Cancel Clear Filters Apply Filters

Price Per Week

$ $

Sleeps

Bedrooms

Bathrooms

Booking Options

Property Type

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

Location Type

Even More Filters

Features

Managed By

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

Wailea Long Term Vacation Rentals(172)

172 Results
$99 - $125
per night
2 night minimum stay
  • Studio,
  • 1 BA,
  • Sleeps 4
2 night minimum stay
(64)
$187 - $312
per night
7 - 10 night minimum stay
  • 1 BR,
  • 2 BA,
  • Sleeps 4
7 - 10 night minimum stay
(33)
$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)
$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)
$149 - $299
per night
4 - 7 night minimum stay
  • 1 BR,
  • 2 BA,
  • Sleeps 4
4 - 7 night minimum stay
(5)
$149 - $329
per night
1 - 14 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
1 - 14 night minimum stay
(5)
$139 - $329
per night
3 - 7 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
3 - 7 night minimum stay
(4)
$185 - $225
per night
5 - 7 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 5
5 - 7 night minimum stay
(6)
$350 - $500
per night
1 - 5 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
1 - 5 night minimum stay
(10)
$995 - $2,093
per week
7 - 14 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 5
7 - 14 night minimum stay
(3)
$155 - $225
per night
5 - 7 night minimum stay
  • 1 BR,
  • 2 BA,
  • Sleeps 4
5 - 7 night minimum stay
(5)
  • 2 BR,
  • 2 BA,
  • Sleeps 6
5 - 14 night minimum stay
(33)
$1,575 - $2,730
per week
7 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
7 night minimum stay
1 Review
  • 2 BR,
  • 2 BA,
  • Sleeps 6
7 night minimum stay
(4)
  • 1 BR,
  • 1 BA,
  • Sleeps 4
5 - 14 night minimum stay
(22)
$500 - $675
per night
5 night minimum stay
  • 2 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 6
5 night minimum stay
(11)
$129 - $289
per night
3 - 5 night minimum stay
  • 1 BR,
  • 2 BA,
  • Sleeps 2
3 - 5 night minimum stay
(4)
$709 - $903
per night
4 night minimum stay
  • 7 BR,
  • 3 BA,
  • Sleeps 22
4 night minimum stay
(16)
  • 2 BR,
  • 2 BA,
  • Sleeps 5
7 - 14 night minimum stay
(39)
  • 2 BR,
  • 2 BA,
  • Sleeps 8
3 night minimum stay
(5)
  • 1 BR,
  • 2 BA,
  • Sleeps 5
4 night minimum stay
(18)
  • 2 BR,
  • 2 BA,
  • Sleeps 6
3 - 10 night minimum stay
(64)
$250 - $295
per night
5 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 4
5 night minimum stay
(13)
  • 2 BR,
  • 2 BA,
  • Sleeps 6
4 - 14 night minimum stay
(18)
$400 - $550
per night
5 - 7 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 6
5 - 7 night minimum stay
(16)
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

Rent a piece of Paradise

4 of 5
The grounds at the complex are lush and tropical and well maintained. The patio overlooks a tropical jungle. There are many birds and we enjoyed listening to them in the morning. The home is very inviting, nicely decorated with granite countertops throughout and tropical pictures and artwork. There are three HDTVs which is helpful if the family has different viewing tastes. There are ceiling fans and air conditioner if needed. The owners thought of everything to make our stay enjoyable. There is anything you would need for a trip to the beach: snorkel gear, beach chairs, umbrella and towels. There is a very nice beach just one mile away with free parking. It has a nice little reef with a good variety of fish. This is a very good location which is very close to shopping, dining and beaches. There are many restaurants in the area from five stars to casual. The owners have a book with some recommendations. We would definitely stay there again.
  • Submitted: Nov 3, 2014
  • Stayed: Oct 2014

Outstanding Stay

5 of 5
Our family of four, with two "tween" girls, really enjoyed our trip and this property. The condo was clean, well located, and nested in a beautiful setting with a short 5 minute walk to the pool and the beach. A real gem!
  • Submitted: Sep 30, 2014
  • Stayed: Jun 2014