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Wailea Beach Vacation Rentals Vacation Rentals(347)

347 Results
$800 - $1,650
per night
5 - 7 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
5 - 7 night minimum stay
(27)
$187 - $312
per night
1 - 7 night minimum stay
  • 1 BR,
  • 2 BA,
  • Sleeps 4
1 - 7 night minimum stay
(32)
$240 - $375
per night
5 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
5 night minimum stay
(42)
$195 - $275
per night
5 - 14 night minimum stay
  • 1 BR,
  • 2 BA,
  • Sleeps 4
5 - 14 night minimum stay
(11)
  • 2 BR,
  • 2 BA,
  • Sleeps 6
5 - 14 night minimum stay
(32)
$500 - $675
per night
5 night minimum stay
  • 2 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 6
5 night minimum stay
(11)
$700 - $1,500
per night
5 - 10 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
5 - 10 night minimum stay
(11)
  • 2 BR,
  • 2 BA,
  • Sleeps 6
3 - 7 night minimum stay
(32)
$1,095 - $2,295
per night
3 - 7 night minimum stay
  • 3 BR,
  • 3 BA,
  • Sleeps 8
3 - 7 night minimum stay
(19)
$650 - $1,950
per night
6 - 10 night minimum stay
  • 3 BR,
  • 3 BA,
  • Sleeps 6
6 - 10 night minimum stay
(6)
$139 - $329
per night
1 - 14 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
1 - 14 night minimum stay
(5)
$395 - $900
per night
5 - 14 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 7
5 - 14 night minimum stay
1 Review
$650 - $1,950
per night
6 - 10 night minimum stay
  • 3 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 8
6 - 10 night minimum stay
(13)
$275 - $375
per night
3 - 14 night minimum stay
  • 1 BR,
  • 2 BA,
  • Sleeps 5
3 - 14 night minimum stay
(3)
$650 - $1,950
per night
6 - 10 night minimum stay
  • 3 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 6
6 - 10 night minimum stay
(7)
$650 - $1,950
per night
6 - 10 night minimum stay
  • 3 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 6
6 - 10 night minimum stay
2 Reviews
  • 2 BR,
  • 2 BA,
  • Sleeps 5
7 - 14 night minimum stay
(38)
$395 - $485
per night
5 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 5
5 night minimum stay
(71)
$2,495 - $5,000
per night
5 - 14 night minimum stay
  • 3 BR,
  • 4 BA,
  • Sleeps 6
5 - 14 night minimum stay
(3)
$119 - $289
per night
3 - 5 night minimum stay
  • 1 BR,
  • 2 BA,
  • Sleeps 2
3 - 5 night minimum stay
(4)
$725 - $1,095
per night
5 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
5 night minimum stay
(16)
$145 - $329
per night
6 - 7 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
6 - 7 night minimum stay
2 Reviews
$1,550 - $2,195
per night
5 night minimum stay
  • 3 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 6
5 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
7 night minimum stay
(4)
$350 - $550
per night
5 - 7 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 6
5 - 7 night minimum stay
(16)
$190 - $250
per night
5 - 7 night minimum stay
  • 1 BR,
  • 2 BA,
  • Sleeps 4
5 - 7 night minimum stay
(29)
  • 4 BR,
  • 3 BA,
  • Sleeps 8
5 night minimum stay
$119 - $169
per night
5 - 14 night minimum stay
  • 1 BR,
  • 1 BA,
  • Sleeps 4
5 - 14 night minimum stay
(22)
  • 1 BR,
  • 2 BA,
  • Sleeps 5
4 - 7 night minimum stay
(7)
$1,450 - $2,950
per night
5 night minimum stay
  • 3 BR,
  • 3 BA,
  • Sleeps 6
5 night minimum stay
2 Reviews
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Recent Wailea Reviews

Wish I was there now!

5 of 5
We had perhaps the most relaxing vacation ever. We loved the condo and it's location. We took wonderful, scenic walks along the ocean each morning. My daughter and I read books on the lanai as well as by the pool over-looking the ocean. The grounds were impeccable and made you feel like you were truly in paradise. Randy was a pleasure to work with. Prompt and responsive to needs or questions. I loved and appreciated all of his recommendations for activities and restaurants. The condo itself was super comfortable for our family of four. I sure hope we can plan another trip here soon!
  • Submitted: Sep 12, 2014
  • Stayed: Jun 2014

Stunning, amazing, perfect & I'm ready to go back

5 of 5
We had a fabulous stay at this house. It was exactly as advertised, only better. Because when you open up the glass siding doors and take in the ocean breeze and the gorgeous maui sunsets you will feel like you're in heaven. It's an easy 20 feet walk to a beautiful beach and you're right off a 1.5 mile walking/running trail that takes you right by the Fairmont, Grand Wailea & Four Seasons (you're in pretty good company when you stay here). We will be back for sure -- Janna, thank you so much for taking such great care of us. We're home and missing the house already!
  • Submitted: Jul 27, 2014
  • Stayed: Jul 2014

Paradise for a week

5 of 5
Our party of two adult couples stayed for a week at 2A at the beginning of May, and thoroughly enjoyed this lovely and immaculately-maintained condo. The location allows easy access to two pools, is a short walk to the beach, and parking is close and very convenient. We appreciated the fact that there are two master bedroom suites, and that they are separated so that early risers don’t disturb anyone who wants to sleep in. The kitchen is updated and fully equipped, and it is very pleasant to fix meals while admiring the panoramic view of the ocean out the dining room window. The lanai is wonderful, with a gorgeous view as well as privacy that is provided by the lush plantings around the space. Furniture was very comfortable, there was excellent cross-ventilation which made the air conditioning almost unnecessary, and the bathrooms had been completely renovated. We would highly recommend this condo, and wouldn’t hesitate to stay here again!
  • Submitted: Jun 26, 2014
  • Stayed: May 2014