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Villas in Wailea and Condos - Holiday Lettings - Holiday Rentals Wailea

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190 Holiday homes

Holiday condo in Wailea

Wailea condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £270 / night

£1,888 / week

1 / 11

Holiday condo in Wailea

Wailea condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £224 / night

£1,567 / week

1 / 71

Condo rental in Wailea

Wailea condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from £382 / night

£2,675 / week

1 / 12

Holiday condo with shared pool, golf nearby in Wailea

Wailea condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from £349 / night

£2,442 / week

1 / 8

Holiday home with shared pool in Wailea

Wailea house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from £939 / night

£6,568 / week

1 / 48

Holiday apartment with shared pool in Wailea

Wailea apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

“Wonderful” This space was spotless. The recent renovations made others seem like camping. The unit was fully equipped and very comfortable. The walk to the beach and common pool was only a few minutes. The view was like a golf fairway to the ocean. We would like to return.

from £765 / night

£5,350 / week

1 / 21

Holiday villa with swimming pool in Wailea

Wailea villa

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 8

“wonderful and would do it again.” If you love Wailea, and you're staying for a week, these units are the only place to stay. So much better than a hotel. It really was a "home" away from home. Kitchen fully stocked with utensils and many (but not all) items we all use everyday. Get the rest by yourself. Rent one of these units - you will never regret it.

from £942 / night

£6,590 / week

1 / 50

Holiday home rental

Wailea house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 8

from £1,826 / night

£12,779 / week

1 / 50

Holiday villa with shared pool in Wailea

Wailea villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from £782 / night

£5,469 / week

1 / 48

Holiday apartment with shared pool in Wailea

Wailea apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from £491 / night

£3,200 / week

1 / 31

Holiday apartment in Wailea

Wailea apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £179 / night

£1,253 / week

1 / 21

Holiday condo in Wailea

Wailea condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from £224 / night

£1,567 / week

1 / 18

Holiday condo in Wailea

Wailea condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

from £299 / night

£2,089 / week

1 / 16

Holiday condo rental

Wailea condo

  • 1 bedroom
  • 2 bathrooms
  • sleeps 2

from £257 / night

£1,794 / week

1 / 17

Holiday apartment with shared pool in Wailea

Wailea apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“It was great. Modern room and very convenient location” We had a great time and it was a wonderful facility. It was so easy to get to and from our location. Overall great experience.

from £965 / night

£6,112 / week

1 / 54

Condo rental in Wailea with shared pool

Wailea condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from £351 / night

£2,455 / week

1 / 15

Holiday apartment in Wailea

Wailea apartment

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 8

from £189 / night

£1,322 - £1,700 / week

1 / 17

Holiday apartment with golf nearby in Wailea

Wailea apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

from £298 / night

£2,083 / week

1 / 24

Apartment rental in Wailea with golf nearby

Wailea apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from £588 / night

£4,117 / week

1 / 44

Holiday apartment with golf nearby in Wailea

Wailea apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“nice, comfy, homey atmosphere” Wonderful experience! It's like home away from home! Awesome, helpful staff! Thank you!!!

from £243 / night

£1,699 / week

1 / 24

Holiday apartment with shared pool in Wailea

Wailea apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 7

from £1,114 / night

£7,798 / week

1 / 19

Holiday camper van in Wailea

Wailea camper van

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £99 / night

£693 / week

1 / 43

Villa rental in Wailea with shared pool

Wailea villa

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 8

from £854 / night

£5,979 / week

1 / 33

Wailea holiday condo rental

Wailea condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from £630 / night

£4,406 / week

1 / 23

Apartment rental in Wailea with shared pool

Wailea apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from £491 / night

£3,200 / week

1 / 43

Apartment letting in Wailea with shared pool

Wailea apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from £775 / night

£4,907 / week

1 / 58

Holiday apartment in Wailea

Wailea apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from £530 / night

£3,357 / week

1 / 52

Holiday apartment with golf nearby in Wailea

Wailea apartment

  • 1 bedroom
  • 2 bathrooms
  • sleeps 2

from £471 / night

£3,293 / week

1 / 26

Wailea holiday apartment accommodation

Wailea apartment

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

from £424 / night

£2,963 / week

1 / 47

Holiday home rental

Wailea house

  • 4 bedrooms
  • 6 bathrooms
  • sleeps 8

“A paradise for our family vacation” We have rented this house for our family vacation for the past 3 years and it is truly perfect. The location is great...close to lots of restaurants and easy base to explore all of Maui. Wonderful house, terrific layout, lovely and comfortable furnishings and the beautiful waterfront yard is great for our grandkids. We love kayaking with the whales and turtles and then relaxing in the pool or on the lanai for stunning sunsets. House and kitchen are well extremely equipped and everyone at Tropical Villa Vacations makes sure that your vacation is trouble free. We will be back next year!

from £1,963 / night

£13,735 / week

1 / 50

Holiday home in Wailea

Wailea house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

“Our getaway to the beauty of the ocean & Maui.” A spectacular view from the balcony that draws you to it when you enter Regal Mandalay. Every amenity is provided to make our stay stress free and enjoyable. The beds are comfortable for a great nights sleep. The location to the pools, beach, & walking path bring us back every year. The friendliness & helpfullness of the staff is like talking to family. We felt at home the entire stay and will return. We find the convenience to the golf courses as well as great eateries the best on the island.

from £1,017 / night

£7,118 / week

1 / 50

Apartment rental in Wailea

Wailea apartment

  • 2 bedrooms
  • sleeps 6

from £322 / night

£2,248 / week

1 / 16

Wailea holiday condo let

Wailea condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

from £320 / night

£2,234 - £2,675 / week

1 / 41

Holiday condo in Wailea

Wailea condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £540 / night

£3,776 / week

1 / 35

Holiday apartment with golf nearby in Wailea

Wailea apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from £722 / night

£5,051 / week

1 / 43

Holiday apartment in Wailea

Wailea apartment

  • 2 bedrooms
  • sleeps 6

from £390 / night

£2,727 / week

1 / 17

Wailea holiday apartment rental

Wailea apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from £761 / night

£5,326 / week

1 / 33

Holiday apartment with golf nearby in Wailea

Wailea apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from £824 / night

£5,766 / week

1 / 32

Holiday condo in Wailea

Wailea condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £176 / night

£1,192 - £1,524 / week

1 / 16

Holiday apartment in Wailea

Wailea apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

“Great Condo in Wailea” We stayed in unit 2110 July 1-8 and really enjoyed ourselves. This was our first trip to Maui and were definitely happy to stay in the Wailea area. While the south shore is a relatively dry part of the island, the Wailea Elua community is beautifully landscaped and is a tropical paradise. The condo was just a short walk down the hill through the community to the beach but there was also a parking lot so you could drive down if you have a lot of stuff to carry like we did with our 2 small children and all the beach stuff. We would definitely recommend this condo and will return here on our next trip to Maui.

from £1,407 / night

£8,914 / week

1 / 40

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Wailea holidays

Famous for its five half-moon shaped beaches and world-class golf courses, Wailea is five times the size of Honolulu’s Waikiki with unmatched Pacific Ocean views. For a luxurious Hawaiian holiday in a very sought-after location, visit Holiday Lettings where you will find a Wailea holiday rental to suit all your needs.

About Wailea

Wailea is located on the south-western part of Hawaiian Island of Maui, just 14 miles from Kahului Airport.

Meticulously laid out over 1,500 acres of lush tropical vegetation, the beach at Wailea is one of the most visited on Maui. The popularity of the beach is partly due to the area’s luxurious oceanfront resorts and spas, as well as its legendary year-round average temperature of 82 degrees!

Even the shopping at Wailea has an up-market feel with Gucci, Louis Vuitton, Prada and Tiffany & Co all represented next to surfing boutiques such as Quicksilver, Rip Curl and the Honolulu Surfing Company.

When it comes to fine dining, you will be spoilt for choice with American, international and Hawaiian specialities all available.

Top Wailea events include the February Whale Week and the Maui Film Festival. See if you can catch one during your stay!

What to do

Avid golfers flock to Wailea just to play the Gold Course (one of the top golfing destinations in the country!). Robert Trent Jones II designed championship course that takes advantage of the natural surroundings, while incorporating stunning ocean views from every tee. A true thinking man’s course, and considered one of the best designed courses in the world.

Hawaii is, of course, all about surfing and Maui has its fair share of top spots where the pros come to catch big winter waves. But on the south of the island, the waves are around three feet in height, making them perfect for beginners.

Go hiking in the Haleakala National Park and climb to the top of the world’s largest dormant volcano, Haleakala, where you will be rewarded with fantastic views of the island.

Top Wailea travel tips

With almost perfect weather all year round, there is no bad time to visit Wailea.

For beach attire, avoid the fancy stores and ask the locals where they go shopping, instead. Consider buying a snorkel, mask, and fins as it can actually work out cheaper than renting.

Hawaii is a no-brainer for a tropical beach holiday, but with so many great amenities, Wailea truly is a world-class destination. To find your slice of paradise, Holiday Lettings has dozens of Wailea holiday rentals to suit all budgets.

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