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(677)

677 Results
$750 - $1,950
per night
6 - 10 night minimum stay
  • 3 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 8
6 - 10 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)
$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
3 - 5 night minimum stay
(33)
  • 2 BR,
  • 2 BA,
  • Sleeps 6
6 - 14 night minimum stay
(7)
$149 - $299
per night
4 - 7 night minimum stay
  • 1 BR,
  • 2 BA,
  • Sleeps 4
4 - 7 night minimum stay
(5)
$350 - $500
per night
1 - 5 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
1 - 5 night minimum stay
(10)
$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
$339 - $495
per night
4 - 7 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
4 - 7 night minimum stay
1 Review
$695 - $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
  • 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)
$709 - $903
per night
4 night minimum stay
  • 7 BR,
  • 3 BA,
  • Sleeps 22
4 night minimum stay
(16)
  • 2 BR,
  • 2 BA,
  • Sleeps 8
3 night minimum stay
(5)
  • 1 BR,
  • 2 BA,
  • Sleeps 4
5 night minimum stay
(4)
  • 2 BR,
  • 2 BA,
  • Sleeps 5
5 - 7 night minimum stay
(5)
$194 - $360
per night
2 - 4 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
2 - 4 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 4
3 - 5 night minimum stay
$1,088 - $3,388
per night
3 - 7 night minimum stay
  • 3 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 8
3 - 7 night minimum stay
(6)
  • 3 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 8
3 - 7 night minimum stay
1 Review
$2,495 - $5,000
per night
5 - 14 night minimum stay
  • 3 BR,
  • 3 BA,
  • Sleeps 6
5 - 14 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
$1,950 - $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
$1,450 - $3,450
per night
4 - 12 night minimum stay
  • 3 BR,
  • 3 BA,
  • Sleeps 6
4 - 12 night minimum stay
2 Reviews
$1,995 - $4,150
per night
5 - 12 night minimum stay
  • 3 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 6
5 - 12 night minimum stay
1 Review
  • 3 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 8
(55)
$0
per night
5 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
5 night minimum stay
(5)
Advertisement
 

Recent Wailea Reviews

The Best of The Best!

5 of 5
This is our third stay at this beautiful condo and it won't be our last! You won't be disappointed with your choice! The home is very clean, well-maintained and the view is beyond words! The beds are comfortable, and the kitchen has everything you need to prepare breakfasts to dinners! The owners are a pleasure to work with and Hope, their property manager, is absolutely the best and there for your every need! Can't wait to return to what we feel is our home away from home! Thank you so much for sharing your home with us!
  • Submitted: Oct 24, 2014
  • Stayed: Oct 2014

Great Wailea Condo to family

5 of 5
We have a very finicky toddler that will not sleep with us in the room, so this 2 bedroom condo was perfect! The room that she stayed in had an A/C unit with a fan that we left on for her to sleep comfortably. So, with a well slept toddler through the night, you got happy parents! The kitchen is very well updated and stocked with all the utensils and cookware. Having A/C in the living area would have been nice as it was pretty hot when we were there. But, they do have a great powerful fan in the living room that helped tremendously. Having an washer and dryer was a major plus! Its a very nice washer and dryer too which is super quiet. A note to future renters: Leave the washer door open after use to air it out to prevent mold growth. Mold grows fast in the tropics with the humidity and heat. The previous renters didn't air it out and when we got there, there was bad mold which is common in front load washers. The condo is well stocked with all the goodies for the beach and the pool. We will definently be returning to this condo!!!
  • Submitted: Aug 6, 2014
  • Stayed: Jul 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