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 rentals, Kapalua condo rentals, Kihei rentals and Lahaina condo rentals.



Wailea Hawaii Vacation Rentals

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Wailea condo rental - Queen bed with high quality linens
1 Bedroom, Sleeps 4
  • Condo
  • 1 Bathroom
  • beach, near the ocean
  • swimming pool
Rates per property (USD)
$159 - $179/night
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Wailea condo rental - Good Morning Paradise in Wailea!
2 Bedrooms, Sleeps 6
  • Condo
  • 2 Bathrooms
  • near the ocean, resort
  • accept credit card
Rates per property (USD)
$225 - $250/night
View Property Details Contact the Owner
SPECIAL OFFER! Maui Oct -Mar Special $159/night October 1 - March 31
Wailea condo rental - Hawaiian Luxury Living room
2 Bedrooms, Sleeps 6
  • Condo
  • 2 Bathrooms
  • accept credit card
  • swimming pool
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SPECIAL OFFER! !!!!! FALL SPECIAL !!!!! 25-35% OFF September 22 - December 16
Wailea house rental - View from pool at sunset
4 Bedrooms, Sleeps 8
  • House
  • 3 Bathrooms, 1 Half Bath
  • near the ocean, resort
  • accept credit card
Rates per property (USD)
$1,250/night
$8,750/week
$30,000/month
View Property Details Contact the Owner
Wailea cottage rental - saline pool
2 Bedrooms, Sleeps 5
  • Cottage
  • 2 Bathrooms
  • near the ocean, rural
  • accept credit card
Rates per person (USD)
$2,020/week
View Property Details Contact the Owner
SPECIAL OFFER! Last Minute Vacation in Maui October 27 - November 8
Wailea condo rental - Beachside Pool and Pavilion Next to the Ocean
1 Bedroom, Sleeps 5
  • Condo
  • 2 Bathrooms
  • beach, resort
  • swimming pool
Rates per property (USD)
$200 - $275/night
$1,400 - $1,925/week
$5,100 - $7,350/month
View Property Details Contact the Owner
Wailea condo rental - Living/Dining Room
1 Bedroom, Sleeps 5
  • Condo
  • 1 Bathroom
  • near the ocean, resort
  • accept credit card
Rates per property (USD)
$150 - $170/night
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Wailea condo rental - Mokapu Beach - 1/4 mile away
2 Bedrooms, Sleeps 8
  • Condo
  • 2 Bathrooms
  • near the ocean, resort
  • accept credit card
Rates per property (USD)
$270 - $290/night
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Wailea condo rental - One of the pools on the lush landscape of Ekahi
1 Bedroom, Sleeps 4
  • Condo
  • 2 Bathrooms
  • beach, resort
  • swimming pool
Rates per property (USD)
$175 - $250/night
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Wailea condo rental
2 Bedrooms, Sleeps 4
  • Condo
  • 2 Bathrooms
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Wailea villa rental - View of ocean from our lanai taken July 2007
1 Bedroom, Sleeps 4
  • Villa
  • 2 Bathrooms
  • beach, near the ocean
  • accept credit card
Rates per property (USD)
$210 - $275/night
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Wailea condo rental - Private Living Area with Sofa/chaise
1 Bedroom, Sleeps 2
  • Condo
  • 1 Bathroom
  • near the ocean, resort
  • accept credit card
Rates per property (USD)
$150/night
$1,015 - $1,225/week
View Property Details Contact the Owner
Wailea condo rental
1 Bedroom, Sleeps 4
  • Condo
  • 2 Bathrooms
  • near the ocean, resort
  • swimming pool
Rates per property (USD)
$175 - $195/night
View Property Details Contact the Owner
Wailea condo rental
1 Bedroom, Sleeps 4
  • Condo
  • 1 Bathroom
  • beach, near the ocean
  • swimming pool
View Property Details Contact the Owner
Wailea condo rental - Beautiful View From The Lanai
2 Bedrooms, Sleeps 6
  • Condo
  • 2 Bathrooms
  • beach, near the ocean
  • swimming pool
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Wailea condo rental -  Breathtaking Oceanview
2 Bedrooms, Sleeps 6
  • Condo
  • 2 Bathrooms
  • beach, near the ocean
  • swimming pool
Rates per property (USD)
$309/night
$2,025/week
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Wailea condo rental
2 Bedrooms, Sleeps 6
  • Condo
  • 2 Bathrooms
  • swimming pool
  • air-conditioning
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Wailea condo rental - Tropically Manicured Grounds
1 Bedroom, Sleeps 4
  • Condo
  • 2 Bathrooms
  • beach, near the ocean
  • swimming pool
Rates per property (USD)
$279/night
$1,895/week
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Wailea condo rental
3 Bedrooms, Sleeps 8
  • Condo
  • 2 Bathrooms
  • beach
  • swimming pool
Rates per property (USD)
$349/night
$2,395/week
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Wailea condo rental
2 Bedrooms, Sleeps 6
  • Condo
  • 2 Bathrooms
  • beach
  • accept credit card
Rates per property (USD)
$375/night
$2,495/week
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Wailea condo rental - Ocean View from Lanai
2 Bedrooms, Sleeps 6
  • Condo
  • 2 Bathrooms
  • beach, near the ocean
  • accept credit card
Rates per property (USD)
$175 - $300/night
$1,225 - $2,100/week
$4,725 - $8,400/month
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Wailea condo rental - View from Lanai
2 Bedrooms, Sleeps 6
  • Condo
  • 2 Bathrooms
  • accept credit card
  • swimming pool
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Wailea condo rental - Beautiful Greenbelt And Ocean Views
2 Bedrooms, Sleeps 6
  • Condo
  • 2 Bathrooms
  • beach, resort
  • swimming pool
Rates per property (USD)
$385 - $440/night
$2,695 - $3,080/week
View Property Details Contact the Owner
Wailea condo rental - Dining Room Area
2 Bedrooms, Sleeps 6
  • Condo
  • 2 Bathrooms
  • near the ocean, village
  • swimming pool
Rates per property (USD)
$164/night
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Wailea condo rental - Spectacular actual sunset view from lanai
2 Bedrooms, Sleeps 6
  • Condo
  • 2 Bathrooms
  • near the ocean, resort
  • accept credit card
Rates per property (USD)
$160 - $300/night
$1,120 - $2,100/week
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Wailea condo rental - A nightly treat from your lanai at Wailea Ekolu!
1 Bedroom, Sleeps 4
  • Condo
  • 2 Bathrooms
  • beach, near the ocean
  • accept credit card
Rates per property (USD)
$225 - $300/night
$1,470 - $1,855/week
$6,626 - $7,950/month
View Property Details Contact the Owner
SPECIAL OFFER! Owner Direct Specials Available September 12 - June 30
Wailea villa rental - Ocean View from Lanai
4 Bedrooms, Sleeps 9
  • Villa
  • 3 Bathrooms
  • beach, waterfront
  • accept credit card
Rates per property (USD)
$1,200 - $3,150/night
$9,975 - $22,050/week
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Wailea condo rental - Queen size pillow top bed with high quality linens
Studio, Sleeps 2
  • Condo
  • 1 Bathroom
  • beach, near the ocean
  • swimming pool
Rates per property (USD)
$125 - $140/night
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Wailea condo rental - Oceanfront Elua Village with sandy Ulua Beach
1 Bedroom, Sleeps 4
  • Condo
  • 2 Bathrooms
  • beach, resort
  • accept credit card
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Wailea condo rental - Grand champion welcomes you.
2 Bedrooms, Sleeps 6
  • Condo
  • 2 Bathrooms
  • near the ocean, resort
  • accept credit card
Rates per property (USD)
$175 - $295/night
View Property Details Contact the Owner
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