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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November Special!-$179 a night INCLUDING Thanksgiving

— Property 167604
Wailea condo rental - Good Morning Paradise in Wailea!
2 Bedrooms, Sleeps 6,
Condo, 2 Bathrooms, near the ocean, resort, pool
Rates - per property (USD)
$225 - $250/night
Calendar Updated Nov 9 2009

Property Review

Wow...what can we say about this beautiful property! Having been to Maui many times in the past, we wanted a beautiful and quiet area as well as nice beaches nearby. We got all of that. The condo...
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Wailea Ekolu - Ocean View - Special March/April $155 NT

— Property 205827
Wailea condo rental - Wailea Ekolu Village
2 Bedrooms, Sleeps 6,
Condo, 2 Bathrooms, beach, near the ocean, air-conditioning
Rates - per property (USD)
$164/night
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Wailea condo rental - Grand champion welcomes you.
2 Bedrooms, Sleeps 6,
Condo, 2 Bathrooms, near the ocean, resort, tennis court
Rates - per property (USD)
$175 - $295/night
Calendar Updated Nov 9 2009

Property Review

My wife and I enjoyed our stay at this beautifully decorated unit on the ground floor. The condo had everything we needed to save money by making dinner every night. We'll definitely plan to...
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Exclusive Oceanfront Condo Nestled Between 2 World Class Maui Beaches

— Property 7019171h
Wailea condo rental - Lanai View
2 Bedrooms, Sleeps 4,
Condo, 3 Bathrooms, adventure, air-conditioning
Rates - per condo (USD)
$17,000 - $25,000/month
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Ginger & Palm Suite L109 Wailea Beach Villas

— Property 93017h
Wailea villa rental - Partial Ocean View Terrace with Viking Gas Grill and Family Dining at Teak Table for eight guests
4 Bedrooms, Sleeps 8,
Villa, 3 Bathrooms, adventure, air-conditioning
Rates - per villa (USD)
$850 - $1,200/night
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Golden Mandarin D102 Wailea Beach Villas

— Property 93031h
Wailea villa rental - Fabulous view from D102 Golden Mandarin
3 Bedrooms, Sleeps 6,
Villa, 3 Bathrooms, 1 Half Bath, adventure, air-conditioning
Rates - per villa (USD)
$1,250 - $1,500/night
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Floral Gardens Villa G102 Wailea Beach Villas

— Property 93262h
Wailea villa rental - Expansive Great Room
3 Bedrooms, Sleeps 6,
Villa, 3 Bathrooms, 1 Half Bath, adventure, air-conditioning
Rates - per villa (USD)
$1,095 - $1,950/night
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Bella Luna D302 Wailea Beach Villas

— Property 93258h
Wailea villa rental - Master Bedroom with Ocean View and Cal King Bed
3 Bedrooms, Sleeps 6,
Villa, 3 Bathrooms, 1 Half Bath, adventure, air-conditioning
Rates - per villa (USD)
$1,350 - $1,850/night
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Regal Mandalay M511 Wailea Beach Villas

— Property 93261h
Wailea villa rental - Great Room Includes a well-equipped kitchen, living room, and private terrace
3 Bedrooms, Sleeps 6,
Villa, 2 Bathrooms, air-conditioning, balcony
Rates - per villa (USD)
$850 - $1,650/night
Calendar Updated Nov 9 2009

Property Review

We enjoyed our stay very much. I think the best highlights were eating fresh island papayas for breakfast and having coconut for the first time. Your kitchen was so bright we just felt like...
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Sun Splash J506 Wailea Beach Villas

— Property 95988h
Wailea villa rental - Stunning Ocean Views From Your Own Private Terrace
2 Bedrooms, Sleeps 6,
Villa, 2 Bathrooms, adventure, air-conditioning
Rates - per villa (USD)
$850 - $1,650/night
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Royal Ilima A201 Wailea Beach Villas

— Property 95985h
Wailea villa rental - A twilight view towards The Royal Ilima Upper Corner
3 Bedrooms, Sleeps 6,
Villa, 3 Bathrooms, 1 Half Bath, adventure, air-conditioning
Rates - per villa (USD)
$3,025/night
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Island Oasis M111 Wailea Beach Villas

— Property 95987h
Wailea villa rental - Expansive Great Room
3 Bedrooms, Sleeps 6,
Villa, 2 Bathrooms, adventure, air-conditioning
Rates - per villa (USD)
$600 - $1,250/night
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Wailea Sunset Bungalow

— Property 95991h
Wailea cottage rental - Stunning Sunsets Along Maui''s Southshore
2 Bedrooms, Sleeps 4,
Cottage, 1 Bathroom, adventure, air-conditioning
Rates - per cottage (USD)
$450 - $650/night
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Wailea Sunset Estate

— Property 95990h
Wailea house rental - Oceanside Pool
3 Bedrooms, Sleeps 10,
House, 4 Bathrooms, 1 Half Bath, adventure, air-conditioning
Rates - per house (USD)
$1,650 - $2,550/night
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Beautiful Beach House with All the Comforts of Luxury Living

— Property 313906
Wailea villa rental - Your back yard!
3 Bedrooms, Sleeps 6,
Villa, 2 Bathrooms, beach, near the ocean, pool
Calendar Updated Nov 9 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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A Bit of Paradise - Ocean View- Near Grand Wailea

— Property 153990
Wailea condo rental - Hawaiian Luxury Living room
2 Bedrooms, Sleeps 6,
Condo, 2 Bathrooms, jacuzzi, air-conditioning
Calendar Updated Nov 9 2009

Property Review

The website of this property does not do it justice. The unit was beautiful, in excellent condition and very well-stocked and situated in a lovely complex. Our family came to Maui for our...
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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 8 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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Wailea Tropical Forest Studio JAN 7-23rd NOW OPEN $125 SPECIAL

— Property 307780
Wailea condo rental - Queen size pillow top bed with high quality linens
Studio, Sleeps 2,
Condo, 1 Bathroom, beach, near the ocean, pool
Rates - per property (USD)
$115 - $135/night
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'Tommy Bahama' Style Luxury Condo on Greenbelt, Ocean View

— Property 239232
Wailea condo rental - View from Lanai
1 Bedroom, Sleeps 4,
Condo, 2 Bathrooms, beach, near the ocean, pool
Rates - per property (USD)
$300 - $325/night
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Most Popular Wailea Beach Villa Trip Advisor Rates Perfect-$750/nite for 8

— Property 164181
Golf
Wailea villa rental - Panoramic Ocean View from Huge Lanai-Wailea Beach
4 Bedrooms, Sleeps 10,
Villa, 3 Bathrooms, beach, waterfront, pool
Rates - per property (USD)
$995 - $1,500/night
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Wailea Beach Villa, Luxury w/Beautiful Ocean Views

— Property 141228
Wailea villa rental - Adult pool
3 Bedrooms, Sleeps 6,
Villa, 3 Bathrooms, beach, resort, jacuzzi
Rates - per property (USD)
$900 - $1,800/night
$6,300 - $12,600/week
Calendar Updated Nov 7 2009

Property Review

The condo has everything you could need to have a great time in a home away from home. The amenities are better than most homes. The decor is beautiful and the villa is very clean. The kitchen,...
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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 6 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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Impressive Elua Village Condo 3/2

— Property 7023916h
Wailea condo rental
3 Bedrooms, Sleeps 8,
Condo, 2 Bathrooms, adventure, air-conditioning
Rates - per condo (USD)
$650 - $850/night
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Panoramic Oceanviews in Wailea

— Property 7023915h
Wailea condo rental
2 Bedrooms, Sleeps 6,
Condo, 2 Bathrooms, adventure, air-conditioning
Rates - per condo (USD)
$445 - $655/night
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Amazing Views in Wailea

— Property 7023913h
Wailea condo rental
2 Bedrooms, Sleeps 6,
Condo, 2 Bathrooms, adventure, air-conditioning
Rates - per condo (USD)
$395 - $550/night
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Remodeled Condo w/Wonderful Ocean Views in Wailea

— Property 7023914h
Wailea condo rental
2 Bedrooms, Sleeps 6,
Condo, 2 Bathrooms, adventure, air-conditioning
Rates - per condo (USD)
$445 - $655/night
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Oceanview Elua Village Condo Sleeps 6

— Property 7023911h
Wailea condo rental
2 Bedrooms, Sleeps 6,
Condo, 2 Bathrooms, adventure, air-conditioning
Rates - per condo (USD)
$445 - $655/night
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2 Minutes to Beautiful Ulua Beach, Wailea

— Property 7023923h
Wailea condo rental
1 Bedroom, Sleeps 4,
Condo, 1 Bathroom, adventure, air-conditioning
Rates - per condo (USD)
$445 - $595/night
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Marvelous Ocean Views - Elua 1102

— Property 7023921h
Wailea condo rental
1 Bedroom, Sleeps 4,
Condo, 1 Bathroom, adventure, air-conditioning
Rates - per condo (USD)
$380 - $495/night
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Wailea Condo with Gorgeous Ocean Views and Amazing Ocean Breezes

— Property 7023920h
Wailea condo rental
2 Bedrooms, Sleeps 6,
Condo, 2 Bathrooms, adventure, air-conditioning
Rates - per condo (USD)
$545 - $850/night