479 Results
Cancel Clear Filters Apply Filters

Price Per Week

$ $

Sleeps

Bedrooms

Bathrooms

Booking Options

Property Type

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

Booking Options

Location Type

Even More Filters

Features

Managed By

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

Wailea Vacation Rentals(479)

479 Results
  • 1 BR,
  • 1 BA,
  • Sleeps 4
2 night min stay
(56)
$110 - $135
per night
2 night min stay
  • Studio,
  • 1 BA,
  • Sleeps 4
2 night min stay
(67)
  • 2 BR,
  • 2 BA,
  • Sleeps 6
5 - 14 night min stay
(35)
$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)
$700 - $1,600
per night
5 - 10 night min stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
5 - 10 night min stay
(13)
  • 1 BR,
  • 2 BA,
  • Sleeps 4
4 night min stay
(71)
  • 1 BR,
  • 2 BA,
  • Sleeps 4
5 - 14 night min stay
(11)
  • 1 BR,
  • 2 BA,
  • Sleeps 4
5 - 14 night min stay
(14)
  • 1 BR,
  • 2 BA,
  • Sleeps 2
4 - 14 night min stay
(14)
  • 2 BR,
  • 2 BA,
  • Sleeps 6
5 night min stay
(42)
  • 1 BR,
  • 2 BA,
  • Sleeps 4
6 - 7 night min stay
(36)
  • 1 BR,
  • 1 BA,
  • Sleeps 4
4 - 5 night min stay
(13)
$495 - $1,495
per night
5 - 12 night min stay
  • 2 BR,
  • 2 BA,
  • Sleeps 7
5 - 12 night min stay
(4)
  • 2 BR,
  • 2 BA,
  • Sleeps 6
3 - 7 night min stay
(32)
$210 - $260
per night
5 - 7 night min stay
  • 1 BR,
  • 2 BA,
  • Sleeps 4
5 - 7 night min stay
(30)
  • 2 BR,
  • 2 BA,
  • Sleeps 8
2 night min stay
(16)
$1,195 - $2,295
per night
3 - 7 night min stay
  • 3 BR,
  • 3 BA,
  • Sleeps 8
3 - 7 night min stay
(21)
  • 2 BR,
  • 2 BA,
  • Sleeps 6
5 - 12 night min stay
(47)
  • 1 BR,
  • 1 BA,
  • Sleeps 3
3 night min stay
(55)
$795 - $1,850
per night
3 - 10 night min stay
  • 3 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 8
3 - 10 night min stay
(15)
$225 - $375
per night
3 - 14 night min stay
  • 1 BR,
  • 2 BA,
  • Sleeps 5
3 - 14 night min stay
(5)
$250 - $400
per night
3 - 7 night min stay
  • 1 BR,
  • 2 BA,
  • Sleeps 4
3 - 7 night min stay
(24)
$825 - $895
per night
5 - 7 night min stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
5 - 7 night min stay
(30)
$225 - $295
per night
2 night min stay
  • 1 BR,
  • 2 BA,
  • Sleeps 2
2 night min stay
(26)
$160 - $250
per night
7 - 12 night min stay
  • 1 BR,
  • 2 BA,
  • Sleeps 4
7 - 12 night min stay
(17)
$265 - $275
per night
1 - 5 night min stay
  • 1 BR,
  • 2 BA,
  • Sleeps 4
1 - 5 night min stay
(21)
  • 1 BR,
  • 2 BA,
  • Sleeps 5
4 - 14 night min stay
(15)
$250 - $355
per night
5 night min stay
  • 2 BR,
  • 2 BA,
  • Sleeps 5
5 night min stay
(16)
 View map Map
Advertisement
 

Recent Wailea Reviews

Fabulous and unique!

5 of 5
What can we say about this fabulous cottage and the owners! We have been traveling to Hawaii for over 30 years, staying in condos at the various islands. This cottage surpasses them all! Clean, lots of amenities, comfortable, private, with a nice BBQ area and hot tub. One couldn't ask for more, except there is more - Stewart and Andrea - the home owners. They were available when needed but were never intrusive. We had all the privacy we could ask for. The uniqueness of the cottage is worth seeing with the large rock walls and big wood beams and a mote! We had a few friends over to visit and they even loved it. There is a hose in front to wash off beach toys which is very convenient. We will be staying at this cottage for many years to come!
  • Submitted: Apr 25, 2015
  • Stayed: Feb 2015

Wailea Beach Villas are the best!

5 of 5
We just finished our 7th year staying in a Wailea Beach Villa unit and can say that this is the best place to stay on the island. The property is beautiful, quite and access to beach chairs and umbrellas is fantastic! The owners, Helen and Steve, are great to work with and the views from their 4th floor unit are amazing.
  • Submitted: Apr 10, 2015
  • Stayed: Mar 2015

TOP NOTCH CONDO

5 of 5
This condo was so perfect for my husband and me. Not only was it clean and comfortable, it convenient to many restaurants, beaches and activities. The owners provide their guests with a comprehensive list of places to dine, things to do and many other helpful tips to add to enjoyment of Maui. We ate at Sarento's on the Beach; Monkeypod Kitchen and experienced an authentic luau and show depicting the history of Havaii at Old Lahaini Luau. We also laughed nonstop at Annabelle & Warren's magic show--an unforgettable 2-hour show of illusion combiined with raucous humor. The condo is equipped with everything you couuld ask for, including beach chairs, towels and umbrella. The view from both lanais is breathtaking---spectacular sunrises and sunsets. Pool is a short walk down a path. We would, wiithout hesitation, stay here again and recommend this others.
  • Submitted: Apr 8, 2015
  • Stayed: Mar 2015