
House vacation rentals in Wailea-Makena
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Top-rated house rentals in Wailea-Makena
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Popular amenities for Wailea-Makena house rentals
House rentals with a pool

Aloha Aku CoCoPalm Suite – Experience Tropical Bli
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!

Newly Remodeled Cottage
Look no more!! Vans place is absolutely stunning. We stayed here with our four kids & we cannot wait to return. The location is so peaceful and extremely spacious. Thank you Van for hosting our stay. We look forward to staying here again.

ICC 20 Remodeled 2BD Hawaiian Cottage w Pool AC
Beautiful property with a great deck. Was perfect for a family vacation. So close to all the resorts and the beach. Great location to get around Maui. Would highly recommend!

Luana Kai C209
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!

Your Beachfront Island Home Awaits! #1A2
This place is terrific! It's clean, very comfortable, nicely laid out. The rooms are spacious and all have AC units and ceiling fans - and an AC unit in the main living/eating area. The linens and towels are high quality. There is a wonderful deck that overlooks the pool and the ocean with easy access to a small grassy area and beach. The house has lots of amenities for guests' use incl boogie boards, snorkel equipment, sand toys for kids. There are also a lot of spices and other items in the pantry which is always nice when you cook in. The hosts are responsive and friendly. The only downside is the condo sits on a pretty high traffic road and it can be noisy. You can walk to some restaurants but a car is a must. I would come back here for sure.

Centrally located and steps to the beach!
Mike and Ashley’s place was perfect for our little getaway. It was one of our birthdays and they had a little balloon and card for us. They were very responsive when we needed a couple of things and I 10/10 recommend to stay here!

3BR/3BA Pualei Beach House
Ryan's place was exactly as pictured. The neighborhood and townhouse was very quiet and family friendly. Ryan was very responsive to the small things that can sometimes come up when traveling. Lahaina is still in process of rebuilding but even so there was more than enough to stay busy. Would highly recommend.

Oceanfront 2BR Condo w/ Pool Access & Sunset Views
Very highly recommend this listing! the views were stunning and with obstruction. The suite feels very private and the lanai is ideal for anyone looking to relax while looking out and watching the ocean. The unit is also very near attractions and beaches on West Maui with great parking access (included which is rare) and calm roads. Even during higher surf days, the sound proofing in the suite didn't disturb our sleep. we had a very enjoyable time!
Weekly house rentals

Mahalo Pono @ Ka 'anapali Royal
We absolutely loved Jay and Amy’s place. It had everything we needed and more. The location was perfect ( 5 minute walk to the shopping center), restaurants and beach were also a short drive away. The house was pristine. It’s better in person than in the pictures to be honest. Amy was very helpful and super responsive with any questions we had. We truly felt at home. Would definitely stay here again. Thank you, Jay and Amy for your hospitality. You truly made our vacation very special.

Island-Inspired 2BD Oceanfront ~ Quam Properties
We stayed in two units at Hololani. This one was my fav. More spacious. Wonderful lanai. Unit is comfortable and we felt at home. Made some great dinners and enjoyed the view. This is a neighborhood condo not the high end resort. Pool amazing. 90 degrees! We loved our stay! Note units are Not air conditioned. Fans adequate. A couple of big box fans would have gone a long way to making us more comfortable.

Hunter Hales KALA cottage Haiku Maui
Mikes spot was amazing! Spotlessly clean, had anything you can think of (from glass food containers, cooking supplies, filtered water, everything…) and was perfectly located to hop on the road to Hana. It’s walkable to a few cafes but is very private and secluded from the road. We loved hearing the sounds of the toads at night as well as the rooster saying hello in the morning. A perfect place to relax 😎

3-bed 2-bath Beach Bungalow w/ Bikes & Pickleball!
Dan & Steph’s place was the perfect getaway location for me! It was so close to amazing beaches and restaurants, and the seemingly remote nature or the house made it seem I returned to a private island when I returned!

5 Star 4 Bdrm Private Home in Kihei! 2 K 2 Q
We had a great stay at our “Hawaii” house. We made good use of the covered lanai where we sat and visited while the kids ran around in the yard looking for the rooster and the cat. The daily visit of the geckos was also a highlight. The bedrooms were spacious especially the master which had enough room for two blowup mattresses for the kids. Location was perfect making it easy to get to the Kamaole beaches. We also loved that we could walk to Kalama park. It was also a short drive to the outdoor pool. We swam in the morning and built sand castles in the afternoon. My 5 year old grandson met a playmate at the pool and they arranged a play date at Kamaole 3 in the afternoon. The sand toys were well used. With Foodland so close by, we were able to shop every second day and eat as much poke, pineapples, and papayas as we wanted. We also walked to the food trucks and the South Maui gardens. Deb was very responsive to inquiries and we appreciated that she gave us a late checkout.

Charming 2bd/1ba downstairs Unit with AC
Rina’s place was great for us. It had all the basic amenities that we needed. The place is a quick walk to the town of Paia and a few local beaches. All the food in the town is great and the beaches were awesome. It was a good place to rest after a long day of being out and about. No complaints here.
Private house rentals

Clean, Ocean Front, Big 1 Bd, 1st Fl, Royal Kahana
First time in Maui was a success. Only thing we would change is the length of stay. Recommend 10 days minimum. Will definitely be looking to stay here again.

Stunning Ocean View Napili Bay!
Kris & Kirk were fantastic from the start with their communication. We had a little hiccup with the door code BUT I still gave them 5 stars because it was not their fault by any means. The entire property just happened to change their door code system that day. Even on an airplane, they communicated through text and they had maintenance there within an hour or two to open it up, PLUS their renters left earlier in the morning so they let us check-in early anyway. The place was so cute and perfect for our family. It was clean and gave the Hawaiian condo vibe I love. Location was great and so close to Napili Bay with gorgeous views less than 500 feet (give or take) from their sliding back door and the Gazebo restaurant about the same distance. The grounds were clean and absolutely gorgeous plumeria trees everywhere! The bed was comfy and my girls loved having a “sleepover” on the pull out couch and loveseat. I would definitely stay there again and recommend it to my friends and family.

3 Bedroom Private House Kihei /Wailea Maui
The coconut cottage is an ideal base for Maui adventures! Large, spacious property to easily accommodate up to 6-8 people - with a full functioning kitchen, 2.5 baths, large backyard and a lovely front-facing deck. We had the most luxurious and comfy stay, and lots of fun family memories in the main living area. The property is located in Kihei, with quick access to the beach, shopping and local markets. Marc is the most gracious host, and was incredibly accommodating, easily accessible and super kind. 10/10 recommend!!!! Would love to come back at some stage :)

One Block to the Beach! Cozy Beach House in Kihei
Wonderful to stay at Leanne’s place! Great spot to work remotely while enjoying Maui. And such a responsive and helpful host! Strongly recommend!

Gratitude Bed and Breakfast BBWK2022/0001
We had such a lovely week long stay here!This house is peaceful, quiet, clean, and very comfortable- a hidden gem for sure. It truly felt like a home away from home and the perfect place for us to relax, unwind and enjoy. The house was furnished with all the amenities that we needed and is walkable to restaurants and shops. Rhonda was so welcoming and was always available if we had questions or needed anything. We would happily stay at the Gratitude Bed and Breakfast again.

Come Back to Puamana Nani
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.

Exclusive Beachfront Cottage, Ocean Views, WiFi/AC
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.

Sunshine house (Ka Lā Hale)
Our 3 families had a wonderful stay at Shannon's property! The house has a nice open area combining the living room and dining table making a comfortable area to relax and hang out. Location was convenient as we were able to walk to Nipili Bay and a few restaurants in the area. Nipili Market and other restaurants both fast/local (Joeys and Mamas) and nicer (Merrimans and The Sea House) were just a couple minute drive away. Shannon had quick responses to all my questions and great suggestions! Would definitely stay again if we're in the area!
Quick stats about house rentals in Wailea-Makena
Total rentals
50 properties
Nightly prices starting at
$97 CAD before taxes and fees
Total number of reviews
2.3K 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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