9 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

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

Wailea Villa Rentals with Online Payment(9)

9 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)
$342 - $599
per night
5 - 14 night min stay
  • 2 BR,
  • 2 BA,
  • Sleeps 5
5 - 14 night min stay
  • 3 BR,
  • 3 BA,
  • Sleeps 7
(10)
 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

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

A Fabulous Home Away from Home

5 of 5
We rented this property for two weeks in December 2014 and our family of 5 met up from all parts of the globe to spend the holiday season together. It was everything we had hoped for and more! Eric checked us in and ensured that all our queries were answered before we kicked off what was an amazing vacation in an amazing home and location. Our days started with early morning gym visits, followed by energizing walks all through Wailea with a stop off at Honolulu Coffee before we went back home to get ready for the day. The beach was just across the street so it was easy to pack a cooler and head out for the day. Days ended with a dip in the pool and a soak in the jacuzzi. The villa itself is beautiful. Well equipped and beautifully decorated- we lived in luxury while there. The kitchen was exceptionally well equipped and we always cooked a meal together at the end of the day and enjoyed dinner on the balcony. Beach chairs, cooler, snorkel gear,picnic basket, beach toys and towels...everything was there. We are a family of 5 adults and the home was more than spacious enough for us all. It truly is a beautiful home away from home. We really enjoyed ourselves and would highly recommend this home.
  • Submitted: Jan 10, 2015
  • Stayed: Dec 2014