Wonderful Wailea

It doesn’t seem quite fair that Hawaii has so many fabulous features. This chain of islands puts other destinations to shame with abundant charms and fun-loving activities; even the smaller regions, like Wailea, have the power to outshine most, if not all, of your previous vacations.


Located on the desirable and sunny southern shores of Maui, the crescent-shaped beach, top-notch shopping and unbelievable culinary delights lay the foundation for a consistently relaxing time. Add in a few picturesque golf courses, romantic nooks and crannies perfect for watching the sun go down and the lure of nearby horseback rides, luaus and volcanoes and you can start to see why other places struggle to measure up.


When it comes time to build an itinerary, consider a helicopter tour, a snorkeling session at Molokini Crater, a trip to The Shops at Wailea and a nice long stroll that ends with a scrumptious seafood dinner. That’s just one path of many that you can take to find your bliss, a commodity that isn’t hard to come by in this privileged part of the planet.


It’s safe to say that Wailea will most definitely dazzle you with its wham-bam combinations of entertaining engagements; from sunrise to sunset you’ll be as busy as you want to be and perpetually pleased with yourself for making your way to the top of the list.


That’s right, your invitation has been issued, your vacation condo awaits, and it’ll soon be your turn to experience a place that, too bad for all the other wannabe-amazing locations in the world, doesn’t apologize for being fantastic.

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Vacation Rentals in Wailea

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Architect's Own Estate in South Maui – Property 159525

  • Wailea rental - house, 4 bedrooms, sleeps 10, 3 bathrooms, 1 half bath, near the ocean, resort, pool
  • Calendar Last Updated On: Nov 20, 2009
*Welcome to Nani Pulelehua ('Beautiful Butterfly'), a luxurious panoramic ocean view estate. 1.5 miles from beaches, dining and shopping.

Deluxe Oceanview Wailea Condo – Property 192613

  • Wailea rental - condo, 2 bedrooms, sleeps 6, 2 bathrooms, beach, near the ocean, pool
  • Calendar Last Updated On: Nov 20, 2009
Christmas and New Years Reservations Now Available - Call Today! Experience the Upscale Resort Community of Wailea on the Stunning South Shore.

Luxury Beachfront Wailea Condo – Property 152894

  • Wailea rental - condo, 2 bedrooms, sleeps 6, 2 bathrooms, beach, air-conditioning
  • $2,750/week
  • Calendar Last Updated On: Nov 20, 2009
Christmas and New Years Reservations Now Available - Call Today! Bask in Tropical Luxury Just Steps from the Sapphire-Blue, Crystal Clear Waters of Stunning Ulua...

Exquisite 'Aloha Kai Suite' 3BD/3BA! Wailea Beach Villa PH205 by Owner Direct! – Property 163269

  • Wailea rental - villa, 3 bedrooms, sleeps 8, 3 bathrooms, beach, resort, daily maid service
  • Calendar Last Updated On: Nov 19, 2009
Fabulous three bedroom, three full baths, Penthouse Villa 205 with gorgeous ocean view. The Aloha Kai Suite is elegant and refined to the last detail--sophisticated...

Special Discounts at Luxury Wailea Condo Rental in Maui – Property 234928

  • Wailea rental - condo, 2 bedrooms, sleeps 4, 2 bathrooms, near the ocean, resort, pool
  • Calendar Last Updated On: Nov 19, 2009
Enticing condo rental in Wailea with two bedrooms and two baths. Ideal for small families and couples, this Wailea condo rental has a fully stocked kitchen,...

Grand Champions Ocean View. Tempur-Pedic Beds, Remodeled, Family friendly,CLEAN! – Property 154811

  • Wailea rental - condo, 2 bedrooms, sleeps 6, 2 bathrooms, near the ocean, tennis court
  • $1,645 - $2,093/week
  • Calendar Last Updated On: Nov 19, 2009
Located on the 7th Fairway of the Wailea Blue Golf Course, in sunny south Maui, our Grand Champions Villas Ocean & Fairway Views Condo awaits you.

Enjoy Dinner and Wine on the Beach for a Maui Sunset Treat! – Property 188896

  • Wailea rental - condo, 2 bedrooms, sleeps 8, 2 bathrooms, beach, village, tennis court
  • $2,555 - $2,765/week
  • Calendar Last Updated On: Nov 19, 2009
Located in the lower village, ground floor unit #20C has three lanais. Use the tropical lawn area as your own backyard. Very light and airy condo situated on the...

Wailea Condo with Fabulous Ocean View – Property 160004

  • Wailea rental - condo, 1 bedroom, sleeps 4, 2 bathrooms, near the ocean, resort, balcony
  • Calendar Last Updated On: Nov 20, 2009
Completely remodeled late 2007. New tile, granite, plumbing, electrical and all new appliances and paint. Like NEW! Imagine yourself sitting on the living room sofa...

More Than One Life Has Been Changed by a Visit to Maui – Property 147336

  • Wailea rental - condo, 1 bedroom, sleeps 2, 2 bathrooms, near the ocean, resort, pool
  • $1,050 - $1,200/week
  • Calendar Last Updated On: Nov 20, 2009
Imagine yourself sitting on the living room sofa or on the private deck, overlooking the emerald green expanse of the beautiful Wailea Blue Golf Course, and beyond,...

Elua Village - Ulua Beach Utopia - 1703 – Property 7023935

  • Wailea rental - condo, 2 bedrooms, sleeps 6, 2 bathrooms, adventure, air-conditioning
  • Calendar Last Updated On: Nov 19, 2009
Whether you enjoy strolling along the beautiful Wailea paved walking path, on Ulua, Maui's most gentle beach, or in the 24 acre Maui condo village itself, Wailea...

Luxury Grand Champions Villa - on 7th Fairway- Blue Golf Course – Property 134937

  • Wailea rental - condo, 2 bedrooms, sleeps 6, 2 bathrooms, near the ocean, resort, pool
  • Calendar Last Updated On: Nov 19, 2009
Our luxury, partial ocean view, 2-bedroom, 2- bath villa is tropical living at its best! Only minutes from the Ulua Beach (ranked eighth in the nation-world class...
SPECIAL OFFER! Great Rate For Thanksgiving Special November 20 - December 3

Beautiful Beach House with All the Comforts of Luxury Living – Property 313906

  • Wailea rental - villa, 3 bedrooms, sleeps 6, 2 bathrooms, beach, near the ocean, pool
  • Calendar Last Updated On: Nov 18, 2009
* Beautiful Home across the street from South Maui Beaches. * 3 Bedrooms, 2.5 baths. * Master has King and deluxe duel-head shower.

Wailea Gem DEC 1-5th SPECIAL $130 – Property 110076

  • Wailea rental - condo, 1 bedroom, sleeps 4, 1 bathroom, beach, near the ocean, pool
  • Calendar Last Updated On: Nov 18, 2009
Free High Speed Wireless Internet and Unlimited Long Distance Calling to US Mainland and Canada!! Experience island life in our upscale tropical hideaway - a...

Seaview Sanctuary M311 Wailea Beach Villas – Property 95986

  • Wailea rental - villa, 3 bedrooms, sleeps 6, 2 bathrooms, adventure, air-conditioning
  • Calendar Last Updated On: Nov 20, 2009
Available from November until early December at just $750 per night, nearly 50% off regular rates for this full panoramic ocean view deluxe villa in the heart of...

Welcome to Reds Wailea Maui Vacation Rental Home – Property 320487

  • Wailea rental - house, 4 bedrooms, sleeps 11, 3 bathrooms, beach, town, pool
  • $3,010/week
  • Calendar Last Updated On: Nov 18, 2009
Aloha and Welcome to Reds 4 Bedroom Luxury Maui Vacation Rental House Above Wailea! This comfortable and spacious 4 bedroom, 3 bath Maui vacation rental with pool &...

November Special!-$179 a night INCLUDING Thanksgiving – Property 167604

  • Wailea rental - condo, 2 bedrooms, sleeps 6, 2 bathrooms, near the ocean, resort, pool
  • Calendar Last Updated On: Nov 17, 2009
Located in a premier location of Wailea, South Maui, this first-class luxury development with beautifully landscaped grounds, overlooks a top-rated golf course with...

Wailea Ekahi Luxury 1bd/2ba Beachfront resort – Property 188652

  • Wailea rental - condo, 1 bedroom, sleeps 4, 2 bathrooms, beach, resort, pool
  • Calendar Last Updated On: Nov 17, 2009
This beautiful condo is in Wailea Ekahi Village. The condo number is 52C. Ekahi is one of the few beachfront resorts in Wailea, and is just steps from Keawakapu...

Most Romantic Place on Maui – Property 241440

  • Wailea rental - condo, 1 bedroom, sleeps 4, 2 bathrooms, near the ocean, pool
  • Calendar Last Updated On: Nov 17, 2009
Bring the romantic person in your life. You will not be disappointed!! You will love this place. Oh, the view,incredible and very romantic! Completely...

Spectacular Sunset Ocean View in Peaceful Wailea, Ekolu Village – Property 166599

  • Wailea rental - condo, 1 bedroom, sleeps 4, 2 bathrooms, beach, resort, pool
  • $1,225 - $1,925/week
  • Calendar Last Updated On: Nov 20, 2009
We recently (May 2009) remodeled our condo with all new upgraded tumbled travertine flooring and tropical faux painting. Why stay in a resort hotel like the Four...

Exclusive Oceanfront Condo Nestled Between 2 World Class Maui Beaches – Property 7019171

  • Wailea rental - condo, 2 bedrooms, sleeps 4, 3 bathrooms, adventure, air-conditioning
  • Calendar Last Updated On: Nov 17, 2009
Wailea Point is a approximately 30 acre property that boasts world renowned design, meticulously manicured tropical landscape, and expert craftsmanship.
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