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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Grand Champions, Remodeled, Ocean Views, Thanksgiving Special $225/nt

— Property 186208
Wailea condo rental - Maui's best beaches are next door
2 Bedrooms, Sleeps 5,
Condo, 2 Bathrooms, beach, near the ocean, pool
Rates - per property (USD)
$199 - $280/night
Calendar Updated Nov 28 2009

Property Review

This was our 5th year in Maui and our 5th different vacation rental spot, and all I can say is... we'll be back next year to stay in this unit if we don't purchase one first. Anyone who is...
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Magnificent Panoramic Views!! Luxury Private Corner End Unit!!

— Property 229269
Wailea condo rental - Incredible views of Haleakala and the Fairway
2 Bedrooms, Sleeps 6,
Condo, 2 Bathrooms, balcony, air-conditioning
SPECIAL OFFER! Wailea Beach Villa Luxury 4BR $750/nite (November 1 - December 15)
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Wailea Beach Villa for 8- Rated Perfect on TripAdvisor

— Property 230622
Special Offer
Golf
Wailea villa rental - Wailea Beach Villa is living in paradise!
4 Bedrooms, Sleeps 10,
Villa, 3 Bathrooms, beach, resort, pool
Rates - per property (USD)
$995 - $1,500/night
$7,665 - $10,500/week
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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 27 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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Luxury Maui Ocean View, Grand Wailea Resort Amenities

— Property 246371
Wailea townhome rental - Enjoy beautiful ocean views from the lanai
3 Bedrooms, Sleeps 10,
Townhome, 3 Bathrooms, 1 Half Bath, near the ocean, resort, pool
Rates - per property (USD)
$995 - $2,495/night
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Beach Breezes H201 Wailea Beach Villas

— Property 7017686h
Wailea villa rental - Ocean View Great Room and Indoor Dining
3 Bedrooms, Sleeps 6,
Villa, 3 Bathrooms, accept credit card, activities guide
Rates - per villa (USD)
$900 - $1,095/night
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Mer Et Soleil K408 Wailea Beach Villas

— Property 7017689h
Wailea villa rental - Stunning Views!
4 Bedrooms, Sleeps 8,
Villa, 3 Bathrooms, accept credit card, activities guide
Rates - per villa (USD)
$1,250 - $1,500/night
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Aqua Lani J305 Wailea Beach Villas

— Property 7017685h
Wailea villa rental - Spacious Ocean View Great Room with 50" Plasma Flat-Panel HDTV
3 Bedrooms, Sleeps 6,
Villa, 3 Bathrooms, accept credit card, activities guide
Rates - per villa (USD)
$900 - $1,795/night
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Blue Horizons K308 Wailea Beach Villas

— Property 7017687h
Wailea villa rental - Ocean view Great Room
4 Bedrooms, Sleeps 8,
Villa, 3 Bathrooms, accept credit card, activities guide
Rates - per villa (USD)
$995 - $1,950/night
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Grand Seascape K407 Wailea Beach Villas

— Property 7017688h
Wailea villa rental - Incredible Great Room Oceanviews!
3 Bedrooms, Sleeps 6,
Villa, 2 Bathrooms, accept credit card, activities guide
Rates - per villa (USD)
$850 - $995/night
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Hoku At Ho`olei Wailea

— Property 7017693h
Wailea villa rental - Lower Queen Bedroom
3 Bedrooms, Sleeps 6,
Villa, 3 Bathrooms, 1 Half Bath, accept credit card, activities guide
Rates - per villa (USD)
$750 - $950/night
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Ocean Pearl E202 Wailea Beach Villas

— Property 7017695h
Wailea villa rental - Set Atop Beautiful Waterfalls
3 Bedrooms, Sleeps 6,
Villa, 3 Bathrooms, 1 Half Bath, accept credit card, activities guide
Rates - per villa (USD)
$950 - $1,300/night
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Modern Maui At Ho`olei Wailea

— Property 7017694h
Wailea villa rental - Great Room with HD digital cable, Blu-Ray DVD/CD, DVR, Surround sound, Plush seating
3 Bedrooms, Sleeps 6,
Villa, 3 Bathrooms, 1 Half Bath, accept credit card, activities guide
Rates - per villa (USD)
$850 - $995/night
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Bird Of Paradise Cottage

— Property 7017711h
Wailea house rental - Pool and Jacuzzi with Bar/Lounge
2 Bedrooms, Sleeps 4,
House, 2 Bathrooms, accept credit card, activities guide
Rates - per house (USD)
$375 - $450/night
Calendar Updated Nov 27 2009

Property Review

This property would be nice for the typical tourist who only needs a place to sleep. You cannot see the sunset from the cottage and very little of the ocean. The property description said...
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Designer Wailea Studio in Heart of Wailea

— Property 230085
Wailea studio rental - Entry to Secret Studio
Studio, Sleeps 2,
Studio, 1 Bathroom, near the ocean, resort, pool
Rates - per property (USD)
$110 - $130/night
$750 - $910/week
$2,600/month
Calendar Updated Nov 26 2009

Property Review

We stayed in the apartment during late August/early September 2009 and had a WONDERFUL time. The apartment is spacious and VERY well equipped, super comfortable and simply had everything we...
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Wailea condo rental - Take in the fabulous ocean view from our lanai.
1 Bedroom, Sleeps 4,
Condo, 1 Bathroom, beach, village, balcony
Rates - per property (USD)
$215 - $355/night
Calendar Updated Nov 25 2009

Property Review

Our stay at 53D was absolutely amazing! My wife, 4-year-old son, and myself we're blown away for the moment we drove up and saw the manicured landscape with amazing flowers, trees and bushes. ...
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The Palms- $150/nt for Remaining Dates in 2009!!

— Property 163145
Golf
Wailea condo rental - Ocean View from Lanai
2 Bedrooms, Sleeps 6,
Condo, 2 Bathrooms, beach, near the ocean, pool
Rates - per property (USD)
$195 - $350/night
$1,365 - $2,450/week
$5,850 - $10,500/month
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Great Wailea Family Vacation Condo

— Property 188978
Wailea condo rental - Mokapu Beach - 1/4 mile away
2 Bedrooms, Sleeps 8,
Condo, 2 Bathrooms, near the ocean, resort, pool
Rates - per property (USD)
$270 - $290/night
Calendar Updated Nov 25 2009

Property Review

We just returned from Maui and all I can say is WOW! Everything was perfect and it all started with our accommodations. The condo was absolutely perfect in every way. The location is excellent...
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Wailea Ekahi 33D

— Property 257747
Wailea condo rental
1 Bedroom, Sleeps 2,
Condo, 2 Bathrooms, near the ocean, satellite or cable
Rates - per property (USD)
$275/night
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Wailea apartment rental
2 Bedrooms, Sleeps 4,
Apartment, 2 Bathrooms, beach, pool
Rates - per property (USD)
$846/night
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Spectacular Sunset Ocean View in Peaceful Wailea, Ekolu Village

— Property 166599
Wailea condo rental - A nightly treat from your lanai at Wailea Ekolu!
1 Bedroom, Sleeps 4,
Condo, 2 Bathrooms, beach, resort, pool
Rates - per property (USD)
$175 - $275/night
$1,225 - $1,925/week
$5,000 - $6,000/month
Calendar Updated Nov 27 2009

Property Review

7-12-09 Dear Tim and Carolyn, Our two weeks in Maui were amazing, and to always come home to the comfort of your condominium was truly the best thing about our trip. We snorkeled, we saw...
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Seaview Sanctuary M311 Wailea Beach Villas

— Property 95986h
Wailea villa rental - Ocean view Living Area
3 Bedrooms, Sleeps 6,
Villa, 2 Bathrooms, accept credit card, activities guide
Rates - per villa (USD)
$750 - $1,500/night
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Polo Beach Club,Cabana Style, Luxury Ground Floor on Beach

— Property 194292
Wailea condo rental - Oceanside Swimming Pool and Hot Tub
2 Bedrooms, Sleeps 6,
Condo, 2 Bathrooms, beach, waterfront, air-conditioning
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2 Bedroom condo pool and hottub

— Property 255552
Wailea condo rental
2 Bedrooms, Sleeps 4,
Condo, 2 Bathrooms, beach, near the ocean, pool
Rates - per property (USD)
$910/night
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Wailea Beach Villas Penthouse only 5 min walk to Wailea Beach

— Property 255433
Wailea condo rental - Lanai
2 Bedrooms, Sleeps 4,
Condo, 2 Bathrooms, beach, near the ocean, pool
Rates - per property (USD)
$695 - $1,200/night
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Wailea Ekahi 39D

— Property 257748
Wailea condo rental
1 Bedroom, Sleeps 2,
Condo, 1 Bathroom, near the ocean, air-conditioning
Rates - per property (USD)
$275/night
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Welcome to Reds Wailea Maui Vacation Rental Home

— Property 320487
Wailea house rental - Gorgeous Home on Large Lot with New Pool & Jacuzzi
4 Bedrooms, Sleeps 11,
House, 3 Bathrooms, beach, town, pool
Rates - per property (USD)
$430/night
$3,010/week
Calendar Updated Nov 25 2009

Property Review

Our stay was with our son & daughter in law who made the arrangements. Red's web site gives you accurate information about this beautiful spot. The location is ideal. The property is very well...
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Wailea Ekahi 46F

— Property 257745
Wailea condo rental
2 Bedrooms, Sleeps 6,
Condo, 2 Bathrooms, near the ocean, air-conditioning
Rates - per property (USD)
$280/night
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Elua Village 1BR/2BA Ocean Front Condominium

— Property 226394
Wailea condo rental - View from Lanai
1 Bedroom, Sleeps 4,
Condo, 1 Bathroom, beach, near the ocean, pool
Rates - per property (USD)
$450 - $500/night
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Wailea Elua 2BR/2BA Condo Just Steps to the Beach!

— Property 226393
Wailea condo rental - Sunsets
2 Bedrooms, Sleeps 6,
Condo, 2 Bathrooms, beach, near the ocean, pool
Rates - per property (USD)
$425 - $460/night