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Vacation Rentals in Wailea, HI

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All 228 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
$695
Per Night
3 Bedrooms, 4 Bathrooms, Sleeps 10
44 photos Details Reviews (27) Make Inquiry
From
$199
Per Night
1 Bedroom, 1 Bathroom, Sleeps 2
Booking
21 photos Details Reviews (4) Make Inquiry
Also consider
Wailea, Maui , Hawaii The Palms Deluxe #706
2 Bedrooms, sleeps 6
$240 - $375 / night
Wailea Ekahi 7G Luxury Ocean Front S Maui Condo
1 Bedroom, sleeps 3
$340 - $450 / night
Great Ocean View, Remodeled, Stuff for Kids
2 Bedrooms, sleeps 6
$250 - $325 / night
Spectacular Ocean view-Stuff for Kids-Ekahi 32D
1 Bedroom, sleeps 4
$290 - $325 / night
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
$369
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
19 photos Details Reviews (1) Make Inquiry
From
$225
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
Booking
22 photos Details Make Inquiry
From
$190
Per Night
2 Bedrooms, 3 Bathrooms, Sleeps 8
Bookings
11 photos Details Make Inquiry
From
$190
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 4
Booking
17 photos Details Make Inquiry
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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
$195
Per Night
1 Bedroom, 2 Bathrooms, Sleeps 4
13 photos Details Make Inquiry
From
$210
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
24 photos Details Make Inquiry
From
$195
Per Night
1 Bedroom, 2 Bathrooms, Sleeps 4
15 photos Details Make Inquiry
From
$149
Per Night
1 Bedroom, 2 Bathrooms, Sleeps 4
25 photos Details Make Inquiry
From
$295
Per Night
1 Bedroom, 2 Bathrooms, Sleeps 3
7 photos Details Make Inquiry
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
$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
$695
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
30 photos Details Reviews (18) Make Inquiry
From
$995
Per Night
3 Bedrooms, 3 Bathrooms, Sleeps 8
32 photos Details Reviews (5) 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
$120
Per Night
1 Bedroom, 1 Bathroom, Sleeps 4
20 photos Details Reviews (10) Make Inquiry
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
$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
$240
Per Night
1 Bedroom, 2 Bathrooms, Sleeps 4
21 photos Details Reviews (2) 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
$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
$550
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 4
20 photos Details Reviews (33) Make Inquiry
5 of 5 stars Reviewed October 2, 2012
We booked this condo through the web site www.makenasurf.com and dealt with Jim Osgood during the booking process. Mr. Osgood was quickly responsive to my initial inquiry about...
3 of 5 stars Reviewed September 5, 2012
We were very excited to stay in this unit at Makena Surf but had a very disappointing experience. Our hope is to prevent other families from having a similar experience. First...
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From
$115
Per Night
1 Bedroom, 1 Bathroom, Sleeps 2
24 photos Details Reviews (9) Make Inquiry
5 of 5 stars Reviewed June 13, 2013
My boyfriend and I stayed at Wailea Grand Champions for a couple of nights and we loved it. The property is beautifully maintained and it is located very close to several great...
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From
$200
Per Night
1 Bedroom, 2 Bathrooms, Sleeps 4
14 photos Details Reviews (9) Make Inquiry
4 of 5 stars Reviewed August 17, 2014
Skip and Mickey were fantastic from the beginning. They have taken special care to stock the condo with everything you might need for a relaxing, fun trip to the beach. From...
5 of 5 stars Reviewed June 15, 2013
This was our first visit to Maui and Skip and Mickey's condo was the perfect home away from home. They have it stocked with everything we needed for the beach - beach chairs...
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From
$175
Per Night
3 Bedrooms, 2 Bathrooms, Sleeps 6
29 photos Details Reviews (2) Make Inquiry
From
$199
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
19 photos Details Reviews (16) Make Inquiry
5 of 5 stars Reviewed November 7, 2011
The condo and resort exceeded our expectations with the rental agent for the owners going above and beyond. Grand Champions is so convenient to the beautiful Shops of Wailea, the...
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From
$410
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
21 photos Details Reviews (24) Make Inquiry
4 of 5 stars Reviewed August 19, 2014
Highly recommend this condo unit. would have given it an "excellent" if it had a good ocean view-- which it once did, until some new construction between it and the ocean...
5 of 5 stars Reviewed January 26, 2012
We are a family of 4 adults and booked Ekahi 20A for 12 nights over Christmas. The suite was lovely and just as depicted in the photos on line. Communication with the Owner is...
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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
$265
Per Night
1 Bedroom, 2 Bathrooms, Sleeps 4
10 photos Details Reviews (9) Make Inquiry
4 of 5 stars Reviewed September 8, 2014
The condo was very nice , well maintained with quality renovations. The BQ was electric and I am a chef so that was one thing I didn't like and the towels were not very clean. The...
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From
$595
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 4
24 photos Details Reviews (9) Make Inquiry
5 of 5 stars Reviewed November 22, 2012
My mother, wife, and I stayed here from Nov. 11th till Nov. 16th, 2012. This is a lovely and nice place you should definately consider staying when making a trip to Wailea, Maui...
5 of 5 stars Reviewed January 12, 2012
My thank you note to the owners: I just want to say thank you for opening up your Maui home to fortunate people such as us. Your home there is lovely! You did a beautiful job...
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From
$290
Per Night
1 Bedroom, 2 Bathrooms, Sleeps 4
19 photos Details Reviews (11) Make Inquiry
From
$199
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 6
20 photos Details Reviews (37) Make Inquiry
5 of 5 stars Reviewed January 26, 2014
My husband and I, along with our 1 year-old daughter, stayed at this condo for a week Jan 14 - 21, 2014. The condo was clean and very well appointed. The lanai overlooks the...
5 of 5 stars Reviewed September 6, 2013
The photos are accurate and show a beautifully decorated home, but they don't show you how well stocked this home is. It's not "just a rental" with low quality/bare minimum...
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From
$170
Per Night
1 Bedroom, 2 Bathrooms, Sleeps 4
Bookings
23 photos Details Reviews (9) Make Inquiry
1 of 5 stars Reviewed September 27, 2014
I booked this condo in July as 3 of us are attending a conference. I was notified that my final payment was due, which I paid promptly. On Mon. I received a notification that my...
5 of 5 stars Reviewed April 3, 2014
We ran across this particular condo because we needed to fill in 3 additional days on our recent stay in Maui. The only regret is we didn't know about it earlier. The condo itself...
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From
$195
Per Night
1 Bedroom, 1 Bathroom, Sleeps 2
14 photos Details Reviews (14) Make Inquiry
5 of 5 stars Reviewed December 11, 2013
Wonderful, wonderful studio condo on second floor. Super clean, and newly refurnished and redecorated including the lanai which was fabulous for BBQing in the evening and...
5 of 5 stars Reviewed August 2, 2013
Gorgeous condo with walking distance to gorgeous beaches with great snorkeling, newly renovated kitchen including everything from soy sauce to Tupperware, a small gas BBQ grill...
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From
$450
Per Night
2 Bedrooms, 2 Bathrooms, Sleeps 4
41 photos Details Reviews (17) Make Inquiry
5 of 5 stars Reviewed October 1, 2014
Communication and booking was very smooth and easy by working through Peggy the owner, she is very prompt and informative and a very nice person. The condo unit has obviously been...
5 of 5 stars Reviewed June 11, 2014
From the time of booking this condo (Ekahi 11F) through the stay and afterward, the experience was flawless. Contact with Peggy Kay all went smoothly. The condo is BEAUTIFUL...
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From
$295
Per Night
1 Bedroom, 2 Bathrooms, Sleeps 2
16 photos Details Reviews (2) Make Inquiry
5 of 5 stars Reviewed July 2, 2014
This was a beautiful Condo with all the amenities. It had a beautiful view of the garden an ocean. Great lanai to sit and have breakfast and dinner at. Even had a gas grill to...
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Suitability

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

Amenities

  • Grill (188)
  • Internet (184)
  • All pools (162)
  • Air Conditioning (158)
  • Public pool (155)
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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 (188)
  • Internet (184)
  • All pools (162)
  • Air Conditioning (158)
  • Public pool (155)
  • 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.