360 Results
Cancel Clear Filters Apply Filters

Price Per Week

$ $

Sleeps

Bedrooms

Bathrooms

Booking Options

Property Type

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

Booking Options

Location Type

Even More Filters

Features

Managed By

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

Wailea Vacation Rentals with Online Payment(360)

360 Results
$995 - $1,995
per night
5 - 14 night min stay
  • 2 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 6
5 - 14 night min stay
(15)
$245 - $375
per night
6 - 14 night min stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
6 - 14 night min stay
(31)
$750 - $1,950
per night
6 - 10 night min stay
  • 3 BR,
  • 3 BA,
  • Sleeps 6
6 - 10 night min stay
(6)
  • 2 BR,
  • 2 BA,
  • Sleeps 6
6 - 14 night min stay
(16)
  • 2 BR,
  • 2 BA,
  • Sleeps 6
4 - 7 night min stay
(11)
$149 - $299
per night
3 - 7 night min stay
  • 1 BR,
  • 2 BA,
  • Sleeps 4
3 - 7 night min stay
(7)
  • 2 BR,
  • 2 BA,
  • Sleeps 4
3 - 7 night min stay
(9)
  • 3 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 8
7 - 10 night min stay
(13)
$1,695 - $5,000
per night
4 - 14 night min stay
  • 3 BR,
  • 4 BA,
  • Sleeps 6
4 - 14 night min stay
(4)
$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)
$290 - $699
per night
3 - 7 night min stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
3 - 7 night min stay
(5)
$1,225 - $1,295
per week
7 night min stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
7 night min stay
(5)
$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)
$1,795 - $5,000
per night
4 - 10 night min stay
  • 3 BR,
  • 3 BA,
  • Sleeps 6
4 - 10 night min stay
(5)
  • 1 BR,
  • 2 BA,
  • Sleeps 4
5 - 7 night min stay
(7)
  • 2 BR,
  • 2 BA,
  • Sleeps 4
4 - 7 night min stay
(10)
$194 - $378
per night
2 - 10 night min stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
2 - 10 night min stay
2 Reviews
  • 2 BR,
  • 2 BA,
  • Sleeps 4
3 - 7 night min stay
(3)
  • 2 BR,
  • 2 BA,
  • Sleeps 8
3 night min stay
(7)
  • 3 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 8
5 night min stay
(29)
$250 - $350
per night
5 - 7 night min stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
5 - 7 night min stay
2 Reviews
$180 - $300
per night
3 - 14 night min stay
  • 2 BR,
  • 2 BA,
  • Sleeps 4
3 - 14 night min stay
(28)
$250 - $360
per night
3 - 14 night min stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
3 - 14 night min stay
(31)
$200 - $285
per night
3 - 14 night min stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
3 - 14 night min stay
(12)
$208 - $515
per night
2 - 10 night min stay
  • 1 BR,
  • 1 BA,
  • Sleeps 4
2 - 10 night min stay
  • 2 BR,
  • 2 BA,
  • Sleeps 5
2 - 10 night min stay
$128 - $247
per night
2 - 7 night min stay
  • 1 BR,
  • 1 BA,
  • Sleeps 2
2 - 7 night min stay
$185 - $357
per night
2 - 10 night min stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
2 - 10 night min stay
1 Review
  • 2 BR,
  • 2 BA,
  • Sleeps 6
2 - 10 night min stay
$211 - $420
per night
2 - 10 night min stay
  • 2 BR,
  • 2 BA,
  • Sleeps 4
2 - 10 night min stay
1 Review
 View map Map
Advertisement
 

Recent Wailea Reviews

A great location for a wonderful vacation!

4 of 5
Our stay at the Palms of Wailea was wonderful! The condo was fabulous, just as advertised. The common area was spacious and very comfortable. We loved the picture window - the view of the ocean, watching the whales, the beautiful rainbows and sunsets. The lanai (with the same view) was a great place to enjoy morning coffee and afternoon cocktails. We really appreciated the opportunity to try a sleep number bed! There were plenty of ocean chairs and boogie boards for our use. The pool area was also very nice. The complex was well-maintained and quite beautiful. Joe and his team on the island were great, very helpful and accommodating. While in Maui we golfed, went to the beach, sailed and snorkeled. We attended a luau, which was a lot of fun. We cooked in and ate out - lots of choices including the Kihei Cafe, the Monkey Pod and Ferraro's at the Four Seasons. We came to Maui for a celebration and it was the vacation of a life-time!!!!
  • Submitted: Mar 21, 2015
  • Stayed: Feb 2015

Awesome home - great to work with! H

5 of 5
We had an awesome time with our children, their spouses & our 4 small grandchildren. The house was beautiful with an amazing kitchen area. So roomy & comfortable for our family and especially enjoyed the grassy area right outside the bottom patio- perfect for our grandkids! Upstairs the lanai area is perfect to enjoy family and BBQ too! The beach is a quick walk away & the pool is very close - grandkids loved it! Thanks to Chrissy & Sara for all their help. Their family favorite list was very helpful! We will be back!
  • Submitted: Feb 6, 2015
  • Stayed: Jan 2015

Spectacular!

5 of 5
We were met at the house at the start of our stay by Janna. She’s extremely informative and gave us a full walk through of the home/property. She was also very responsive and accommodating to special requests. The views are spectacular, and I don’t think it’s possible to rent a home closer to the beach than this one. Looking down the shoreline it felt like we had the best possible location to take in the waves. The home itself is lovely. Very private driveway, garage, amazing kitchen and stunning patio. The spool is the perfect size for cooling off in, or warming up in. Lots of great beach equipment was available to borrow in the garage. We spent many evenings enjoying dinner on the back patio, whale watching, BBQ’ing and enjoying the secluded nature of the back yard. Truly wonderful vacation – and more than we’d hoped for. We really struggled to find something “wrong” to say about the rental in order to provide a balanced review. So we came up with two things. The house could use a bigger toaster, it just had a two-slice, and we were a big group. End of the world, I know. The pathway access point behind the home to the sand beach (Polo Beach) could be a bit tricky to navigate with some loose rock. Not a problem for our group, but I think if you were senior citizens, or tiny kids, you’d possibly want to walk around the front of the house to get to the beach versus accessing through the back yard. Overall, this home is a gem. We are so glad we found it, and would definitely return!!! Thanks Janna!
  • Submitted: Feb 2, 2015
  • Stayed: Jan 2015