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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Wailea villa rental - Living Room
2 Bedrooms, Sleeps 6
  • Villa
  • 2 Bathrooms
  • beach, resort
  • accept credit card
Rates per property (USD)
$700 - $1,100/night
$4,550 - $7,700/week
$15,000 - $18,000/month
Wailea condo rental - 'Great Room' spacious living room
2 Bedrooms, Sleeps 6
  • Condo
  • 2 Bathrooms
  • beach, near the ocean
  • accept credit card
Wailea condo rental - Beach Front Pool and Spa
2 Bedrooms, Sleeps 6
  • Condo
  • 2 Bathrooms
  • beach, waterfront
  • accept credit card
Wailea house rental - Gorgeous Home on Large Lot with New Pool & Jacuzzi
3 Bedrooms, Sleeps 8
  • House
  • 2 Bathrooms
  • beach, town
  • accept credit card
Wailea estate rental - 4 Bedroom Wailea Sunset Estate
3 Bedrooms, Sleeps 9
  • Estate
  • 5 Bathrooms, 1 Half Bath
  • beach, waterfront
  • accept credit card
Rates per property (USD)
$1,850 - $3,000/night
Wailea villa rental - Beautiful Sunsets from the Wrap-Around Lanai
3 Bedrooms, Sleeps 6
  • Villa
  • 3 Bathrooms, 1 Half Bath
  • beach, resort
  • accept credit card
Rates per property (USD)
$1,200 - $1,650/night
Wailea villa rental - Adult Infinity Pool with Hot Tub Spa
3 Bedrooms, Sleeps 6
  • Villa
  • 3 Bathrooms
  • beach, resort
  • accept credit card
Rates per property (USD)
$1,200 - $2,500/night
Wailea villa rental - Family Pool & Spa Hot Tub From K408 Mer Et Soleil
3 Bedrooms, Sleeps 8
  • Villa
  • 3 Bathrooms
  • beach, resort
  • accept credit card
Rates per property (USD)
$1,250 - $2,500/night
Wailea villa rental - Panoramic Views from L409 Pacific Sunset Villa
4 Bedrooms, Sleeps 8
  • Villa
  • 3 Bathrooms
  • beach, resort
  • accept credit card
Rates per property (USD)
$1,250 - $3,350/night
Wailea villa rental - Private, outdoor terrace with beautiful ocean view
3 Bedrooms, Sleeps 6
  • Villa
  • 3 Bathrooms
  • beach, resort
  • accept credit card
Rates per property (USD)
$1,150 - $2,350/night
Wailea cottage rental - Bird of Paradise Pool overlooking the Ocean
2 Bedrooms, Sleeps 4
  • Cottage
  • 2 Bathrooms
  • beach, near the ocean
  • accept credit card
Rates per property (USD)
$375 - $400/night
$2,625/week
$6,000/month
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
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
Wailea condo rental - This is the view from the lanai
1 Bedroom, Sleeps 4
  • Condo
  • 1 Bathroom
  • beach, village
  • swimming pool
Rates per property (USD)
$275 - $345/night
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
Wailea condo rental
2 Bedrooms, Sleeps 6
  • Condo
  • 2 Bathrooms
  • beach
  • swimming pool
Rates per property (USD)
$525 - $750/night
Wailea condo rental - Queen bed with high quality linens
1 Bedroom, Sleeps 4
  • Condo
  • 1 Bathroom
  • beach, near the ocean
  • swimming pool
Rates per property (USD)
$159 - $179/night
Wailea villa rental - Spectacular Maui sunset from lanai
2 Bedrooms, Sleeps 6
  • Villa
  • 2 Bathrooms
  • beach, waterfront
  • swimming pool
Rates per property (USD)
$1,050 - $2,000/night
Wailea condo rental - Beautiful Polo Beach
2 Bedrooms, Sleeps 8
  • Condo
  • 2 Bathrooms
  • beach, waterfront
  • accept credit card
Wailea condo rental - Great ocean view from the Lanai
2 Bedrooms, Sleeps 5
  • Condo
  • 2 Bathrooms
  • beach, near the ocean
  • swimming pool
Wailea cottage rental - saline pool
2 Bedrooms, Sleeps 5
  • Cottage
  • 2 Bathrooms
  • near the ocean, rural
  • accept credit card
Rates per person (USD)
$2,020/week
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
Wailea condo rental - Views of Kahoolawe & Lanai from your balcony
2 Bedrooms, Sleeps 6
  • Condo
  • 2 Bathrooms
  • near the ocean
  • accept credit card
Rates per property (USD)
$195 - $295/night
$1,365 - $2,065/week
Wailea villa rental - Adult pool
3 Bedrooms, Sleeps 6
  • Villa
  • 3 Bathrooms
  • beach, resort
  • accept credit card
Rates per property (USD)
$1,100 - $2,200/night
$7,700 - $15,400/week
Wailea condo rental - Hawaiian Luxury Living room
2 Bedrooms, Sleeps 6
  • Condo
  • 2 Bathrooms
  • accept credit card
  • swimming pool
Wailea condo rental - Ocean view complx pool/spa
2 Bedrooms, Sleeps 6
  • Condo
  • 2 Bathrooms
  • near the ocean, resort
  • accept credit card
Rates per property (USD)
$1,820 - $2,310/week
Wailea condo rental
2 Bedrooms, Sleeps 8
  • Condo
  • 2 Bathrooms
  • beach, village
  • swimming pool
Wailea condo rental - Bedroom with private Lanai
1 Bedroom, Sleeps 4
  • Condo
  • 1 Bathroom
  • beach
  • accept credit card
Rates per property (USD)
$199 - $250/night
$1,393 - $1,750/week
Wailea condo rental - New living room furniture.
2 Bedrooms, Sleeps 6
  • Condo
  • 2 Bathrooms
  • near the ocean
  • accept credit card
Rates per property (USD)
$175/night
Wailea condo rental - Grand champion welcomes you.
2 Bedrooms, Sleeps 6
  • Condo
  • 2 Bathrooms
  • near the ocean, resort
  • accept credit card
Rates per property (USD)
$175 - $295/night