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, 204 reviews

Mana Kai 608: Oceanfront Remod! Summer now OPEN!

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 clear blue pool is surrounded by palm trees, creating a relaxing atmosphere. Lounge chairs are positioned along the deck, offering spots for sunbathing. Umbrellas provide shade for outdoor dining tables nearby, all with a scenic view of the ocean in the background.

4.95 out of 5 average rating, 213 reviews

Maui's Best - Wailea Ekahi 47A

Ekahi says it all. Don't come all the way to Maui to stay in a bargain space. Unit 47A is a one bedroom (with sleeper sofa), two-bath renovated on the ground floor. This means a larger lanai than upper units. It also means that when you step off that lanai, you step onto A LOT of grass. Our condo is a 5-minute (barefoot) walk to the most wonderful of all Maui beaches; a ten-minute walk to the shops at Wailea. Restaurants nearby. Convenient yet without the road noise.2067153903 Privacy and peace.

4.99 out of 5 average rating, 124 reviews

Beachfront Oceanview Wailea Ekahi 16B Studio W/AC

Wailea Ekahi is a luxurious resort fronting onto beautiful Keawakapu Beach with acres of tropical grounds and 4 pools. Unit 16B is a mid property, renovated ground floor ocean view studio unit (500 sq feet) with a King sized bed, walk in shower and full kitchen. Enjoy your morning coffee and meals from the peaceful, shaded lanai which opens onto the lush greenspace and gardens while enjoying ocean views. A short walk to the beach, pools, luxury shopping, highend dining and golf courses.

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, 110 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, 176 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, 121 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 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, 146 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, 131 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!

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, 206 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, 441 reviews

A welcoming living area features a comfortable sectional sofa beside a modern coffee table, with natural light filtering through large windows. An outdoor patio is visible, with an umbrella-shaded table and chairs overlooking lush tropical gardens and ocean views.

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, 127 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

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, 118 reviews

Grand Champions - King Bed - Close to Wailea Beach

We are located in the heart of Wailea at the Grand Champions Villas, close to Maui's best beaches and within walking distance to great restaurants, the Shops of Wailea and surrounded by Championship Golf Courses. Grand Champions is a serene 12-acre park-like resort next to the Wailea Tennis Club and Wailea Blue Golf Course. Have fun with the whole family at this stylish place.

Popular amenities for Wailea family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

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, 133 reviews

Newly Remodeled 1bed/1bath, Kihei/Wailea

A serene bedroom is visible, featuring a spacious bed with white linens and a teal accent blanket. A piece of wall art depicting ocean waves enhances the decor. Natural light flows in through a window, and a ceiling fan provides ventilation.

4.98 out of 5 average rating, 151 reviews

Chic Maui Condo Steps From Beach & Ocean

4.96 out of 5 average rating, 162 reviews

Luxury Vacationing Modern Condo Nov. Specials $275

4.98 out of 5 average rating, 291 reviews

A single-story cottage is surrounded by a lush tropical garden, featuring vibrant flowers and palm trees. A spacious green lawn invites relaxation, while the wooden deck area, partially shaded, offers a welcoming space for outdoor activities.

Cottage in Kihei

Luxury Cottage,Saltwater Spa-Close to Beach,Dining

The oceanfront view captures gentle waves rolling onto a sandy beach, with vibrant shades of turquoise blending into deeper blue hues. A coastal landscape in the background features distant hills under a canvas of partly cloudy skies.

4.98 out of 5 average rating, 129 reviews

Beach/Oceanfront Property, Sleeps 5, Kihei Maui

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, 172 reviews

Grand Champions 169 Beautiful 3 BR on the Fairway!

Superhost

A spacious living area is furnished with two light-colored sofas adorned with patterned cushions. A glass coffee table sits at the center, complemented by a potted plant in the corner. Natural light enters through large windows with sheer curtains, enhancing the inviting atmosphere.

4.83 out of 5 average rating, 148 reviews

Beautiful Palms At Wailea #608-SEPT/OCT Discount

4.94 out of 5 average rating, 168 reviews

An outdoor dining table is set for four, featuring plates and cutlery, with a backdrop of lush greenery and panoramic ocean views. Palm trees frame the scene, and the sky displays soft hues of sunrise or sunset, enhancing the tranquil atmosphere.

Condo in Wailuku

Boho Beach Retreat *OCEAN VIEWS*

Family- and pet-friendly home rentals

4.98 out of 5 average rating, 116 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, 56 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, 504 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, 128 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

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.

4.98 out of 5 average rating, 66 reviews

Oceanfront renovated luxury-best location! SBR 404

4.86 out of 5 average rating, 115 reviews

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

Two Bedroom Green Turtle House

A sandy path leads from lush greenery to a serene beach. Palm trees sway gently in the foreground, framing views of calm blue waters and distant islands under a clear sky with scattered clouds.

4.97 out of 5 average rating, 32 reviews

*Rare Find* Quiet Ocean View Condo in Sunny Kihei

Family-friendly home rentals with a pool

A bright living area features sliding glass doors that open to a private lanai with ocean views. Comfortable seating options include a cozy sofa and armchair, complemented by a round coffee table and decorative pillows. Natural light fills the space, creating a welcoming ambiance.

4.98 out of 5 average rating, 140 reviews

Stunning Ocean Views · Steps to Beach · Comfort

The spacious living area features vaulted ceilings with exposed beams and large glass doors that open to stunning ocean views. Comfortable seating includes two patterned armchairs and a cozy sofa. A coffee table is centered in the room, and the dining area is illuminated by pendant lights.

4.96 out of 5 average rating, 111 reviews

Upscale and Elegant Vistas

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

Superhost

A modern kitchen features sleek white cabinets and a spacious granite countertop, with stainless steel appliances. A decorative arrangement of tropical flowers is positioned on the counter. A sliding glass door leads to a private lanai with ocean views, furnished with a dining table and chairs.

4.95 out of 5 average rating, 176 reviews

Wailea Gem-Remodeled Ocean View

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, 58 reviews

Gorgeous Condo in Wailea Ekahi Village!

4.97 out of 5 average rating, 39 reviews

Apartment in Wailea

Wailea Ocean View Escape

An open-concept living area displays a modern sofa and coffee table, surrounded by greenery visible through large sliding glass doors. A dining table is set with a woven basket centerpiece, creating a warm and inviting space that blends indoor and outdoor elements.

4.97 out of 5 average rating, 91 reviews

Modern Renovated Palms at Wailea Condo!

A modern dining area features a polished wooden table surrounded by six chairs. Natural light floods the space, highlighting the contemporary kitchen with granite countertops in the background. Large sliding glass doors open to a scenic view of the ocean and lush surroundings.