Wailea Holidays from £1,388

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

Kahana Villa

3 out of 5
per person
2 Sept - 9 Sept
found 17 hours ago
Return direct flight included
London (LON) to Kahului (OGG)
8/10 Very Good! (338 reviews)
Great location. Stay away from condos close to the road because it gets noisy. WiFi and washing machine was fixed fairly quickly. Nice pool and tennis/pickel court.

Reviewed on 16 Jul 2025

Mana Kai Maui- Official Onsite Rental

Mana Kai Maui- Official Onsite Rental

3.5 out of 5
Save 100% on your flight
per person
18 Sept - 25 Sept
found 1 day ago
Return flight included
London (LON) to Kahului (OGG)
8.8/10 Excellent! (1,001 reviews)
The property was a great place to stay. The beach are was great. They had to shut off water for maintenance. I understand the need but caused some inconvenience. It was not easy to watch local news or any descent entertainment on the TV. I would recommend this place

Reviewed on 16 Jul 2025

Napili Kai Beach Resort

Napili Kai Beach Resort

3.5 out of 5
Save 100% on your flight
per person
18 Sept - 25 Sept
found 1 day ago
Return flight included
London (LON) to Kahului (OGG)
9.4/10 Exceptional! (1,001 reviews)
Fantastic property, beach, amenities, friendliness and helpfulness of staff!

Reviewed on 18 Jul 2025

Royal Lahaina Resort & Bungalows

Royal Lahaina Resort & Bungalows

4 out of 5
per person
18 Sept - 25 Sept
found 1 day ago
Return flight included
London (LON) to Kahului (OGG)
8.2/10 Very Good! (1,358 reviews)
The best location in Kaanapali! Two great outdoor bars on the beach, two awesome pools and endless views.

Reviewed on 18 Jul 2025

OUTRIGGER Kaanapali Beach Resort

OUTRIGGER Kaanapali Beach Resort

3.5 out of 5
per person
18 Sept - 25 Sept
found 1 day ago
Return flight included
London (LON) to Kahului (OGG)
9.2/10 Wonderful! (1,177 reviews)
Property is right on the beach. Hotel is kept clean and staff is friendly. Will definitely be back.

Reviewed on 17 Jul 2025

Top hotels in 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 £831 per night from 1 Aug to 2 Aug
£831
1 Aug - 2 Aug
includes taxes & fees
8.8/10 Excellent! (1,000 reviews)
"We had the best time! The property is absolutely gorgeous and the weather was perfect."

Reviewed on 17 Jun 2025

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 £753 per night from 11 Aug to 12 Aug
£753
11 Aug - 12 Aug
includes taxes & fees
9.4/10 Exceptional! (1,004 reviews)
"We lives the Fairmont"

Reviewed on 13 Jul 2025

Fairmont Kea Lani Maui
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 £655 per night from 24 Jul to 25 Jul
£655
24 Jul - 25 Jul
includes taxes & fees
9.6/10 Exceptional! (999 reviews)
"Ms ging, Vee and almira, and the rest of staff are awesome… Management 🏆"

Reviewed on 7 Jul 2025

Four Seasons Resort Maui at Wailea
See all 1,194 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 travel package cost?
Get your credit card ready, because a getaway to Wailea starts from just £1,388. 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 featuring rocky coastline, a pebble beach and mountains

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

Guided Turtle Town Snorkeling Tour with Underwater Photos

Snorkel with Turtles and Free Underwater Photos - Turtle Town

£95
per adult
100% of travellers recommend
Snorkel with Turtles and Free Underwater Photos - Turtle Town
Wailea Beach: Guided Sea Scooter Snorkeling Tour

Wailea Beach: Guided Sea Scooter Snorkeling Tour

£109
per adult
100% of travellers recommend
Wailea Beach: Guided Sea Scooter Snorkeling Tour
Morning views at Haleakalā National Park

Haleakala National Park Sunrise Tour

£177
per adult
92% of travellers recommend
Haleakala National Park Sunrise Tour
See all activities in Kihei