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.

Destination: Search

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Vacation Rentals in Wailea

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Most Popular Wailea Beach Villa Trip Advisor Rates Perfect-$750/nite for 8 – Property 164181

  • Wailea rental - villa, 4 bedrooms, sleeps 10, 3 bathrooms, beach, waterfront, pool
  • Calendar Last Updated On: Nov 7, 2009
Wailea Beach Villa Rated Perfect on Trip Advisor. $750/ night to 12/15/09 (excludesThanksgiving for $1200) on this 4BR (3 Kings & 1 Queen, or 2 Kings, 2 Twins & 1...

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 6, 2009
*Welcome to Nani Pulelehua ('Beautiful Butterfly'), a luxurious panoramic ocean view estate. 1.5 miles from beaches, dining and shopping.

Wailea Ekahi Village: 10E – Property 7023740

  • Wailea rental - condo, 1 bedroom, sleeps 2, 2 bathrooms, adventure, air-conditioning
  • Calendar Last Updated On: Nov 6, 2009
This spacious 1BR/2BA beautiful garden view condo is only steps away to the reknowned Keawekapu Beach and Pool Pavilion. Great for honeymooner's, anniversary stays,...

Wailea Ekahi Village: 03A – Property 7023739

  • Wailea rental - condo, 2 bedrooms, sleeps 6, 3 bathrooms, adventure, air-conditioning
  • Calendar Last Updated On: Nov 6, 2009
People return again and again to this wonderful Wailea Maui condo resort location for it's convenience to golf, tennis and the beauty of Keawakapu Beach.

Wailea Ekahi Village: 12E – Property 7023742

  • Wailea rental - condo, 1 bedroom, sleeps 4, 1 bathroom, adventure, air-conditioning
  • Calendar Last Updated On: Nov 6, 2009
People return again and again to this wonderful Wailea Maui condo resort location for it's convenience to golf, tennis and the beauty of Keawakapu Beach.

Wailea Ekahi Village: 10F – Property 7023741

  • Wailea rental - condo, 1 bedroom, sleeps 4, 1 bathroom, adventure, air-conditioning
  • Calendar Last Updated On: Nov 6, 2009
People return again and again to this wonderful Wailea Maui condo resort location for it's convenience to golf, tennis and the beauty of Keawakapu Beach.

Wailea Ekahi Village: 51D – Property 7023747

  • Wailea rental - condo, 2 bedrooms, sleeps 6, 2 bathrooms, adventure, air-conditioning
  • Calendar Last Updated On: Nov 6, 2009
People return again and again to this wonderful Wailea Maui condo resort location for it's convenience to golf, tennis and the beauty of Keawakapu Beach.

Wailea Ekahi Village: 22F – Property 7023743

  • Wailea rental - condo, 2 bedrooms, sleeps 4, 2 bathrooms, adventure, air-conditioning
  • Calendar Last Updated On: Nov 6, 2009
People return again and again to this wonderful Wailea Maui condo resort location for it's convenience to golf, tennis and the beauty of Keawakapu Beach.

Wailea Ekahi Village: 28F – Property 7023744

  • Wailea rental - condo, 1 bedroom, sleeps 4, 2 bathrooms, adventure, air-conditioning
  • Calendar Last Updated On: Nov 6, 2009
People return again and again to this wonderful Wailea Maui condo resort location for it's convenience to golf, tennis and the beauty of Keawakapu Beach.

Wailea Ekahi Village: 38F – Property 7023745

  • Wailea rental - condo, 2 bedrooms, sleeps 6, 2 bathrooms, adventure, air-conditioning
  • Calendar Last Updated On: Nov 6, 2009
People return again and again to this wonderful Wailea Maui condo resort location for it's convenience to golf, tennis and the beauty of Keawakapu Beach.

Wailea Ekahi Village: 54B – Property 7023748

  • Wailea rental - condo, 1 bedroom, sleeps 4, 2 bathrooms, adventure, air-conditioning
  • Calendar Last Updated On: Nov 6, 2009
People return again and again to this wonderful Wailea Maui condo resort location for it's convenience to golf, tennis and the beauty of Keawakapu Beach.

Wailea Ekahi Village: 50F – Property 7023746

  • Wailea rental - condo, 1 bedroom, sleeps 4, 1 bathroom, adventure, air-conditioning
  • Calendar Last Updated On: Nov 6, 2009
People return again and again to this wonderful Wailea Maui condo resort location for it's convenience to golf, tennis and the beauty of Keawakapu Beach.

Impressive Elua Village Condo 3/2 – Property 7023916

  • Wailea rental - condo, 3 bedrooms, sleeps 8, 2 bathrooms, adventure, air-conditioning
  • Calendar Last Updated On: Nov 6, 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...

Panoramic Oceanviews in Wailea – Property 7023915

  • Wailea rental - condo, 2 bedrooms, sleeps 6, 2 bathrooms, adventure, air-conditioning
  • Calendar Last Updated On: Nov 6, 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...

Amazing Views in Wailea – Property 7023913

  • Wailea rental - condo, 2 bedrooms, sleeps 6, 2 bathrooms, adventure, air-conditioning
  • Calendar Last Updated On: Nov 6, 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...

Remodeled Condo w/Wonderful Ocean Views in Wailea – Property 7023914

  • Wailea rental - condo, 2 bedrooms, sleeps 6, 2 bathrooms, adventure, air-conditioning
  • Calendar Last Updated On: Nov 6, 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...

Oceanview Elua Village Condo Sleeps 6 – Property 7023911

  • Wailea rental - condo, 2 bedrooms, sleeps 6, 2 bathrooms, adventure, air-conditioning
  • Calendar Last Updated On: Nov 6, 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...

2 Minutes to Beautiful Ulua Beach, Wailea – Property 7023923

  • Wailea rental - condo, 1 bedroom, sleeps 4, 1 bathroom, adventure, air-conditioning
  • Calendar Last Updated On: Nov 6, 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...

Marvelous Ocean Views - Elua 1102 – Property 7023921

  • Wailea rental - condo, 1 bedroom, sleeps 4, 1 bathroom, adventure, air-conditioning
  • Calendar Last Updated On: Nov 6, 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...

Wailea Condo with Gorgeous Ocean Views and Amazing Ocean Breezes – Property 7023920

  • Wailea rental - condo, 2 bedrooms, sleeps 6, 2 bathrooms, adventure, air-conditioning
  • Calendar Last Updated On: Nov 6, 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...
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