157 Results
Cancel Clear Filters Apply Filters

Price Per Week

$ $

Sleeps

Bedrooms

Bathrooms

Booking Options

Property Type

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

Booking Options

Location Type

Even More Filters

Features

Managed By

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

Wailea Beach Vacation Rentals with Online Payment(157)

157 Results
  • 2 BR,
  • 2 BA,
  • Sleeps 6
7 - 14 night min stay
(36)
$825 - $925
per night
5 - 7 night min stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
5 - 7 night min stay
(30)
$700 - $1,600
per night
5 - 10 night min stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
5 - 10 night min stay
(13)
  • 1 BR,
  • 2 BA,
  • Sleeps 4
5 - 14 night min stay
(11)
  • 2 BR,
  • 2 BA,
  • Sleeps 6
5 night min stay
(43)
  • 1 BR,
  • 2 BA,
  • Sleeps 4
6 - 7 night min stay
(38)
$395 - $1,495
per night
5 - 12 night min stay
  • 2 BR,
  • 2 BA,
  • Sleeps 7
5 - 12 night min stay
(4)
  • 2 BR,
  • 2 BA,
  • Sleeps 6
3 - 7 night min stay
(32)
  • 1 BR,
  • 2 BA,
  • Sleeps 5
4 night min stay
(19)
$1,195 - $2,295
per night
3 - 7 night min stay
  • 3 BR,
  • 3 BA,
  • Sleeps 8
3 - 7 night min stay
(21)
$189 - $269
per night
3 night min stay
  • 1 BR,
  • 1 BA,
  • Sleeps 2
3 night min stay
(56)
$225 - $375
per night
3 - 14 night min stay
  • 1 BR,
  • 2 BA,
  • Sleeps 5
3 - 14 night min stay
(7)
$750 - $1,950
per night
6 - 10 night min stay
  • 3 BR,
  • 3 BA,
  • Sleeps 6
6 - 10 night min stay
(6)
  • 1 BR,
  • 2 BA,
  • Sleeps 5
4 - 14 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)
$210 - $260
per night
5 - 7 night min stay
  • 1 BR,
  • 2 BA,
  • Sleeps 4
5 - 7 night min stay
(31)
  • 3 BR,
  • 3 BA,
  • Sleeps 6
(4)
  • 3 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 8
7 - 10 night min stay
(13)
  • 2 BR,
  • 2 BA,
  • Sleeps 5
7 night min stay
(7)
$750 - $1,950
per night
7 - 10 night min stay
  • 3 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 6
7 - 10 night min stay
(8)
  • 2 BR,
  • 2 BA,
  • Sleeps 6
4 - 14 night min stay
(5)
$525 - $725
per night
5 night min stay
  • 2 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 6
5 night min stay
(15)
$1,225 - $1,295
per week
7 night min stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
7 night min stay
(5)
$1,795 - $5,000
per night
4 - 10 night min stay
  • 3 BR,
  • 3 BA,
  • Sleeps 6
4 - 10 night min stay
(5)
$950 - $2,250
per night
5 - 14 night min stay
  • 3 BR,
  • 3 BA,
  • Sleeps 8
5 - 14 night min stay
(7)
$845 - $2,445
per night
1 - 7 night min stay
  • 4 BR,
  • 4 BA,
  • Sleeps 8
1 - 7 night min stay
2 Reviews
  • 1 BR,
  • 2 BA,
  • Sleeps 4
5 - 14 night min stay
(35)
  • 3 BR,
  • 2 BA,
  • Sleeps 6
5 - 7 night min stay
(16)
 View map Map
Advertisement
 

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

Great unit

5 of 5
Beautiful view and spacious condo. Great for our family of 5. Kids room has queen size bed and a single bed. Perfect for 3 children. Short walk to pool/beach. Would stay here again.
  • Submitted: Apr 28, 2015
  • Stayed: Mar 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