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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SPECIAL OFFER! Wailea Beach Villa-Best Unit & Price (May 18 - December 18)
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Special Offer
Golf
Wailea villa rental - Panoramic Ocean View from Huge Lanai-Wailea Beach
4 Bedrooms, Sleeps 9,
Villa, 3 Bathrooms, beach, waterfront, accept credit card
Rates - per property (USD)
$1,100 - $2,300/night
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The Palms at Wailea Resort Maui

— Property 189272
Wailea condo rental
2 Bedrooms, Sleeps 6,
Condo, 2 Bathrooms, beach, resort, swimming pool
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Wailea condo rental - It just doesn't get any better than this!
1 Bedroom, Sleeps 4,
Condo, 2 Bathrooms, beach, waterfront, swimming pool
Rates - per property (USD)
$160 - $225/night
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Wailea, Oceanfront, Luxury, Polo Beach Club Condo

— Property 245567
Wailea condo rental - Ocean front pool & jacuzzi at Polo Beach Club.
2 Bedrooms, Sleeps 5,
Condo, 2 Bathrooms, beach, waterfront, accept credit card
Rates - per property (USD)
$2,700 - $3,750/week
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New Lower Rates!! Ocean View Grand Champions Condo!

— Property 155264
Wailea condo rental - Ocean View from Lanai with Island of Lanai in Dist
2 Bedrooms, Sleeps 6,
Condo, 2 Bathrooms, near the ocean, resort, accept credit card
Rates - per property (USD)
$195 - $300/night
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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, accept credit card, swimming pool
Calendar Updated Jul 3 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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Wailea Luxury 1BR Vacation Condo - Lots of Recommendations

— Property 188977
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
Calendar Updated Jul 2 2009

Property Review

This condo was perfect for our family of three. Our son especially liked the fact that the pool was close by. Beautiful surroundings and great location. We liked that it was away from the hustle...
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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, swimming pool
Rates - per property (USD)
$365 - $390/night
$2,500 - $2,695/week
Calendar Updated Jul 2 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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Modern Maui At Ho`olei Wailea

— Property 7017694h
Wailea villa rental - Amazing view from Modern Maui at Ho`olei
3 Bedrooms, Sleeps 6,
Villa, 3 Bathrooms, 1 Half Bath, coffee maker, toaster
Rates - per villa (USD)
$850 - $1,750/night
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Grand Seascape K407 Wailea Beach Villas

— Property 7017688h
Wailea villa rental - Stqinless Steel BBQ on Lanai with Oceanviews!
3 Bedrooms, Sleeps 6,
Villa, 2 Bathrooms, coffee maker, toaster
Rates - per villa (USD)
$900 - $2,150/night
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Mer Et Soleil K408 Wailea Beach Villas

— Property 7017689h
Wailea villa rental - Intimate contemporary Master Bedroom
4 Bedrooms, Sleeps 8,
Villa, 3 Bathrooms, coffee maker, toaster
Rates - per villa (USD)
$1,200 - $2,850/night
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Beach Breezes H201 Wailea Beach Villas

— Property 7017686h
Wailea villa rental - Ocean View Dining and Great Room
3 Bedrooms, Sleeps 6,
Villa, 3 Bathrooms, coffee maker, toaster
Rates - per villa (USD)
$900 - $2,250/night
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Wailea Sunset Bungalow

— Property 95991h
Wailea cottage rental - Upscale Vintage Bungalow on Priceless Oceanfront Property
2 Bedrooms, Sleeps 4,
Cottage, 1 Bathroom, coffee maker, toaster
Rates - per cottage (USD)
$450 - $650/night
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Wailea Sunset Estate

— Property 95990h
Wailea house rental - Ocean view Gas Firepit
3 Bedrooms, Sleeps 10,
House, 4 Bathrooms, 1 Half Bath, toaster, children welcome
Rates - per house (USD)
$1,650 - $3,500/night
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Island Oasis M111 Wailea Beach Villas

— Property 95987h
Wailea villa rental - Exceptional free-form private pool for Wailea Beach Villas
3 Bedrooms, Sleeps 6,
Villa, 2 Bathrooms, coffee maker, toaster
Rates - per villa (USD)
$650 - $1,500/night
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Royal Ilima A201 Wailea Beach Villas

— Property 95985h
Wailea villa rental - Wailea Beach from your private dining terrace
3 Bedrooms, Sleeps 6,
Villa, 3 Bathrooms, 1 Half Bath, coffee maker, toaster
Rates - per villa (USD)
$3,025 - $4,000/night
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Seaview Sanctuary M311 Wailea Beach Villas

— Property 95986h
Wailea villa rental - Stunning Oceanview Terrace
3 Bedrooms, Sleeps 6,
Villa, 2 Bathrooms, coffee maker, toaster
Rates - per villa (USD)
$800 - $1,950/night
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Golden Mandarin D102 Wailea Beach Villas

— Property 93031h
Wailea villa rental - Private Villa Cold Splash Plunge Pool
3 Bedrooms, Sleeps 8,
Villa, 3 Bathrooms, 1 Half Bath, coffee maker, toaster
Rates - per villa (USD)
$1,375 - $2,750/night
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Regal Mandalay M511 Wailea Beach Villas

— Property 93261h
Wailea villa rental - Covered Ocean View Terrace Looking West and South over Wailea Beach
3 Bedrooms, Sleeps 6,
Villa, 2 Bathrooms, coffee maker, toaster
Rates - per villa (USD)
$950 - $2,500/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, toaster, children welcome
Rates - per villa (USD)
$1,550 - $2,200/night
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Floral Gardens Villa G102 Wailea Beach Villas

— Property 93262h
Wailea villa rental - Covered Patio and Sitting Area Opens to the Garden
3 Bedrooms, Sleeps 6,
Villa, 3 Bathrooms, 1 Half Bath, coffee maker, toaster
Rates - per villa (USD)
$1,100 - $2,750/night
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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, coffee maker, toaster
Rates - per villa (USD)
$1,000 - $1,350/night
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Luxury Villa, Ho'olei with Grand Wailea Resort amenities

— Property 241380
Wailea villa rental - Nighttime views from our unit
3 Bedrooms, Sleeps 6,
Villa, 3 Bathrooms, 1 Half Bath, beach, near the ocean, accept credit card
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Luxury 2BR with Ocean View -- Location & New Summer Discounts!

— Property 212306
Wailea condo rental - Great ocean view from the Lanai
2 Bedrooms, Sleeps 5,
Condo, 2 Bathrooms, beach, near the ocean, swimming pool
Rates - per property (USD)
$395 - $485/night
Calendar Updated Jul 2 2009

Property Review

I am reluctant to write this review as I don't want the condo to get booked up but feel it's only fair to let others know what a great place this is. We had a wonderful stay here, the condo is...
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Luxury Wailea Studio Hideaway - Many, Many Recommendations

— Property 188831
Wailea studio rental - Queen Size Bed
Studio, Sleeps 4,
Studio, 1 Bathroom, near the ocean, resort, accept credit card
Rates - per property (USD)
$125 - $140/night
Calendar Updated Jul 1 2009

Property Review

My wife and 2 daughters recently returned from a stay to the Wailea Hideaway studio. Wow! It was great. Everything we wanted. Cleaner than most hotels. Great swimming pool. Very close to the...
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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, accept credit card
Rates - per property (USD)
$270 - $290/night
Calendar Updated Jul 2 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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Rent a Luxury Beachfront Condo in Wailea Beach, Maui, Hawaii

— Property 215250
Wailea condo rental - Polo Beach Club
2 Bedrooms, Sleeps 6,
Condo, 2 Bathrooms, beach, swimming pool
Calendar Updated Jul 1 2009

Property Review

We were two couples staying at the condo which was nicely appointed. Our only disappointment was that there is too much furniture in the 2nd bedroom, making it very crowded. Perhaps they should...
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Wailea condo rental - Ocean View from Dining Rm
2 Bedrooms, Sleeps 6,
Condo, 2 Bathrooms, beach, waterfront, swimming pool
Rates - per property (USD)
$395/night
$2,765/week
Calendar Updated Jun 30 2009

Property Review

We have just returned from a week in this very well apppointed condo. Spectacular views from the master bedroom, living rooms and lanais of the ocean and beautifully kept gardens. The whole...
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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, accept credit card
Rates - per property (USD)
$995 - $1,750/night
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Big Ocean View Ekahi 17f Remodeled 2007

— Property 177634
Wailea condo rental - 180 Degreed HUGE Ocean Island views from the lanai
1 Bedroom, Sleeps 4,
Condo, 1 Bathroom, beach, village, swimming pool
Calendar Updated Jun 30 2009

Property Review

We had a wonderful week in Maui - the condo was great. We're planning to stay here again on our next trip. The grounds are beautiful, the pools are great (especially with kids), and the view is...