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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
$1,383
Per Night
3 Bedrooms, 4 Bathrooms, Sleeps 8
45 photos Details
Reviews (1) Make Enquiry
From
$231
Per Night
1 Bedroom, 2 Bathrooms, Sleeps 4
19 photos Details
Reviews (4) Make Enquiry
From
$214
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
19 photos Details
Reviews (16) Make Enquiry
Also consider
Ekahi 32D  Ocean View 7th night free thru-Aug.
1 Bedroom, sleeps 4
$311 - $349 / night
Ekahi-2A Lower Village, Ocean Views and Sunsets
2 Bedrooms, sleeps 6
$440 - $564 / night
AFFORDABLE LUXURYt Avail  JUL 16-20 $115 SPECIAL
1 Bedroom, sleeps 2
$140 - $209 / night
Beautifully remodeled 2 bedroom!Near pool and spa!
2 Bedrooms, sleeps 6
$263 - $446 / night
From
$171
Per Night
1 Bedroom, 2 Bathrooms, Sleeps 4
31 photos Details
Reviews (6) Make Enquiry
From
$311
Per Night
1 Bedroom, 1 Bathroom, Sleeps 4
19 photos Details
Reviews (11) Make Enquiry
From
$268
Per Night
1 Bedroom, 2 Bathrooms, Sleeps 5
12 photos Details
Reviews (12) Make Enquiry
From
$188
Per Night
1 Bedroom, 2 Bathrooms, Sleeps 4
13 photos Details
Reviews (2) Make Enquiry
From
$118
Per Night
Studio, 1 Bathroom, Sleeps 2
14 photos Details
Reviews (21) Make Enquiry
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From
$365
Per Night
1 Bedroom, 2 Bathrooms, Sleeps 3
18 photos Details
Reviews (26) Make Enquiry
From
$199
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
21 photos Details
Reviews (6) Make Enquiry
From
$285
Per Night
1 Bedroom, 2 Bathrooms, Sleeps 4
26 photos Details
Reviews (4) Make Enquiry
From
$430
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 6
23 photos Details
Reviews (9) Make Enquiry
From
$639
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 4
24 photos Details
Reviews (9) Make Enquiry
From
$192
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
26 photos Details
Reviews (5) Make Enquiry
From
$643
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 4
12 photos Details
Reviews (4) Make Enquiry
From
$150
Per Night
1 Bedroom, 1 Bathroom, Sleeps 4
25 photos Details
Reviews (10) Make Enquiry
From
$370
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
38 photos Details
Reviews (6) Make Enquiry
From
$1,176
Per Night
3 Bedrooms, 3 Bathrooms, Sleeps 6
75 photos Details
Reviews (1) Make Enquiry
From
$171
Per Night
1 Bedroom, 2 Bathrooms, Sleeps 4
25 photos Details
Reviews (17) Make Enquiry
From
$1,713
Per Night
4 Bedrooms, 3 Bathrooms, Sleeps 6
80 photos Details
Reviews (1) Make Enquiry
From
$961
Per Night
3 Bedrooms, 3 Bathrooms, Sleeps 8
41 photos Details
Reviews (78) Make Enquiry
From
$1,391
Per Night
3 Bedrooms, 4 Bathrooms, Sleeps 6
74 photos Details
Reviews (8) Make Enquiry
From
$139
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
37 photos Details
Reviews (13) Make Enquiry
From
$1,068
Per Night
3 Bedrooms, 3 Bathrooms, Sleeps 8
32 photos Details
Reviews (5) Make Enquiry
From
$779
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
24 photos Details
Reviews (21) Make Enquiry
From
$424
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
14 photos Details
Reviews (34) Make Enquiry
From
$214
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
26 photos Details
Reviews (17) Make Enquiry
From
$746
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 6
59 photos Details
Reviews (14) Make Enquiry
From
$171
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
29 photos Details
Reviews (13) Make Enquiry
From
$375
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 7
35 photos Details
Reviews (14) Make Enquiry
From
$1,176
Per Night
3 Bedrooms, 4 Bathrooms, Sleeps 8
37 photos Details
Reviews (4) Make Enquiry
From
$271
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
16 photos Details
Reviews (9) Make Enquiry
From
$424
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 5
23 photos Details
Reviews (16) Make Enquiry
From
$188
Per Night
1 Bedroom, 1 Bathroom, Sleeps 3
29 photos Details
Reviews (3) Make Enquiry
From
$187
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
32 photos Details
Reviews (29) Make Enquiry
From
$247
Per Night
1 Bedroom, 2 Bathrooms, Sleeps 4
16 photos Details
Reviews (1) Make Enquiry
From
$367
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 5
16 photos Details
Reviews (15) Make Enquiry
From
$965
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 6
65 photos Details
Reviews (10) Make Enquiry
From
$279
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 4
16 photos Details
Reviews (3) Make Enquiry
From
$209
Per Night
1 Bedroom, 1 Bathroom, Sleeps 2
16 photos Details
Reviews (5) Make Enquiry
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Suitability

  • Wheelchair access (15)
  • Elder access (61)
  • Suitable for children (54)
  • Pet friendly (1)
  • Smoking allowed (0)

Amenities

  • Internet (204)
  • Grill (181)
  • Air Conditioning (157)
  • All pools (154)
  • Public pool (147)
  • 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.