
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
We had a wonderful week long stay here with the kids and grandparents. The house was spacious and exactly as described in the listing. I really appreciated how responsive Van was the few times we reached out. It was also a big bonus that they had a great selection of beach toys, good quality beach chairs, a boogey board and noodles that we could use. The house was well stocked with everything needed for our stay. The walk to the beach was a bit far for our small kids (all under 5), but it would be an easy walk for big kids and adults.

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!

Oceanview Home with Private pool and hot tub
Steve’s place is great and he is an excellent communicator and very invested in ensuring his guests have a great experience. We loved watching the sunset from the deck and the pool and game room were both so fun for our family. Lots of pantry staples on hand as well as some yummy snacks to greet us. The location is private and peaceful and we loved all the beautiful Hawaiian plants and geckos in the yard. Thanks for a great stay!

Luxury Panoramic Ocean Views!
Kapalua Ridge is an incredible development and Kevin’s place was absolutely stunning. The entire setup gives all the resorts in the area a run for their money. The place itself was clean, well equipped, massive and luxurious. The views of the coast and islands was beautiful and we enjoyed stunning views everyday. It’s a short walk to the beach and few steps past the nearby beach gets you to Kapalua bay which is where the restaurants are. The bathrooms were very large and luxurious - which we loved. Our host Kevin was super responsive and was very helpful with recommendations and helping us find things in the airbnb. Will come back here if in Maui - amazing place.

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.

Kapalua Ridge 622 Luxe Ocean and Coastal Views
Perfect location with beautiful beaches nearby. Not a lot of restaurants around but if you have a car - it’s easy to navigate. The view from the bedroom and living room is brilliant 😍 We really enjoyed the stay. Definitely recommend 🙌🏻
Weekly house rentals

Mahalo Pono @ Ka 'anapali Royal
We throughly enjoyed our stay and the place was super nice! Nice of them to let us use their beach chairs, towels and boogie board. Owners accommodating to let us check in a little early. Little bit of a walk to beaches but we’re walkers and really enjoyed it. Pretty centralized and beach accessible.

Paia Family Cottage
We loved Maria’s place! Open plan with lots of space to relax and socialize. We loved having a washer and dryer! The beach chairs were an added bonus. The lanai was my favorite place. It faces due east so we were able to watch the sunrise every day while listening to the birds and drinking our coffee. The beds were very comfortable. A lovely neighborhood within walking distance to town, which we did every day. I highly recommend this lovely home!

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 😎

Maalaea Kai 307 - Maui Prime Oceanfront
This was a fantastic place to spend our week in Maui. The condo was amazing and spacious with all the amenities you would need to enjoy your time. The location is perfect, relatively close to the airport and well situated next to route 30 so you could go everywhere on the island quite easily. The view from the condo is second to none, from the patio you can easily see the Haleakalā mountain and from the front door is a great sight of the western Maui mountains. And on top of everything this condo was much more peaceful than the huge resort areas. There were not too many people around, and even when we did go to the beach we were able to find a spot easily. I’d recommend this condo for anyone who wants to spend a week or a few days in Maui - the price is quite good compared to the normal resorts, you get a great view and anything you don’t pick up on your way from the airport you can grab on a 20 minute drive to Kihei. This place was perfect for us.

Papakea Oceanfront Resort L103
We had a wonderful stay in Papakea. The views right from the Lanai were perfect, the space was exactly as pictured, and the property was lovely. We could easily walk to the fish market or the grocery store to get anything we needed. Brand new grills at the pool made for easy dinners.

3BR Loft Beach Bungalow w/ Bikes & Pickleball gear
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.

Hale Nanea
The beach nearby was great for children. Came with four large turtles and plenty of fish. Go snorkeling for the grown ups and safe place for 3 year olds.
Private house rentals

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 :)

House of light
Audrey's place was excellent, from the location, amenities, and geckos; all around really great spot away from busy touristy areas.

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.

The Art Estate, Haiku Maui Hawaii
We are so grateful to have found Mana House! This place is truly magical. We loved the peaceful beauty of the house and surrounding area. It’s very private and there was always a nice breeze that kept things cool. The sound of the birds and the laughing goats added an extra “mood elevator” as Tom puts it! Highly, highly recommend staying here!

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.

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.

Beautiful ocean view home with central A/C
Had a great 1 night stay here. Slept 6 comfortably and was an easy walk into town. No complaints!!

Peaceful and Spacious; North Shore Maui
Great place, having a home cooked meal in this deck with some evening sun was amazing. I would recommend staying here!
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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