
Family-friendly holiday 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

Spectacular Oceanfront views!
Beautiful space- views and ocean front sounds of crashing waves were amazing. And so much sea turtle activity. Never stayed in a place with such a well stocked kitchen with pans and cooking implements. First rate. Very quiet area and a larger beach for swimming is a couple blocks walk away.

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!

Sugar Beach Resort #532 - Maui HI
We came here for our 20th anniversary. The views and beach are unparalleled. It is a more private setting and not walkable to downtown Kihei. This was perfect for us because we just wanted a chill place to be. It is still very accessible to the entire island and Kihei is really easy to get to. We will absolutely stay here again when we come back to Maui!

Tropical & Lush Paradise Vistas
An excellent place to stay on Maui. Was exactly as described and was perfect for my wife and me. Absolute gem and will stay again.

Gorgeous New 1BR condo w Ocean View
Adams place was everything we hoped it would be and I checked out dozens in the area before we picked this one. Walkable (within 5 min) to many great restaurants and cool little shops for t-shirts and beachy wear at great prices. The beaches are pristine and start right across the street running in both directions. Watching the surfers was a daily activity as well as the watching the beautiful sunsets. The condo had all of the beach toys you might want and even though it's a one bedroom I can see a family staying here. Adam was responsive and got back to us almost immediately with the couple of questions I had.

3 minutes walk to the beach 2BR/2BA Top floor
Mike's place is exactly as described. So close to the beach! He provides all sorts of things like beach chairs, a few beach towels, paddle boards a cooler, etc. Fully stocked kitchen with everything you could imagine that you need. He let us check in early which was a huge help! He's kind and fast on the replies. One thing to note, it can get toasty in the front bed room. He has a big fan which we used to suck in the air and that worked well! I highly recommend his place.

Beautiful Palms At Wailea #608-May/June Discount
Had a wonderful, relaxing stay at Elise and Bruce's condo. Explored different beaches (walkable and drive to), did some biking, hiking, many books read, weather perfect as it usually is in S Kihei, enjoyed sunsets at the pool, and cribbage matches on the lanai after a day outside. Appreciated some food staples already in the cupboards and Safeway store not far away. Tried a Bruce-recommended Sushi restaurant (Avo was the name, I believe in Wailea) which we liked and also pre-booked at Star Noodle in Lahaina to enjoy another wonderful asian meal, otherwise cooking in and at the condo community BBQ. Well set up for a small family and recommend it.

Convenient, Comfortable Sunny Kihei 1BR Beach Pool
All 5 Stars from CROSIER family.. Brandon place was great. When arriving everything was clean and accommodating! Would stay here again and suggest it! Mahalo!Great place for a family of 4 .!!!!!!!
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!

Maui Beach House
The stay was special to say the least. It was private and the walkable beach was quiet and beautiful. The town of Kihei has everything you need with close stores, restaurants, gas stations and snorkel rental. The house was perfect for our family with a space our child could sleep free of noise from the rest of the house while we were awake so we could enjoy the ocean from the porch and the jacuzzi tub. Would definitely stay again while on Maui!

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

Maui Westin Kaanapali Ocean Resort Studio
Robert was amazing to deal with! Great communicator, very accommodating of the guest, and seemed very genuine. The Westin at Kaanapali speaks for itself! It has everything…pools, great location, awesome beach front ! Had a great ocean view! And view of the pools! The room was very spacious. It was just two of us but we could have had two more people on the sofa bed easily. Small kitchen with full fridge and ice maker allowed for in room meal accommodations and cold refreshments. Spacious bathroom . It was five star plus! We had a hard time leaving… it was perfect and there is always so much to do in Hawaii.

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.

Kula Jewel - Pool, Hot Tub & Awesome Views!
Pamela was a fantastic host. She was responsive and so friendly. She truly loved the area and making guests feel at home. The space itself was such a dream. It had everything we needed and then some. The location and views were stunning. we sat on the porch almost every night just to take it all in. We loved staying at the Kula Jewel and would stay here again!

Kahana Falls resort on the beach,
The resort is older but well maintained. Beautiful landscaping, friendly staff. nice pool area, BBQ & sand bottom hot tub. we did not have a lanai but there is a group BBQ area. I enjoyed the gym and the peaceful surroundings. The beach is across the street. All in all a wonderful vacation experience.
Family-friendly home rentals with a pool

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.

Beautiful Resort Condo w/ AC @ Kam III Beach
Stayed here for the weekend after deciding to extend our trip. Really lucked out! This place is perfectly located — right across / walking distance to Kam III, a great beach, and a short drive to grocery stores, restaurants, and anything you need. The resort area was clean and friendly with a great pool, and the unit feels private and quiet. Didn’t hear anything but birds chirping. Perfect for families or couples. The unit is much bigger than it looks in photos! Super comfortable bed, nice clean shower, lovely lanai, and a huge kitchen stocked with everything you need. Thanks so much Rob, will definitely stay with you again on our next trip!

Beautiful Oceanfront Condo- Great View, A/C,Wi-Fi
Our stay was wonderful. The accommodations were very comfortable and clean. The ocean view was beautiful and we enjoyed looking out over the water every night. I’d definitely stay here again!

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.

Can be 2 Units! Modern On Beach Ocean View Balcony
Our stay in Kihei was lovely. We enjoyed walking the quiet beach each morning and getting into town was easy from the Airbnb. We did not have any issues with parking on site despite a very late (overnight) arrival. It was a quick trip down from the airport as well.

Cute one BR ground floor. Long & short term rates
Is our second time at Lori’s place and it was amazing, you can walk everywhere (restaurants, beaches), make your own food and beach gear is so convenient to have. I hope to be back soon!

Tropical Resort Across Beach With Turtles!
Wonderful Airbnb! Katie was very responsive, helpful, and kind. It was a plus for us that this place had a washer dryer, because we didn’t want to check bags. Had beach towels, umbrellas, and boogie boards for us to use as well!

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 holiday rentals that are family-friendly in Wailea-Makena
Total rentals
1K properties
Nightly prices starting at
₹8,654 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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