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Wailea Waterfront Vacation Rentals(178)

178 Results
$187 - $322
per night
6 - 7 night minimum stay
  • 1 BR,
  • 2 BA,
  • Sleeps 4
6 - 7 night minimum stay
(36)
$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)
  • 1 BR,
  • 2 BA,
  • Sleeps 4
3 - 7 night minimum stay
(23)
  • 1 BR,
  • 2 BA,
  • Sleeps 5
4 - 14 night minimum stay
(13)
$2,800 - $4,200
per week
7 - 14 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
7 - 14 night minimum stay
(16)
$169 - $329
per night
2 - 6 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
2 - 6 night minimum stay
(5)
  • 3 BR,
  • 3 BA,
  • Sleeps 6
(4)
$1,695 - $5,000
per night
4 - 14 night minimum stay
  • 3 BR,
  • 4 BA,
  • Sleeps 6
4 - 14 night minimum stay
(3)
  • 2 BR,
  • 2 BA,
  • Sleeps 5
7 night minimum stay
(5)
$375 - $600
per night
4 - 7 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
4 - 7 night minimum stay
(4)
$395 - $1,495
per night
5 - 12 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 7
5 - 12 night minimum stay
(4)
$275 - $450
per night
3 - 14 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
3 - 14 night minimum stay
2 Reviews
$950 - $2,250
per night
5 - 14 night minimum stay
  • 3 BR,
  • 3 BA,
  • Sleeps 8
5 - 14 night minimum stay
(5)
  • 1 BR,
  • 2 BA,
  • Sleeps 4
3 - 7 night minimum stay
2 Reviews
  • 2 BR,
  • 2 BA,
  • Sleeps 5
4 - 7 night minimum stay
(10)
$703 - $909
per night
4 night minimum stay
  • 7 BR,
  • 3 BA,
  • Sleeps 22
4 night minimum stay
(16)
  • 2 BR,
  • 2 BA,
  • Sleeps 4
3 - 14 night minimum stay
(9)
$625 - $795
per night
3 - 14 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 4
3 - 14 night minimum stay
(9)
  • 2 BR,
  • 2 BA,
  • Sleeps 6
5 - 14 night minimum stay
(34)
  • 2 BR,
  • 2 BA,
  • Sleeps 6
5 night minimum stay
(16)
$1,195 - $2,650
per night
5 - 12 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 6
5 - 12 night minimum stay
1 Review
$650 - $1,150
per night
4 - 5 night minimum stay
  • 2 BR,
  • 1 BA,
  • Sleeps 4
4 - 5 night minimum stay
1 Review
$1,450 - $3,450
per night
5 - 12 night minimum stay
  • 3 BR,
  • 3 BA,
  • Sleeps 6
5 - 12 night minimum stay
2 Reviews
$475
per night
3 - 6 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
3 - 6 night minimum stay
(3)
$1,995 - $4,350
per night
5 - 7 night minimum stay
  • 3 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 6
5 - 7 night minimum stay
1 Review
$159 - $319
per night
1 - 14 night minimum stay
  • 1 BR,
  • 1 BA,
  • Sleeps 4
1 - 14 night minimum stay
$2,650 - $3,850
per night
5 night minimum stay
  • 3 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 6
5 night minimum stay
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Recent Wailea Reviews

Amazing vacation home!!

5 of 5
Amazing vacation rental!! Awesome beach views, great locations near a ton of restaurants and shopping. Our family had an amazing time during our Thanksgiving holiday.
  • Submitted: Jan 23, 2015
  • Stayed: Nov 2014

Margie

5 of 5
This was now our 4th stay in this outstanding condo! We had a family reunion with members coming from as far away as Rhode Island, as well as Southern California and Montana. Two of our sons stayed with us while others stayed elsewhere...but we had the BEST place in all of Wailea and Kiehi!! Love the two master suites as well as the comfortable beds, outstanding kitchen and amazing ocean views! The owner keeps things updated and has just put in new lanai tiles and plantings! This condo is immaculate and comfortable and has the best location to pools and the beach! Hope we can return a 5th time!
  • Submitted: Dec 22, 2014
  • Stayed: Nov 2014

BEAUTIFULLY appointed unit in the PERFECT location

5 of 5
We have stayed in numerous rentals/hotels on Maui over the years and we both agreed that this was, without a doubt, the most enjoyable stay. The owners of this unit have done an incredible job of providing every amenity imaginable to their guests. The website doesn't do this unit justice. Our jaws literally dropped when we walked in and saw the view from the living area and out past the lanai. The building, while not new, is immaculate and, like the grounds (including pool and BBQ area), are very well maintained. The location could not be more perfect with the best hotels and restaurants in Hawaii a short (and beautiful) walk away along the shore path. Because it's not in the middle of the hotels, it seems very secluded and quiet. The beach feels private (even though it's not) and provided the soothing sound of waves at night. Snorkeling was EXCELLENT not 100 yards from the building! I saw numerous species of fish, coral, sea urchin, a moray eel and even the state's official fish, the humu humu. The Shops at Wailea are less than a mile away and grocery shopping is in nearby Kihei. Neither of us golf, but if that's your thing, the Weilea Golf Club is right across the street. Simply put, now that we've stayed in this unit in this location, we won't be staying anywhere else in the future when we visit Maui.
  • Submitted: Nov 8, 2014
  • Stayed: Oct 2014