Wailea Holidays from £1,769

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Your Wailea Holiday

Lock in a holiday package to Wailea and get set to experience its surfing, coastal beaches and views. However you'd like to spend your break in this picturesque neighbourhood, you'll find plenty of opportunities to mix relaxation and fun. Wondering what to see and do during your trip to Wailea? Nearby attractions such as Wailea Beach, Kamaole Beach Park and Keawakapu Beach North are good places to start. No matter your travel plans or the size of your budget, booking your dream Wailea holiday has never been easier with Expedia.

Price found within the past 48 hours. Click for updated prices.
Mana Kai Maui- Official Onsite Rental

Mana Kai Maui- Official Onsite Rental

3.5 out of 5
South Kihei
Price was £2,069, price is now £1,769 per person
£1,769
per person
8 Jun - 14 Jun
found 13 hours ago
Return direct flight included
London (LHR) to Kahului (OGG)
9/10 Wonderful! (1,003 reviews)
Absolutely exceeded our expectations. Super clean room, helpful staff, and amazing views right from the balcony. Can’t wait to come back!

Reviewed on 4 May 2026

Wailea Beach Resort - Marriott, Maui

Wailea Beach Resort - Marriott, Maui

4.5 out of 5
Wailea
Price was £2,955, price is now £2,740 per person
£2,740
per person
5 Jun - 10 Jun
found 4 hours ago
Return direct flight included
London (LON) to Kahului (OGG)
9.2/10 Wonderful! (1,003 reviews)
Too many cockroaches too many fruit flies rooms were not clean

Reviewed on 6 May 2026

Lahaina Shores #218 Condo

Lahaina Shores #218 Condo

3 out of 5
Price was £2,103, price is now £2,046 per person
£2,046
per person
5 Jun - 10 Jun
found 4 hours ago
Return direct flight included
London (LON) to Kahului (OGG)
No reviews

Where to stay in Wailea

Find the best Wailea areas and neighborhoods for the activities you enjoy most. Learn more about Wailea
South Kihei

South Kihei

3 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.

Find hotels in South Kihei

Top hotels in Wailea

Four Seasons Resort Maui at Wailea

Four Seasons Resort Maui at Wailea

5 out of 5
3900 Wailea Alanui Drive Kihei HI
The price is £740 per night from 25 May to 26 May
£740
25 May - 26 May
includes taxes & fees
9.6/10 Exceptional! (1,001 reviews)
Clean room Quite room Kindful staff

Reviewed on 25 Apr 2026

Four Seasons Resort Maui at Wailea
Grand Wailea Maui, A Waldorf Astoria Resort

Grand Wailea Maui, A Waldorf Astoria Resort

5 out of 5
3850 Wailea Alanui Drive Kihei HI
The price is £827 per night from 15 May to 16 May
£827
15 May - 16 May
includes taxes & fees
8.8/10 Excellent! (1,006 reviews)
Pool was Great

Reviewed on 5 May 2026

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

Fairmont Kea Lani Maui

5 out of 5
4100 Wailea Alanui Dr Kihei HI
The price is £1,006 per night from 3 Jun to 4 Jun
£1,006
3 Jun - 4 Jun
includes taxes & fees
9.6/10 Exceptional! (1,002 reviews)
BEAUTIFUL PROPERTY!! Worth every cent. The staff was first class and took care of our every need.

Reviewed on 6 May 2026

Fairmont Kea Lani Maui
See all 1,217 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.
All Inclusive Holidays
All Inclusive Holidays
Beach Holidays
Beach Holidays
Family Friendly Holidays
Family Friendly Holidays

Frequently asked questions

How much does a Wailea travel package cost?
Get your credit card ready, because a getaway to Wailea starts from just £1,769. When you combine your hotels, flights and car rentals into a travel package, you'll land the best bargains.
If I'm not able to travel, can I cancel my Wailea travel package?
Yes, you can cancel your Wailea booking if your plans have changed. Whether you'll be charged a fee or not depends on your airline, hotel or car rental company. You may be able to change or cancel free of charge if you booked in the last 24 hours. Head to our Customer Service Portal for more information.
How do I get a cheap travel package to Wailea?
One of the easiest ways to save dollars (and time) is to combine your bookings with Expedia. Hotels, flights, rental cars and activities — we've got them all. Pick and choose a combination that suits you and see your savings stack up. Of course, a package deal is never a one-size-fits-all. That's why Expedia offers over 550 partner airlines and 1,000,000 properties throughout the world, which lets you customize your Wailea adventure.
Does Expedia offer Book Now, Pay Later Wailea holidays?
Expedia has joined forces with online lender Klarna to make your next getaway easier on your hip pocket. Paying by instalment means you can spread the costs of your next big adventure, leaving you with more cash to splash while you're travelling. Klarna has several payment plans to choose from, so you're sure to find something that falls within your budget. Take a look at these flexible payment options:

  • Pay monthly holidays: Klarna offers manageable monthly payment plans that suit all types of budgets, so you can take that well-earned holiday sooner.
  • Pay in instalments holidays: With this Book Now, Pay Later option, Klarna makes it easy to pay off your trip across multiple transactions.
  • Low deposit holidays: When you see an amazing deal but don't have the full amount yet, Klarna's low deposit holiday plan will help you secure your getaway.

Where should I stay in Wailea?
Stay close to the action. Many people book hotels around popular attractions, such as Wailea Beach, Kamaole Beach Park 3 and Makena State Park Beach.
What are the top hotels in Wailea?
If this will be your first time in Wailea, reserve a room at Grand Wailea Maui, A Waldorf Astoria Resort or Maui Coast Hotel. Both will make you feel at home and are favourites with many savvy travellers.
How far in advance should I book my Wailea holiday?
While not all air carriers release ticket prices early, you can normally look up international flights on Expedia up to a year in advance. This is the time you can score some incredible deals. If you're booking at the last minute, you might still be in luck. Low prices sometimes emerge just weeks prior to departure.
What does an Expedia Wailea travel package include?
Hotels, rental cars and flights, or any combination of them — it's totally up to you. Whether you're headed to Wailea on a family road trip or travelling by yourself, there's a package to suit your style and budget. Once you've made your booking, why not add on a couple of tours and experiences?
What should I know before booking a Wailea travel package?
Our prices are always low. However, you'll enjoy an even better deal if you book your flights, hotels and car rentals together. With an Expedia travel package, you'll always get transparent pricing and tons of choice.
Can I choose my airline with a Wailea Expedia travel package?
Yes, so take your pick! Expedia has access to more than 550 partner airlines across the globe, so you can tailor your Wailea trip according to your budget and travel needs.

Popular places to visit

Maluaka Beach

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.

Maluaka Beach

Things to do

Molokini Island

Maui Snorkeling Adventure to Molokini and Turtle Town

£118
per adult
90% of travellers recommend
Maui Snorkeling Adventure to Molokini and Turtle Town
Deluxe Inclusive Hana Day Tour

Small Group Road to Hana, and Waterfall Swim, The Ultimate Maui Experiences

£160
per adult
98% of travellers recommend
Small Group Road to Hana, and Waterfall Swim, The Ultimate Maui Experiences
Maui: Molokini & Turtle Town Snorkel & Waterslide Adventure

Maui: Molokini & Turtle Town Snorkel & Waterslide Adventure

£145
per adult
94% of travellers recommend
Maui: Molokini & Turtle Town Snorkel & Waterslide Adventure
See all activities in Kihei

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Flight-inclusive packages are ATOL protected.