80 Results
Cancel Clear Filters Apply Filters

Price Per Week

$ $

Sleeps

Bedrooms

Bathrooms

Booking Options

Property Type

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

Booking Options

Location Type

Even More Filters

Features

Managed By

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

Wailea Villa Rentals(80)

80 Results
$700 - $1,600
per night
5 - 10 night min stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
5 - 10 night min stay
(13)
  • 2 BR,
  • 2 BA,
  • Sleeps 6
3 - 7 night min stay
(32)
$1,195 - $2,295
per night
3 - 7 night min stay
  • 3 BR,
  • 3 BA,
  • Sleeps 8
3 - 7 night min stay
(21)
$250 - $355
per night
5 night min stay
  • 2 BR,
  • 2 BA,
  • Sleeps 5
5 night min stay
(16)
$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 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)
  • 2 BR,
  • 2 BA,
  • Sleeps 6
3 - 10 night min stay
(6)
  • 4 BR,
  • 3 BA,
  • Sleeps 10
5 - 7 night min stay
$1,995 - $4,350
per night
4 - 7 night min stay
  • 3 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 8
4 - 7 night min stay
1 Review
$1,695 - $2,500
per night
4 - 5 night min stay
  • 3 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 8
4 - 5 night min stay
$1,650 - $3,950
per night
5 - 12 night min stay
  • 4 BR,
  • 3 BA,
  • Sleeps 8
5 - 12 night min stay
  • 3 BR,
  • 3 BA,
  • Sleeps 4
5 night min stay
  • 3 BR,
  • 3 BA,
  • Sleeps 8
5 night min stay
 View map Map
Advertisement
 

Recent Wailea Reviews

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

lovely place but...

4 of 5
We traveled with 3 kids age 14, 10 and 8 and grandma. The interior was gorgeous and outfitted with the finest cookware and furnishings. It would have been my absolute favorite all time vacation rental except that the beautiful pool which was situated on the ocean was not open to children. This was a deal breaker for us as we had to leave the property daily. The beach was nice but crowded and we ended up paying a fortune to use the pool the grand wailea...something we did not budget given he cost of this unit. The children's pool was just ok, situated way up on top of the property, with no ocean view and buildings all around. I could have swam in this pool at home. The policy would have been understandable if the no kid rule was for certain hours during the day and not all the time. Anyhow, go...it's beautiful....but don't go with kids.
  • Submitted: Apr 8, 2015
  • Stayed: Mar 2015

A perfect vacation

5 of 5
The property was in great condition with everything we needed on arrival. The managers and greeters were very accommodating. We will be coming back!!
  • Submitted: Apr 5, 2015
  • Stayed: Mar 2015