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Wailea Rentals with Online Payment(89)

89 Results
$1,350 - $1,650
per night
6 - 14 night min stay
  • 4 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 10
6 - 14 night min stay
(37)
$700 - $1,600
per night
5 - 10 night min stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
5 - 10 night min stay
(13)
  • 2 BR,
  • 2 BA,
  • Sleeps 6
3 - 7 night min stay
(32)
$1,195 - $2,295
per night
3 - 7 night min stay
  • 3 BR,
  • 3 BA,
  • Sleeps 8
3 - 7 night min stay
(21)
$250 - $355
per night
5 night min stay
  • 2 BR,
  • 2 BA,
  • Sleeps 5
5 night min stay
(16)
  • 3 BR,
  • 2 BA,
  • Sleeps 10
5 night min stay
(18)
$1,695 - $5,000
per night
4 - 14 night min stay
  • 3 BR,
  • 4 BA,
  • Sleeps 6
4 - 14 night min stay
(4)
  • 2 BR,
  • 2 BA,
  • Sleeps 6
5 - 7 night min stay
(9)
$4,200 - $7,000
per week
7 - 14 night min stay
  • 4 BR,
  • 3 BA,
  • Sleeps 8
7 - 14 night min stay
(14)
$750 - $1,950
per night
7 - 10 night min stay
  • 3 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 8
7 - 10 night min stay
(3)
$1,795 - $5,000
per night
4 - 10 night min stay
  • 3 BR,
  • 3 BA,
  • Sleeps 6
4 - 10 night min stay
(5)
  • 3 BR,
  • 3 BA,
  • Sleeps 6
(4)
  • 3 BR,
  • 2 BA,
  • Sleeps 6
5 - 7 night min stay
(16)
  • 2 BR,
  • 2 BA,
  • Sleeps 5
3 night min stay
(17)
$419 - $505
per night
4 - 12 night min stay
  • 3 BR,
  • 3 BA,
  • Sleeps 8
4 - 12 night min stay
$319 - $434
per night
4 - 12 night min stay
  • 2 BR,
  • 2 BA,
  • Sleeps 4
4 - 12 night min stay
$245 - $345
per night
4 - 12 night min stay
  • 1 BR,
  • 2 BA,
  • Sleeps 2
4 - 12 night min stay
  • 2 BR,
  • 2 BA,
  • Sleeps 4
5 - 12 night min stay
$213 - $294
per night
4 - 12 night min stay
  • 1 BR,
  • 2 BA,
  • Sleeps 4
4 - 12 night min stay
$331 - $446
per night
4 - 12 night min stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
4 - 12 night min stay
$306 - $421
per night
4 - 12 night min stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
4 - 12 night min stay
  • 1 BR,
  • 1 BA,
  • 1 HF BA,
  • Sleeps 4
4 - 12 night min stay
$306 - $421
per night
4 - 12 night min stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
4 - 12 night min stay
  • 2 BR,
  • 2 BA,
  • Sleeps 4
5 - 12 night min stay
$230 - $268
per night
4 - 12 night min stay
  • 1 BR,
  • 2 BA,
  • Sleeps 2
4 - 12 night min stay
$310 - $409
per night
5 - 12 night min stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
5 - 12 night min stay
$238 - $312
per night
4 - 12 night min stay
  • 1 BR,
  • 2 BA,
  • Sleeps 4
4 - 12 night min stay
$169 - $253
per night
4 - 12 night min stay
  • Studio,
  • 1 BA,
  • Sleeps 2
4 - 12 night min stay
$297 - $417
per night
4 - 12 night min stay
  • 1 BR,
  • 1 BA,
  • 1 HF BA,
  • Sleeps 4
4 - 12 night min stay
$245 - $320
per night
4 - 12 night min stay
  • 1 BR,
  • 2 BA,
  • Sleeps 4
4 - 12 night min stay
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Recent Wailea Reviews

Wonderful time

5 of 5
We had a fantastic stay there with our family. We have three kids (6yrs, 3yrs and a baby) and the place worked out perfectly with the pool being perfectly supervisable from the patio. Teri was a wonderful host and made us feel so welcome. She gave us a ton of great ideas where to go and how to best explore the island with kids. It is also great that she keeps sand toys, boogie boards, pool noodles and other things around for guests to use so we did not need to bring or buy any of that. If you are looking for a perfect place to relax with a great pool and an amazing view we cannot recommend this place enough! We would certainly love to come back and our kids are still talking about the easter egg hunt in the garden and the plush easter rabbits that Teri got them along with hiding eggs she had painted the night before!!!
  • Submitted: Apr 24, 2015
  • Stayed: Mar 2015

Wailea Beach Villas are the best!

5 of 5
We just finished our 7th year staying in a Wailea Beach Villa unit and can say that this is the best place to stay on the island. The property is beautiful, quite and access to beach chairs and umbrellas is fantastic! The owners, Helen and Steve, are great to work with and the views from their 4th floor unit are amazing.
  • Submitted: Apr 10, 2015
  • Stayed: Mar 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