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Wailea Beach Vacation Rentals Vacation Rentals with Online Payment(140)

140 Results
$800 - $1,650
per night
5 - 7 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
5 - 7 night minimum stay
(28)
$187 - $312
per night
7 - 10 night minimum stay
  • 1 BR,
  • 2 BA,
  • Sleeps 4
7 - 10 night minimum stay
(32)
$240 - $375
per night
5 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
5 night minimum stay
(42)
  • 2 BR,
  • 2 BA,
  • Sleeps 6
5 - 14 night minimum stay
(33)
$195 - $275
per night
5 - 14 night minimum stay
  • 1 BR,
  • 2 BA,
  • Sleeps 4
5 - 14 night minimum stay
(11)
$500 - $675
per night
5 night minimum stay
  • 2 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 6
5 night minimum stay
(11)
  • 1 BR,
  • 1 BA,
  • Sleeps 4
5 - 14 night minimum stay
(22)
  • 2 BR,
  • 2 BA,
  • Sleeps 6
3 - 7 night minimum stay
(32)
$700 - $1,500
per night
5 - 10 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
5 - 10 night minimum stay
(11)
$1,095 - $2,295
per night
3 - 7 night minimum stay
  • 3 BR,
  • 3 BA,
  • Sleeps 8
3 - 7 night minimum stay
(19)
$210 - $260
per night
5 - 7 night minimum stay
  • 1 BR,
  • 2 BA,
  • Sleeps 4
5 - 7 night minimum stay
(29)
$650 - $1,950
per night
6 - 10 night minimum stay
  • 3 BR,
  • 3 BA,
  • Sleeps 6
6 - 10 night minimum stay
(6)
$225 - $375
per night
3 - 14 night minimum stay
  • 1 BR,
  • 2 BA,
  • Sleeps 5
3 - 14 night minimum stay
(4)
$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
  • 6 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 8
6 - 10 night minimum stay
(13)
$145 - $329
per night
6 - 7 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
6 - 7 night minimum stay
(4)
$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
$1,595 - $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)
  • 1 BR,
  • 2 BA,
  • Sleeps 5
4 - 7 night minimum stay
(8)
$995 - $1,890
per week
7 - 14 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 5
7 - 14 night minimum stay
1 Review
$2,495 - $5,000
per night
5 - 14 night minimum stay
  • 3 BR,
  • 3 BA,
  • Sleeps 6
5 - 14 night minimum stay
$950 - $1,950
per night
5 - 14 night minimum stay
  • 3 BR,
  • 3 BA,
  • Sleeps 8
5 - 14 night minimum stay
(5)
$199 - $299
per night
3 - 5 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
3 - 5 night minimum stay
$350 - $550
per night
5 - 7 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 6
5 - 7 night minimum stay
(16)
  • 3 BR,
  • 3 BA,
  • Sleeps 6
(3)
  • 2 BR,
  • 2 BA,
  • Sleeps 6
4 - 7 night minimum stay
1 Review
  • 2 BR,
  • 2 BA,
  • Sleeps 6
7 night minimum stay
(4)
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Recent Wailea Reviews

Outstanding Stay

5 of 5
Our family of four, with two "tween" girls, really enjoyed our trip and this property. The condo was clean, well located, and nested in a beautiful setting with a short 5 minute walk to the pool and the beach. A real gem!
  • Submitted: Sep 30, 2014
  • Stayed: Jun 2014

Beautiful Wailea home in the perfect location.

5 of 5
My family had a wonderful week in this beautiful Ho'olei home in Wailea. It is a beautiful home and the perfect location. We enjoyed the beaches, walking path, pool and the local restaurants were all good. We have already recommended it to a few friends. Our granddaughter really enjoyed the pool and sand toys. Everyone loved the view and we were all up early every morning to enjoy the sunrise and of course mai tai's on the lanai watching the sunset! Thank you for greeting us upon our arrival and making your property so welcoming. BRH
  • Submitted: Aug 21, 2014
  • Stayed: Aug 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