92 Results
Cancel Clear Filters Apply Filters

Price Per Week

$ $

Sleeps

Bedrooms

Bathrooms

Booking Options

Property Type

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

Booking Options

Location Type

Even More Filters

Features

Managed By

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

Wailea Long Term Vacation Rentals with Online Payment(92)

92 Results
$99 - $125
per night
2 night minimum stay
  • Studio,
  • 1 BA,
  • Sleeps 4
2 night minimum stay
(65)
$1,350 - $1,650
per night
6 - 14 night minimum stay
  • 4 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 10
6 - 14 night minimum stay
(33)
$187 - $322
per night
6 - 7 night minimum stay
  • 1 BR,
  • 2 BA,
  • Sleeps 4
6 - 7 night minimum stay
(36)
$750 - $1,950
per night
7 - 10 night minimum stay
  • 3 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 8
7 - 10 night minimum stay
(13)
$795 - $1,850
per night
3 - 7 night minimum stay
  • 3 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 8
3 - 7 night minimum stay
(13)
  • 1 BR,
  • 2 BA,
  • Sleeps 4
3 - 7 night minimum stay
(23)
$225 - $295
per night
2 night minimum stay
  • 1 BR,
  • 2 BA,
  • Sleeps 2
2 night minimum stay
(23)
$750 - $1,950
per night
7 - 10 night minimum stay
  • 3 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 6
7 - 10 night minimum stay
(7)
$149 - $329
per night
1 - 14 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
1 - 14 night minimum stay
(6)
$165 - $299
per night
3 - 7 night minimum stay
  • 1 BR,
  • 2 BA,
  • Sleeps 4
3 - 7 night minimum stay
(5)
$169 - $329
per night
2 - 6 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
2 - 6 night minimum stay
(5)
  • 2 BR,
  • 2 BA,
  • Sleeps 5
7 night minimum stay
(5)
$525 - $725
per night
5 night minimum stay
  • 2 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 6
5 night minimum stay
(11)
  • 2 BR,
  • 2 BA,
  • Sleeps 6
5 - 7 night minimum stay
(5)
$350 - $500
per night
1 - 5 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
1 - 5 night minimum stay
(11)
  • 1 BR,
  • 1 BA,
  • Sleeps 4
5 - 14 night minimum stay
(22)
$185 - $220
per night
5 - 7 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 5
5 - 7 night minimum stay
(6)
$275 - $350
per night
4 night minimum stay
  • 1 BR,
  • 2 BA,
  • Sleeps 5
4 night minimum stay
(18)
$189 - $489
per night
5 - 7 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
5 - 7 night minimum stay
(5)
$275 - $450
per night
3 - 14 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
3 - 14 night minimum stay
2 Reviews
$155 - $225
per night
5 - 7 night minimum stay
  • 1 BR,
  • 2 BA,
  • Sleeps 4
5 - 7 night minimum stay
(5)
$1,225 - $1,295
per week
7 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
7 night minimum stay
(4)
$129 - $249
per night
3 - 5 night minimum stay
  • 1 BR,
  • 2 BA,
  • Sleeps 2
3 - 5 night minimum stay
(5)
  • 2 BR,
  • 2 BA,
  • Sleeps 8
3 night minimum stay
(5)
  • 2 BR,
  • 2 BA,
  • Sleeps 6
5 - 14 night minimum stay
(34)
$400 - $450
per night
5 - 7 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 6
5 - 7 night minimum stay
(16)
$206 - $360
per night
2 - 4 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
2 - 4 night minimum stay
$159 - $289
per night
6 - 10 night minimum stay
  • 1 BR,
  • 2 BA,
  • Sleeps 4
6 - 10 night minimum stay
1 Review
  • 2 BR,
  • 2 BA,
  • Sleeps 5
3 night minimum stay
(14)
$175 - $225
per night
6 night minimum stay
  • 1 BR,
  • 2 BA,
  • Sleeps 4
6 night minimum stay
(6)
Advertisement
 

Recent Wailea Reviews

A LITTLE PIECE OF PARADISE

5 of 5
What a lovely piece of paradise Maui Joy Villa is! On short notice, to our great fortune, we were able to stay at Maui Joy Villa from Jan 1-10/15. We had plenty of room for 2 couples, 2 youngsters and a baby. It was perfect for our two families, complete with full kitchen, 2 bedrooms, 2 bathrooms, a futon for the kids; and a wonderful lanai adjacent to the spectacular pool overlooking the magnificent ocean view. We enjoyed many home cooked meals right on the lanai watching the Maui sunset. The location, only minutes from shopping, restaurants, and the beach was perfect. The hospitality our hostess extended was not only beyond our expectations, but we found her giving and caring nature a real pleasure. She went out of her way to ensure we had everything we needed. Needless to say, we would definitely book again without hesitation and look forward to returning again some day - hopefully next year!
  • Submitted: Jan 21, 2015
  • Stayed: Jan 2015

Margie

5 of 5
This was now our 4th stay in this outstanding condo! We had a family reunion with members coming from as far away as Rhode Island, as well as Southern California and Montana. Two of our sons stayed with us while others stayed elsewhere...but we had the BEST place in all of Wailea and Kiehi!! Love the two master suites as well as the comfortable beds, outstanding kitchen and amazing ocean views! The owner keeps things updated and has just put in new lanai tiles and plantings! This condo is immaculate and comfortable and has the best location to pools and the beach! Hope we can return a 5th time!
  • Submitted: Dec 22, 2014
  • Stayed: Nov 2014

Maui Excellence

5 of 5
I cannot say enough about our stay in this beautiful condo. This was our 4th trip to Maui. The first two trips we stayed at the Grand Wailea and the last trip we stayed at the Wailea Marriott. We wanted to stay in a condo for our next trip and we hit the jackpot! My husband describes me as very high maintenance; and this condo met all my expectations! The condo is decorated and furnished with great style and elegance. The condo has everything you could need from kitchen supplies with everything you would need to have picnic at the beach, beach chairs, umbrellas and even a few sun hats! The bathrooms were very well stocked and even had high quality blow dryers and a curling iron! The condo owner was fabulous to work with from the first inquiry I had last year when we were deciding to book until we checked out. You will have no regrets on booking this condo! It is truly Maui excellence! Mahalo!
  • Submitted: Nov 21, 2014
  • Stayed: Nov 2014