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Wailea Long Term Vacation Rentals(218)

218 Results
$110 - $135
per night
2 night min stay
  • Studio,
  • 1 BA,
  • Sleeps 4
2 night min stay
(68)
  • 2 BR,
  • 2 BA,
  • Sleeps 6
7 - 14 night min stay
(36)
$1,350 - $1,650
per night
6 - 14 night min stay
  • 4 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 10
6 - 14 night min stay
(37)
  • 1 BR,
  • 2 BA,
  • Sleeps 4
6 - 7 night min stay
(38)
  • 1 BR,
  • 2 BA,
  • Sleeps 5
4 night min stay
(19)
$189 - $269
per night
3 night min stay
  • 1 BR,
  • 1 BA,
  • Sleeps 2
3 night min stay
(56)
$795 - $1,850
per night
3 - 10 night min stay
  • 3 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 8
3 - 10 night min stay
(16)
$250 - $400
per night
3 - 7 night min stay
  • 1 BR,
  • 2 BA,
  • Sleeps 4
3 - 7 night min stay
(26)
$225 - $295
per night
2 night min stay
  • 1 BR,
  • 2 BA,
  • Sleeps 2
2 night min stay
(28)
  • 3 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 8
7 - 10 night min stay
(13)
  • 2 BR,
  • 2 BA,
  • Sleeps 6
5 - 7 night min stay
(9)
  • 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)
$525 - $725
per night
5 night min stay
  • 2 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 6
5 night min stay
(15)
$165 - $240
per night
5 - 7 night min stay
  • 2 BR,
  • 2 BA,
  • Sleeps 5
5 - 7 night min stay
(7)
$1,225 - $1,295
per week
7 night min stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
7 night min stay
(5)
  • 1 BR,
  • 1 BA,
  • Sleeps 3
5 - 14 night min stay
(24)
  • 1 BR,
  • 2 BA,
  • Sleeps 4
5 - 7 night min stay
(8)
$189 - $489
per night
5 - 7 night min stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
5 - 7 night min stay
(6)
$300 - $450
per night
3 - 14 night min stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
3 - 14 night min stay
(4)
$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)
$159 - $289
per night
6 - 10 night min stay
  • 1 BR,
  • 2 BA,
  • Sleeps 4
6 - 10 night min stay
(3)
  • 2 BR,
  • 2 BA,
  • Sleeps 8
3 night min stay
(7)
$503 - $903
per night
2 - 5 night min stay
  • 7 BR,
  • 3 BA,
  • Sleeps 22
2 - 5 night min stay
(16)
  • 2 BR,
  • 2 BA,
  • Sleeps 5
3 - 14 night min stay
(44)
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Recent Wailea Reviews

Spacious Condo in prime location.

5 of 5
We really enjoyed our stay at this Wailea condo. We were a party of 4 adults and 1 child and we fit comfortably in this spacious unit. The unit is nicely renovated and situated on the second floor. The lanai is large and faces a green space providing good privacy. The location is our favorite so far with beaches and food a few minutes away driving. The mall near by offered a great place to walk to for some afternoon ice cream or coffee. If you get a chance, visit Horhitos taco truck in Kihei for some amazing tacos and be sure to stop by Chez Meme Bistro in Kihei for some outstanding breakfast. The owner was very helpful and responded promptly to questions I had about the unit and the island. We would gladly stay here again. Thanks!
  • Submitted: May 18, 2015
  • Stayed: Apr 2015

King of Your Own Castle

5 of 5
Do Not Pass This One Up! This charming cottage has it all. From the moment you drive up, you feel transported to a lovely English cottage in the forest of Maui. Beautiful trees, flowers and bird songs. Lovely patio with BBQ and a large hot tub. It even has it's own MOTE! WOW!!! The mote trickles to a sitting pool for two for those days when you need to cool off. The owners Stewart and Andrea have thought of everything. There was nothing we wanted for. Do nothing but buy your meat, potatoes and a bottle of wine. The pictures don't do the cottage justice. The decor is lovely and the furniture is comfy, the beds are incredibly comfortable, clean clean clean kitchen, floors and bathrooms. And NO BUGS!!! Yea! Cable TV, WiFi, BluRay/DVD, surround sound for those techie folks and a nice book selection for us quiet types. All of this is and more is situated behind a private security gate. We didn't want to leave. Stewart and Andrea couldn't have been sweeter host. I know we've made new friends for life. We've already made our next reservation. Mahalo to you both!
  • Submitted: May 12, 2015
  • Stayed: May 2015

Wonderful Relaxing Retreat

5 of 5
This was our first trip to Maui and we couldn't have picked a better location. The condo is so nicely decorated and well stocked with everything you need. We throughly enjoyed our time in Maui. The condo has great beach options within a short drive or walk. We found some great restaurants nearby, Monkey Pod Kitchen was our favorite, you have to try their strawberry cream pie. I don't think we could have found a better location to explore Maui from. We look forward to returning.
  • Submitted: May 11, 2015
  • Stayed: Apr 2015