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Wailea Long Term Vacation Rentals(169)

169 Results
$99 - $125
per night
2 night minimum stay
  • Studio,
  • 1 BA,
  • Sleeps 4
2 night minimum stay
(63)
$187 - $312
per night
1 - 7 night minimum stay
  • 1 BR,
  • 2 BA,
  • Sleeps 4
1 - 7 night minimum stay
(32)
  • 1 BR,
  • 2 BA,
  • Sleeps 4
2 - 7 night minimum stay
(21)
$750 - $1,895
per night
1 - 10 night minimum stay
  • 3 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 8
1 - 10 night minimum stay
(12)
  • 2 BR,
  • 2 BA,
  • Sleeps 6
5 - 14 night minimum stay
(32)
$195 - $295
per night
2 - 5 night minimum stay
  • 1 BR,
  • 2 BA,
  • Sleeps 2
2 - 5 night minimum stay
(18)
$500 - $675
per night
5 night minimum stay
  • 2 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 6
5 night minimum stay
(11)
$139 - $329
per night
1 - 14 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
1 - 14 night minimum stay
(5)
$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)
  • 2 BR,
  • 2 BA,
  • Sleeps 8
3 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)
$170 - $225
per night
3 - 7 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 5
3 - 7 night minimum stay
(4)
  • 2 BR,
  • 2 BA,
  • Sleeps 5
7 - 14 night minimum stay
(38)
$350 - $500
per night
1 - 5 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
1 - 5 night minimum stay
(10)
$119 - $289
per night
3 - 5 night minimum stay
  • 1 BR,
  • 2 BA,
  • Sleeps 2
3 - 5 night minimum stay
(4)
$159 - $299
per night
6 - 7 night minimum stay
  • 1 BR,
  • 2 BA,
  • Sleeps 4
6 - 7 night minimum stay
(3)
$189 - $489
per night
5 - 7 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
5 - 7 night minimum stay
(5)
$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)
  • 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)
  • 2 BR,
  • 2 BA,
  • Sleeps 6
1 - 7 night minimum stay
$169 - $360
per night
2 - 4 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
2 - 4 night minimum stay
$1,450 - $2,950
per night
5 night minimum stay
  • 3 BR,
  • 3 BA,
  • Sleeps 6
5 night minimum stay
2 Reviews
$270 - $325
per night
3 night minimum stay
  • 1 BR,
  • 2 BA,
  • Sleeps 4
3 night minimum stay
(14)
  • 2 BR,
  • 2 BA,
  • Sleeps 4
7 night minimum stay
$250 - $300
per night
4 night minimum stay
  • 1 BR,
  • 2 BA,
  • Sleeps 5
4 night minimum stay
(17)
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Recent Wailea Reviews

Maui Family Vacation

4 of 5
Our stay at Maui Hill in Byron and Kim's condo was wonderful! The place was cozy and homey and included everything we needed during out stay. We were greeted with fresh leis on each bed along with some Hawaiian snacks and goodies, which were yummy! If you are just exploring Kihei and Wailea then the location is perfect and convenient and close to the beaches. It could be walking distance to one of the beaches, but with our kiddoes it would be a trek so we opted to drive. We also appreciated that the place had beach gears for us to use during our beach days. Kim and Byron were so attentive and accomodated our family with a early check in since we had our 11 month old with us. Thanks so much and we would definitely come back and stay! Mahalo!
  • Submitted: Sep 15, 2014
  • Stayed: Sep 2014

Truly One of a Kind!

5 of 5
We had a wonderful, beautiful 2 weeks at Rose's "slice of heaven". It was perfect for us. As we entered it was "OMG this is beautiful ". Everything was done in great taste ! All very relaxing and soothing. From the totally supplied kitchen, to the very comfortable king bed, to the wonderful art work. The private patio area beautiful, private and quiet. It was by far more than we expected. We have rented in the past thru VRBO and this was by far the best unit we have stayed in thru out our travels. We are now highly recommending this condo to all our friends. It is beautiful, sensual and very relaxing. And the location is absolutely perfect to everything at Wailea, the best area of all Maui. Mahalo, Rose We will be back soon.
  • Submitted: Aug 24, 2014
  • Stayed: Aug 2014

Great Location

4 of 5
The condo was excellent. it had everything that we needed for a comfortable stay. All inquiries to owner and property manager were quickly responded and very helpful. I had a little problem with the internet on the first day, but we got it resolved quickly.
  • Submitted: Aug 4, 2014
  • Stayed: Jul 2014