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Family Friendly Holidays in Wailea - Holiday Lettings

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Holiday condo in Wailea

Wailea condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

from £186 / night

£1,301 / week

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Condo rental in Wailea with shared pool, golf nearby

Wailea condo

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

from £304 / night

£2,125 / week

1 / 17

Holiday camper van in Wailea

Wailea camper van

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £122 / night

£850 / week

1 / 41

Condo rental in Wailea

Wailea condo

  • 1 bedroom
  • 2 bathrooms
  • sleeps 2

from £178 / night

£1,243 / week

1 / 12

Holiday condo with golf nearby in Wailea

Wailea condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from £456 / night

£3,191 / week

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Holiday condo in Wailea

Wailea condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £281 / night

£1,962 / week

1 / 11

Condo rental in Wailea

Wailea condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from £304 / night

£2,125 / week

1 / 12

Condo rental in Wailea with shared pool

Wailea condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from £234 / night

£1,635 / week

1 / 15

Holiday home rental

Wailea house

  • 5 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 £3,794 / night

£26,552 / week

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Holiday home rental

Wailea house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

from £2,652 / night

£18,558 / week

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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 £1,301 / night

£9,108 / week

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Condo rental in Wailea with golf nearby

Wailea condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from £309 / night

£2,158 / week

1 / 12

Wailea holiday apartment rental

Wailea apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

from £522 / night

£3,649 / week

1 / 29

Holiday home rental

Wailea house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

from £3,997 / night

£27,980 / week

1 / 50

Wailea holiday condo rental

Wailea condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from £514 / night

£3,596 / week

1 / 23

Wailea holiday apartment rental

Wailea apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Wonderful Whale Watching Vacation” We spent 11 days in Unit #802 and experienced a fun and relaxing time on Maui. Our whale watching/snorkeling excursion, Old Lahaina Luau experience and trip to the Ocean Center were excellent. Out upcountry drive to the alii lavender Farm and Tedeschi Winery was also fun. We especially loved spending time on the nearby beaches, snorkeling along several different reef zones, kayaking with sea turtles and whales offshore of the Marriott resort,hiking in the lava field at the end of the road, and walking to dinner at the Shops at Wailea. We can't wait to return! We feel fortunate to have found the perfect Maui vacation spot at Wailea Village. This convenient location allowed us to easily participate in all the activities we had planned. Our unit had an ocean view where we could sit on our lanai each evening to watch the sunset. We also ate breakfast here and saw whales spouting, breeching, and cruising in the ocean every day. Having a washer/dryer to use made our trip even more pleasant as did the fully functional kitchen. We much prefer staying in a condo to a hotel room!

from £595 / night

£4,163 / week

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Condo rental in Wailea with shared pool

Wailea condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 5

from £577 / night

£4,034 / week

1 / 39

Condo rental in Wailea with shared pool

Wailea condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 5

from £577 / night

£4,034 / week

1 / 30

Holiday condo rental

Wailea condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 5

from £611 / night

£4,276 / week

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Holiday condo accommodation

Wailea condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 5

from £577 / night

£4,034 / week

1 / 52

Holiday apartment with golf nearby in Wailea

Wailea apartment

  • 1 bedroom
  • 2 bathrooms
  • sleeps 2

from £489 / night

£3,421 / week

1 / 19

Wailea holiday apartment accommodation

Wailea apartment

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

from £489 / night

£3,421 / week

1 / 30

Villa rental in Wailea with shared pool

Wailea villa

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 8

from £934 / night

£6,538 / week

1 / 33

Holiday apartment with golf nearby in Wailea

Wailea apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from £709 / night

£4,963 / week

1 / 23

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 £1,383 / night

£9,679 / week

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Holiday home with shared pool in Wailea

Wailea house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from £1,383 / night

£9,679 / week

1 / 49

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 £252 / night

£1,765 / week

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Wailea holiday villa let

Wailea villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from £975 / night

£6,824 / week

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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 £1,954 / night

£13,676 / week

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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 £1,346 / night

£9,422 / week

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Wailea holiday home rental

Wailea house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

from £1,546 / night

£10,821 / week

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Wailea holiday villa rental

Wailea villa

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

from £2,199 / night

£15,389 / week

1 / 48

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 £894 / night

£6,253 / week

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Holiday home rental

Wailea house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

from £2,325 / night

£16,274 / week

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Holiday villa with shared pool in Wailea

Wailea villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from £1,383 / night

£9,679 / week

1 / 50

Holiday villa with shared pool in Wailea

Wailea villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

from £1,709 / night

£11,963 / week

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Holiday villa with shared pool in Wailea

Wailea villa

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

“Simply Divine in Wailea” Our family of 6, 2 teen boys and 2 teen girls, had the pleasure of staying at Bella Luna in March. It was even better than the pictures. Sure it was a splurge, but there is simply no better accommodations to be had in the Wailea area. The unit was so complete and so well stocked that there was not one single thing we could think of that wasn't already there. The furnishings were spectacular, the view from the lanai was breathtaking, and the sliding glass walls allowed us to enjoy the open air all the time. The appliances, electronics, were all top notch, as were the cookware and dishes. I was impressed too with the management company, Tropical Villa Vacations. They were really on top of everything to make sure our trip was special. We will definitely go back to Wailea and stay in this unit again. I wouldn't want to stay anywhere else!

from £2,570 / night

£17,987 / week

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Wailea holiday condo rental

Wailea condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 5

from £577 / night

£4,034 / week

1 / 30

Holiday apartment with golf nearby in Wailea

Wailea apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from £432 / night

£3,021 / week

1 / 30

Condo accommodation in Wailea

Wailea condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from £352 / night

£2,461 / week

1 / 38

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