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Family-friendly vacation rentals in Wailea-Makena

Find and book unique family-friendly homes on Airbnb

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Popular amenities for Wailea-Makena family-friendly rentals

Family-friendly home rentals with a hot tub

Guest favorite
A private lanai is furnished with a round table and two chairs, overlooking lush greenery and palm trees. The sunset casts a warm glow over the ocean in the distance, creating a serene atmosphere for outdoor dining.
Condo in Wailea
4.82 out of 5 average rating, 105 reviews

Beautiful Ocean View Kamaole Sands

PaoloRating, 5 stars1 month ago
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!
Superhost
A spacious studio features a queen bed adorned with a tropical-patterned quilt, complemented by wooden furniture. Large sliding glass doors open to a private outdoor area, while framed artworks add an island touch. Light from the lamps provides a cozy ambiance.
Apartment in Kihei
4.82 out of 5 average rating, 542 reviews

Hawaiian Paradise Escape Across Street from Beach

WayneRating, 5 stars4 days ago
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.
Top guest favorite
A vibrant room features calming blue walls adorned with artwork. A spacious bed is draped with a colorful patterned quilt. Natural light fills the area through expansive glass doors leading to a lanai. A media console houses a television and amenities for guest convenience.
Condo in Kihei
4.96 out of 5 average rating, 301 reviews

65% Off: TTT#3 of 4 Awarded “Best in Maui” OceanVw

RossRating, 5 stars3 weeks ago
Had a great few days in Kihei!
Superhost
A newly remodeled kitchen is displayed, featuring rich wooden cabinets and sleek granite countertops. Stainless steel appliances, including a refrigerator, microwave, and dishwasher, complement the modern design. Glass-front cabinets showcase dishware, while under-cabinet lighting enhances the overall brightness of the space.
Condo in Wailea
4.88 out of 5 average rating, 187 reviews

Remodeled,Ground Level,King Bed,Walk To Beach

TamsenRating, 5 stars2 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!
Guest favorite
A person stands in the ocean water, silhouetted against a vibrant sunset with shades of orange and gold. Gentle waves lap at the shore, reflecting the warm colors of the sky, while clouds drift above, adding texture to the scene.
Condo in Kihei
4.89 out of 5 average rating, 133 reviews

Incomparable Maui Sunset condo, includes all taxes

DanRating, 5 stars4 weeks 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!
Superhost
Lush greenery surrounds the tropical landscape, featuring vibrant plants and a small pond reflecting plants and trees. A decorative fountain can be seen in the pond. Two stories of a building are visible in the background, nestled among mature trees.
Condo in Kihei
4.79 out of 5 average rating, 388 reviews

Tropical Resort Across Beach With Turtles!

ConnerRating, 5 stars2 weeks ago
Katie was amazing. Such a wonderful place to start me and my friend’s birthday adventure.
Superhost
The open living area features a modern kitchen with light cabinetry and dark granite countertops. A dining area with wicker chairs is adjacent, while a comfortable sofa faces large glass doors leading to the ocean view. Natural light brightens the space, enhancing the serene atmosphere.
Condo in Kihei
4.94 out of 5 average rating, 111 reviews

Beachfront Remodel with 180° Views! Epic Sunsets

JennaRating, 5 stars1 week ago
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.
Guest favorite
A serene coastal scene features a palm tree beside gently lapping waves. Inset images showcase a modern kitchen with stainless steel appliances, a pool area, and a beach view, illustrating the condo's amenities and nearby recreational options.
Apartment in Kihei
4.87 out of 5 average rating, 298 reviews

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

MikeRating, 5 stars1 week ago
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

Guest favorite
A spacious bedroom features a large bed dressed in a light blue quilt, complemented by decorative pillows. Two bedside lamps illuminate the room, while sliding glass doors provide views of the surrounding lush greenery and mountains. A decorative tray with cups and flowers rests on the bed.
Condo in Lahaina
4.89 out of 5 average rating, 131 reviews

Beautiful Views~

RebeccaRating, 5 stars3 weeks 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!
Guest favorite
An outdoor dining area is presented on a spacious deck, featuring a wooden table surrounded by cushioned chairs. The backdrop reveals a stunning view of the ocean and West Maui, bathed in the warm glow of sunset, while palm trees frame the scene.
Guesthouse in Wailea
4.97 out of 5 average rating, 89 reviews

WOW! Stunning Ocean Views, Large Deck &Luxury Beds

CarrieRating, 5 stars4 weeks 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 favorite
A covered balcony features a round mosaic table surrounded by black mesh chairs. Lush greenery is visible in the foreground, with trees framing the view of distant mountains against a clear sky.
Home in Makawao
4.87 out of 5 average rating, 52 reviews

Pookela Paradise-Newly Renovated, Fantastic Views!

AmberRating, 5 stars3 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
A view from the unit features a private patio area with a round table and four cushioned chairs. Lush green grass and flowering plants enhance the outdoor space, while a peaceful garden area is visible in the distance. Clear skies are seen through the glass door.
Apartment in Wailea
5 out of 5 average rating, 9 reviews

Hale Kamaole Maui's Hidden gem! Lower Condo~

LindaRating, 5 stars2 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 favorite
An open living area features a comfortable red leather sofa with decorative pillows. A dining table with wooden chairs is set nearby, and a well-equipped kitchen can be seen in the background. Natural light illuminates the space, enhancing its welcoming ambiance.
Home in Lanai City
4.96 out of 5 average rating, 101 reviews

The Artists House

JohnRating, 5 stars1 week ago
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.
Top guest favorite
A sunlit swimming pool is framed by lush green grass, leading to a well-designed single-story home with a distinct round roof. The expansive landscape stretches in the background, providing a view of the ocean and distant mountains under a clear blue sky.
Home in Kula
4.92 out of 5 average rating, 346 reviews

Kula Jewel - Pool, Hot Tub & Awesome Views!

KellyRating, 5 stars5 days ago
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.
Guest favorite
An inviting bedroom features a spacious bed with a patterned blanket. Two framed paintings adorn the light blue walls, and a bedside lamp provides soft illumination. A doorway leads to a bright living area, with natural light visible from additional outdoor access.
Apartment 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 favorite
A comfortable living area features a green sofa with decorative pillows, complemented by a wooden coffee table and matching lamps. A dining space with a table and chairs is visible in the background, alongside a kitchen area with a bright, airy atmosphere enhanced by natural light.
Home in Paia
4.86 out of 5 average rating, 114 reviews

Two Bedroom Paia North Shore Beach House

MaureenRating, 5 stars3 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 favorite
A modern kitchen is visible, featuring light cabinetry, stainless steel appliances, and a tile backsplash. A round dining table is surrounded by cushioned chairs, while bar stools are positioned at the countertop. The open layout reveals sliding glass doors leading to a covered lanai with tropical views.
Condo in Wailea
4.95 out of 5 average rating, 65 reviews

Gem near Keawakapu Beach - Privacy and Ocean Views

DrewRating, 5 stars1 month ago
Amazing spot and stay
Guest favorite
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.
Superhost
A serene pool area is depicted, surrounded by lush tropical landscaping and swaying palm trees. The pool is framed by a stone deck, with a shallow section visible. Behind the pool, multistory buildings adorned with greenery provide a backdrop, emphasizing the peaceful atmosphere.
Condo in Lahaina
4.93 out of 5 average rating, 143 reviews

Absolute Beachfront with Million-Dollar Views!

MarinaRating, 5 stars2 weeks ago
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!
Guest favorite
A bright living area features a comfortable blue sofa against a wall adorned with framed artwork. A flat-screen TV is mounted nearby, and natural light pours in through sliding glass doors, leading to a small balcony with outdoor seating. Clean, tiled flooring adds to the spacious feel.
Apartment in Kihei
4.83 out of 5 average rating, 186 reviews

Maui View

SelmaRating, 5 stars4 weeks ago
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
Guest favorite
An outdoor area features a stone patio with a pool surrounded by palm trees. Poolside loungers are positioned for relaxation, while a cooking area with a grill is visible. The ocean can be seen in the background under a clear blue sky.
Condo in Wailuku
4.95 out of 5 average rating, 107 reviews

All New Beachy Chic Remodel, Ocean front with AC

KasturiRating, 5 stars1 month ago
The place is amazing, centrally located. View is top notch, we saw turtles from our balcony almost everyday. Leslie was extremely responsive and accommodating.
Superhost
A spacious bedroom features a king bed adorned with a vibrant blue and white floral quilt. Two bedside tables with turquoise lamps flank the bed. Colorful artwork depicting Hawaiian landscapes is displayed above the headboard, complementing the beachy theme.
Condo in Kihei
4.87 out of 5 average rating, 237 reviews

Ocean Bliss: Beach Condo - Walk to Everything!

RicardoRating, 5 stars3 weeks ago
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!
Guest favorite
Condo in Kihei
4.78 out of 5 average rating, 260 reviews

Affordable Accommodations in Maui

AmberRating, 5 stars2 weeks ago
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!
Guest favorite
An aerial view captures the complex's landscaped grounds, featuring a swimming pool surrounded by lounge chairs and tropical plants. Palm trees gently sway in the breeze, while neighboring buildings provide a glimpse of the comfortable accommodations available.
Condo in Lahaina
4.9 out of 5 average rating, 310 reviews

TOP FLOOR!!!! Oceanfront, free Wi-Fi, free parking

MeganRating, 5 stars3 weeks ago
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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