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 condo rental - Take in the fabulous ocean view from our lanai.
1 Bedroom, Sleeps 4
  • Condo
  • 1 Bathroom
  • beach, resort
  • accept credit card
Rates per property (USD)
$255 - $340/night
Wailea condo rental - View from Lanai
2 Bedrooms, Sleeps 6
  • Condo
  • 2 Bathrooms
  • accept credit card
  • swimming pool
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 - Maui's best beaches are next door
2 Bedrooms, Sleeps 5
  • Condo
  • 2 Bathrooms
  • beach, near the ocean
  • accept credit card
Rates per property (USD)
$169 - $260/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 villa rental - View from Makai Lanai/Spectacular Maui Sunset
3 Bedrooms, Sleeps 8
  • Villa
  • 3 Bathrooms
  • beach, resort
  • accept credit card
Rates per property (USD)
$995 - $2,195/night
Wailea condo rental - Huge living/dining area with wide screen TV
1 Bedroom, Sleeps 4
  • Condo
  • 2 Bathrooms
  • beach, resort
  • swimming pool
Rates per property (USD)
$160 - $200/night
$1,120 - $1,400/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 - Dining Room Area
2 Bedrooms, Sleeps 6
  • Condo
  • 2 Bathrooms
  • near the ocean
  • swimming pool
Rates per property (USD)
$164/night
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 - Ocean View from Lanai
2 Bedrooms, Sleeps 6
  • Condo
  • 2 Bathrooms
  • beach, near the ocean
  • accept credit card
Rates per property (USD)
$175 - $300/night
$1,225 - $2,100/week
$4,725 - $8,400/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
2 Bedrooms, Sleeps 6
  • Condo
  • 2 Bathrooms
  • swimming pool
  • air-conditioning
Wailea condo rental
2 Bedrooms, Sleeps 6
  • Condo
  • 2 Bathrooms
  • beach
  • swimming pool
Rates per property (USD)
$525 - $750/night
Wailea condo rental - Big Beach, a 6 minute drive from the condo
1 Bedroom, Sleeps 2
  • Condo
  • 2 Bathrooms
  • near the ocean, resort
  • swimming pool
Wailea condo rental - Enlarged Master Bedroom suite - listen to the surf
1 Bedroom, Sleeps 4
  • Condo
  • 2 Bathrooms
  • beach, resort
  • accept credit card
Rates per property (USD)
$305 - $350/night
Wailea house rental - View from pool at sunset
4 Bedrooms, Sleeps 8
  • House
  • 3 Bathrooms, 1 Half Bath
  • near the ocean, resort
  • accept credit card
Rates per property (USD)
$1,250/night
$8,750/week
$30,000/month
Wailea condo rental - Private Living Area with Sofa/chaise
1 Bedroom, Sleeps 2
  • Condo
  • 1 Bathroom
  • near the ocean, resort
  • accept credit card
Rates per property (USD)
$150/night
$1,015 - $1,225/week
Wailea condo rental - Hawaiian Luxury Living room
2 Bedrooms, Sleeps 6
  • Condo
  • 2 Bathrooms
  • accept credit card
  • swimming pool
Wailea condo rental - One of the pools on the lush landscape of Ekahi
1 Bedroom, Sleeps 4
  • Condo
  • 2 Bathrooms
  • beach, resort
  • swimming pool
Rates per property (USD)
$175 - $225/night
Wailea condo rental - View from the Main Lanai
1 Bedroom, Sleeps 4
  • Condo
  • 1 Bathroom
  • near the ocean
  • swimming pool
Wailea condo rental - Beachside Pool and Pavilion Next to the Ocean
1 Bedroom, Sleeps 5
  • Condo
  • 2 Bathrooms
  • beach, resort
  • swimming pool
Rates per property (USD)
$220 - $275/night
$1,540 - $1,925/week
$5,700 - $7,350/month
Wailea condo rental - A nightly treat from your lanai at Wailea Ekolu!
1 Bedroom, Sleeps 4
  • Condo
  • 2 Bathrooms
  • beach, near the ocean
  • accept credit card
Rates per property (USD)
$225 - $300/night
$1,470 - $1,855/week
$6,626 - $7,950/month
Wailea condo rental - Wailea Ekahi 14F - Upper Left
2 Bedrooms, Sleeps 4
  • Condo
  • 2 Bathrooms
  • near the ocean
  • accept credit card
Wailea condo rental -  Breathtaking Oceanview
2 Bedrooms, Sleeps 6
  • Condo
  • 2 Bathrooms
  • beach, near the ocean
  • swimming pool
Rates per property (USD)
$309/night
$2,025/week
Wailea condo rental - Tropically Manicured Grounds
1 Bedroom, Sleeps 4
  • Condo
  • 2 Bathrooms
  • beach, near the ocean
  • swimming pool
Rates per property (USD)
$279/night
$1,895/week
Wailea condo rental
3 Bedrooms, Sleeps 8
  • Condo
  • 2 Bathrooms
  • beach
  • swimming pool
Rates per property (USD)
$349/night
$2,395/week
Wailea condo rental
2 Bedrooms, Sleeps 6
  • Condo
  • 2 Bathrooms
  • beach
  • accept credit card
Rates per property (USD)
$375/night
$2,495/week
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 - Beach Front Pool and Spa
2 Bedrooms, Sleeps 6
  • Condo
  • 2 Bathrooms
  • beach, waterfront
  • accept credit card