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

Vacation Rentals in Wailea

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Wailea Luxury 1BR Vacation Condo - Lots of Recommendations – Property 188977

  • Wailea rental - condo, 1 bedroom, sleeps 5, 1 bathroom, near the ocean, resort, accept credit card
  • Calendar Last Updated On: Dec 1, 2008
This Grand Champions - One bedroom condominium is new on the rental market and just a short walk to the ocean. This is our personal condominium, and when we are not...

Luxury 2BR with Ocean View -- Location, Location, Location! – Property 212306

  • Wailea rental - condo, 2 bedrooms, sleeps 5, 2 bathrooms, beach, near the ocean, swimming pool
  • Calendar Last Updated On: Dec 1, 2008
Welcome to our home! Enjoy the fantastic ocean views and luxury of our home in Wailea Elua Village - a gated, 24 acre, oceanfront community. Our home is perfectly...

Luxurious Secret Garden One Bedroom – Property 315090

  • Wailea rental - condo, 1 bedroom, sleeps 2, 1 bathroom, near the ocean, resort, accept credit card
  • $1,015 - $1,225/week
  • Calendar Last Updated On: Dec 1, 2008
Just a short walk from the beaches and ocean front walking path, hidden in a tropical oasis, are Grand Champions Villas. A quiet community of well appointed,...

Rent a Luxury Beachfront Condo in Wailea Beach, Maui, Hawaii – Property 215250

  • Wailea rental - condo, 2 bedrooms, sleeps 6, 2 bathrooms, beach, swimming pool
  • Calendar Last Updated On: Dec 1, 2008
Whether you're planning a romantic getaway for two or a family vacation, you'll find everything you need at this prime location! Located on the second floor facing...

Wailea Vacation Rental - Ekahi 53D Fabulous Ocean View Newly Renovated 1BR/1BA – Property 194155

  • Wailea rental - condo, 1 bedroom, sleeps 4, 1 bathroom, beach, resort, accept credit card
  • Calendar Last Updated On: Nov 29, 2008
Encase yourself in the luxury of Unit 53D. From this incredible home base with ocean views you can venture out into the tropical paradise that surrounds you.

Wailea Renovated 2BD. Golf & Mtn. View Condo – Property 182854

  • Wailea rental - condo, 2 bedrooms, sleeps 6, 2 bathrooms, accept credit card, swimming pool
  • Calendar Last Updated On: Nov 29, 2008
Aloha! Welcome to our home away from home! Come and relax and enjoy our two bedroom two bath villa that is new to the rental program.

Escape to Paradise in the Heart of Wailea – Property 168889

  • Wailea rental - condo, 2 bedrooms, sleeps 6, 2 bathrooms, near the ocean, accept credit card
  • Calendar Last Updated On: Dec 1, 2008
Come and enjoy tropical paradise in our lovely villa located in the Grand Champions Resort. Peace and serenity will soon over come you as you settle in to our...

Grand Champion Villas #32 Remodeled – Property 186208

  • Wailea rental - condo, 2 bedrooms, sleeps 5, 2 bathrooms, beach, near the ocean, accept credit card
  • Calendar Last Updated On: Nov 27, 2008
We welcome you to experience our large, newly remodeled 2 Master Suite, 2 Bathroom, 2nd floor condo, located in Wailea, Maui, with beautiful ocean views from our...

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

  • Wailea rental - villa, 3 bedrooms, sleeps 8, 3 bathrooms, beach, resort, accept credit card
  • Calendar Last Updated On: Nov 28, 2008
Fabulous three bedroom, three full baths, Penthouse Villa with gorgeous ocean view. The Aloha Kai Suite is elegant and refined to the last detail--sophisticated...

Great Wailea Family Vacation Condo – Property 188978

  • Wailea rental - condo, 2 bedrooms, sleeps 8, 2 bathrooms, near the ocean, resort, accept credit card
  • Calendar Last Updated On: Dec 1, 2008
The ground floor unit features easy access and a reserved parking space in front of the unit, as well as use of convenient guest parking.

Stunning Oasis in The Palms at Wailea- 2block to beach, world class golf&shops! – Property 156620

  • Wailea rental - condo, 1 bedroom, sleeps 4, 2 bathrooms, beach, resort, swimming pool
  • $1,120 - $1,400/week
  • Calendar Last Updated On: Nov 25, 2008
Wailea is one of the most sought after resort addresses on Maui. Here you can relax in the luxury of the beautiful grounds which feature a sparkling stream, winding...

Luxury Wailea Studio Hideaway - Many, Many Recommendations – Property 188831

  • Wailea rental - studio, sleeps 4, 1 bathroom, near the ocean, resort, accept credit card
  • Calendar Last Updated On: Nov 25, 2008
The studio features a large bedroom/sitting area with a comfortable queen size bed and a full size futon, a kitchenette, full bathroom and a lanai featuring tropical...

Wailea Ekolu - Ocean View - DEC. Special $155. Night – Property 205827

  • Wailea rental - condo, 2 bedrooms, sleeps 6, 2 bathrooms, near the ocean, swimming pool
  • Calendar Last Updated On: Nov 25, 2008
Wailea. There's nothing else on Maui quite like it. Our quiet unit Wailea Ekolu #705, two bedroom, two bath ground level 1316 square foot Condo in Wailea, comes...

Luxurious condo, Wailea, Maui, w/pool/spa and partial ocean view – Property 217632

  • Wailea rental - condo, 2 bedrooms, sleeps 6, 2 bathrooms, near the ocean, resort, accept credit card
  • $1,820 - $2,310/week
  • Calendar Last Updated On: Nov 24, 2008
This magnificently furnished, ocean and garden view, two bedroom, two bathroom condo, is just minutes away from the upscale 'Shops at Wailea,' restaurants, golf...

Palms At Wailea- XMAS/NEW YEAR'S Just Released!! Wailea on Discount – Property 163145

  • Wailea rental - condo, 2 bedrooms, sleeps 6, 2 bathrooms, beach, near the ocean, accept credit card
  • $1,225 - $2,100/week
  • Calendar Last Updated On: Nov 24, 2008
The Palms at Wailea is a quick 1/2 mile walk or drive to the beach. Minutes away is the town of Kihei with abundant shopping, restaurants and activities.

Upgrade to a Great Deal for Dazzling Aloha Contemporary Suite – Property 213130

  • Wailea rental - condo, 2 bedrooms, sleeps 6, 2 bathrooms, beach, near the ocean, accept credit card
  • Calendar Last Updated On: Nov 30, 2008
Luxury and comfort await you in our 2.5 bedroom, 2 bath Aloha Contemporary Suite at Wailea Beach Villas (WBV). Our gorgeous garden view vacation residence is...

The Palms at Wailea Resort Maui – Property 189272

  • Wailea rental - condo, 2 bedrooms, sleeps 6, 2 bathrooms, swimming pool, air-conditioning
  • Calendar Last Updated On: Nov 26, 2008
Our condominium has been called by our numerous return guests as their Maui home away from home. Just steps to the pool and Maui's best beach just minutes away, you...

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, swimming pool
  • Calendar Last Updated On: Nov 23, 2008
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,...

Wailea Ekahi Lower Village Luxury w spectacular ocean, surf & tropical views – Property 177791

  • Wailea rental - condo, 1 bedroom, sleeps 4, 2 bathrooms, beach, resort, accept credit card
  • Calendar Last Updated On: Nov 22, 2008
This is the spot you dream of when you think ocean front island luxury. Our newly remodeled condo is unique at Wailea Ekahi Village and offers quality, comfortable...

Architect's Own Custom Estate in South Maui – Property 159525

  • Wailea rental - house, 4 bedrooms, sleeps 8, 3 bathrooms, 1 half bath, near the ocean, resort, accept credit card
  • $8,750/week
  • Calendar Last Updated On: Nov 28, 2008
Welcome to Nani Pulelehua ('Beautiful Butterfly'), a New luxurious panoramic ocean view estate. The house is fully furnished with an emphasis on comfort & good...
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