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Vacation rentals in Wailea, Maui

Professionally managed typically means…
  • Dedicated on-site help
  • Experienced local staff
  • Professional hospitality services
  • Secure credit card payment
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  • Enhanced property ownership verification in addition to verification of owner name and address via valid credit card
  • Established history of renting online
  • Direct & personal contact
  • Detailed rental knowledge
  • Flexible dates & rates
  • More options in smaller towns
Property owner typically means…
  • Verification of owner name and address via valid credit card
  • Direct & personal contact
  • Detailed rental knowledge
  • Flexible dates & rates
  • More options in smaller towns
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All 222 Rentals in Wailea
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From
$293
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 4
19 photos Details
Reviews (2) Make Enquiry
From
$1,062
Per Night
3 Bedrooms, 3 Bathrooms, Sleeps 6
75 photos Details
Reviews (1) Make Enquiry
From
$469
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 4
16 photos Details
Reviews (9) Make Enquiry
Also consider
Wailea Ekahi 11f:  Ocean View/Remodel 2 BR Condo
2 Bedrooms, sleeps 4
$480 - $640 / night
Wailea Orchid Villa - Panoramic Views!  3 Bd/3 Ba
3 Bedrooms, sleeps 8
$1,062 - $2,449 / night
Experience Grand Champions Best!
1 Bedroom, sleeps 2
$208 - $293 / night
Wailea Ocean View, 2Bed, 2Bath Beautiful Update
2 Bedrooms, sleeps 4
$203 - $373 / night
From
$304
Per Night
1 Bedroom, 2 Bathrooms, Sleeps 4
16 photos Details
Reviews (1) Make Enquiry
From
$800
Per Night
3 Bedrooms, 4 Bathrooms, Sleeps 6
18 photos Details
Reviews (1) Make Enquiry
From
$624
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 4
19 photos Details
Reviews (4) Make Enquiry
From
$1,974
Per Night
3 Bedrooms, 3 Bathrooms, Sleeps 5
77 photos Details
Reviews (1) Make Enquiry
From
$6,386
Per Week
3 Bedrooms, 3 Bathrooms, Sleeps 8
19 photos Details
Reviews (6) Make Enquiry
Get the List
From
$197
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
20 photos Details
Reviews (4) Make Enquiry
From
$191
Per Night
1 Bedroom, 2 Bathrooms, Sleeps 4
25 photos Details
Reviews (13) Make Enquiry
From
$256
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
16 photos Details
Reviews (2) Make Enquiry
From
$437
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
19 photos Details
Reviews (13) Make Enquiry
From
$469
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 5
16 photos Details
Reviews (7) Make Enquiry
From
$1,547
Per Night
3 Bedrooms, 4 Bathrooms, Sleeps 6
88 photos Details
Reviews (4) Make Enquiry
From
$1,920
Per Night
3 Bedrooms, 4 Bathrooms, Sleeps 6
85 photos Details
Reviews (5) Make Enquiry
From
$365
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
16 photos Details
Reviews (3) Make Enquiry
From
$223
Per Night
1 Bedroom, 2 Bathrooms, Sleeps 2
30 photos Details
Reviews (5) Make Enquiry
From
$293
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 4
16 photos Details
Reviews (2) Make Enquiry
From
$212
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 4
25 photos Details
Reviews (16) Make Enquiry
From
$361
Per Night
1 Bedroom, 2 Bathrooms, Sleeps 4
16 photos Details
Reviews (15) Make Enquiry
From
$1,227
Per Night
3 Bedrooms, 4 Bathrooms, Sleeps 6
83 photos Details
Reviews (2) Make Enquiry
From
$123
Per Night
1 Bedroom, 1 Bathroom, Sleeps 2
24 photos Details
Reviews (9) Make Enquiry
From
$224
Per Night
1 Bedroom, 2 Bathrooms, Sleeps 2
13 photos Details
Reviews (1) Make Enquiry
From
$212
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 4
50 photos Details
Reviews (6) Make Enquiry
From
$191
Per Night
1 Bedroom, 2 Bathrooms, Sleeps 4
27 photos Details
Reviews (23) Make Enquiry
From
$245
Per Night
1 Bedroom, 1 Bathroom, Sleeps 2
16 photos Details
Reviews (3) Make Enquiry
From
$427
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 4
16 photos Details
Reviews (1) Make Enquiry
From
$203
Per Night
1 Bedroom, 2 Bathrooms, Sleeps 2
13 photos Details
Reviews (4) Make Enquiry
From
$256
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
14 photos Details
Reviews (17) Make Enquiry
From
$267
Per Night
1 Bedroom, 2 Bathrooms, Sleeps 4
18 photos Details
Reviews (5) Make Enquiry
From
$1,148
Per Night
3 Bedrooms, 3 Bathrooms, Sleeps 6
16 photos Details
Reviews (11) Make Enquiry
From
$315
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
25 photos Details
Reviews (1) Make Enquiry
From
$170
Per Night
1 Bedroom, 2 Bathrooms, Sleeps 4
14 photos Details
Reviews (1) Make Enquiry
From
$421
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 5
37 photos Details
Reviews (13) Make Enquiry
From
$1,860
Per Week
2 Bedrooms, 2 Bathrooms, Sleeps 6
31 photos Details
Reviews (16) Make Enquiry
From
$432
Per Night
1 Bedroom, 2 Bathrooms, Sleeps 4
16 photos Details
Reviews (15) Make Enquiry
From
$229
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 6
21 photos Details
Reviews (2) Make Enquiry
From
$208
Per Night
Studio, 1 Bathroom, Sleeps 2
12 photos Details
Reviews (14) Make Enquiry
From
$176
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 4
25 photos Details
Reviews (4) Make Enquiry
From
$267
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
10 photos Details
Reviews (4) Make Enquiry
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Book Online(69)
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Suitability

  • Wheelchair access (16)
  • Elder access (63)
  • Suitable for children (56)
  • Pet friendly (1)
  • Smoking allowed (0)

Amenities

  • Internet (204)
  • Grill (181)
  • Air Conditioning (157)
  • All pools (156)
  • Public pool (148)
  • View all amenities
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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.