Find Your Way in Wailea

Wailea Vacation Rentals, Wailea Chalets, Condos, Cottages, Villas, Houses & Estates

Plan your next vacation in Wailea, a lovely little town located on Maui’s southern coast. Cramped hotel rooms are fine if you don’t like space or privacy - but what if you’re searching for something more comfortable – like your own home away from home in Hawaii? Consider staying in a vacation rental and experience the island like a local! Types of vacation homes run the gamut from cozy condos to palatial estates and may accommodate any size group, during any season.

Wailea is home to some of the most beautiful beaches in Hawaii, and its high-end resorts lend an air of exclusivity to the area. Stay in a house rental and blend right in.Get wet and take a ride on some jet skis or a banana boat, or just relax on the warm sand while the waves gently crash ashore. If the smell of commerce excites you, make the short trip to The Shops at Wailea. The upscale retail stores and delicious restaurants will make you feel as if you’ve stepped into a shopping paradise.

One benefit of staying in a beach rental is that you can cook meals in your own fully-equipped kitchen. Those who visit Wailea for the deep sea fishing will especially enjoy the convenience of grilling what you catch at home. Preparing food at home is also a great way to save money to spend on other attractions, like the local art galleries and souvenirs. Or, visit one of the local eateries in town – they range from budget seafood shacks to five-star Pacific Rim restaurants. You won’t go hungry or get bored when you vacation in Wailea, so book your vacation home today!

Find more Maui vacation rentals by taking a look at Kaanapali condo rentals, Kahana condos for rent, Kapalua condo rentals, Kihei rentals and Lahaina condo rentals.


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Wailea: Condos, Villas & More(1,006)

1,006 Results
3 - 10 night minimum stay
  • Studio,
  • 1 BA,
  • Sleeps 2
#33820vb
(78)
3 - 14 night minimum stay
  • 1 BR,
  • 1 BA,
  • Sleeps 2
#315090
(72)
2 night minimum stay
  • Studio,
  • Sleeps 4
#188831
(165)
2 night minimum stay
  • 1 BR,
  • Sleeps 4
#188977
(147)
5 night minimum stay
  • 1 BR,
  • 2 BA,
  • Sleeps 4
#212578
(30)
5 - 10 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
#351737
(34)
6 - 14 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
#3165441
(20)
2 night minimum stay
  • 1 BR,
  • 2 BA,
  • Sleeps 4
#457082vb
(17)
1 - 7 night minimum stay
  • 3 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 8
#441129vb
(10)
2 night minimum stay
  • 1 BR,
  • 2 BA,
  • Sleeps 2
#3564788
(12)
2 - 14 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 5
#455674vb
(13)
2 night minimum stay
  • 2 BR,
  • Sleeps 8
#188978
(24)
3 - 7 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
#275052
(79)
3 - 7 night minimum stay
  • 3 BR,
  • 3 BA,
  • Sleeps 8
#370688
(45)
5 - 14 night minimum stay
  • 2 BR,
  • Sleeps 7
#5224vb
(20)
6 - 10 night minimum stay
  • 3 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 8
#272495
(15)
6 - 10 night minimum stay
  • 3 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 6
#272496
(12)
5 - 7 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 6
#283881
(21)
4 - 14 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
#505709vb
(4)
5 - 10 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 4
#485272vb
(7)
7 - 14 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 5
#186208
(34)
$650 - $1,950
per night
6 - 10 night minimum stay
  • 3 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 6
#992675
(6)
3 - 7 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
#497748vb
(10)
3 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 8
#482722vb
(3)
4 - 14 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 6
#322096vb
(25)
  • 3 BR,
  • 3 BA,
  • Sleeps 6
#3498378
(4)
5 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 5
#212306
(63)
5 night minimum stay
  • 2 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 6
#3506190
(9)
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