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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Architect's Own Estate in South Maui

— Property 159525
Wailea house rental - Ocean view, beach entry at pool / spa
4 Bedrooms, Sleeps 10,
House, 3 Bathrooms, 1 Half Bath, near the ocean, resort, pool
Rates - per property (USD)
$1,250 - $1,800/night
Calendar Updated Nov 20 2009

Property Review

From our first views of the property to those last glances at the ocean, our family vacation was perfect in every way. The house is spacious enough for each family member to have his or her own...
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Deluxe Oceanview Wailea Condo

— Property 192613
Wailea condo rental - Breathtaking Oceanview
2 Bedrooms, Sleeps 6,
Condo, 2 Bathrooms, beach, near the ocean, pool
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Luxury Beachfront Wailea Condo

— Property 152894
Wailea condo rental
2 Bedrooms, Sleeps 6,
Condo, 2 Bathrooms, beach, air-conditioning
Rates - per property (USD)
$395/night
$2,750/week
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Wailea villa rental - View from Makai Lanai/Spectacular Maui Sunset
3 Bedrooms, Sleeps 8,
Villa, 3 Bathrooms, beach, resort, daily maid service
Rates - per property (USD)
$895 - $1,995/night
Calendar Updated Nov 19 2009

Property Review

This place took my breath away when I first entered. Both the inside as well as the outside was so beautiful. The views from the lanai were awesome, and having my morning coffee on the lanai...
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Wailea Condo with Fabulous Ocean View

— Property 160004
Wailea condo rental - Ocean view from unit deck
1 Bedroom, Sleeps 4,
Condo, 2 Bathrooms, near the ocean, resort, balcony
Rates - per property (USD)
$219/night
Accepts Online Payments
Calendar Updated Nov 19 2009

Property Review

We rented this unit for our family that was staying with us from California. We Loved it the views were breathtaking and the unit was 5 Star in feel and design. We will definitely use it again.
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Special Discounts at Luxury Wailea Condo Rental in Maui

— Property 234928
Wailea condo rental - Wailea Grand Champions 35
2 Bedrooms, Sleeps 4,
Condo, 2 Bathrooms, near the ocean, resort, pool
Rates - per property (USD)
$185 - $280/night
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Wailea condo rental - Amazing sunset from our lanai...no charge!
2 Bedrooms, Sleeps 6,
Condo, 2 Bathrooms, near the ocean, tennis court
Rates - per property (USD)
$225 - $299/night
$1,645 - $2,093/week
Calendar Updated Nov 19 2009

Property Review

Jackie and Greg, What an amazing time we had. Your place is phenomenal...and so user friendly!!! From the flat screen TV's, ipod player/charger, Tempur-pedic beds, spacious master...
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Enjoy Dinner and Wine on the Beach for a Maui Sunset Treat!

— Property 188896
Wailea condo rental - Beach Pool
2 Bedrooms, Sleeps 8,
Condo, 2 Bathrooms, beach, village, tennis court
Rates - per property (USD)
$365 - $395/night
$2,555 - $2,765/week
Calendar Updated Nov 19 2009

Property Review

This location is the PERFECT blend of access and hideaway. This unit makes you feel like you're on your own estate. Great sunset view over the lawn from the patio. Steps from the pool or the...
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More Than One Life Has Been Changed by a Visit to Maui

— Property 147336
Wailea condo rental - Big Beach, a 6 minute drive from the condo
1 Bedroom, Sleeps 2,
Condo, 2 Bathrooms, near the ocean, resort, pool
Rates - per property (USD)
$160 - $170/night
$1,050 - $1,200/week
Calendar Updated Nov 20 2009

Property Review

Dear Richard, We knew the minute we pulled into our own parking space at the condo that it was going to be GREAT! Everything was just as you described it and the pictures you have don't do it...
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Elua Village - Ulua Beach Utopia - 1703

— Property 7023935h
Wailea condo rental
2 Bedrooms, Sleeps 6,
Condo, 2 Bathrooms, adventure, air-conditioning
Rates - per condo (USD)
$545 - $850/night
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Wailea Ekahi 33D

— Property 7024510h
Wailea condo rental - View from Lanai
1 Bedroom, Sleeps 2,
Condo, 2 Bathrooms, air-conditioning, beach
Rates - per condo (USD)
$1,925 - $2,240/week
$7,590 - $9,298/month
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Palms at Wailea #1606

— Property 7024504h
Wailea condo rental - Lanai
2 Bedrooms, Sleeps 6,
Condo, 2 Bathrooms, balcony, clothes dryer
Rates - per condo (USD)
$245 - $270/night
$1,540 - $1,715/week
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Wailea Ekahi 39D

— Property 7024511h
Wailea condo rental
1 Bedroom, Sleeps 2,
Condo, 1 Bathroom, air-conditioning, beach
Rates - per condo (USD)
$1,925 - $2,240/week
$7,590 - $9,298/month
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Grand Champions #35

— Property 7024505h
Wailea condo rental - Lanai View
2 Bedrooms, Sleeps 4,
Condo, 2 Bathrooms, air-conditioning, balcony
Rates - per condo (USD)
$255 - $280/night
$1,610 - $1,785/week
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Ho'olei

— Property 7024519h
Wailea condo rental
3 Bedrooms, Sleeps 8,
Condo, 3 Bathrooms, 1 Half Bath, air-conditioning, beach
Rates - per condo (USD)
$675/night
$4,725 - $14,875/week
$20,250 - $38,492/month
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Wailea Beach Villas

— Property 7024518h
Wailea condo rental
2 Bedrooms, Sleeps 6,
Condo, 2 Bathrooms, air-conditioning, beach
Rates - per condo (USD)
$595 - $675/night
$4,165 - $4,865/week
$18,750 - $30,266/month
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Azure Dreams at Makena Surf

— Property 7024517h
Wailea condo rental
2 Bedrooms, Sleeps 6,
Condo, 2 Bathrooms, air-conditioning, beach
Rates - per condo (USD)
$3,815 - $4,515/week
$16,350 - $21,179/month
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Luxury Grand Champions Villa - on 7th Fairway- Blue Golf Course

— Property 134937
Wailea condo rental - Living Room and Dining area
2 Bedrooms, Sleeps 6,
Condo, 2 Bathrooms, near the ocean, resort, pool
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Wailea Ekolu #501

— Property 7024503h
Wailea condo rental
2 Bedrooms, Sleeps 4,
Condo, 2 Bathrooms, clothes dryer, DVD
Rates - per condo (USD)
$245 - $270/night
$1,540 - $1,715/week
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Grand Champions #186

— Property 7024506h
Wailea condo rental
2 Bedrooms, Sleeps 4,
Condo, 2 Bathrooms, air-conditioning, balcony
Rates - per condo (USD)
$245 - $270/night
$1,540 - $1,715/week
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Wailea Ekahi 40C

— Property 7024512h
Wailea condo rental - Ekahi Gardenview
1 Bedroom, Sleeps 4,
Condo, 1 Bathroom, air-conditioning, beach
Rates - per condo (USD)
$1,400 - $1,750/week
$5,520 - $7,268/month
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Wailea Ekahi 1A

— Property 7024507h
Wailea condo rental
1 Bedroom, Sleeps 4,
Condo, 2 Bathrooms, air-conditioning, beach
Rates - per condo (USD)
$1,505 - $1,995/week
$5,940 - $8,283/month
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Palms at Wailea #606

— Property 7024516h
Wailea condo rental - Master Bedroom
2 Bedrooms, Sleeps 6,
Condo, 2 Bathrooms, air-conditioning, blender
Rates - per condo (USD)
$1,505 - $2,380/week
$5,850 - $10,119/month
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Wailea Ekahi 52D

— Property 7024515h
Wailea condo rental - A pool at Wailea Ekahi
1 Bedroom, Sleeps 2,
Condo, 1 Bathroom, air-conditioning, beach
Rates - per condo (USD)
$1,400 - $1,750/week
$5,520 - $7,268/month
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Wailea Ekahi 46F

— Property 7024514h
Wailea condo rental - Ekahi Upper Village View
2 Bedrooms, Sleeps 6,
Condo, 2 Bathrooms, air-conditioning, beach
Rates - per condo (USD)
$1,960 - $2,590/week
$7,740 - $10,752/month
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Wailea Ekahi 1B

— Property 7024508h
Wailea condo rental - Wailea Ekahi Beach Pool
1 Bedroom, Sleeps 4,
Condo, 2 Bathrooms, air-conditioning, beach
Rates - per condo (USD)
$1,575 - $2,065/week
$6,210 - $8,571/month
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Wailea Ekahi 48C

— Property 7024513h
Wailea condo rental - Ekahi Upper Village View
1 Bedroom, Sleeps 4,
Condo, 2 Bathrooms, air-conditioning, beach
Rates - per condo (USD)
$1,400 - $1,750/week
$5,520 - $7,268/month
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Wailea Ekahi 27D

— Property 7024509h
Wailea condo rental - OceanView
1 Bedroom, Sleeps 2,
Condo, 2 Bathrooms, air-conditioning, beach
Rates - per condo (USD)
$1,750 - $2,240/week
$6,900 - $9,298/month
SPECIAL OFFER! Great Rate For Thanksgiving Special (November 20 - December 3)
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Beautiful Beach House with All the Comforts of Luxury Living

— Property 313906
Special Offer
Wailea villa rental - Your back yard!
3 Bedrooms, Sleeps 6,
Villa, 2 Bathrooms, beach, near the ocean, pool
Calendar Updated Nov 18 2009

Property Review

WOW- is what we said after entering the property - the pictures didn't do justice to the plush comfort of the home. We really enjoyed our stay and within 4 days we felt as thought we were "living...
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Wailea Gem DEC 1-5th SPECIAL $130

— Property 110076
Wailea condo rental - Queen bed with high quality linens
1 Bedroom, Sleeps 4,
Condo, 1 Bathroom, beach, near the ocean, pool
Rates - per property (USD)
$145 - $169/night