Family-friendly holiday rentals in Wailea, Wailea-Makena

Find and book unique family-friendly homes on Airbnb

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Popular amenities for Wailea, Wailea-Makena family-friendly rentals

Family-friendly home rentals with a hot tub

Superhost
Flat in Kihei
4.83 out of 5 average rating, 249 reviews

Quiet Studio, Great location across from beach

AmandaRating, 5 stars3 weeks ago
The location in Kihei was perfect for our trip to Haleakalā National Park, only a one-hour drive! There were also many beaches and restaurants within walking distance of the condo.
Superhost
Apartment in Kihei
4.81 out of 5 average rating, 314 reviews

Ocean view studio. 1k ft from water!

JohanaRating, 5 stars1 month ago
Very nice place! It’s right across from the beach and very close to great food. The apartment is very cozy and had AC.
Superhost
Apartment in Kihei
4.88 out of 5 average rating, 187 reviews

Remodeled,Ground Level,King Bed,Walk To Beach

TamsenRating, 5 stars3 weeks ago
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!
Superhost
Apartment in Kihei
4.79 out of 5 average rating, 389 reviews

Tropical Resort Across Beach With Turtles!

LaurenRating, 5 stars2 weeks ago
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!
Guest favourite
Apartment in Kihei
4.83 out of 5 average rating, 153 reviews

Ocean-view Maui Condo near Beach

JustinRating, 5 stars2 months ago
We really enjoyed our stay at Sam’s condo. It’s in a fantastic location in Kihei and just a few min walk from the beach. The condo is large, well-kept, very well stocked with everything you could need for a short or long stay. It was very quiet and private as well and Sam is very friendly and helpful.
Guest favourite
Flat in Kihei
4.87 out of 5 average rating, 300 reviews

3 minutes walk to the beach 2BR/2BA Top floor

MeganRating, 5 stars2 weeks ago
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.
Superhost
Apartment in Wailea
4.83 out of 5 average rating, 146 reviews

Beautiful Palms At Wailea #608-May/June Discount

SusanRating, 5 stars3 months ago
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.
Superhost
Apartment in Kihei
4.93 out of 5 average rating, 165 reviews

Beautiful Ocean Views In Maui Kamaole.

AnastasiiaRating, 5 stars3 weeks ago
It is our second stay in this unit ! Just Love it . We had a great time ! Very peaceful and relaxing atmosphere! And Suuuper clean ! A lot of beach gear! Amazing ! 200% Recommended! For sure will come back! 🌺🤙🤗❤️

Family- and pet-friendly home rentals

Guest favourite
Apartment in Lahaina
4.89 out of 5 average rating, 131 reviews

Beautiful Views~

RebeccaRating, 5 stars1 month ago
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!
Townhouse in Kihei
4.92 out of 5 average rating, 86 reviews

Maui Beach House

VanessaRating, 5 stars2 months ago
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!
Guest favourite
Guest house in Wailea-Makena
4.97 out of 5 average rating, 89 reviews

WOW! Stunning Ocean Views, Large Deck &Luxury Beds

CarrieRating, 5 stars1 month ago
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!!!
Guest favourite
Home in Makawao
4.87 out of 5 average rating, 52 reviews

Pookela Paradise-Newly Renovated, Fantastic Views!

AmberRating, 5 stars4 weeks ago
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
Flat in Kihei
5 out of 5 average rating, 9 reviews

Hale Kamaole Maui's Hidden gem! Lower Condo~

LindaRating, 5 stars3 weeks ago
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.
Top guest favourite
Home in Kula
4.92 out of 5 average rating, 348 reviews

Kula Jewel - Pool, Hot Tub & Awesome Views!

AndreaRating, 5 stars2 days ago
Pamela’s place is amazing! As a host Pamela was very welcoming and gave a great tour of her place. The view is beautiful and the pool and hot tub are perfect! We would definitely stay here again. Thank you Pamela!
Guest favourite
Flat in Wailuku
4.88 out of 5 average rating, 242 reviews

2B/2B Cottage/Cozy/Central/Private/Historic town

RainerRating, 5 stars1 month ago
Clean and easy accom, Emma was easy to deal with. The place was relaxing. Outdoor shower a standout.
Top guest favourite
Home in Paia
4.86 out of 5 average rating, 114 reviews

Two Bedroom Paia North Shore Beach House

MaureenRating, 5 stars4 weeks ago
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

Guest favourite
Apartment in Kihei
4.85 out of 5 average rating, 138 reviews

Beautiful Resort Condo w/ AC @ Kam III Beach

SofiaRating, 5 stars2 months ago
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!
Guest favourite
Bungalow in Kihei
4.92 out of 5 average rating, 133 reviews

Go for an Ocean Swim From a Fun Beach Villa

MariRating, 5 stars2 months ago
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.
Guest favourite
Apartment in Wailea
5 out of 5 average rating, 59 reviews

Beautiful Ocean Views and Aloha at Wailea Ekolu!

AlexandraRating, 5 stars4 weeks ago
The pictures and description don’t do justice to this amazing place! We had the most wonderful time and our expectations were surpassed! The ocean view is much better in person, the lanai was perfect because our toddler could play outside while we enjoyed relaxing in the lanai! Perfect place and really kid friendly! :)
Guest favourite
Apartment in Kihei
4.93 out of 5 average rating, 141 reviews

Kihei Akahi D308-Remodeled-Ocean Views-AC

CindyRating, 5 stars2 months ago
Fabulous accommodations with a beautiful view of the water. Really nice new furniture and well stocked with everything we needed. Easy walk down to the beach for the sunset. We appreciated the high speed WiFi for our zoom meetings without a glitch. The host was great - we would stay again and highly recommend this Kihea condo with a view.
Guest favourite
Apartment in Kihei
4.89 out of 5 average rating, 133 reviews

Incomparable Maui Sunset condo, includes all taxes

DanRating, 5 stars1 month ago
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!
Guest favourite
Apartment in Kihei
4.87 out of 5 average rating, 405 reviews

Can be 2 Units! Modern On Beach Ocean View Balcony

SarahRating, 5 stars2 weeks ago
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.
Top guest favourite
Apartment in Kihei
4.89 out of 5 average rating, 110 reviews

Cute one BR ground floor. Long & short term rates

MelisaRating, 5 stars1 month ago
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!
Guest favourite
Apartment in Kihei
4.83 out of 5 average rating, 229 reviews

Beachy Bright Maui Vista location

StephanieRating, 5 stars1 month ago
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!

Quick stats about holiday rentals that are family-friendly in Wailea, Wailea-Makena

  • Total rentals

    1K properties

  • Nightly prices starting at

    ₹8,600 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

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  4. Maui County
  5. Wailea-Makena
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  7. Family-friendly rentals