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Wailea Rentals with Online Payment(10)

10 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
(6)
$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)
$97 - $515
per night
2 - 10 night min stay
  • 1 BR,
  • 1 BA,
  • Sleeps 2
2 - 10 night min stay
$342 - $625
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)
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Recent Wailea Reviews

The BEST family vacation...EVER!

5 of 5
My name is Emma and I am 14 1/2 months old. My grandparents (Mama G. & Papa G.) treated me, my parents, my auntie, and my auntie's boyfriend to a trip to Maui. We stayed at the most beautiful beach house I have ever seen. Mama G. said Janna was a most hospitable and accomodating host, and Janna made sure we had whatever we needed for a perfect, relaxing vacation. My parents loved playing with me in the pool, where I spent most of each day when I wasn't napping. We took so many pictures of all of us having the best time. The house was stocked with everything we could possibly want, from beach towels to large screen TVs. I especially liked playing with the sand bucket and other beach toys. Everyone agreed that the house, location, hospitality and the many amenities made for the best, most relaxing, and fun family vacation. Mama G. and Papa G. plan to return to Ocean Bliss one day. I hope they take me with them.
  • Submitted: May 11, 2015
  • Stayed: Apr 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

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