House vacation rentals in Wailea, Wailea-Makena

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Popular amenities for Wailea, Wailea-Makena house rentals

House rentals with a pool

Guest favorite
Home in Kihei
4.95 out of 5 average rating, 22 reviews

Luana Kai C209

ShriyaRating, 5 stars4 months ago
Beautiful condo in Kihei with every possible amenity to make you feel right at home. Private and peaceful with a pool, beach access. Perfect for getting around to snorkeling which was nearby. Access to stores too. Great place from which to visit Haleakala as well!
Superhost
A refreshing pool is surrounded by palm trees, with the ocean visible in the background. Several lounge chairs are positioned near the poolside for relaxation. The clear blue water reflects the bright sky, creating a vibrant outdoor space.
Home in Kihei
4.9 out of 5 average rating, 80 reviews

Maui Sunset Resort A102 - Aloha Mai, Remodel, Grou

StephanieRating, 5 stars2 months ago
We had a great time at Maui Sunset. The name definitely did not disappoint. Watching the sunset from the pool was amazing. Gary and his team were quick to respond to any message with kindness. The rental was clean and exactly as pictured. Quiet, comfortable place to stay with your family. We will definitely visit again!
Guest favorite
Home in Kihei
5 out of 5 average rating, 8 reviews

Private Home, Saltwater Pool in Kihei!

BetsyRating, 5 stars2 months ago
Mahalo nui loa! The Maui Dolphin House was spectacular, comfortable and exceeded our expectations for our family’s Ohana Christmas vacation. It was a wonderful home enjoyed by three generations of family while vacationing/traveling together. We especially loved the big dining table (to sit our eight people) and very well-stocked kitchen because we took turns preparing epic dinners for one another. The master bedroom was beautiful, with a view of the beautiful property, the sound of a water feature, and a huge rainfall shower and large jacuzzi tub. (We raffled off use of the jacuzzi tub during one of our family card games!) But the icing on the cake, was the salt water pool in the backyard. We loved lounging and playing in it during the week’s 80+ degree weather the week before Christmas. The property was very well maintained, met our every need (from BBQ to sheet pans for cooking to nice linens and comfty beds). We felt like we were on our very own Hawaiian island!
Guest favorite
A spacious living area showcases a blue sectional sofa adorned with colorful cushions. Two ceiling fans circulate air over the room, which is illuminated by natural light. A coffee table rests in front of the sofa, and art pieces decorate the walls.
Home in Wailuku
4.95 out of 5 average rating, 19 reviews

Maalaea Kai 307 - Maui Prime Oceanfront

Mary BethRating, 5 stars1 month ago
We spent a lovely three nights in this condo and it was perfect! We could not have asked for more. The view is just breathtaking, the beds were comfy, and the place was exactly what we’d hoped for. The location was wonderfully central for all our activities around the west side of the island. Our family, who was staying nearby was jealous they hadn’t booked this place, especially given it was more affordable than most. This place is an asset to any trip to Maui.
Guest favorite
A spacious living area features a large wall-mounted television and a distinctive chimney. Natural wood ceilings create an open atmosphere, while a stylish coffee table and comfortable seating provide a welcoming space for relaxation. Large windows allow natural light to brighten the room.
Home in Kihei
5 out of 5 average rating, 73 reviews

Your Own Private Resort with Breathtaking Ocean Views

PatrickRating, 5 stars1 month ago
Don’t pass up an opportunity to rent this house from Troy and Dianna! We have stayed at many rentals around the world and this one is top notch. House was clean, spacious, and kitchen well stocked with plenty of cook ware to cook some meals at home. Spent most of our time outside at the pool and hot tub. Beautiful views of ocean and nearby islands. Outside grill was cleaner than my grill at home. Wonderful outdoor scene. Plenty of beach equipment for beach excursions. There literally wasn’t anything needed at this house. Centrally located between Kihei and wailea. Closer to wailea shopping and restaurants than Kihei. Amazing beaches (Big Beach and Maluaka are our favs) within 10 minutes drive. Absolutely love the location.
Guest favorite
Home in Wailea
4.76 out of 5 average rating, 25 reviews

The Palms 1202 - The most expansive ocean views

GregRating, 5 stars12 months ago
Andre was a tremendous host. He was promptly responsive to our questions and requests. His condo is beautiful and well-equipped. The view from the lanai and every room was spectacular. My wife and I would love to stay here again.
A private pool is surrounded by lush tropical vegetation, creating a serene outdoor space. Bright green lounge chairs are positioned nearby, inviting relaxation under clear blue skies. Sunlight reflects off the water's surface, enhancing the tranquil ambiance.
Home in Kihei
5 out of 5 average rating, 3 reviews

CLOUD 9 BEACH HOUSE - pool, walk to beach, legal

SeanRating, 5 stars1 month ago
We enjoyed our stay in Kihei with Tamara's place serving as a great hub. Being a couple minutes drive from the main street, beaches, and shopping was really convenient. The house was spacious, clean, and had everything we needed. The beach chairs / toys / towels were an added bonus.

Weekly house rentals

Guest favorite
Home in Kihei
5 out of 5 average rating, 15 reviews

Aloha Aku CoCoPalm2 Suite – Cozy Beachfront Escape

AshleyRating, 5 stars4 months ago
This place is absolutely a gem. When we first pulled into the driveway we didn’t know what to expect. The lit up palms leading to the gorgeous Airbnb feels incredibly luxurious. Upon entering the Airbnb we were shocked to see just how spacious the unit is! It is stocked with everything you might need and has the MOST comfortable bed I have ever slept on out of any hotel or airbnb I have ever been to. Stepping out onto the patio was the biggest shock. Pictures do not do this place justice. Out of all of the places we have stayed on all of Hawaiian islands we have been to this was hands down the best. The beach is right out your back door. The sun sets right off the patio. It is breathtaking. The pool and jacuzzi were a great touch and even though it’s a shared space we never once shared it with other guests. We were not sure how private our stay here would feel, but it was perfect for our honeymoon. Our stay here goes down as my favorite vacation spot to date. I hope to visit again!
Superhost
Home in Kihei
5 out of 5 average rating, 6 reviews

Aloha Aku Hula2 Suite – Beachfront Bliss

NicoleRating, 5 stars9 months ago
Aloha Aku has been everything we wanted, and more. The photos and descriptions don't do it justice. We were originally booked for five days, but extended our trip twice, for a total of 10 days because everything here is just so perfect!
Superhost
Home in Kihei
5 out of 5 average rating, 5 reviews

Aloha Aku Ohana2 Suite – Relaxing Garden Views

TimRating, 5 stars22 months ago
When we arrived, we got confused trying to find the entrance, but if you read the instructions carefully, you should be fine! I had the most communication and clearer instructions here than anywhere else I've stayed with AirBnB-like places! The property is beautiful, the beach there is great for walks and sights, but not the best for swimming/snorkeling as it is usually murky. The hot tub and pools are really neat. The accommodations are exactly as described and really well done.
Guest favorite
A cozy living area features a light-colored sofa adorned with blue and white cushions. Two patterned armchairs complement the space, while a round wooden dining table sits nearby. Natural light enters through sheer curtains, and a colorful wall art piece adds visual interest.
Home in Paia
4.92 out of 5 average rating, 200 reviews

Paia cottage walk to town and beach

KirstenRating, 5 stars1 day ago
Jacque’s cottage was a perfect home base while we attended a yoga retreat nearby. It was spotless, cozy, and walking distance to so many cute shops and excellent restaurants along Baldwin Rd. I would highly recommend this cottage for anyone who wants to enjoy the charming town on Paia and the gorgeous North Shore of Maui. Mahalo, Jacque!!
Guest favorite
Home in Kihei
4.86 out of 5 average rating, 7 reviews

Aloha Aku Honu2 Suite – Relax by the Sea

AnthonyRating, 5 stars1 month ago
This was our second stay, we love it. The accommodations are great and the location divine. The on-site bikes and paddle boards and snorkeling gear are such a bonus. Wake up and paddle out…, every morning. The support team are excellent.
Guest favorite
Home in Kihei
4.93 out of 5 average rating, 27 reviews

Aloha Aku Honu Suite – Experience Aloha Spirit

MeaganRating, 5 stars8 months ago
Gary's condo is on a private beach with private pool and hot tub. The common area has all the amenities you could ask for. Very impressed!
Superhost
A spacious living area features a light hardwood floor, comfortable seating arrangements including a gray sofa, and a coffee table. Large windows allow natural light to fill the room, while a ceiling fan provides airflow. The dining area is visible in the background, accommodating six at a wooden table.
Home in Kihei
4.93 out of 5 average rating, 15 reviews

Private Tropical Home, Locally owned and operated!

KarinaRating, 5 stars4 months ago
Alexandra not only provided my friends and I with a beautiful and safe stay but she was quick to respond with any questions that we had. She was accommodating with our needs and met all of our expectations. Great place to explore all sides of the island!
Superhost
Home in Kihei
4.92 out of 5 average rating, 24 reviews

Aloha Aku Hula Suite – Find Peace by the Shore

TracyRating, 5 stars4 months ago
Location was ideal! Right on the beach, access to a small shared pool and hot tub, made it feel like your own private beach house. Kayaks and paddle boards were readily accessible, and were able to launch them right from the yard. We would not hesitate to stay here again.

Private house rentals

Superhost
Home in Kihei
4.71 out of 5 average rating, 7 reviews

Stunning One bedroom Oceanview Condo

JackieRating, 5 stars1 month ago
My husband and I stayed in this unit for 2 weeks over the Christmas period with our two children. we found the unit to be very well equipped with everything we could have needed for our stay. the kitchen in particular was great with newer cabinets and marble-look countertop - it was all very easy to keep clean through our stay. The washer and dryer inside the unit was a plus and super convenient - it meant that we could pack less for our trip since we could do laundry throughout our stay. The suite overlooked the ocean and the pickleball courts, so there was always some people-watching potential. As a relatively small complex, it was nice to recognize faces at the pool or in the parking lot throughout our stay - it does have the feel of a small community. The location of the complex itself was wonderful. it had the convenience of being very close to all the restaurants of Kihei without being directly in the action. This meant less traffic but could pick up takeout within 5 minutes.
Superhost
A spacious living area showcases elegant tile flooring and large sliding glass doors that invite natural light. A comfortable sofa is paired with a glass coffee table, while a flat-screen TV is mounted on the wall. A private outdoor space is visible through the doors.
Home in Kihei
4.85 out of 5 average rating, 13 reviews

Maui Sunset A102 - Aloha Mai 2, Beachfront Resort

LoriRating, 5 stars2 months ago
My sisters and I had a wonderful stay. We grew up on the island and came back to visit for a family event. It was wonderful to stay somewhere that was so convenient. It totally met our needs for location and amenities. Although it is a one bedroom, having a second bathroom was a big plus in choosing a place to stay. The beach is right there and we enjoyed watching the sunsets. The grounds are beautiful. Plenty of restaurants to choose from just a short drive away. We hope to stay again.
Superhost
A comfortable green sofa adorned with colorful floral pillows is positioned next to a wooden side table with a glass lamp. A vibrant piece of wall art depicting figures in a garden adds character, while a glass coffee table displays an assortment of fresh tropical fruits.
Home in Wailuku
4.9 out of 5 average rating, 30 reviews

Vineyard Village Maui House of Aloha

RebeccaRating, 5 stars1 month ago
Todd was an AWESOME host! Will definitely stay here again. 5 stars!!
Lush green lawns are framed by tall palm trees, leading to an unobstructed view of the ocean in the distance. A serene pond is visible among the greenery, enhancing the natural beauty of the landscape.
Home in Kihei
5 out of 5 average rating, 6 reviews

Kamaole Sands FRONT ROW OCEAN Unit 116

MichelleRating, 5 stars2 months ago
Stayed just over 3 weeks in this spectacular unit. Well appointed, incredible views, so clean! It was fully stocked with anything and everything you could possibly need. Full size toiletries in bathrooms, tons of clean linens, soap, detergent, cleaning supplies, and toilet paper to cover our entire stay. We felt right at home. Andre was responsive and immediately assisted when we had an issue with the AC unit in the second bedroom upon arrival. There is ongoing construction in the complex, but it didn't affect our building or interrupt our stay at all. Parking is open season during this construction period, which turned out great because we could choose any open spot - super convenient and tons of availability. Kamaole Sands is our fav complex in Kihei and we are already planning our return visit. Will definitely stay in this unit over and over again.
The exterior of the beach cottage is shown, featuring a light blue facade and a sloped, gray roof. Lush greenery surrounds the property, and multiple window A/C units are visible. A gravel driveway leads to the entrance, which is highlighted by natural landscaping.
Home in Kihei
4.7 out of 5 average rating, 86 reviews

Private Cottage @ Keawakapu Beach Sleeps 6 - MMC2

RebeccaRating, 5 stars2 months ago
We would stay here again in a heartbeat! This is a true beach cottage. Nothing fancy but everything you need. We are a family of 5 adults and a toddler and this house fit all of our needs. The back yard was our favorite space, it is shaded and secluded with a table that seats 6. The downtown area was an easy drive, 10 minutes tops, and had lots of options for eating, drinking, and shopping. The beach was an easy 3 minute walk from the house and it was a beautiful beach! Everything we needed for a fun day on the beach was available to us. There are beach chairs, sand toys, snorkeling equipment, towels, and even an insulated backpack to carry food and drink. My husband loved being able to grab the snorkeling gear he needed and just go. There are window ac units in the bedrooms which means you can't open those windows but it wasn't a problem for us. We loved staying here! I miss my walks on the beach and breakfast on the patio! Oh, and the chicken family who lived in the front yard!

Quick stats about house rentals in Wailea, Wailea-Makena

  • Total rentals

    50 properties

  • Nightly prices starting at

    ﺩ.ﺇ257 before taxes and fees

  • Total number of reviews

    2.2K reviews

  • Family-friendly rentals

    40 properties are a good fit for families

  • Rentals with a pool

    30 properties have a pool

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

Destinations to explore

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  3. Hawaii
  4. Maui County
  5. Wailea-Makena
  6. Wailea
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