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Vacation Rentals in Wailea, HI

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All 229 Rentals in Wailea
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From
$356
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 4
19 photos Details Reviews (2) Make Inquiry
From
$950
Per Night
3 Bedrooms, 3 Bathrooms, Sleeps 6
76 photos Details Reviews (1) Make Inquiry
From
$199
Per Night
1 Bedroom, 1 Bathroom, Sleeps 2
Booking
21 photos Details Reviews (4) Make Inquiry
Also consider
Updated Spacious 3 Bdrm. Wailea Ocean View Condo
3 Bedrooms, sleeps 6
$275 - $320 / night
Totally renovated, closest to the beach!
1 Bedroom, sleeps 5
$250 - $350 / night
Wailea Ekahi 11f:  Ocean View/Remodel 2 BR Condo
2 Bedrooms, sleeps 4
$450 - $600 / night
WOW !  WHAT A GREAT VIEW ! ---Great Reviews !
2 Bedrooms, sleeps 6
$395 - $510 / night
From
$995
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 6
77 photos Details Reviews (7) Make Inquiry
5 of 5 stars Reviewed April 24, 2013
We had a wonderful time staying here. Tropical Villa Vacations does such a great job of taking care of the details. We loved the condo. So much so we had a hard time getting...
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From
$695
Per Night
3 Bedrooms, 4 Bathrooms, Sleeps 10
44 photos Details Reviews (27) Make Inquiry
5 of 5 stars Reviewed April 12, 2014
Our first trip to Maui, Hawaii for our Daughters wedding. We were a family of 8 (including grandparents).Plenty of room,Condo is immaculate, amazing, beautiful, photo's were...
5 of 5 stars Reviewed December 30, 2013
Upon our arrival, we immediately knew we hit the jackpot! The spacious condo was beautiful and full of every necessity needed for our vacation. The views from the lanai were...
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From
$200
Per Night
1 Bedroom, 2 Bathrooms, Sleeps 4
15 photos Details Reviews (2) Make Inquiry
From
$440
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
16 photos Details Reviews (6) Make Inquiry
From
$266
Per Night
1 Bedroom, 2 Bathrooms, Sleeps 4
15 photos Details Reviews (1) Make Inquiry
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From
$270
Per Night
1 Bedroom, 2 Bathrooms, Sleeps 2
19 photos Details Reviews (1) Make Inquiry
5 of 5 stars Reviewed July 16, 2014
Very well appointed unit and beautifully maintained grounds. Went over for my niece's wedding. We had a pre-wedding function with 15 people and everything had we needed...
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From
$190
Per Night
1 Bedroom, 1 Bathroom, Sleeps 2
Bookings
23 photos Details Reviews (1) Make Inquiry
5 of 5 stars Reviewed September 15, 2014
I thoroughly enjoyed my time at the condo, a few little issues which were actually my fault but these were seen to immediately. All the facilities that you would want, Weather...
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From
$195
Per Night
1 Bedroom, 2 Bathrooms, Sleeps 2
13 photos Details Reviews (1) Make Inquiry
5 of 5 stars Reviewed May 14, 2014
We travelled to Maui in March, stayed for two weeks in a lovely condo at Grand Champions, Wailea. We went with 10 other friends, who also rented condos there. The manager...
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From
$325
Per Night
3 Bedrooms, 3 Bathrooms, Sleeps 8
10 photos Details Reviews (2) Make Inquiry
From
$195
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
13 photos Details Reviews (7) Make Inquiry
From
$199
Per Night
1 Bedroom, 2 Bathrooms, Sleeps 4
25 photos Details Reviews (13) Make Inquiry
From
$209
Per Night
1 Bedroom, 2 Bathrooms, Sleeps 2
30 photos Details Reviews (5) Make Inquiry
From
$695
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
30 photos Details Reviews (18) Make Inquiry
From
$210
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
24 photos Details Reviews (5) Make Inquiry
2 of 5 stars Reviewed April 19, 2013
We stayed here April 11 - 20, 2013. This is actually a relatively nice unit. Great patio deck with pass through window from kitchen. Nice decorations and televisions. I like...
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From
$200
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
24 photos Details Reviews (5) Make Inquiry
4 of 5 stars Reviewed August 2, 2014
We loved the location of the property. Maui Car and Condo was great to work with. They are very reliable, retuned my email every quickly and made the process to check in very...
4 of 5 stars Reviewed July 25, 2014
This was our first trip with our grandaughters. The location is ideal for the snorkling beaches with lifegaurds. The location is also close to all types of dining and fine...
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From
$995
Per Night
3 Bedrooms, 3 Bathrooms, Sleeps 8
32 photos Details Reviews (5) Make Inquiry
From
$599
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 4
12 photos Details Reviews (4) Make Inquiry
5 of 5 stars Reviewed August 12, 2013
My husband and 2 sons stayed in this beautiful condo last week. It is quite a place! Every attention to detail is incredible from the beginning correspondence from the owner until...
5 of 5 stars Reviewed July 7, 2013
Since our last review, we have stayed there twice. The owner has not only maintained the condo in pristine condition but has updated the master bedroom and bath. The owner is...
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From
$1,820
Per Week
2 Bedrooms, 2 Bathrooms, Sleeps 6
23 photos Details Reviews (1) Make Inquiry
From
$195
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 4
23 photos Details Reviews (3) Make Inquiry
5 of 5 stars Reviewed December 16, 2013
My wife and I stayed in unit 29 at the Grande Champions Golf Villas for two weeks in December, 2013. The property manager Kathleen was fantastic to deal with and responded...
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From
$255
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
16 photos Details Reviews (1) Make Inquiry
5 of 5 stars Reviewed November 11, 2011
We booked this condo for 8 days. It was everything that had been described to us and more. The view was fantastic. Everything we needed was there, all we had to bring was our food...
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From
$1,088
Per Night
3 Bedrooms, 4 Bathrooms, Sleeps 8
37 photos Details Reviews (5) Make Inquiry
5 of 5 stars Reviewed August 11, 2014
I must say that this was one of the best vacation rentals I've stayed at. The house, staff and property was simply amazing. Everyone there was extremely courteous, friendly and...
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From
$120
Per Night
1 Bedroom, 1 Bathroom, Sleeps 4
20 photos Details Reviews (10) Make Inquiry
From
$345
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
37 photos Details Reviews (8) Make Inquiry
5 of 5 stars Reviewed July 25, 2014
Beautiful ocean view from balcony, living room and kitchen. My family loved unit # 306. Condo was better than photos. Very comfortable for a family of 5. Beds were comfortable...
5 of 5 stars Reviewed July 20, 2014
My husband, daughter, sister and brother-in-law rented Unit 306 at Polo Beach Club in Wailea, Maui. It was a wonderful experience! We were on the 3rd floor with a corner unit that...
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From
$1,295
Per Night
3 Bedrooms, 4 Bathrooms, Sleeps 6
75 photos Details Reviews (8) Make Inquiry
5 of 5 stars Reviewed October 30, 2013
Very spacious, perfect for a family. This villa is finished with high quality furniture/appliances etc. it had everything you need and more! the property is secure, quiet and...
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From
$130
Per Night
1 Bedroom, 1 Bathroom, Sleeps 2
25 photos Details Reviews (19) Make Inquiry
5 of 5 stars Reviewed June 23, 2014
Condo was very clean and with chocolates upon arrival. Beautiful island décor and kitchen was well stocked with basics to prepare meals. Plenty of furniture to store your...
5 of 5 stars Reviewed June 21, 2014
We loved very minute of our stay in the "Secret Garden" apartment. The property is spotlessly clean, well-equipped and beautifully furnished. We enjoyed breakfasts on the lanai...
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From
$1,150
Per Night
3 Bedrooms, 4 Bathrooms, Sleeps 6
83 photos Details Reviews (1) Make Inquiry
5 of 5 stars Reviewed August 14, 2014
We rented Castaway Cove, Unit C201 at the Wailea Beach Villas on Maui in July 2014. This unit is managed by Tropical Villas Vacations. Our first visit to Maui and "wow" what a...
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From
$1,095
Per Night
3 Bedrooms, 3 Bathrooms, Sleeps 6
78 photos Details Reviews (1) Make Inquiry
From
$265
Per Night
1 Bedroom, 2 Bathrooms, Sleeps 4
16 photos Details Reviews (25) Make Inquiry
5 of 5 stars Reviewed October 1, 2014
The condo was beautiful and had all the amenities we could ask for. The grounds were well maintained and had several pools to choose from. The beach was close and excellent. I...
5 of 5 stars Reviewed September 29, 2014
It was wonderful.... Great location and VERY clean. We loved it and will return to this same condo. thanks, Greg
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From
$190
Per Night
1 Bedroom, 2 Bathrooms, Sleeps 4
17 photos Details Reviews (3) Make Inquiry
From
$240
Per Night
1 Bedroom, 2 Bathrooms, Sleeps 4
21 photos Details Reviews (2) Make Inquiry
From
$265
Per Night
1 Bedroom, 2 Bathrooms, Sleeps 4
26 photos Details Reviews (4) Make Inquiry
From
$725
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 6
60 photos Details Reviews (14) Make Inquiry
5 of 5 stars Reviewed January 17, 2012
Spending our 35th anniversary here, in the beautiful Island Oasis Villa, could not have been more perfect. The owners of this villa know what they’re doing. Heavenly beds...
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From
$1,288
Per Night
3 Bedrooms, 4 Bathrooms, Sleeps 8
45 photos Details Reviews (1) Make Inquiry
From
$250
Per Night
1 Bedroom, 2 Bathrooms, Sleeps 5
21 photos Details Reviews (14) Make Inquiry
5 of 5 stars Reviewed September 13, 2014
We loved the condo and the owners are great. We also loved it as a base camp for exploring the island. Very convenient to other resorts and highways. They provide everything you...
5 of 5 stars Reviewed July 24, 2014
My husband and I stayed at 33a in Ekahi for a week long vacation. The condo and surroundings exceeded all of our expectations. It is very tastefully decorated, extremely clean...
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From
$750
Per Night
3 Bedrooms, 4 Bathrooms, Sleeps 8
17 photos Details Reviews (1) Make Inquiry
5 of 5 stars Reviewed August 12, 2013
We stayed in unit 24-1. The accommodations were first class. There aren't enough words to describe the luxury. We took our adult kids and their children. There was lots of...
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From
$115
Per Night
Studio, 1 Bathroom, Sleeps 2
14 photos Details Reviews (21) Make Inquiry
5 of 5 stars Reviewed October 1, 2013
Secret Studio is ideal for two, comfortable, very well equipped and furnished and comes with exhaustive notes on everything inside and locally. The complex is very convenient for...
5 of 5 stars Reviewed September 29, 2012
We enjoyed every minute while staying at the condo. The facility provided everything we wanted or needed including beach toys that we would have had to purchase. The location was...
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From
$295
Per Night
1 Bedroom, 1 Bathroom, Sleeps 2
12 photos Details Reviews (2) Make Inquiry
3 of 5 stars Reviewed November 17, 2011
The condo was just fine, truly just average. We rented from Kumulani Vacations. I notice that since our visit, the unit is no longer on vrbo so we could not review on the vrbo...
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Suitability

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

Amenities

  • Grill (189)
  • Internet (185)
  • All pools (163)
  • Air Conditioning (159)
  • Public pool (156)
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Book Online(74)

Suitability

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

Amenities

  • Grill (189)
  • Internet (185)
  • All pools (163)
  • Air Conditioning (159)
  • Public pool (156)
  • 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.