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

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552 Holiday homes

Condo rental in Wailea with shared pool, golf nearby

Wailea condo

1 bedroom • 2 bathrooms • sleeps 4

from £274 / night

£1,913 / week

1 / 17

Holiday condo in Wailea

Wailea condo

2 bedrooms • 2 bathrooms • sleeps 8

from £168 / night

£1,171 / week

1 / 18

Condo rental in Wailea

Wailea condo

1 bedroom • 2 bathrooms • sleeps 2

from £143 / night

£1,001 / week

1 / 12

Holiday condo with golf nearby in Wailea

Wailea condo

2 bedrooms • 2 bathrooms • sleeps 6

from £413 / night

£2,886 / week

1 / 12

Holiday apartment in Wailea

Wailea apartment

2 bedrooms • 3 bathrooms • sleeps 8

from £169 / night

£1,177 - £1,530 / week

1 / 16

Holiday condo rental

Wailea condo

2 bedrooms • 2 bathrooms • sleeps 6

from £324 / night

£2,266 - £2,560 / week

1 / 25

Holiday condo in Wailea

Wailea condo

1 bedroom • 1 bathroom • sleeps 2

from £254 / night

£1,774 / week

1 / 11

Condo rental in Wailea

Wailea condo

2 bedrooms • 2 bathrooms • sleeps 6

from £261 / night

£1,824 / week

1 / 12

Holiday condo in Wailea

Wailea condo

1 bedroom • 1 bathroom • sleeps 2

from £227 / night

£1,583 / week

1 / 23

Villa rental in Wailea with shared pool

Wailea villa

3 bedrooms • 4 bathrooms • sleeps 8

from £841 / night

£5,884 / week

1 / 33

Apartment rental in Wailea with shared pool, golf nearby

Wailea apartment

1 bedroom • 1 bathroom • sleeps 2

from £194 / night

£1,331 / week

1 / 82

Holiday home with shared pool in Wailea

Wailea house

3 bedrooms • 2 bathrooms • sleeps 6

from £849 / night

£5,939 / week

1 / 50

Holiday home rental

Wailea house

3 bedrooms • 4 bathrooms • sleeps 6

from £1,808 / night

£12,653 / week

1 / 49

Holiday condo in Wailea

Wailea condo

2 bedrooms • 2 bathrooms • sleeps 4

from £634 / night

£4,435 / week

1 / 8

Holiday apartment with golf nearby in Wailea

Wailea apartment

2 bedrooms • 2 bathrooms • sleeps 6

from £538 / night

£3,765 / week

1 / 30

Apartment rental in Wailea with golf nearby

Wailea apartment

2 bedrooms • 2 bathrooms • sleeps 6

from £550 / night

£3,849 / week

1 / 34

Wailea holiday apartment rental

Wailea apartment

2 bedrooms • 2 bathrooms • sleeps 5

from £550 / night

£3,849 / week

1 / 30

Wailea holiday apartment rental

Wailea apartment

2 bedrooms • 2 bathrooms • sleeps 5

from £538 / night

£3,765 / week

1 / 29

Holiday home rental

Wailea house

4 bedrooms • 4 bathrooms • sleeps 8

from £3,615 / night

£25,306 / week

1 / 50

Holiday apartment with golf nearby in Wailea

Wailea apartment

1 bedroom • 1 bathroom • sleeps 4

from £330 / night

£2,308 / week

1 / 30

Wailea holiday condo rental

Wailea condo

2 bedrooms • 2 bathrooms • sleeps 6

from £465 / night

£3,253 / week

1 / 23

Holiday condo rental

Wailea condo

1 bedroom • 2 bathrooms • sleeps 2

from £240 / night

£1,677 / week

1 / 17

Cottage rental in Wailea

Wailea cottage

1 bedroom • 2 bathrooms • sleeps 3

from £210 / night

£1,465 / week

1 / 25

Condo rental in Wailea with shared pool

Wailea condo

1 bedroom • 1 bathroom • sleeps 5

from £443 / night

£3,095 / week

1 / 39

Condo rental in Wailea with shared pool

Wailea condo

1 bedroom • 1 bathroom • sleeps 5

from £441 / night

£3,083 / week

1 / 30

Holiday condo rental

Wailea condo

1 bedroom • 1 bathroom • sleeps 5

from £443 / night

£3,099 / week

1 / 34

Holiday condo accommodation

Wailea condo

1 bedroom • 1 bathroom • sleeps 5

from £441 / night

£3,083 / week

1 / 52

Condo rental in Wailea with shared pool

Wailea condo

2 bedrooms • 2 bathrooms • sleeps 6

from £211 / night

£1,477 / week

1 / 15

Holiday apartment with golf nearby in Wailea

Wailea apartment

1 bedroom • 2 bathrooms • sleeps 2

from £440 / night

£3,078 / week

1 / 19

Wailea holiday apartment accommodation

Wailea apartment

1 bedroom • 2 bathrooms • sleeps 4

from £440 / night

£3,078 / week

1 / 30

Wailea holiday condo let

Wailea condo

1 bedroom • 1 bathroom • sleeps 3

from £219 / night

£1,677 - £2,148 / week

1 / 41

Holiday apartment with golf nearby in Wailea

Wailea apartment

2 bedrooms • 2 bathrooms • sleeps 6

from £741 / night

£5,185 / week

1 / 23

Holiday villa with shared pool in Wailea

Wailea villa

3 bedrooms • 3 bathrooms • sleeps 6

from £956 / night

£6,688 / week

1 / 49

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 £1,398 / night

£9,787 / week

1 / 49

Holiday home in Wailea

Wailea house

2 bedrooms • 1 bathroom • sleeps 4

“Outstanding” My family and I stayed at the Wailea Sunset Bungalow. Amazing property, very clean, extremely well stocked, and all the amenities you would ever expect/need (the water and Chapstick on each nightstand was a thoughtful touch). The property is properly maintained both inside and out. It's private, and in an excellent location. We have stayed in Hana, Makena, Paia, Wailea, Ka'anapali, Haiku, Lahaina, and Kapalua, in Hotels and private homes, over a period of 10 years. This place was our favorite! If prodded, the only thing I would like to see, is a small price reduction. It's not competitively priced for the area. If you can get past the price, you will not be disappointed. This is as good as it gets... really!

from £734 / night

£5,139 / week

1 / 50

Villa rental in Wailea with shared pool

Wailea villa

4 bedrooms • 3 bathrooms • sleeps 8

“The perfect vacation spot” The villa has everything you could need with a view that is breath taking.

from £1,291 / night

£9,038 / week

1 / 50

Holiday home letting

Wailea house

4 bedrooms • 3 bathrooms • sleeps 8

“excellent” We had a wonderful stay made more relaxing by the great service and close proximity to the beach. We would definitely stay again

from £2,062 / night

£14,435 / week

1 / 50

Holiday villa with swimming pool in Wailea

Wailea villa

3 bedrooms • 4 bathrooms • sleeps 6

“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 £1,398 / night

£9,787 / week

1 / 49

Holiday villa with shared pool in Wailea

Wailea villa

3 bedrooms • 2 bathrooms • sleeps 6

“Definitely earned a 5-Star rating with us!” My husband and I went with my brother and sister-in-law, so having 2 Master Suites was ideal. The condo was absolutely gorgeous and immaculately clean. The view was magnificent. There were 2 full size refrigerators, 1 was already pre-stocked with wine and beer upon our arrival (which was very much appreciated after the long plane trip). The staff was pleasant and always available. The pictures you see on the website are true to what you walk into. We highly recommend.

from £1,177 / night

£8,238 / week

1 / 49

Wailea holiday condo accommodation

Wailea condo

1 bedroom • 1 bathroom • sleeps 4

from £126 / night

£883 / week

1 / 27

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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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