Cancel Clear Filters Apply Filters

Price Per Week

$ $

Sleeps

Bedrooms

Bathrooms

Booking Options

Property Type

Apartments
Bungalows
Condos
Cottages
Estates
Hotels
Homes
Townhomes
Villas
Barns
Boats
Cabins
Castles
Chalets
Farmhouses
Lodges
Studios
Yachts

Location Type

Even More Filters

Features

Managed By

Cancel Clear Filters Apply Filters
Use filters to narrow your search results!

Wailea Vacation Rentals(597)

597 Results
  • 2 BR,
  • 2 BA,
  • Sleeps 6
3 - 5 night minimum stay
(34)
$235 - $375
per night
6 - 14 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
6 - 14 night minimum stay
(26)
$249 - $399
per night
4 - 5 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 4
4 - 5 night minimum stay
(18)
$199 - $299
per night
3 - 5 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
3 - 5 night minimum stay
(14)
$255 - $375
per night
6 - 14 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
6 - 14 night minimum stay
(5)
$650 - $1,950
per night
6 - 10 night minimum stay
  • 3 BR,
  • 3 BA,
  • Sleeps 6
6 - 10 night minimum stay
(6)
  • 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)
$650 - $1,950
per night
6 - 10 night minimum stay
  • 6 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 8
6 - 10 night minimum stay
(13)
$159 - $299
per night
6 - 7 night minimum stay
  • 1 BR,
  • 2 BA,
  • Sleeps 4
6 - 7 night minimum stay
(4)
$99 - $189
per night
3 - 5 night minimum stay
  • 1 BR,
  • 2 BA,
  • Sleeps 4
3 - 5 night minimum stay
(28)
$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)
$650 - $1,950
per night
6 - 10 night minimum stay
  • 3 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 6
6 - 10 night minimum stay
2 Reviews
$350 - $500
per night
1 - 5 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
1 - 5 night minimum stay
(10)
$703 - $903
per night
3 - 4 night minimum stay
  • 7 BR,
  • 3 BA,
  • Sleeps 22
3 - 4 night minimum stay
(8)
  • 2 BR,
  • 2 BA,
  • Sleeps 6
3 - 5 night minimum stay
2 Reviews
$1,425 - $3,950
per night
5 - 12 night minimum stay
  • 3 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 6
5 - 12 night minimum stay
$1,495 - $3,750
per night
4 - 12 night minimum stay
  • 4 BR,
  • 3 BA,
  • Sleeps 8
4 - 12 night minimum stay
$339 - $495
per night
4 - 7 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
4 - 7 night minimum stay
1 Review
  • 2 BR,
  • 2 BA,
  • Sleeps 4
3 - 5 night minimum stay
1 Review
$131 - $280
per night
2 - 4 night minimum stay
  • 1 BR,
  • 2 BA,
  • Sleeps 4
2 - 4 night minimum stay
$194 - $360
per night
2 - 4 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
2 - 4 night minimum stay
$1,450 - $3,450
per night
4 - 12 night minimum stay
  • 3 BR,
  • 3 BA,
  • Sleeps 6
4 - 12 night minimum stay
2 Reviews
$2,495 - $5,000
per night
5 - 14 night minimum stay
  • 3 BR,
  • 3 BA,
  • Sleeps 6
5 - 14 night minimum stay
$1,150 - $1,650
per night
5 night minimum stay
  • 3 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 6
5 night minimum stay
$650 - $1,250
per night
6 - 12 night minimum stay
  • 2 BR,
  • 1 BA,
  • Sleeps 4
6 - 12 night minimum stay
1 Review
$1,750 - $5,250
per night
5 - 12 night minimum stay
  • 4 BR,
  • 5 BA,
  • 1 HF BA,
  • Sleeps 10
5 - 12 night minimum stay
1 Review
$1,395 - $3,350
per night
4 - 12 night minimum stay
  • 4 BR,
  • 3 BA,
  • Sleeps 8
4 - 12 night minimum stay
$899 - $2,500
per night
5 - 12 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 6
5 - 12 night minimum stay
$2,500 - $3,250
per night
5 night minimum stay
  • 3 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 6
5 night minimum stay
Advertisement
 

Recent Wailea Reviews

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

Beautiful view!

5 of 5
This place is great and was a perfect fit for our family of five! The rooms were spacious, and we loved the beautiful picture window and the well equipped kitchen. The lanai was our favorite place to hang out with lots of seating we ate all of our meals outside and played games out there in the evenings. An added bonus beach chairs and 3 sets of snorkel equipment were available for use. The washer and dryer was also nice to have in the condo. The location was great about a five -10 minute walk to the beach which even my six year old made to and from with ease. The property itself is well maintained. Joe the owner was quick to respond to our inquiry when we booked on short notice. Would love to go back! The Mendler's Chula Vista , CA
  • Submitted: Jun 15, 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