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Holiday homes - Holiday rentals

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68 Holiday homes

Holiday condo with shared pool, golf nearby in Wailea

Wailea condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from £354 / night

£2,479 / week

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Holiday home with shared pool in Wailea

Wailea house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from £956 / night

£6,689 / week

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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 £776 / night

£5,430 / 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 £797 / night

£5,574 / week

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Holiday home rental

Wailea house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 8

from £1,431 / night

£10,014 / week

1 / 50

Holiday villa with shared pool in Wailea

Wailea villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from £797 / night

£5,574 / week

1 / 50

Holiday apartment with shared pool in Wailea

Wailea apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from £499 / night

£3,248 / week

1 / 31

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 £884 / night

£4,383 / week

1 / 54

Condo rental in Wailea with shared pool

Wailea condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from £356 / night

£2,492 / week

1 / 15

Villa rental in Wailea with shared pool

Wailea villa

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 8

from £867 / night

£6,069 / week

1 / 33

Apartment rental in Wailea with shared pool

Wailea apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from £499 / night

£3,248 / week

1 / 43

Apartment letting in Wailea with shared pool

Wailea apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from £710 / night

£3,509 / week

1 / 58

Holiday apartment in Wailea

Wailea apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from £538 / night

£3,407 / week

1 / 51

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 £637 / night

£4,458 / week

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Holiday condo in Wailea

Wailea condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £178 / night

£1,210 / 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 £1,289 / night

£6,412 / week

1 / 40

Home rental in Wailea with swimming pool

Wailea house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 8

from £1,156 / night

£8,090 / week

1 / 48

Holiday apartment with shared pool in Wailea

Wailea apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from £371 / night

£2,595 / week

1 / 40

Holiday condo with shared pool in Wailea

Wailea condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from £578 / night

£3,766 / week

1 / 51

Wailea holiday villa let

Wailea villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from £678 / night

£4,742 / 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 £876 / night

£6,132 / week

1 / 49

Holiday home letting

Wailea house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

from £957 / night

£6,695 / week

1 / 50

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 £678 / night

£4,742 / week

1 / 50

Wailea holiday home rental

Wailea house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 8

from £1,032 / night

£7,225 / week

1 / 50

Holiday apartment in Wailea

Wailea apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from £715 / night

£3,973 / week

1 / 52

Wailea holiday apartment rental

Wailea apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from £756 / night

£3,762 / week

1 / 25

Wailea holiday villa rental

Wailea villa

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 8

from £1,315 / night

£9,205 / week

1 / 49

Wailea holiday villa rental

Wailea villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

“Very Nice Trip” I can surely attest that you will not be unhappy with your stay in J305 and will be pleased with the resort facilities as a whole. There are always a few items that can use improvement but the nice extras and superlatives outweigh the negatives. They could use some sharper knives and I am not a big fan of electric stove tops. The grill only got marginally hot and this obviously made grilling difficult. The elevator to our unit was broken on and off our first few days on property and I would strongly recommend the use of Wailea Beach Villas own concierge Tracy, in lieu of using the concierge assigned to you by Tropical Villa Vacations. Tracy is outstanding. Overall we had a lovely vacation and would certainly visit again and be happy to book through Tropical Villa Vacations.

from £677 / night

£4,737 / week

1 / 50

Holiday condo in Wailea

Wailea condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

from £1,109 / night

£5,514 / week

1 / 53

Holiday condo with shared pool in Wailea

Wailea condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

from £395 / night

£2,762 / week

1 / 29

Villa rental in Wailea with shared pool

Wailea villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from £717 / night

£5,016 / week

1 / 50

Holiday villa with shared pool in Wailea

Wailea villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

from £1,036 / night

£7,247 / week

1 / 49

Holiday home rental

Wailea house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

from £1,192 / night

£8,341 / week

1 / 48

Holiday villa with shared pool in Wailea

Wailea villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

from £1,036 / night

£7,247 / week

1 / 50

Wailea holiday home rental

Wailea house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 8

from £797 / night

£5,574 / week

1 / 49

Holiday apartment with shared pool in Wailea

Wailea apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Unit 2303” Great accommodations very private with all the amenities. Highly recommend.

from £777 / night

£4,317 / week

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Holiday apartment with shared pool in Wailea

Wailea apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from £479 / night

£3,102 / week

1 / 34

Apartment rental in Wailea with shared pool

Wailea apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from £849 / night

£4,497 / week

1 / 48

Holiday apartment accommodation

Wailea apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from £828 / night

£4,116 / week

1 / 36

Apartment rental in Wailea with shared pool

Wailea apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

“Tranquil Living with an Oceanview” We very much enjoyed our stay at 805 Wailea Ekolu. Great view as well as access for an older couple. The view was wonderful. The management company were very acommodating in supplying some things we needed to make our stay a great hoiiday!

from £704 / night

£3,910 / week

1 / 49

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