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 stars5 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
Home in Kihei
4.9 out of 5 average rating, 81 reviews

Maui Sunset Resort A102 - Aloha Mai, Remodel, Grou

NonaRating, 5 stars3 months ago
This was a good place, I would have liked to have seen more detail to some of the cleaning,, i.e. corners & draperies. We found a huge Palmetto bug the first night! Ewww This is a very well maintained complex & the grounds are delightful.
Guest favorite
Home in Wailuku
4.95 out of 5 average rating, 20 reviews

Maalaea Kai 307 - Maui Prime Oceanfront

MikeRating, 5 stars3 days ago
Great place in a great location. 15 minute drive from the airport, cute area, reasonable drives to all of the places we went (Road to Hana, Kaanapali, Ioa Valley). My family of 4 were very happy there! We saw whales from our lanai several times. Great trip!
Top guest favorite
Home in Kihei
4.98 out of 5 average rating, 50 reviews

Centrally located and steps to the beach!

AmandaRating, 5 stars1 week ago
We had a great stay at Ashley and Mike’s! Lots of great food places and grocery stores/ coffee shops within quick walking distance. We utilized the provided beach chairs, coolers and umbrella pretty much daily. Ashley and Mike were easy to communicate with. The place was super clean and comfortable. We would definitely return :)
Guest favorite
Home in Lahaina
5 out of 5 average rating, 7 reviews

Pualei Beach House

PierrickRating, 5 stars1 month ago
The house was beautiful and clean, located in a quiet neighborhood close to everything you may need. Ryan is a wonderful host and was very responsive with great communication. We will definitely try to book this place when we come back! The house was very cute, modern with a great kitchen and spacious. There were extra snorkeling gear, games and everything you would want for a beach day We all had an amazing time!
Home in Lahaina
5 out of 5 average rating, 4 reviews

Come Back to Puamana Nani

NicoleRating, 5 stars1 month ago
Annie is a great host, the home was clean and comfortable. The beach a minute or two walk. The pool is close to the condo, about a minute too. We slept peacefully in the comfortable beds, the kitchen was well stocked, and the place is beautiful and comforting. We sat outside to drink coffee in the mornings and it felt like home, but better.
Top guest favorite
Home in Wailea
4.76 out of 5 average rating, 25 reviews

The Palms 1202 - The most expansive ocean views

GregRating, 5 stars13 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.
Home in Kihei
4.8 out of 5 average rating, 5 reviews

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

StaceyRating, 5 stars3 weeks ago
We are a family of 7. 6 adults and one teenager. Tamara's home has a Homey feeling. We felt right at home. She provided so many amenities. She was extremely friendly and responsive as if she was part of your family. Beds were very comfortable, and she supplied many daily used items. Don't just take my word. Book her home and see for yourself. We will definitely book with her again in the near future.

Weekly house rentals

Home in Kihei
New place to stay

Kihei 533 Ocean View Condo

HershRating, 5 stars2 weeks ago
Great stay!
Home in Wailuku
4.64 out of 5 average rating, 227 reviews

Charming Direct Oceanfront North Shore Beach House

JessicaRating, 5 stars1 week ago
Excellent place to stay. The land is alive and well. 🌀
Home in Kihei
4.76 out of 5 average rating, 29 reviews

Oceanfront Koa Lagoon Condo w/ Sunset Views

MeganRating, 5 stars1 day ago
Enjoyed the view and spacious quarters. Would definitely stay here again!
Guest favorite
Home in Paia
4.7 out of 5 average rating, 193 reviews

Kuau Beachy Family Cottage Maui

LindsayRating, 5 stars15 months ago
John’s place was perfect for what we wanted. We didn’t want to stay in a resort, but wanted access to all the island had to offer- this was the spot. Easy to access upcountry, get to the swimmable beaches, watch world Class surfing, good food. Being across the street from the store made grabbing breakfast, poke and sandwiches a breeze. The cottage was clean, quiet, and cozy.
Guest favorite
Home in Kihei
4.9 out of 5 average rating, 86 reviews

Chez Maui Kihei Beach House, 1 Block to the Beach!

AlisaRating, 5 stars17 months ago
Thank you for this amazing stay Leanne! We had such a great time and enjoyed the close beach at sunset, went snorkeling during the day and even saw turtles just 5min away (by car). All rooms have air condition which we enjoyed during the night. It’s a pretty quiet neighborhood so this will be a really relaxing holiday. Perfect area to explore the island. If Germany wouldn’t be as far away, we would love to come back!
Home in Kihei
4.87 out of 5 average rating, 39 reviews

Cottage Keawakapu Beach

GrantRating, 5 stars3 weeks ago
We really enjoyed our stay at the Maui Mango cottages. It’s a very spacious 2 bedroom unit, it feels more spacious than the photos make it appear, which was a great surprise. The yard is huge and really well shaded which is great because it’s pretty much non-stop sunny in Kihei. It’s a super quick walk to a really nice beach. The only shower is an outdoor shower, which we didn’t realize initially, but turned out to be a fun surprise. A smidge chilly if you shower at night but still fun to look at the moon and stars while you shower. Overall would definitely stay here again!
Home in Kihei
4.97 out of 5 average rating, 67 reviews

Exclusive Beachfront Cottage, Ocean Views, WiFi/AC

MariRating, 5 stars9 months ago
Absolutely perfect! Beautiful beach access with great walkability to local restaurants and shops. This place was peaceful and quiet! Great sunset view from the balcony. The space was clean and very easy to find. The beach made for great turtle watching.

Private house rentals

Superhost
Home in Kihei
5 out of 5 average rating, 3 reviews

Aloha Aku CoCoPalm Suite – Tropical Bliss

AshleyRating, 5 stars73 months ago
We had the most amazing time. All of the small touches were there, and we were constantly surprised by the high level of service and pride in the property. You cannot beat the view, and the hot tub is awesome! The unit was stocked with the nessesities, as well as delightful extras. The bed was incredibly comfortable, and the cherry on top was the ducks!! So charming. We cannot wait to come back!
Superhost
Home in Haiku-Pauwela
4.93 out of 5 average rating, 41 reviews

Private cottage with hot-tub

AlexandraRating, 5 stars4 months ago
Our stay at this up country Air B&B was absolutely perfect! The property is private, peaceful, and tucked away in such a serene location. We loved how cool and quiet it was, making it the perfect place to unwind and recharge. One of the highlights was the jacuzzi—relaxing under the stars was a magical experience, and the beautiful sunrise each morning was the perfect way to start the day. The space was well-appointed, comfortable, and everything we needed for a memorable stay. If you’re looking for tranquility and a touch of luxury, this is the spot. Highly recommended, and we can’t wait to return!
Guest favorite
Home in Paia
4.85 out of 5 average rating, 41 reviews

Huge views, one minute to beach

SarahRating, 5 stars1 month ago
We will be back!! This was the best location, the views were breathtaking and having walking access to a quiet beach was so special. Thank you, Cathy!
Top guest favorite
Home in Paia
4.92 out of 5 average rating, 204 reviews

Paia cottage walk to town and beach

NadyaRating, 5 stars4 days ago
This is a great find. Everything was as described. Very good location. Nice clean cottage that is equipped with everything we needed for 8 days stay. I would highly recommend.
Guest favorite
Home in Paia
4.95 out of 5 average rating, 66 reviews

Hale Ho'okipa Kai Cottage, County Licensed

KatrinaRating, 5 stars4 months ago
Fabulous Maui oasis. A beautiful cottage overlooking the ocean, just a couple minutes drive from the awesome town of Paia. We loved this place and would absolutely stay here again. The house itself has been kept in excellent condition -- photos reflect reality! And the garden and ocean are sublime. Paia is really fun little town full of restaurants and shops, perfect place to have as a Maui home base and explore the rest of the island -- or stay put in your oasis. The only negative is the garden is shared with the AirBnB apartment behind. This could have been intrusive as anyone in the garden looks directly into the cottage and is close to the lanai. That said, our neighbors were very discrete and hardly used the outdoor space so it was not a problem. Just worth noting. All that said, just love this place and hope to return!
Superhost
Home in Haiku-Pauwela
4.93 out of 5 average rating, 14 reviews

Hale Pola'i, County Licensed

TaylorRating, 5 stars15 months ago
This is a lovely house with lots of space. We had six people but plenty of room to spread out. The outdoor space was also a huge plus.
Top guest favorite
Home in Kihei
5 out of 5 average rating, 67 reviews

Cute Cottage-Large Outdoor Deck

KatieRating, 5 stars2 weeks ago
Brandon’s place is perfectly located for everything we wanted to do: whale watching, snorkeling, eating good food, beach relaxing, etc. Other Maui highlights like the volcano and the Road to Hana are a reasonable distance away too. This place was soooo cozy with lots of cute Hawaiian touches, and the bed was fantastic and comfortable after a long day of exploring. It’s also just a short half mile walk to the beach, which I did on foot every day to catch the sunset. Towels and beach chairs are provided which was so helpful. It was just the right size for my boyfriend and I for a week long trip!
Guest favorite
Home in Haiku-Pauwela
4.9 out of 5 average rating, 29 reviews

Nature lovers cottage with tennis

MatiasRating, 5 stars1 month ago
We loved this gorgeous cottage even more than we thought we would! We vacationed with my in-laws and there was plenty of space for everyone even with sharing the one bathroom between four people. The location is really beautiful in a gated property with a great deal of privacy and amazing grounds with a great view over a verdant gorge with the mountain in the distance. Everything is in pristine condition. The outdoor shower was awesome! My in-laws were excited to play pickle ball on the tennis court but apparently the surface was not the right kind for pickle ball (I don't play so I can't comment directly). Highly recommend!

Quick stats about house rentals in Wailea, Wailea-Makena

  • Total rentals

    50 properties

  • Nightly prices starting at

    $70 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

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