
Family-friendly holiday rentals in Wailea-Makena
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Wailea-Makena
Guests agree: These family-friendly homes are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
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.

Luxury with a view at a reasonable price
Ray and Elsa’s place was perfect for our Hawaiian get away! It is a quick walk across the street from a beautiful beach and quick drive to many more. Amenities listed in the condo, including fins, snorkels, water shoes, chairs, and more as well as activity recommendations from the hosts made for an easy adventure filled trip.

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 & 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.

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

Grand Champions 169 Beautiful 3 BR on the Fairway!
We loved and had an amazing time staying at this 3bdrm condo. Was great to be on the golf course with a large lanai and beautiful views. Condo was stocked with beach gear and nice welcome basket. AC worked great. Walkable to restaurants and the beach!

Luxury Modern 2-Bedroom Condo, Amazing Ocean Views
We had a fantastic time in Kihei and all around Maui! The Knowles' condo was centrally located to a lot of great spots, many that were recommended by the Knowles. Our family enjoyed staying in the condo, which was well stocked with everything we needed. No details were missed here! There is also a beautiful view of the ocean from the lanai. Mahalo to the Knowles for their hospitality!
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!!!

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.

Puamana 80-4 Superior Garden View
We had a wonderful visit! This condo is clean and nice and extremely well located. Puamana is quiet and beautiful. Whalers was helpful and supplied us with extra blankets. Cannot recommend highly enough.

Walk to Front St., ALOHA CABANA, "PEOPLES CHOICE"
Great location. Had a minor issue, but Lisa was on top of it . Making sure we were enjoying our trip. Would recommend to anyone visiting Maui! Mahalo!

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

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.

Beautiful Oceanfront Condo- Great View, A/C,Wi-Fi
The apartment was as advertised. Most everything was new or nicely updated. The view from the balcony was beautiful

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

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!

Beachy Bright Maui Vista location
The location was perfect! Right in the middle of great restaurants & beaches. Also with comfortable driving distances to other beaches. Mary has in her binder & all throughout the condo, information & instructions- all very helpful. I will definitely book with her again!

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.

Maui Condo across fm Kam II beach
KKN is a wonderful community to spend your vacation. The staff are kind and take pride in their work. Beautiful, mature landscaping. Nice alternative to a sterile resort. Location is excellent and walkable to many beaches. Host was very kind and helpful. Condo is the perfect space for a couple. Had many luxury amenities - king size bed, A/C, beach accessories, 2 TV's. Perfect and affordable.
Quick stats about holiday rentals that are family-friendly in Wailea-Makena
Total rentals
1K properties
Nightly prices starting at
$167 NZD 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
Destinations to explore
- Waikiki Beach Holiday rentals
- Kailua-Kona Holiday rentals
- Kona Holiday rentals
- Kihei Holiday rentals
- Kaanapali Holiday rentals
- North Kona Holiday rentals
- Kailua Holiday rentals
- Napili-Honokowai Holiday rentals
- Island of Hawai'i Holiday rentals
- Honolulu Holiday rentals
- Kauai Holiday rentals
- O‘ahu Holiday rentals
- Villa rentals Wailea-Makena
- Apartment rentals Wailea-Makena
- Rentals with outdoor seating Wailea-Makena
- Pet-friendly rentals Wailea-Makena
- Hotel rentals Wailea-Makena
- House rentals Wailea-Makena
- Waterfront rentals Wailea-Makena
- Rentals with beach access Wailea-Makena
- Rentals with a patio Wailea-Makena
- Rentals with a hot tub Wailea-Makena
- Rentals with an EV charger Wailea-Makena
- Fitness-friendly rentals Wailea-Makena
- Rentals with a sauna Wailea-Makena
- Serviced apartment rentals Wailea-Makena
- Condo rentals Wailea-Makena
- Townhouse rentals Wailea-Makena
- Beach condo rentals Wailea-Makena
- Beachfront rentals Wailea-Makena
- Rentals with pools Wailea-Makena
- Rentals with a washing machine and dryer Wailea-Makena
- Luxury rentals Wailea-Makena
- Kid-friendly rentals Wailea-Makena
- Family-friendly rentals Maui County
- Family-friendly rentals Hawaii
- Family-friendly rentals United States
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- Maui
- Kaanapali Beach
- Kahului Beach
- Lahaina Beach
- Sandy Beach
- Kaipukaihina
- Laie
- Honolua Bay
- Spreckelsville Beach
- Kapalua Bay Beach
- Olowalu Beach
- Pahoa Beach
- Wailea Beach
- Manele Golf Course
- Hāmoa Beach
- Oneloa Beach
- Maui Ocean Center
- Palauea Beach
- Old Lahaina Luau
- Wailau Valley
- Mokulau Beach
- Wailea Golf Club
- Kaulahao Beach
- Ka'anapali Golf Courses
- Things to do Wailea-Makena
- Nature and outdoors Wailea-Makena
- Sports activities Wailea-Makena
- Art and culture Wailea-Makena
- Things to do Maui County
- Art and culture Maui County
- Sports activities Maui County
- Tours Maui County
- Nature and outdoors Maui County
- Things to do Hawaii
- Nature and outdoors Hawaii
- Art and culture Hawaii
- Tours Hawaii
- Wellness Hawaii
- Entertainment Hawaii
- Food and drink Hawaii
- Sightseeing Hawaii
- Sports activities Hawaii
- Things to do United States
- Sightseeing United States
- Food and drink United States
- Nature and outdoors United States
- Sports activities United States
- Tours United States
- Art and culture United States
- Entertainment United States
- Wellness United States