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!

Wailea Vacation Rentals

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» Grand Champions Upgraded Unit on Wailea Blue Course — Property 131169

  • Condo
  • 2 bedrooms, sleeps 6
  • 2 bathrooms
  • near the ocean, resort
  • swimming pool
Rates (shown in USD)
$175 - $295/night

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

  • Condo
  • 2 bedrooms, sleeps 6
  • 2 bathrooms
  • beach
  • swimming pool
Rates (shown in USD)
$525 - $750/night

The Palms - 2BR/2BA in Wailea — Property 189940

  • Condo
  • 2 bedrooms, sleeps 6
  • 2 bathrooms
  • swimming pool
  • air-conditioning
Rates (shown in USD)
$220 - $300/night

Beautiful, Newly Remodeled, Luxury, 2BDRM/2BA Condo — Property 171032

  • Condo
  • 2 bedrooms, sleeps 6
  • 2 bathrooms
  • beach, near the ocean
  • swimming pool

Welcome to Reds Wailea Maui Vacation Rental Home — Property 320487

  • House
  • 3 bedrooms, sleeps 8
  • 2 bathrooms
  • beach, town
  • accept credit card

Wailea Ekolu - Ocean View in Every Room! See It Now-Live Webcam — Property 166599

  • Condo
  • 1 bedroom, sleeps 4
  • 2 bathrooms
  • beach, near the ocean
  • accept credit card
Rates (shown in USD)
$225 - $300/night
$1,470 - $1,855/week
$6,626 - $7,950/month

Palms At Wailea-Closest Palms to the Beach! Jun & Aug Available! — Property 163145

  • Condo
  • 2 bedrooms, sleeps 6
  • 2 bathrooms
  • beach, near the ocean
  • accept credit card
Rates (shown in USD)
$150 - $325/night
$1,050 - $2,275/week
$4,200 - $10,075/month

Big Ocean View Ekahi 17f Remodeled 2007 — Property 177634

  • Condo
  • 1 bedroom, sleeps 4
  • 1 bathroom
  • beach, village
  • swimming pool
Rates (shown in USD)
$275 - $345/night

Introducing the Finest Ocean Views at the Palms — Property 164587

  • Condo
  • 2 bedrooms, sleeps 6
  • 2 bathrooms
  • near the ocean
  • swimming pool

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

  • Condo
  • 2 bedrooms, sleeps 4
  • 2 bathrooms
  • near the ocean, resort
  • swimming pool

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

  • Condo
  • 1 bedroom, sleeps 2
  • 2 bathrooms
  • near the ocean, resort
  • swimming pool

New to the Market - Gorgeous 2 Bedroom in Wailea! — Property 189345

  • Condo
  • 2 bedrooms, sleeps 5
  • 2 bathrooms
  • swimming pool
  • air-conditioning
Rates (shown in USD)
$250 - $275/night

The Palms at Wailea Resort Maui — Property 189272

  • Condo
  • 2 bedrooms, sleeps 6
  • 2 bathrooms
  • swimming pool
  • air-conditioning

Exquisite 'Aloha Kai Suite' 3BD/3BA! Wailea Beach Villa — Property 163269

  • Villa
  • 3 bedrooms, sleeps 8
  • 3 bathrooms
  • beach, resort
  • accept credit card
Rates (shown in USD)
$6,965 - $15,365/week

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

  • Condo
  • 2 bedrooms, sleeps 8
  • 2 bathrooms
  • beach, village
  • swimming pool
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