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Save time when booking: choose rentals that accept online reservations or online payments

Wailea Vacation Rentals with Online Payment(343)

343 Results
  • 3 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 8
5 - 7 night minimum stay
(13)
$240 - $375
per night
6 - 14 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
6 - 14 night minimum stay
(28)
$650 - $1,550
per night
5 - 7 night minimum stay
  • 3 BR,
  • 3 BA,
  • Sleeps 6
5 - 7 night minimum stay
(6)
$255 - $375
per night
5 - 14 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
5 - 14 night minimum stay
(9)
$165 - $299
per night
4 - 7 night minimum stay
  • 1 BR,
  • 2 BA,
  • Sleeps 4
4 - 7 night minimum stay
(5)
$214 - $236
per night
4 - 7 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
4 - 7 night minimum stay
(10)
$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
(3)
$155 - $225
per night
5 - 7 night minimum stay
  • 1 BR,
  • 2 BA,
  • Sleeps 4
5 - 7 night minimum stay
(5)
$99 - $189
per night
3 - 5 night minimum stay
  • 1 BR,
  • 2 BA,
  • Sleeps 4
3 - 5 night minimum stay
(28)
  • 2 BR,
  • 2 BA,
  • Sleeps 4
3 - 5 night minimum stay
2 Reviews
$650 - $1,550
per night
5 - 7 night minimum stay
  • 3 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 6
5 - 7 night minimum stay
2 Reviews
  • 2 BR,
  • 2 BA,
  • Sleeps 6
7 night minimum stay
(4)
  • 3 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 8
5 night minimum stay
(25)
  • 2 BR,
  • 2 BA,
  • Sleeps 8
3 night minimum stay
(5)
$2,495 - $5,000
per night
5 - 14 night minimum stay
  • 3 BR,
  • 3 BA,
  • Sleeps 6
5 - 14 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 4
3 - 5 night minimum stay
$206 - $360
per night
2 - 4 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
2 - 4 night minimum stay
  • 3 BR,
  • 3 BA,
  • Sleeps 8
30 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
3 night minimum stay
(7)
$150 - $285
per night
3 - 5 night minimum stay
  • 1 BR,
  • 1 BA,
  • 1 HF BA,
  • Sleeps 4
3 - 5 night minimum stay
(24)
  • 2 BR,
  • 2 BA,
  • Sleeps 4
(34)
$150 - $275
per night
3 - 5 night minimum stay
  • 1 BR,
  • 1 BA,
  • 1 HF BA,
  • Sleeps 2
3 - 5 night minimum stay
(155)
$125 - $285
per night
3 - 5 night minimum stay
  • 1 BR,
  • 1 BA,
  • Sleeps 4
3 - 5 night minimum stay
(14)
$165 - $285
per night
3 - 5 night minimum stay
  • 1 BR,
  • 1 BA,
  • 1 HF BA,
  • Sleeps 3
3 - 5 night minimum stay
  • 1 BR,
  • 1 BA,
  • Sleeps 3
3 - 5 night minimum stay
$115 - $255
per night
3 - 5 night minimum stay
  • 1 BR,
  • 1 BA,
  • Sleeps 4
3 - 5 night minimum stay
$159 - $209
per night
1 - 7 night minimum stay
  • 1 BR,
  • 2 BA,
  • Sleeps 4
1 - 7 night minimum stay
(18)
  • 2 BR,
  • 2 BA,
  • Sleeps 4
7 - 14 night minimum stay
(14)
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Recent Wailea Reviews

Perfect stay

5 of 5
This place was fantastic. The place is really spacious, with high ceilings and large picture windows giving the effect of even more space. We had 4 adults and 2 small kids and everyone was really comfortable with the kids having lots of room to roam around. Very clean. Very practical with a great lanai for meals and a grill. The views and property are beautiful, and the location is really convenient - 5 minute walk to a very nice beach that if you continue walking will take you down a path along all the big resorts. You can also take about a 30 minute walk (or very short car drive) to the Wailea shops. Finally, the owners are supernice, very responsive and accommodating with requests. Definitely would stay here again!
  • Submitted: Dec 5, 2014
  • Stayed: Nov 2014

Fantastic rental!

5 of 5
You won't want to go home. No really, you won't. Pictures don't do justice to this home. Venue is close (waking distance) to many attractions. This is one of the best Ho'olei units because of location, management company, owner, and rates. The Ho'olei pool may not have 35 water slides, but it does have a waterfall, it's nearly under the patio of this home, it's large, and there are typically not many people in it. This property will cause you to mumble "wow" when you walk in the door. We have stayed here more than once and will likely return. The owners maintain the property and the management company does a great job- they are both very responsive. We take advantage of the beach vouchers for umbrellas, the beach chairs and boogie boards at the site.
  • Submitted: Jun 30, 2014
  • Stayed: Jun 2014

Lovely Condo

5 of 5
This condo was perfect for our family of 6 (me and my husband, our two kids (ages 2 and 10 months), and my parents). It is very comfortable and child friendly while being beautifully decorated. It is clean and updated with a fabulous well-appointed kitchen. It is open and airy and has a huge lanai with a gas grill. The condo is located near the Ho'olei pool and also close to the Grand Wailea Resort and the beach access. There is not an ocean view from this condo, but we spent a lot of time at the beach so we did not miss having a view. We shopped around quite a bit and found this to be the very best rate for a luxury condo in Weilea. A pack and play, a high chair and a stroller were provided so we did not have to pack or rent any baby equipment. Beach chairs, umbrellas and towels were also provided. We really enjoyed spending time at the smaller beach in Makenna, just down the road. The Ho'olei pool is wonderful with a waterfall and a hot tub. it was perfect for our kids and we loved that it was not as crazy and noisy as some of the big resort pools. We really enjoyed eating at Cafe Au Lei in Kihei. The food was excellent and the price was very reasonable. It is popular with locals. Booking this condo and working with Innovar homes was really easy. Chrissy and Daisy were really nice and helpful. We will stay here again and I certainly recommend it.
  • Submitted: May 15, 2014
  • Stayed: Feb 2014