Wailea-Makena Holiday Rentals

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Holiday Rentals in Wailea-Makena

Aston Maui Hill
3.0 star property
9.0 out of 10, Wonderful, (697)
"Extremely happy with our recent stay at Aston Maui Hill! We are a family of 3 - Mom, dad and 1.5yo baby. The accommodations provided were perfect for our family! From a full-size kitchen with all dishware, etc., needed included, to a handy washer and dryer, our stay was both easier and more affordable than had we not had both those options. The layout of our reservation was perfect, including a master suite and a small bedroom. This allowed us to put the baby to bed at a reasonable time, still...
Aston Maui Hill
Maui Banyan Vacation Club
3.0 star property
8.0 out of 10, Very good, (289)
"Location was perfect if you like quiet beach towns. The beach was so beautiful and totally within walking distance. The pool was also very clean."
Maui Banyan Vacation Club
Maui Kamaole
3.5 star property
8.8 out of 10, Excellent, (794)
"This was first time staying condo and we liked the place. The place was clean, provided beach towels, snorkeling gear, beach umbrella and others. The location is great. "
Maui Kamaole
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Castle Kama'ole Sands
3.0 star property
8.0 out of 10, Very good, (2143)
"This was a perfect way to lay your head for my stay. "
Castle Kama'ole Sands
Wailea Ekahi - CoralTree Residence Collection
3.0 star property
9.2 out of 10, Wonderful, (468)
"Close to the beach and beautiful"
Wailea Ekahi - CoralTree Residence Collection
Kihei Akahi
3.0 star property
8.2 out of 10, Very good, (569)
"We love this part of the beach and Kihei Akahi meets all our needs. The unit is spacious enough and has been remodeled. Everything was in good working order. This is our 4th stay at Kihei Akahi. "
Kihei Akahi
Palms at Wailea Maui
3.5 star property
8.4 out of 10, Very good, (464)
"This condo was absolutely gorgeous! The air conditioner was wonderful. I would definitely recommend this place. Amazing view from the Lani. "
Palms at Wailea Maui
Wailea Grand Champions - CoralTree Residence Collection
3.0 star property
9.0 out of 10, Wonderful, (661)
"WiFi had issue and Technical support had to come to condo to repair. Master bathroom toilet had to been leaking and owner had to be contacted fir approval to be replaced during our stay and left us with 1 toilet to share for 24 hours. We had to inconvenience our invited guest with this situation. "
Wailea Grand Champions - CoralTree Residence Collection
Hale Kamaole
3.0 star property
8.4 out of 10, Very good, (321)
"Great location, amazing room! One thing to improve on is to get another fan or AC in the living room because that area gets hot easily"
Hale Kamaole
Absolutely Incredible Penthouse Front Facing Ocean Views with Pickleball!
9.8 out of 10, Exceptional, (262)
"Centrally located in South Kihei, beautiful sunsets and breakfasts on the lanai. Clean unit and communicative owners. We hope to be back!"
Absolutely Incredible Penthouse Front Facing Ocean Views with Pickleball!
Wailea Beach Villas
4.5 star property
9.8 out of 10, Exceptional, (154)
"Incredible! Excellent from start to finish!"
Wailea Beach Villas
Maui Kamaole by VTrips
4.0 star property
9.0 out of 10, Wonderful, (27)
"The pool was perfect for kids and the grounds beautiful and well kept. "
Maui Kamaole by VTrips
Kihei Akahi by VTrips
4.0 star property
7.6 out of 10, Good, (24)
"Central location for Kehie Town. Bed was hard, bathroom small. TV hard to work. Bedroom warm not air conditioned (room). Overall good. "
Kihei Akahi by VTrips
Wailea Ekolu - CoralTree Residence Collection
3.5 star property
8.8 out of 10, Excellent, (241)
"Loved the ocean view. Although our unit was old it was well kept and offered us every amenity."
Wailea Ekolu - CoralTree Residence Collection
Maui Vista 3210 Wonderful unit With New Split AC, Low VO and New Paint and Carpet
8.4 out of 10, Very good, (26)
"We had an amazing time in Maui and loved staying in your place. It is perfectly located near great local shops and beaches, with our favourite shave ice and gelato place just down the street. It is a very nice place and well stocked. We made great use of the cooler and beach chairs. Shower head is a little low for taller people, but a minor factor on a great vacation. Our family is already looking forward to planning another trip to Maui!"
The price is NZ$874
includes taxes & fees
2 Jun - 3 Jun
Maui Vista 3210 Wonderful unit With New Split AC, Low VO and New Paint and Carpet
Beautiful Quiet Unit Steps From Maui's Finest beaches
9.4 out of 10, Exceptional, (131)
"This was our first time to Maui, and I am so glad I stumbled into this place. It was a great base camp for all of the Adventures Maui has to offer. We went to a ton of beaches and some of our favorites were within walking distance from the condo (down the parking lot) the beach chairs, umbrella and boogie boards were a bonus. Kitchen was well stock with pots and pans, bed was comfortable and my kid said she slept well on the pull out couch. Bathroom was nice and clean. Shops and restaurants all...
Beautiful Quiet Unit Steps From Maui's Finest beaches
Wailea Ekahi Studio #52-E Beautifully Renovated Studio on Keawakapu Beach
9.8 out of 10, Exceptional, (13)
"Excellent property! The bed and pillows were so comfortable! The street noise is the only negative comment and that’s really minor. Decorated just as you would expect for Hawaii."
Wailea Ekahi Studio #52-E Beautifully Renovated Studio on Keawakapu Beach
Kamaole Sands by VTrips
4.0 star property
9.0 out of 10, Wonderful, (24)
"This property is in a great walkable location to the ocean. Very clean and pretty. We had here very good time. Love this place and will be happy to return back. I would definitely recommend it to my friends. "
Kamaole Sands by VTrips
Private 2BR Cottage House with Waterfall Pool Maui Meadows Permitted
10.0 out of 10, Exceptional, (130)
"Beautiful property in Wailea. We enjoyed the pool all day and Elaine was so sweet. Will stay here again."
Private 2BR Cottage House with Waterfall Pool Maui Meadows Permitted
New Listing! GC 30- Fabulous Updated Condo! Ideal Wailea Location!
10.0 out of 10, Exceptional, (3)
"Our family has enjoyed GC many times before and enjoy this well situated property. Tastefully refinished unit is well stocked and comfortable. Property managers are excellent."
New Listing! GC 30- Fabulous Updated Condo! Ideal Wailea Location!
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See all available properties in Wailea-Makena
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Other types of properties in Wailea-Makena you may be interested in

Grand Wailea Maui, A Waldorf Astoria Resort
5.0 star property
9.0 out of 10, Wonderful, (1000)
"Best resort in Maui. Views everywhere that are spectacular. Amazing guest experience with fantastic rooms. Pool area was lots of fun and adjacent to the best beach in Wailea! Unbelievable resort. "
The price is NZ$1,684
includes taxes & fees
7 Jun - 8 Jun
Grand Wailea Maui, A Waldorf Astoria Resort
Fairmont Kea Lani Maui
4.5 star property
9.4 out of 10, Exceptional, (1001)
"Easily some of the best service at any resort we’ve ever stayed. Start to finish everyone was fantastic. Front desk. Valet. Pool. Restaurants. Everyone went above and beyond. Will definitely return. "
The price is NZ$1,850
includes taxes & fees
3 Jun - 4 Jun
Fairmont Kea Lani Maui
Wailea Beach Resort - Marriott, Maui
4.5 star property
9.0 out of 10, Wonderful, (829)
"Very nice location and environment!"
The price is NZ$1,589
includes taxes & fees
30 Jun - 1 Jul
Wailea Beach Resort - Marriott, Maui
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Wailea-Makena holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Wailea-Makena. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Wailea-Makena. Seeing all the best attractions is bound to make you fall in love with Wailea-Makena. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Wailea-Makena short-term rentals, that won’t be hard to do.

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