Cancel Clear Filters Apply Filters

Price Per Week

$ $

Sleeps

Bedrooms

Bathrooms

Booking Options

Property Type

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

Location Type

Even More Filters

Features

Managed By

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

Wailea Vacation Rentals(519)

519 Results
$105 - $145
per night
5 - 10 night minimum stay
  • Studio,
  • 1 BA,
  • Sleeps 2
5 - 10 night minimum stay
(35)
  • 1 BR,
  • 1 BA,
  • Sleeps 4
4 - 5 night minimum stay
(10)
$125 - $150
per night
2 night minimum stay
  • 1 BR,
  • 1 BA,
  • Sleeps 4
2 night minimum stay
(51)
$99 - $125
per night
2 night minimum stay
  • Studio,
  • 1 BA,
  • Sleeps 4
2 night minimum stay
(64)
  • 1 BR,
  • 2 BA,
  • Sleeps 4
5 - 14 night minimum stay
(11)
$125 - $189
per night
3 - 14 night minimum stay
  • 1 BR,
  • 1 BA,
  • Sleeps 2
3 - 14 night minimum stay
(35)
$195 - $275
per night
5 - 14 night minimum stay
  • 1 BR,
  • 2 BA,
  • Sleeps 4
5 - 14 night minimum stay
(10)
$187 - $312
per night
7 - 10 night minimum stay
  • 1 BR,
  • 2 BA,
  • Sleeps 4
7 - 10 night minimum stay
(33)
$695 - $1,850
per night
2 - 7 night minimum stay
  • 3 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 10
2 - 7 night minimum stay
(14)
$225 - $250
per night
2 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 8
2 night minimum stay
(16)
$750 - $1,950
per night
6 - 10 night minimum stay
  • 3 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 8
6 - 10 night minimum stay
(13)
$240 - $375
per night
6 - 14 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
6 - 14 night minimum stay
(28)
$750 - $1,950
per night
6 - 10 night minimum stay
  • 3 BR,
  • 3 BA,
  • Sleeps 6
6 - 10 night minimum stay
(6)
$750 - $1,895
per night
7 - 10 night minimum stay
  • 3 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 8
7 - 10 night minimum stay
(13)
  • 1 BR,
  • 2 BA,
  • Sleeps 4
2 - 7 night minimum stay
(22)
$129 - $279
per night
2 - 7 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 5
2 - 7 night minimum stay
(16)
$195 - $295
per night
2 - 5 night minimum stay
  • 1 BR,
  • 2 BA,
  • Sleeps 2
2 - 5 night minimum stay
(23)
$260 - $280
per night
5 night minimum stay
  • 1 BR,
  • 2 BA,
  • Sleeps 4
5 night minimum stay
(21)
$250 - $275
per night
5 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 5
5 night minimum stay
(12)
  • 2 BR,
  • 2 BA,
  • Sleeps 6
3 - 5 night minimum stay
(34)
  • 1 BR,
  • 2 BA,
  • Sleeps 5
4 - 7 night minimum stay
(10)
$2,800 - $4,200
per week
7 - 14 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
7 - 14 night minimum stay
(11)
$165 - $225
per night
5 - 7 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
5 - 7 night minimum stay
(10)
  • 3 BR,
  • 2 BA,
  • Sleeps 10
5 night minimum stay
(10)
  • 2 BR,
  • 2 BA,
  • Sleeps 6
6 - 14 night minimum stay
(7)
  • 2 BR,
  • 2 BA,
  • Sleeps 6
3 - 7 night minimum stay
(32)
$205 - $320
per night
4 - 14 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 4
4 - 14 night minimum stay
(9)
$149 - $299
per night
4 - 7 night minimum stay
  • 1 BR,
  • 2 BA,
  • Sleeps 4
4 - 7 night minimum stay
(5)
$240 - $375
per night
5 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
5 night minimum stay
(42)
Advertisement
 

Recent Wailea Reviews

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

Clean, quiet and comfortable condo

5 of 5
We had a wonderful time in Maui and enjoyed your condo very much. The location was perfect - the view of the ocean and Molikini from the lanai was beautiful - as were the grounds and peace and quiet. We really appreciated having the beach chairs, towels, umbrella and cooler to use - and the safe and lots of extra hangers was great! The distance to the beach may prove to be a longer walk than some may handle - but there is plenty of parking if you want to go there - and some of the nicest beaches and walkways we've seen on the islands. We will definitely suggest your condo to anyone we know visiting Maui. Much thanks for the wine and Aloha!
  • Submitted: Aug 11, 2014
  • Stayed: May 2014

Exceeded our Expectations!

5 of 5
Fabulous!! This is certainly a wonderful villa that exceeded our expectations....beyond what the photos reflect!! We had an amazing family vacation celebrating our daughter's college graduation. The villa worked great for our family of 5 which includes 3 college-aged students. The villa was extremely clean, well equipped with everything we needed, the staff so very nice and helpful and the grounds just beautiful. The complex is very quiet and we enjoyed sitting on the lanai, relaxing by the pools and the beach. These villas are well located with shops and great restaurants just a few minutes walk away. Helen was very prompt and helpful in answering all of our questions. This villa is certainly one we would like to vacation in again!! Thank you for sharing your home with us.
  • Submitted: Jun 9, 2014
  • Stayed: May 2014