33 Results
Cancel Clear Filters Apply Filters

Price Per Week

$ $

Sleeps

Bedrooms

Bathrooms

Booking Options

Property Type

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

Booking Options

Location Type

Even More Filters

Features

Managed By

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

Wailea Luxury Vacation Rentals(33)

33 Results
$1,395 - $3,150
per night
4 - 12 night minimum stay
  • 3 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 8
4 - 12 night minimum stay
1 Review
$650 - $1,150
per night
4 - 5 night minimum stay
  • 2 BR,
  • 1 BA,
  • Sleeps 4
4 - 5 night minimum stay
1 Review
$2,750 - $5,150
per night
5 - 12 night minimum stay
  • 4 BR,
  • 5 BA,
  • 1 HF BA,
  • Sleeps 10
5 - 12 night minimum stay
1 Review
$2,195 - $4,350
per night
4 - 7 night minimum stay
  • 3 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 8
4 - 7 night minimum stay
1 Review
$1,495 - $3,650
per night
5 - 7 night minimum stay
  • 4 BR,
  • 3 BA,
  • Sleeps 8
5 - 7 night minimum stay
$2,650 - $3,850
per night
5 night minimum stay
  • 3 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 8
5 night minimum stay
$1,495 - $3,650
per night
5 - 12 night minimum stay
  • 3 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 8
5 - 12 night minimum stay
$695 - $1,395
per night
4 - 5 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 6
4 - 5 night minimum stay
$1,095 - $1,750
per night
4 - 5 night minimum stay
  • 3 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 8
4 - 5 night minimum stay
$995 - $2,950
per night
4 - 12 night minimum stay
  • 3 BR,
  • 3 BA,
  • Sleeps 8
4 - 12 night minimum stay
$1,595 - $2,195
per night
4 - 5 night minimum stay
  • 4 BR,
  • 3 BA,
  • Sleeps 9
4 - 5 night minimum stay
$1,695 - $3,850
per night
5 - 12 night minimum stay
  • 3 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 8
5 - 12 night minimum stay
$995 - $1,495
per night
4 - 5 night minimum stay
  • 3 BR,
  • 3 BA,
  • Sleeps 8
4 - 5 night minimum stay
$1,195 - $3,050
per night
4 - 12 night minimum stay
  • 3 BR,
  • 3 BA,
  • Sleeps 6
4 - 12 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 6
5 night minimum stay
9 more choices from the HomeAway Network
$169 - $259
per night
3 night minimum stay
  • 1 BR,
  • 1 BA,
  • Sleeps 3
3 night minimum stay
(54)
$235 - $315
per night
3 - 10 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
3 - 10 night minimum stay
1 Review
  • 1 BR,
  • 2 BA,
  • Sleeps 4
  • 3 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 8
1 Review
  • 3 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 6
  • 3 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 8
Advertisement
 

Recent Wailea Reviews

Fantastic beach front vacation rental

5 of 5
We had an incredible trip and we highly recommend staying at Wailea Beach Villas. Thanks to Tropical Villa Vacations for their top notch service. Our villa easily accommodated 3 couples. Located in the heart of Wailea, we were able to walk to all the resorts and shops for dining and entertainment. We'll be back.
  • Submitted: Feb 12, 2015
  • Stayed: Feb 2015

Amazing vacation home!!

5 of 5
Amazing vacation rental!! Awesome beach views, great locations near a ton of restaurants and shopping. Our family had an amazing time during our Thanksgiving holiday.
  • Submitted: Jan 23, 2015
  • Stayed: Nov 2014