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Vacation Rentals in Wailea, Maui

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$199
Per Night
1 Bedroom, 1 Bathroom, Sleeps 2
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$190
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1 Bedroom, 1 Bathroom, Sleeps 2
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$225
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2 Bedrooms, 2 Bathrooms, Sleeps 6
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Also consider
Wailea - Beachfront Luxury Polo Beach Club #408
2 Bedrooms, sleeps 4
$595 - $769 / night
Luxurious Oceanfront Wailea Beach Villa
4 Bedrooms, sleeps 10
$950 - $1,450 / night
Modern Stylish Condo, Designer Touches Throughout!
2 Bedrooms, sleeps 6
$185 - $275 / night
Ocean View, Studio, Ekahi Condo 53E
1 Bedroom, sleeps 2
$195 - $275 / night
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$190
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2 Bedrooms, 3 Bathrooms, Sleeps 8
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$356
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2 Bedrooms, 2 Bathrooms, Sleeps 4
19 photos Details
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$695
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3 Bedrooms, 4 Bathrooms, Sleeps 10
44 photos Details
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$369
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2 Bedrooms, 2 Bathrooms, Sleeps 6
19 photos Details
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$294
Per Night
1 Bedroom, 2 Bathrooms, Sleeps 4
17 photos Details
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From
$190
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 4
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17 photos Details
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$195
Per Night
1 Bedroom, 2 Bathrooms, Sleeps 2
13 photos Details
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$195
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1 Bedroom, 2 Bathrooms, Sleeps 4
13 photos Details
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From
$210
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2 Bedrooms, 2 Bathrooms, Sleeps 6
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From
$195
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1 Bedroom, 2 Bathrooms, Sleeps 4
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From
$295
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1 Bedroom, 2 Bathrooms, Sleeps 3
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From
$139
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1 Bedroom, 2 Bathrooms, Sleeps 4
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$210
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2 Bedrooms, 2 Bathrooms, Sleeps 6
24 photos Details
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$265
Per Night
1 Bedroom, 2 Bathrooms, Sleeps 4
26 photos Details
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$200
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2 Bedrooms, 2 Bathrooms, Sleeps 6
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$250
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1 Bedroom, 2 Bathrooms, Sleeps 5
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$995
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3 Bedrooms, 3 Bathrooms, Sleeps 8
32 photos Details
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$250
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1 Bedroom, 2 Bathrooms, Sleeps 5
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$290
Per Night
1 Bedroom, 2 Bathrooms, Sleeps 4
19 photos Details
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$265
Per Night
1 Bedroom, 2 Bathrooms, Sleeps 4
10 photos Details
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$250
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2 Bedrooms, 2 Bathrooms, Sleeps 6
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$345
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
37 photos Details
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$130
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1 Bedroom, 1 Bathroom, Sleeps 2
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$235
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2 Bedrooms, 2 Bathrooms, Sleeps 6
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$120
Per Night
1 Bedroom, 1 Bathroom, Sleeps 4
20 photos Details
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$1,288
Per Night
3 Bedrooms, 4 Bathrooms, Sleeps 8
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$265
Per Night
1 Bedroom, 2 Bathrooms, Sleeps 4
16 photos Details
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$1,088
Per Night
3 Bedrooms, 4 Bathrooms, Sleeps 8
37 photos Details
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From
$900
Per Night
3 Bedrooms, 3 Bathrooms, Sleeps 8
20 photos Details
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$395
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
14 photos Details
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From
$700
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
14 photos Details
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From
$199
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
19 photos Details
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From
$755
Per Night
3 Bedrooms, 4 Bathrooms, Sleeps 8
15 photos Details
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From
$295
Per Night
1 Bedroom, 2 Bathrooms, Sleeps 2
16 photos Details
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From
$750
Per Night
3 Bedrooms, 4 Bathrooms, Sleeps 6
18 photos Details
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From
$159
Per Night
1 Bedroom, 2 Bathrooms, Sleeps 4
31 photos Details
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From
$115
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Studio, 1 Bathroom, Sleeps 2
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Reviews (21) Make Inquiry
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Suitability

  • Wheelchair access (15)
  • Elder access (60)
  • Suitable for children (55)
  • Pet friendly (1)
  • Smoking allowed (0)

Amenities

  • Internet (179)
  • All pools (157)
  • Grill (157)
  • Air Conditioning (155)
  • Public pool (153)
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Book Online(72)

Suitability

  • Wheelchair access (15)
  • Elder access (60)
  • Suitable for children (55)
  • Pet friendly (1)
  • Smoking allowed (0)

Amenities

  • Internet (179)
  • All pools (157)
  • Grill (157)
  • Air Conditioning (155)
  • Public pool (153)
  • View all amenities
Wailea Vacation Rentals

Wailea is a great destination if you are looking to relax, unwind, and soak up some sun. With its amazing beaches and luxurious spas, it is a pampering and refreshing vacation that you will never want to return from. Why go back to a simple hotel room when your accommodations can make you continue feeling like royalty even after the activities of the day are done? With a wide variety of vacation rentals, from cozy condos to large beachside villas, you can experience Wailea like one of the locals in your very own rental home no matter what your budget or space needs are.

A Wailea Vacation

No matter how you like to relax, there is sure to be a great place to do it in Wailea. From an indulgent day at the Spa Grande to tee time at Wailea Old Blue Course, it is full of ways to treat yourself and have a great time. If you're feeling adventurous, Hawaiian Sailing Canoe Adventures allows small groups to enjoy sailing in an outrigger canoe, or if you just want to relax on the beach, Keawakapu is a perfect choice for everything from sunning to snorkeling. Whatever the day's adventures bring, choosing a vacation rental to stay in means you can go back to the privacy and comfort of your very own rental home away from home for a truly authentic experience.

Family-Friendly Wailea

From exploring the beaches to catching a dinner show at Honua'ula Luau, there are a variety of great experiences for children when vacationing to Wailea. With vacation rentals, you can rent a property to accommodate nearly any size family, and it is a fantastic excuse to bring everyone along. Without having to pay for extra hotel rooms, it can also be a great money saver when traveling with a large group. Enjoying a Wailea vacation with the entire family at your very own rental home will be sure to create wonderful memories for years to come.