castle

Lahaina Shores Beach Resort By Castle

CA $1,759
per person
Nov 9 - Nov 14
found 2 hours ago
Roundtrip flight included
Edmonton (YEG) to Kahului (OGG)
No reviews
Royal Lahaina Bungalows & Spa

Royal Lahaina Bungalows & Spa

CA $2,170
per person
Nov 17 - Nov 24
found 1 day ago
Roundtrip flight included
Toronto (YTO) to Kahului (OGG)
8.2/10 Very good! (24 reviews)

Things to do in and around Wailea

Wailea offers a perfect escape for beach lovers and outdoor enthusiasts alike. Visitors can enjoy a variety of activities, including world-class golf at nearby courses, shopping at local malls, and exciting resort activities. Don't miss the opportunity for a memorable day trip, kayak tours, or the lively Te Au Moana Luau, showcasing Hawaiian culture. Whether you're seeking relaxation or adventure, Wailea has something for everyone.

Shopping

The Shops at Wailea offers a vibrant shopping experience with a mix of entertainment and family-friendly vibes. For a local touch, visit Kihei Kalama Village, just 4.8km away, or explore the Hali'imaile Farmer's Market, located 22.5km from Wailea, for unique souvenirs and treats.

Recreation

At Wailea Gold Golf Course, enjoy a challenging round of golf amidst breathtaking landscapes, perfect for outdoor enthusiasts. For family fun, visit Maui Fish Pipe, an exciting aquatic centre offering thrilling water activities. Lastly, indulge in rejuvenating treatments at Makena Kai Day Spa, where relaxation and wellness await.

Adventure

The Makamakaole Trail, located 6.4km from Wailea, offers breathtaking scenery and an exhilarating hiking experience. For a leisurely stroll with stunning coastal views, explore the Kealia Coastal Boardwalk, situated 12.9km away. Science City, an arcade adventure zone 19.3km from Wailea, is perfect for family fun and excitement.

Nightlife

Wailea’s nightlife offers a blend of elegance and relaxation. Enjoy a cocktail at the upscale Monkeypod Kitchen or unwind with live music at the charming Mulligan's on the Blue. For a more laid-back vibe, visit The Shops at Wailea for boutique bars and casual dining options.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Find the best attractions in and around Wailea

Wailea, located on the beautiful island of Maui, is perfect for beach and outdoor enthusiasts seeking stunning scenery. Visitors can explore popular attractions like Wailea Beach, Ulua Beach, and the Wailea Gold golf course. The area also features a welcoming resort community, making it an ideal destination for families looking to enjoy the sun and surf. Whether you're lounging on the beach or discovering the Hawaiian Islands, Wailea promises a memorable vacation experience.

  • Wailea Beach: Wailea Beach is a stunning, picturesque beach that embodies the quintessential Hawaiian experience. With soft golden sands and crystal-clear waters, it offers a perfect spot for sunbathing, swimming, and enjoying breathtaking sunsets. The relaxed beach vibes create an inviting atmosphere for visitors to unwind and soak in the natural beauty of the area.
  • Makena State Park Beach: Renowned for its romantic vibes, Makena State Park Beach is a beautiful nudist beach that provides a sense of freedom and tranquility. Surrounded by lush landscapes and pristine waters, this beach is an ideal getaway for couples seeking intimacy and connection with nature.
  • Kamaole Beach Park 3: Located 3.2km away from Wailea, Kamaole Beach Park 3 is a vibrant urban park perfect for families. With picnic areas, grassy spaces, and easy beach access, it offers a fun, outdoor atmosphere for children and adults alike to enjoy various activities and beach games.

Best time to go to Wailea

The best time to visit Wailea can depend on the weather and when visitor numbers rise and fall. The hottest average temperature around Wailea falls in August and September. September has average visitor numbers and mostly sunny weather. The coolest average temperature around Wailea falls in February, visitor numbers are average and weather is mostly sunny with no rain.

calendarCalendar MonthtemperatureTemperaturerainPrecipitationmostlyCloudinessoccupationOccupancypricePricing
January72.7°F (22.6°C)No RainMostly SunnySlightly HighAverage
February72.3°F (22.4°C)No RainMostly SunnyAverageSlightly High
March72.7°F (22.6°C)No RainMostly SunnySlightly HighAverage
April74.1°F (23.4°C)No RainMostly SunnySlightly HighAverage
May75.6°F (24.2°C)No RainMostly SunnyAverageAverage
June76.8°F (24.9°C)No RainMostly SunnyAverageAverage
July77.9°F (25.5°C)No RainMostly SunnyAverageSlightly High
August78.4°F (25.8°C)No RainMostly SunnyAverageAverage
September78.4°F (25.8°C)No RainMostly SunnyAverageSlightly Low
October77.7°F (25.4°C)No RainMostly SunnySlightly LowSlightly Low
November75.7°F (24.3°C)No RainMostly SunnySlightly LowSlightly Low
December73.8°F (23.2°C)Light RainMostly SunnySlightly LowSlightly High

Tips to save on your trip to Wailea

  • Combine your flights, hotels and car rentals on Expedia—bundling can result in significant savings.
  • Consider traveling to Wailea during the low season (September to November) for more affordable options.
  • Use the Price per traveler filter on Expedia to find a package deal that suits your budget.
  • Check the VIP Access properties filter to discover outstanding hotels with added member perks at select properties.

Where to stay in Wailea

Find the best Wailea areas and neighborhoods for the activities you enjoy most. Learn more about Wailea
A sunset over a beach with palm trees and a few people walking.

South Kihei

4 out of top 10 points of interest in this area

While visiting South Kihei, you might make a stop by sights like Kamaole Beach Park 2 and Kamaole Beach Park 3.

A yellow and red canoe with six paddlers on a calm sea.

Central Kihei

1 out of top 10 points of interest in this area

If you're spending some time in Central Kihei, Kihei Regional Park and Makamakaole Trail are top sights worth seeing.

A sunset over a calm sea with a distant mountain range and a rocky shoreline.

North Kihei

If you're spending some time in North Kihei, Sugar Beach and Hawaiian Islands Humpback Whale National Marine Sanctuary Headquarters are top sights worth seeing.

A coastal landscape with a rocky shoreline, palm trees, and a clear sky.

Makena

A noteworthy feature of Makena is its stunning beaches. While you're in town, be sure to stop and check out Makena State Park Beach and Maluaka Beach.

Default Image

Halama Street

If you're spending some time in Halama Street, Kihei Town Center Shopping Center and Coast Guard Beach are top sights worth seeing.

Wailea Hotel Deals

Grand Wailea Maui, A Waldorf Astoria Resort

Grand Wailea Maui, A Waldorf Astoria Resort

3850 Wailea Alanui Drive Kihei HI
CA $1,012
CA $1,291 total
Sep 8 - Sep 9
includes taxes & fees
8.6/10 Excellent! (1,006 reviews)
"It’s a great resort . The only disappointment was a couple things were closed like the game room , Tarzan swing . And the water elevator is no longer in operation. But the staff was great . The pools are great . The aesthetic is great . Food is wildly expensive at any of the restaurants related to ..."

Reviewed on Aug 25, 2026

Grand Wailea Maui, A Waldorf Astoria Resort
Fairmont Kea Lani Maui

Fairmont Kea Lani Maui

4100 Wailea Alanui Dr Kihei HI
CA $1,534
CA $1,918 total
Aug 27 - Aug 28
includes taxes & fees
Fairmont Kea Lani Maui
Wailea Beach Resort - Marriott, Maui

Wailea Beach Resort - Marriott, Maui

3700 Wailea Alanui Dr Kihei HI
CA $798
CA $1,045 total
Sep 8 - Sep 9
includes taxes & fees
Wailea Beach Resort - Marriott, Maui
See all 1,193 properties in Wailea
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.

Frequently asked questions

How much does a Wailea vacation package cost?
The most affordable Wailea package is CA $1,744, so your dream vacation can become a reality — without it costing a fortune. Combine flights, hotels, car rentals and more to custom build a package that matches your traveling style.
How do I get a cheap travel package to Wailea?
Crafting your own Wailea vacation package with Expedia is the easiest way to save. We have access to more than 550 airlines and 1,000,000 properties across the globe. With such an extensive range to select from, you'll have no trouble pulling together your ideal escape.
Where should I stay in Wailea?
A vacation in Wailea isn't complete without checking out Wailea Beach, Kamaole Beach Park and Makena State Park Beach. Spend your nights close to these top sights and make sightseeing easy.
What are the top hotels in Wailea?
Lock in a room at Ocean And Golf Course View 3 Bed. It's one of this area's most sought-after hotels. Another top-rated option in Wailea is Wailea Ekahi 36b One Of The Best Locations In Wailea.
How far in advance should I book my Wailea vacation?
While prices change from time to time, we generally recommend booking your spot as soon as possible. Most international fares can be compared on Expedia up to a year in advance. If you're booking last minute, you might still be in luck. Discount prices to Wailea occasionally appear in the weeks prior to departure.
What does an Expedia Wailea travel package include?
Car rentals, hotels and flights — we connect you to the very best deals. All you'll have to do is decide on your preferred combination. Once you've made your booking, you can add on the fun stuff like experiences and tours. Our travel packages make it simple to craft an awesome Wailea getaway.
What should I know before booking a Wailea travel package?
You'll pick up amazing savings when you bundle your flights, hotels and rental cars into a package. Plus, booking everything in one spot makes trip planning much easier. So why waste time or money? Whether you're organizing an upscale romantic escape or a budget family adventure, browse our vacation packages today.
If I'm not able to travel, can I cancel my Wailea vacation package?
Yes, you can. We realize life doesn't always go to plan, so we're here to help if you need to make changes to your Wailea vacation package. It may be possible to cancel or change your itinerary for free if you've booked within 24 hours. Your hotel, airline or car rental company may charge you a fee if you booked more than 24 hours ago. Visit our Customer Service Portal for further information. Also, check your itinerary for the finer details on change fees.

Stay near popular Wailea attractions

A tropical beach with palm trees, a sandy shore, and the ocean.

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.
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A beach with clear turquoise water, a person in the water, and a mountain in the background.

Maluaka Beach

9.4/10 (731 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.
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A sandy beach with a large tree and a clear blue sky.

Makena State Park Beach

9.4/10 (1,787 reviews)
Three distinct, undeveloped beaches and a dormant volcano crater form this scenic southern region of Maui.
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A dessert on a white plate with a strawberry and mint garnish.
Photo by Quintin Doroquez

Shops at Wailea

9.2/10 (381 reviews)
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.
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A beach with waves, a clear sky, and distant land.

Makena Beaches

9.0/10 (18 reviews)
Why not spend a lazy afternoon at Makena Beaches during your trip to Kihei? Stroll along the beautiful beaches or discover the beautiful sunsets in this relaxing area.
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A beach with lush greenery, palm trees, and a clear blue ocean.
Photo by Torrey Kwok

Polo Beach

9.2/10 (186 reviews)
If a restful vacation is part of your travel plans, Polo Beach might be the perfect place to seek out during your trip to Kihei. Wander the seaside or discover the beautiful sunsets in this relaxing area.
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A calm sea with a rainbow, palm trees, and a cloudy sky.
Photo by Kathie Mercier

Ulua Beach

8.8/10 (53 reviews)
Why not spend a carefree afternoon at Ulua Beach during your travels in Kihei? Discover the beautiful sunsets in this romantic area, or enjoy its snorkeling spots.
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Wailea Gold Golf Course

Play a round of golf at Wailea Gold Golf Course and enjoy other activities in Kihei such as snorkeling. Stroll along the seaside or discover the beautiful sunsets in this romantic area.
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Things to do

Maui: Road to Hana Adventure with Farm to Table Lunch

Maui: Road to Hana Adventure with Farm to Table Lunch

CA $364
per adult
94% of travellers recommend
Maui: Road to Hana Adventure with Farm to Table Lunch
Lahaina Sunset Dinner Cruise

Sunset Dinner Cruise aboard Quicksilver: Prime Rib, Fish, Chicken or Pasta

CA $187
per adult
84% of travellers recommend
Sunset Dinner Cruise aboard Quicksilver: Prime Rib, Fish, Chicken or Pasta
Maui Ocean Center All Day Admission Ticket

Maui Ocean Center All Day Admission Ticket

CA $78
per adult
90% of travellers recommend
Maui Ocean Center All Day Admission Ticket
See all activities in Kihei

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.