231 Results
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

Booking Options

Location Type

Even More Filters

Features

Managed By

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

Wailea Mountain Vacation Rentals(231)

231 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)
$210 - $335
per night
4 - 14 night min stay
  • 2 BR,
  • 2 BA,
  • Sleeps 4
4 - 14 night min stay
(13)
  • 1 BR,
  • 2 BA,
  • Sleeps 2
4 - 14 night min stay
(15)
  • 2 BR,
  • 2 BA,
  • Sleeps 6
5 night min stay
(43)
  • 1 BR,
  • 2 BA,
  • Sleeps 4
6 - 7 night min stay
(38)
  • 2 BR,
  • 2 BA,
  • Sleeps 6
5 - 12 night min stay
(48)
$189 - $269
per night
3 night min stay
  • 1 BR,
  • 1 BA,
  • Sleeps 2
3 night min stay
(56)
$225 - $295
per night
2 night min stay
  • 1 BR,
  • 2 BA,
  • Sleeps 2
2 night min stay
(28)
$160 - $260
per night
7 - 10 night min stay
  • 1 BR,
  • 2 BA,
  • Sleeps 4
7 - 10 night min stay
(17)
  • 2 BR,
  • 2 BA,
  • Sleeps 4
6 - 7 night min stay
(15)
  • 3 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 8
7 - 10 night min stay
(13)
$290 - $699
per night
3 - 7 night min stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
3 - 7 night min stay
(6)
  • 2 BR,
  • 2 BA,
  • Sleeps 6
5 - 7 night min stay
(9)
  • 2 BR,
  • 2 BA,
  • Sleeps 5
7 night min stay
(7)
$750 - $1,950
per night
7 - 10 night min stay
  • 3 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 6
7 - 10 night min stay
(8)
$525 - $725
per night
5 night min stay
  • 2 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 6
5 night min stay
(15)
$4,200 - $7,000
per week
7 - 14 night min stay
  • 4 BR,
  • 3 BA,
  • Sleeps 8
7 - 14 night min stay
(14)
$185 - $355
per night
5 - 10 night min stay
  • 2 BR,
  • 2 BA,
  • Sleeps 4
5 - 10 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)
$845 - $2,445
per night
1 - 7 night min stay
  • 4 BR,
  • 4 BA,
  • Sleeps 8
1 - 7 night min stay
2 Reviews
$175 - $315
per night
5 night min stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
5 night min stay
(3)
  • 2 BR,
  • 2 BA,
  • Sleeps 8
4 night min stay
(22)
$503 - $903
per night
2 - 5 night min stay
  • 7 BR,
  • 3 BA,
  • Sleeps 22
2 - 5 night min stay
(16)
  • 2 BR,
  • 2 BA,
  • Sleeps 5
3 - 14 night min stay
(44)
  • 2 BR,
  • 2 BA,
  • Sleeps 5
5 - 7 night min stay
(7)
  • 2 BR,
  • 2 BA,
  • Sleeps 6
3 - 10 night min stay
(66)
$250 - $350
per night
4 - 7 night min stay
  • 2 BR,
  • 2 BA,
  • Sleeps 5
4 - 7 night min stay
(7)
  • 2 BR,
  • 2 BA,
  • Sleeps 6
5 night min stay
(12)
  • 2 BR,
  • 2 BA,
  • Sleeps 6
3 night min stay
(8)
$600 - $1,295
per night
5 - 6 night min stay
  • 2 BR,
  • 1 BA,
  • Sleeps 4
5 - 6 night min stay
2 Reviews
 View map Map
Advertisement
 

Recent Wailea Reviews

Amazing

5 of 5
My wife and I stayed in the Bungalow for 5 days, and the place is amazing. The pictures are spot on. It is really very private, and the back yard is very large. The cottage is quaint, and in great condition. It is also well provisioned with everything needed, except groceries. It only has one bath, so I would not recommend it to a larger group, 4 people is probably max. The place is very appropriately named as the sunsets were fantastic. We took the lawn chairs right down to the water’s edge every night, and there was a small turtle swimming around the rocks every morning for coffee. When we were there, the two homes on either side were unoccupied, so it was absolutely quiet and practically private other than a few beach combers, or a passing kayak.
  • Submitted: May 20, 2015
  • Stayed: May 2015

A perfect home base in a beautiful setting!

5 of 5
Our family thoroughly enjoyed our stay at this impressive condominium! The unit itself was very clean and well maintained with all sorts of conveniences such as some cooking essentials (spices, oil, vinegar), coolers, beach towels and body surfing boards for the beach, a washer/dryer and even an extra propane tank for all the BBQing that we did on the large, comfortable Lanai! The complex itself is very well looked after and the pool made for a great place to relax later in the afternoon after a day at the beach. There are beautiful walking paths beachside nearby and the beach is just a short walk from the condo. Make sure you check out the Five Palms for Happy Hour about a 5 minute drive away. We would highly recommend this home for your next family getaway to Maui!
  • Submitted: May 12, 2015
  • Stayed: Mar 2015

Wonderful Relaxing Retreat

5 of 5
This was our first trip to Maui and we couldn't have picked a better location. The condo is so nicely decorated and well stocked with everything you need. We throughly enjoyed our time in Maui. The condo has great beach options within a short drive or walk. We found some great restaurants nearby, Monkey Pod Kitchen was our favorite, you have to try their strawberry cream pie. I don't think we could have found a better location to explore Maui from. We look forward to returning.
  • Submitted: May 11, 2015
  • Stayed: Apr 2015