Cancel Clear Filters Apply Filters

Price Per Week

$ $

Sleeps

Bedrooms

Bathrooms

Booking Options

Property Type

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

Location Type

Even More Filters

Features

Managed By

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

Wailea Waterfront Vacation Rentals Vacation Rentals(171)

171 Results
$187 - $312
per night
1 - 7 night minimum stay
  • 1 BR,
  • 2 BA,
  • Sleeps 4
1 - 7 night minimum stay
(32)
  • 2 BR,
  • 2 BA,
  • Sleeps 6
5 - 14 night minimum stay
(33)
  • 1 BR,
  • 2 BA,
  • Sleeps 4
2 - 7 night minimum stay
(21)
$395 - $900
per night
5 - 14 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 7
5 - 14 night minimum stay
1 Review
$145 - $329
per night
6 - 7 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
6 - 7 night minimum stay
(4)
$1,595 - $5,000
per night
5 - 14 night minimum stay
  • 3 BR,
  • 4 BA,
  • Sleeps 6
5 - 14 night minimum stay
(3)
$950 - $1,950
per night
5 - 14 night minimum stay
  • 3 BR,
  • 3 BA,
  • Sleeps 8
5 - 14 night minimum stay
(5)
  • 1 BR,
  • 2 BA,
  • Sleeps 5
4 - 7 night minimum stay
(8)
  • 2 BR,
  • 2 BA,
  • Sleeps 6
5 night minimum stay
(16)
$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
$225 - $390
per night
1 - 7 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
1 - 7 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 5
7 night minimum stay
1 Review
  • 1 BR,
  • 2 BA,
  • Sleeps 4
3 - 7 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
$1,395 - $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
$1,500 - $3,450
per night
5 - 12 night minimum stay
  • 3 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 6
5 - 12 night minimum stay
$725 - $1,895
per night
4 - 12 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 6
4 - 12 night minimum stay
$1,150 - $2,950
per night
5 - 10 night minimum stay
  • 3 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 6
5 - 10 night minimum stay
$1,850 - $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
$995 - $2,750
per night
4 - 12 night minimum stay
  • 3 BR,
  • 3 BA,
  • Sleeps 6
4 - 12 night minimum stay
$1,295 - $3,150
per night
5 - 12 night minimum stay
  • 3 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 6
5 - 12 night minimum stay
$1,095 - $2,950
per night
5 - 12 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 6
5 - 12 night minimum stay
Advertisement
 

Recent Wailea Reviews

Outstanding Stay

5 of 5
Our family of four, with two "tween" girls, really enjoyed our trip and this property. The condo was clean, well located, and nested in a beautiful setting with a short 5 minute walk to the pool and the beach. A real gem!
  • Submitted: Sep 30, 2014
  • Stayed: Jun 2014

Stunning, amazing, perfect & I'm ready to go back

5 of 5
We had a fabulous stay at this house. It was exactly as advertised, only better. Because when you open up the glass siding doors and take in the ocean breeze and the gorgeous maui sunsets you will feel like you're in heaven. It's an easy 20 feet walk to a beautiful beach and you're right off a 1.5 mile walking/running trail that takes you right by the Fairmont, Grand Wailea & Four Seasons (you're in pretty good company when you stay here). We will be back for sure -- Janna, thank you so much for taking such great care of us. We're home and missing the house already!
  • Submitted: Jul 27, 2014
  • Stayed: Jul 2014

Picture perfect view

5 of 5
Janet and Hugh were great with the reservation and condo walk through process. They provided recommendations to local restaurants, shopping, and activities for the family to enjoy. Their condo is 5 stars with the amenities and decor, they had everything we needed for our one week family vacation in Maui. The beach as shown on homeaway website was within minutes walking from the condo and was an excellent snorkeling spot for the family. The kids were able to see turtles on every snorkeling trip. Every morning, several tour boats and kayaker would stop at the same location to snorkel and you can do it for free! The view from the balcony was picture perfect! The condo was also a short drive (5-10 minutes) to some of the great shopping, restaurants, and beaches in Wailea and Kihei. Overall, great condo, location, and owners. I would rent again when we go back to Maui.
  • Submitted: Jun 25, 2014
  • Stayed: Jun 2014