81 Results
Cancel Clear Filters Apply Filters

Price Per Week

$ $

Sleeps

Bedrooms

Bathrooms

Booking Options

Property Type

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

Booking Options

Location Type

Even More Filters

Features

Managed By

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

Wailea Rentals(81)

81 Results
$700 - $1,600
per night
5 - 10 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
5 - 10 night minimum stay
(13)
  • 2 BR,
  • 2 BA,
  • Sleeps 6
3 - 7 night minimum stay
(32)
$1,195 - $2,295
per night
3 - 7 night minimum stay
  • 3 BR,
  • 3 BA,
  • Sleeps 8
3 - 7 night minimum stay
(20)
$250 - $355
per night
5 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 5
5 night minimum stay
(13)
$1,695 - $5,000
per night
4 - 14 night minimum stay
  • 3 BR,
  • 4 BA,
  • Sleeps 6
4 - 14 night minimum stay
(4)
$750 - $1,950
per night
7 - 10 night minimum stay
  • 3 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 8
7 - 10 night minimum stay
(3)
$1,795 - $5,000
per night
4 - 10 night minimum stay
  • 3 BR,
  • 3 BA,
  • Sleeps 6
4 - 10 night minimum stay
1 Review
$1,188 - $3,388
per night
3 - 7 night minimum stay
  • 3 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 8
3 - 7 night minimum stay
(6)
$575 - $1,150
per night
3 - 10 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
3 - 10 night minimum stay
(6)
  • 3 BR,
  • 3 BA,
  • Sleeps 8
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
$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
$1,595 - $2,195
per night
4 - 5 night minimum stay
  • 4 BR,
  • 3 BA,
  • Sleeps 9
4 - 5 night minimum stay
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

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

Best place ever!

5 of 5
We just returned from a week at this lovely home. Best place ever! The photos can't convey the beauty of this penthouse. Each morning, we'd rise before the sun and sit on the lanai and watch the water shimmer with streaks of orange. The whales gave us a front row show! The palm trees, the fragrant flowers, all were a wonderful way to start our day. The property location is perfect and the grounds are amazing. We walked the Wailea beach area and while there are some top-notch hotels nearby, my husband and I agreed--we would only come back to the Wailea Beach Villas for their beauty, serenity and the luxury of this unit. Simply amazing! Helen was so gracious and helpful leading up to our stay. A very professional contact and everything went smoothly. Can't wait to come back one day!
  • Submitted: Feb 1, 2015
  • Stayed: Jan 2015