Family-friendly vacation rentals in Wailea

A bright living area offers ocean views through expansive sliding glass doors. Comfortable chairs are positioned towards the balcony, where coastal scenery includes palm trees swaying in the breeze. Neutral decor is accented with beach-themed cushions, and a TV set is present on a stylish console.

4.99 out of 5 average rating, 205 reviews

Mana Kai 608- Oceanfront Remod! Modern Surf Vibe

Mana Kai 608 is a remodeled oceanfront condo DIRECTLY on Keawakapu beach! Mana Kai is a hotel zoned resort in the ideal location, right on the border of Wailea and Kihei! Our condo is designed with a modern surf feel in mind, we are excited to share it with you! If you enjoy Wailea's 5 star resorts but crave a kitchen, less fees, better views, or don't want to cross the street to get to the beach, stay with us! We have the best Property Mgr. in Maui, Tracy O'Reilly to take amazing care of you!

A spacious living area features a light grey sectional sofa adorned with decorative cushions. A wooden coffee table sits in front, accompanied by a textured area rug. A piece of wall art depicting a boat on water is displayed above the sofa, complemented by a floor lamp and a plant on a side table.

4.98 out of 5 average rating, 113 reviews

Spacious tropical oasis near beautiful beaches!

Aloha! Welcome to our beautiful home at Maui Kamaole, an upscale complex located across Kamaole 3 Beach and minutes to Wailea. Our condo is perfectly suited for couples and small families wanting space with stylish comfort in a prime location. Relax on a luxurious king-sized bed, sectional sofa w/ memory foam sleeper, and a pack and play for toddlers! Enjoy the essentials of modern connectivity, a fully stocked kitchen, with two full bathrooms. Unwind in paradise on two lush garden patios!

A stunning beach scene captures vibrant sunset colors reflecting off wet sand. Rocky outcrops frame the tranquil waters, while palm trees sway gently in the foreground. Wispy clouds stretch across the sky, adding depth to the evening landscape.

4.99 out of 5 average rating, 178 reviews

Romantic, Luxury Retreat w/Ocean View-Couples Only

Luxury 1 bedroom 2 bath condo which has been fully renovated. Our condo has lovely ocean views as well as views of the lush tropical gardens and the pool. It has a fully stocked gourmet kitchen with high end appliances, assorted spices, coffee and tea. Sunset views from the lanai are stunning. If our condo is not available during the days of your travel, please check availability at our other Wailea Palms condo at https://www.airbnb.com/rooms/1728525 Not suitable for children or infants.

4.99 out of 5 average rating, 122 reviews

An expansive covered lanai features comfortable seating with plush cushions, accented by a decorative table. String lights adorn the ceiling, and panoramic ocean views showcase a vibrant sunset over palm trees and neighboring properties.

Guest suite in Wailea

Sweeping Panoramic Ocean Views - Private Ohana

Live like a local at the Ocean Blue Ohana - the private first floor of this amazing Hawaiian pole home on a half acre property in South Maui. As you enter the space, you will be drawn to the sweeping panoramic ocean views. You are sky-high, perched 500 feet above sea level, looking at the most glorious views of the neighboring islands, mountains, coastline, and Maui's amazing skyline. To top it off, you are 5 minutes from the Wailea Resorts and beautiful golden sand, crystal clear beaches.

A modern kitchen is shown with sleek gray cabinetry and stainless steel appliances. An island seating area with two wooden stools is present, topped with a decorative tray and two cups. Pendant lights with blue shades illuminate the space, enhancing the open and functional layout.

4.96 out of 5 average rating, 185 reviews

Renovated Condo | 3 Min Walk to Toes in the Sand!

Welcome to Pacific Pearl — your serene Maui escape just steps from golden-sand Kamaole Beach Park II. Set in the lush, resort-style Maui Banyan complex, this fully remodeled ground-floor condo offers peaceful garden views, a walkable location near dining and shops, and all the comforts of home. Spend your mornings snorkeling, your afternoons lounging by the pool, and your evenings with sunset walks on the shore. Perfect for couples, families, or friends seeking the effortless Maui getaway.

A modern kitchen and dining area are visible, featuring a round table set for four with woven placemats and plates. Stainless steel appliances are arranged in the sleek kitchen design, while large sliding glass doors open to reveal views of lush gardens and the ocean beyond.

4.96 out of 5 average rating, 150 reviews

A.R.A Retreats: Big Blue Pacific

Nicknamed “Big Blue Pacific” for its absolutely stunning view of the Pacific Ocean from the living room, kitchen and master bedroom. Our vacation rental condo is located in Wailea Ekolu, the well-known luxury resort community of Wailea. It offers a relaxing space for you to unwind after you spend all day taking in the sunshine around the island. Sit and enjoy your coffee whilst taking in our amazing views and when the sun goes down, watch your favorite shows on on our smart tvs!

An open-concept living area features a spacious dining table with blue upholstered chairs, complemented by a calming color palette. The kitchen, equipped with modern appliances, is visible in the background, while natural light fills the space through large windows.

4.95 out of 5 average rating, 133 reviews

MAUI BLISS! RARE Wailea 3-bedroom...sleeps 10!

This is the one you've been waiting for! Perfect for families, couples, or anyone who loves to spread out, this 1700 sq ft Grand Champions 3 bedroom has been painstakingly remodeled with luxury finishes throughout. Two kings, two pull-out queens, plus...bunk beds! Nestled in the most peaceful corner of the resort, boasting stunning ocean views from the lanai, and minutes away from Wailea beaches, restaurants, and shopping, this is truly what Maui vacation dreams are made of!

4.94 out of 5 average rating, 131 reviews

A scenic outdoor space features a table set for dining, overlooking a vibrant green lawn and an expansive ocean view. Nearby, comfortable seating invites relaxation. The kitchen area is equipped with modern appliances, while a stylish clock adorns the wall.

Condo in Wailuku

Oceanfront Getaway, Brand New, Steps To Beach

Enjoy the panoramic ocean view directly from the living room. This wonderful ground floor unit offers privacy and tranquility with expansive ocean views, where you can enjoy seasonal whale watching, paddle boarding, surfing, snorkeling as well as many other activities just outside your door. The unit is also adjacent to one of the longest beaches on Maui, Sugar Beach. And just down the road you will find great shopping, restaurants, nightlife and the Maui Ocean Center.

A modern loft interior features a spacious living area with a light grey sectional sofa adorned with various blue and white throw pillows. A simple wooden dining table with teal seating is visible alongside a kitchen with a white island. Large windows allow natural light, and a decorative wall clock adds charm.

4.98 out of 5 average rating, 178 reviews

Live, Love, Loft in Beautiful Maui

Experience the beautiful island of Maui and all its wonder in this modern loft in Central Kihei. You’re just minutes away from stunning beaches, local markets, and some of the best food on island. Nothing feels like you’ve arrived in Maui like the welcoming sand and warm waters of Charlie Young Beach, just across the street. Head down to The Cove to surf or paddle board with the locals. Or simply relax, put on a classic record and enjoy the sunset from the balcony.

A dining table set for four is positioned on the private lanai, surrounded by lush greenery. A bottle of wine sits center stage, accompanied by a plate of fresh fruit and pastries. Bright blue skies provide a serene backdrop.

4.96 out of 5 average rating, 208 reviews

Top 5% Home with King Bed + Steps to Beach & Shops

Exquisitely remodeled top floor condo in one of the most desirable condo complexes in South Maui. Enjoy sunsets and peekaboo ocean views from your private lanai, walk to some of the finest beaches, shops & restaurants and lounge in the multiple pools & hot tubs on property with this perfect Hawaiian oasis! Everything (and we mean everything) is fully remodeled. From a peaceful island getaway to your next Hawaiian adventure, Makana Condo is ready for your enjoyment!

4.96 out of 5 average rating, 442 reviews

Home in Wailea

Stunning ocean view, heated pool at home by Wailea

Ocean, sunset views, unique home reminiscent of a Victorian villa with heated private pool for guests in the villa, tropical gardens. Home renovated and maintained by designer. Cal King in main, second has twin beds. Pac n play and high chair are available. Open plan living with dining and relaxing on the lanai. Keawakapu beach, Wailea shops and restaurants 5 minutes drive. Your private view retreat. #BBMK 2016/0003

An open-concept living area showcases a modern kitchen island with a fruit bowl. A sectional sofa is positioned beside a Samsung Smart TV, with beach-themed artwork adorning the walls. Natural light floods the space, highlighting the neutral tones and inviting layout.

4.98 out of 5 average rating, 128 reviews

*Fully Remodeled* Modern Island Style*

I am looking forward to hosting you at the Palms at Wailea 606 and making your vacation fun and enjoyable. The Palms is an upscale community that offers you great shopping, dining, golfing, world-class resorts, and beaches all within a few minutes. I offer you a clean, comfortable and memorable stay on the island. I want to make your Maui dreams come true! Mahalo and looking forward to seeing you! -Aini

Popular amenities for Wailea family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

An inviting pool area is surrounded by lush tropical landscaping. The clear blue water of the pool is complemented by several lounge chairs and tables with umbrellas, providing shaded seating. A serene atmosphere is created by the vibrant greenery in the background.

4.91 out of 5 average rating, 119 reviews

Grand Champions - King Bed - Close to Wailea Beach

A clear view of a swimming pool is presented, surrounded by lounge chairs arranged neatly on a stone patio. Lush greenery and palm trees frame the area, with ocean views visible in the distance under a bright blue sky.

4.94 out of 5 average rating, 135 reviews

Newly Remodeled 1bed/1bath, Kihei/Wailea

A vibrant sunset is captured over the Pacific Ocean, with clouds in shades of orange and purple. Silhouettes of palm trees frame the foreground, while lush greenery and homes are visible at the edge of the golf course, enhancing the tropical setting.

4.91 out of 5 average rating, 145 reviews

Sale! Gorgeous 3BR/2BA with Ocean & Sunset views

An expansive view of the Sugar Beach Resort is displayed, showcasing a spacious outdoor pool surrounded by lounge chairs. The building features numerous balconies with oceanfront views, complemented by lush greenery and palm trees along the coastline.

5 out of 5 average rating, 103 reviews

Luxury 1BR Beachfront Condo @ Sugar Beach unit 505

A sandy beach stretches along the coastline, leading to a distant rocky outcrop separating the water from the shore. A multi-level building stands nearby, surrounded by greenery, with gentle waves lapping at the beach under a clear blue sky.

4.82 out of 5 average rating, 188 reviews

Charming Maui Beach Condo Steps from the Shore!

An inviting sleeping area features a spacious bed with blue striped bedding. A small table and two chairs are positioned nearby, with a decorative rug underfoot. A television is placed on a low shelf, and a glass door leads to an outdoor balcony surrounded by greenery.

4.94 out of 5 average rating, 112 reviews

Your Island Home Too

An outdoor lanai is equipped with a decorative table and six chairs, providing a comfortable area for dining. Lush greenery is visible in the surrounding landscape, alongside sweeping views of the fairway and the ocean in the distance, under a clear blue sky.

4.98 out of 5 average rating, 175 reviews

Grand Champions 169 Beautiful 3 BR on the Fairway!

A scenic view reveals the ocean with soft waves meeting sandy shores, framed by palm trees. In the foreground, tennis courts are visible against a backdrop of rolling hills, showcasing lush greenery under a clear blue sky.

4.98 out of 5 average rating, 105 reviews

Maui is Open - Come Support the Locals

Family- and pet-friendly home rentals

4.98 out of 5 average rating, 117 reviews

The exterior of a spacious home is framed by lush tropical plants and trees. A charming pathway leads to a welcoming front deck illuminated by soft lighting. Large sliding doors enhance visibility into the interior, where comfortable seating is visible in a cozy living space.

Home in Wailea

Mana Hale Vacation Rental

4.98 out of 5 average rating, 57 reviews

The cottage exterior presents a light green facade with a sloped roof, complemented by vibrant flowering shrubs. A private carport is visible beside the entrance, and a shaded seating area is provided under an umbrella on the porch. The scene is surrounded by lush greenery.

Cottage in Wailea

Maui Meadows Ocean View Cottage

4.89 out of 5 average rating, 510 reviews

An open living space features a comfortable bed with soft blue linens, a stylish fold-out loveseat, and a large area rug. A fully equipped kitchen with wooden cabinets and a breakfast bar is visible, complemented by natural light from nearby windows.

Guest suite in Wailuku

Oceanview, Banana Bread, Hot Tub & Sauna near OGG

4.97 out of 5 average rating, 129 reviews

The open living area showcases vaulted ceilings and warm wood beams. A modern kitchen island with a marble finish is complemented by stylish pendant lights. A cozy seating area invites relaxation, while large windows offer views of the surrounding landscape, enhancing the bright and airy atmosphere.

Townhouse in Wailea

Beautiful Wailea Ekolu Townhouse-Perfect Get-Away

A cozy studio condo includes two double beds covered with white bedding and a blue accent thrown. Large glass doors lead to a private patio, offering natural light. A small seating area and a TV are visible, adding to the comfort of the space.

4.85 out of 5 average rating, 130 reviews

Resort 2-Bed Studio- Steps to Beach/Shops/Dining

Superhost

A private lanai is showcased with woven seating and a wooden table, offering a view of vibrant green grass that leads to the ocean. Palm trees frame the scene against a clear blue sky, enhancing the relaxing beachside atmosphere.

5 out of 5 average rating, 5 reviews

Breathtaking Location-Sugar Beach #129

4.88 out of 5 average rating, 251 reviews

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

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

A modern living area features a comfortable sofa and a chair, with a flat-screen TV situated on a wooden media console. Large sliding glass doors provide access to a private lanai, with views of palm trees and the ocean in the background.

4.99 out of 5 average rating, 67 reviews

Oceanfront renovated luxury-best location! SBR 404

Family-friendly home rentals with a pool

A spacious living area features large windows offering views of the surrounding greenery. The open floor plan includes a dining table set for six, with a central decorative piece. A modern kitchen with stainless steel appliances is visible, complemented by stylish light fixtures and ceiling fan.

4.92 out of 5 average rating, 50 reviews

Stunning Wailea 2/2, AC, Upper Fl , walk to beach

A dining area features a circular bar with four woven stools and multi-colored pendant lights overhead. The textured orange walls and bamboo ceiling create a warm ambiance. A small desk with a chair is visible against the wall, along with decorative artwork and shelving.

4.95 out of 5 average rating, 61 reviews

Gorgeous Condo in Wailea Ekahi Village!

4.98 out of 5 average rating, 41 reviews

Apartment in Wailea

Wailea Ocean View Escape

An outdoor patio space features comfortable wooden seating and a decorative rug. Lush greenery and vibrant flowers surround the area, while ocean views are visible in the background under a clear blue sky.

5 out of 5 average rating, 15 reviews

Wailea Elua condo - Ocean Views | Gym | Pickleball

4.97 out of 5 average rating, 93 reviews

Modern Renovated Palms at Wailea Condo!

An expansive view of Kamaole Beach is visible from the lanai, framed by swaying palm trees. The vibrant blue ocean meets the sandy shoreline, with people enjoying the beach below. The lush green landscape adds a tranquil touch to this coastal scene.

4.97 out of 5 average rating, 281 reviews

200 Steps from the Beach | Sunset views!

A panoramic view showcases the coastline meeting the Pacific Ocean under a vibrant sunset. Lush palm trees frame the scene, while the 10th fairway of the Wailea Blue Golf Course runs through the foreground. The sky is filled with soft clouds reflecting warm tones.

4.98 out of 5 average rating, 46 reviews

Wailea Ekolu Ocean Suite 207 AC and Ocean Views

A modern kitchen area showcases a large island with a striking marble countertop, complemented by warm wood cabinetry. Pendant lights hang above, providing additional illumination. In the background, sliding glass doors lead to an outdoor terrace featuring scenic views.