
Family-friendly vacation rentals in Wailea-Makena
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Top-rated family-friendly rentals in Wailea-Makena
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Popular amenities for Wailea-Makena family-friendly rentals
Family-friendly home rentals with a hot tub

Beautiful Ocean View Kamaole Sands
Wow. What an amazing place to stay in Kihei. Everything is within walking distance -- coffee shops, shaved ice, shopping and especially the beach! This condo is across the street from Kamaole 3, which has great sand, snorkeling, waves for bodysurfing and daily turtle sightings. We honestly didn't leave the square mile from the condo except for drives to Foodland for grocery shopping and poke. :) The condo itself was squeaky clean upon arrival, which is impressive considering the sand that is easy to track in. The condo had all the amenities we needed for our family of four and sleeping arrangements were easy with the upstairs master loft and the two beds in the proper bedroom. As this condo is on the top floor, it stays warm and there's not whole-condo air conditioning, especially if you're used to A/C that really cools off rooms, but humidity was never bad and we slept well. Just keep the patio and front door open for the cross-breeze in the morning and before bedtime. Mahalo!

Hawaiian Paradise Escape Across Street from Beach
A++++++ owners, place was great for what we needed. Sleeps 2-3 comfy, might be able to squeeze in a 4th. Full mini kitchen, patio, pool/spa/BBQ’s, tennis courts. 1/4 mile walking distance to beach. Cute wildlife w/ birds & chicken all over property. Everyone was friendly. 5-10min from downtown Kihei shopping & grocery stores.

65% Off: TTT#3 of 4 Awarded “Best in Maui” OceanVw
Had a great few days in Kihei!

Remodeled,Ground Level,King Bed,Walk To Beach
Really cute and well appointed space. Everything you could want in the kitchen. Bed and linens were very comfortable. I will definitely book again with Ted!

Incomparable Maui Sunset condo, includes all taxes
First and foremost was the excellent, prompt communication with the host. Kyra always responded to any questions, and offered suggestions that encouraged us to explore the beautiful island. The condo itself has everything one would expect, from a very comfortable bed, to a fully equipped kitchen, BBQ's cleaned daily in the beautifully maintained grounds, and a short walk to the beach. Also, with a security guard present, one feels very safe. Definitely recommend!

Tropical Resort Across Beach With Turtles!
Katie was amazing. Such a wonderful place to start me and my friend’s birthday adventure.

Beachfront Remodel with 180° Views! Epic Sunsets
Beautiful location! Wish we would have stayed longer so we could have tried our hand at pickleball. Lots to do in Kihei, would definitely go back. The views from the private deck were amazing and so many restaurants within a close distance.

3 minutes walk to the beach 2BR/2BA Top floor
Mike’s place was super convenient! Short walk to the beach, and he basically had all the supplies we needed so we didn’t need to rent anything. One of the beach chairs has seen better days, but it was still useable and my daughter loved the boogie boards. The apartment was extremely clean as well. There are plenty of restaurants and food trucks within walking distance. It’s an easy drive to all the major sights — we basically hit all the highlights in Maui easily. Would definitely recommend Mike’s place.
Family- and pet-friendly home rentals

Beautiful Views~
Beautiful place and area. Right on the beach, which was amazing. Lots of towels, no need to bring your own shampoo, etc. as those are provided. Well stocked kitchen too. Beach chairs, etc. were also provided. Great trip! We will be back!

WOW! Stunning Ocean Views, Large Deck &Luxury Beds
Has an awesome view with a relatively short walk to the beach. (We actually saw sea turtles there!!) The location was not far from wherever we wanted to go. The beds were comfy (a big plus for us after multiple back surgeries), as was the sectional sofa. Plenty of room for us to hang out. The kitchen was well stocked and having a washer/dryer available was extremely helpful. I may have missed this in the posting, but the first floor is a separate rentable area than the second floor. Luckily no one was in the first floor so we basically had the place to ourselves. We'd definitely stay again and had a wonderful time!!!

Pookela Paradise-Newly Renovated, Fantastic Views!
Our ohana had the best time at Pookela Paradise. Mark was extremely helpful and so much aloha. Our family was well accommodated and was so nice to have a place for us to stay in Makawao. Mahalo again Mark! We will definitely be back

Hale Kamaole Maui's Hidden gem! Lower Condo~
Beautiful condo, had everything we needed. Well stocked kitchen, condo was clean and comfortable. Air conditioning unit in living room and bedroom kept us cool and comfortable. Great location with park and beach right across the street and walking distance to lots of restaurants and shops. I'll definitely be coming back.

The Artists House
Jordanne's house was was perfect. Open and comfortable. Fully equipped kitchen. fenced in -making it feel private even out doors. good parking area. waking distance to restaurants or really anywhere in town.

Kula Jewel - Pool, Hot Tub & Awesome Views!
Staying at the Kula Jewel is nothing short of the perfect experience. Pamela made sure to personally welcome us, show us around and direct us to local shops. We should have just spent our entire time in Hawaii here, as the views and perfect design of the home gave us the experience of staying with a close friend. Stocked kitchen, great linens, pool and hot tub, bbq and all of the perfect details that make vacations special, Pamela really takes care in making her guests feel at home. The stunning interiors partner with the unique shape of the house, making the Maui landscape picturesque from sunrise to sunset. We will have a place to call our Maui spot when visiting from now on.

2B/2B Cottage/Cozy/Central/Private/Historic town
Clean and easy accom, Emma was easy to deal with. The place was relaxing. Outdoor shower a standout.

Two Bedroom Paia North Shore Beach House
The Turtle House was welcoming, comfortable, and spacious for four adults. Peacefully located between Paia and beautiful beaches, it was a perfect base. We especially enjoyed quiet mornings and lunches on the side porch.
Family-friendly home rentals with a pool

Gem near Keawakapu Beach - Privacy and Ocean Views
Amazing spot and stay

Go for an Ocean Swim From a Fun Beach Villa
Gal’s place was wonderful. We enjoyed staying there taking Maui’s beauty and especially kihei’s in and then even extending our stay. We’d always come back and will definitely recommend his place. The place is just as pictured. We were grateful for the beach equipment and also that there was a washing machine and dryer that we could use. He and the staff of the place took really good care of us. Don’t hestitate - it’s really the place to be.

Absolute Beachfront with Million-Dollar Views!
When searching for a nice place to stay sight unseen, especially after such a loss to the community, we were pleasantly surprised. We wanted something private yet still in the heart of the activity for our wedding and honeymoon. Maui is breathtaking, and the views from the balcony were incredible. Every day, we could see sea turtles in the water from our private beach, and we were even greeted by a few that spent the night on the beach during our stay. The space was fantastic, and the bed was really comfortable. It was also conveniently close to necessities like the ABC store and a few shopping centers. Heidi was very prompt when we reported a minor issue, and she resolved it quickly while keeping us updated throughout the process. Thank you for hosting us! We will definitely be recommending this spot to all our friends and family, and we hope to visit again sometime!

Maui View
The place was just as described. It was within walking distance to a really nice beach. The chairs/umbrella for the beach were great and we used them extensively. We really liked that the washer and dryer were in the unit so we had fresh towels when needed. Would definitely come back

All New Beachy Chic Remodel, Ocean front with AC
The place is amazing, centrally located. View is top notch, we saw turtles from our balcony almost everyday. Leslie was extremely responsive and accommodating.

Ocean Bliss: Beach Condo - Walk to Everything!
This condo is where you want to stay at while in Maui. You will have absolutely everything you need to be comfortable and more. The floor plan is spacious, very well decorated with details that make you feel at home away from home. The kitchen has everything you need to cook and bake. The bedroom has a very comfortable bed, amazing views of the ocean, full closet with hangers and all sorts of things the host provides so you can enjoy yourself at the beach or parks. Things like a cooler, beach chairs, tennis balls and rackets, you name it, it’s in there. The bathroom is very practical and well designed too. The shower has amazing water pressure!! The lanai is one of the best parts, IMO. You can get to it through a glass door in the living room or the bedroom. The windows and glass doors are floor to sealing giving you natural light all day. I didn’t tun on the TV once, but there is one. I’m running out of space in this review and want to say so much more!! I’m coming back for sure!

Affordable Accommodations in Maui
My boyfriend and I had such a wonderful stay here! The space was clean and in a great location. Walking distance to shops and great food spots. Elizabeth is very responsive and made the check in and out process very easy! We were even able to get an early check in. Highly recommend this Airbnb to anyone visiting!

TOP FLOOR!!!! Oceanfront, free Wi-Fi, free parking
Wonderful stay! Great location, quiet with ocean views, and a lovely breeze that really does mean no A/C necessary. Jennifer was super responsive and the place was perfect for us.
Quick stats about vacation rentals that are family-friendly in Wailea-Makena
Total rentals
1K properties
Nightly prices starting at
G$20,922 GYD before taxes and fees
Total number of reviews
25K reviews
Pet-friendly rentals
10 properties allow pets
Rentals with a pool
1K properties have a pool
Rentals with dedicated workspaces
590 properties have a dedicated workspace
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