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Wailea Vacation Rentals(672)

672 Results
$995 - $1,995
per night
5 - 14 night minimum stay
  • 2 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 6
5 - 14 night minimum stay
(13)
$245 - $375
per night
6 - 14 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
6 - 14 night minimum stay
(30)
$750 - $1,950
per night
6 - 10 night minimum stay
  • 3 BR,
  • 3 BA,
  • Sleeps 6
6 - 10 night minimum stay
(6)
  • 2 BR,
  • 2 BA,
  • Sleeps 6
5 - 14 night minimum stay
(14)
$159 - $299
per night
3 - 7 night minimum stay
  • 1 BR,
  • 2 BA,
  • Sleeps 4
3 - 7 night minimum stay
(6)
$1,695 - $5,000
per night
4 - 14 night minimum stay
  • 3 BR,
  • 4 BA,
  • Sleeps 6
4 - 14 night minimum stay
(4)
  • 2 BR,
  • 2 BA,
  • Sleeps 4
3 - 7 night minimum stay
(7)
$214 - $236
per night
4 - 7 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
4 - 7 night minimum stay
(10)
$750 - $1,950
per night
7 - 10 night minimum stay
  • 3 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 8
7 - 10 night minimum stay
(13)
$750 - $1,950
per night
7 - 10 night minimum stay
  • 3 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 6
7 - 10 night minimum stay
(8)
$750 - $1,950
per night
7 - 10 night minimum stay
  • 3 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 8
7 - 10 night minimum stay
(3)
$350 - $500
per night
1 - 5 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
1 - 5 night minimum stay
(11)
$349 - $495
per night
4 - 7 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
4 - 7 night minimum stay
(4)
$155 - $225
per night
5 - 7 night minimum stay
  • 1 BR,
  • 2 BA,
  • Sleeps 4
5 - 7 night minimum stay
(6)
$99 - $180
per night
3 - 7 night minimum stay
  • 1 BR,
  • 2 BA,
  • Sleeps 4
3 - 7 night minimum stay
(30)
  • 2 BR,
  • 2 BA,
  • Sleeps 8
3 night minimum stay
(6)
$1,795 - $5,000
per night
4 - 10 night minimum stay
  • 3 BR,
  • 3 BA,
  • Sleeps 6
4 - 10 night minimum stay
1 Review
  • 3 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 8
5 night minimum stay
(29)
$503 - $895
per night
3 - 4 night minimum stay
  • 7 BR,
  • 3 BA,
  • Sleeps 22
3 - 4 night minimum stay
(16)
  • 1 BR,
  • 2 BA,
  • Sleeps 4
5 night minimum stay
(4)
  • 2 BR,
  • 2 BA,
  • Sleeps 5
5 - 7 night minimum stay
(5)
$315 - $360
per night
5 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
5 night minimum stay
(6)
  • 2 BR,
  • 2 BA,
  • Sleeps 4
3 - 7 night minimum stay
1 Review
  • 3 BR,
  • 3 BA,
  • Sleeps 7
5 night minimum stay
(26)
$206 - $270
per night
2 - 4 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
2 - 4 night minimum stay
$250 - $350
per night
5 - 7 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
5 - 7 night minimum stay
1 Review
$1,188 - $3,388
per night
3 - 7 night minimum stay
  • 3 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 8
3 - 7 night minimum stay
(6)
  • 1 BR,
  • 2 BA,
  • Sleeps 4
5 - 17 night minimum stay
(4)
  • 3 BR,
  • 3 BA,
  • Sleeps 8
1 Review
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Recent Wailea Reviews

Awesome home - great to work with! H

5 of 5
We had an awesome time with our children, their spouses & our 4 small grandchildren. The house was beautiful with an amazing kitchen area. So roomy & comfortable for our family and especially enjoyed the grassy area right outside the bottom patio- perfect for our grandkids! Upstairs the lanai area is perfect to enjoy family and BBQ too! The beach is a quick walk away & the pool is very close - grandkids loved it! Thanks to Chrissy & Sara for all their help. Their family favorite list was very helpful! We will be back!
  • Submitted: Feb 6, 2015
  • Stayed: Jan 2015

Spectacular!

5 of 5
We were met at the house at the start of our stay by Janna. She’s extremely informative and gave us a full walk through of the home/property. She was also very responsive and accommodating to special requests. The views are spectacular, and I don’t think it’s possible to rent a home closer to the beach than this one. Looking down the shoreline it felt like we had the best possible location to take in the waves. The home itself is lovely. Very private driveway, garage, amazing kitchen and stunning patio. The spool is the perfect size for cooling off in, or warming up in. Lots of great beach equipment was available to borrow in the garage. We spent many evenings enjoying dinner on the back patio, whale watching, BBQ’ing and enjoying the secluded nature of the back yard. Truly wonderful vacation – and more than we’d hoped for. We really struggled to find something “wrong” to say about the rental in order to provide a balanced review. So we came up with two things. The house could use a bigger toaster, it just had a two-slice, and we were a big group. End of the world, I know. The pathway access point behind the home to the sand beach (Polo Beach) could be a bit tricky to navigate with some loose rock. Not a problem for our group, but I think if you were senior citizens, or tiny kids, you’d possibly want to walk around the front of the house to get to the beach versus accessing through the back yard. Overall, this home is a gem. We are so glad we found it, and would definitely return!!! Thanks Janna!
  • Submitted: Feb 2, 2015
  • Stayed: Jan 2015

Great Condo!

5 of 5
We stayed in July 2014 and had a great experience. There were 4 of us. My husband cancelled at the last minute because of work. So, had a friend, granddaughter and her friend. We had a great time. The pictures do not do the condo justice. It is immaculate and sitting on the balcony enjoying coffee and/or a meal is fabulous. The walk in the morning from the Marriott to the other end is very enjoyable. Thank you!
  • Submitted: Feb 2, 2015
  • Stayed: Jul 2014