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, 207 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 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, 216 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.

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.

4.94 out of 5 average rating, 183 reviews

Wailea Ekolu Village 2/2 with stunning ocean view!

Halloween Special! 20% off all days October 28 - November 5! Beautiful, spacious, modern 2/2 condo located in the heart of the Wailea Resort area with gorgeous, far-reaching ocean and island views, and surrounded by brilliant, lush, flowery grounds. Super-close to dining, golf, shopping, and only a short stroll to award-winning Wailea and Ulua beaches! Please note that this condo is in the Wailea Resort area, and does not infringe upon nor remove housing from the local neighborhoods of Maui.

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

Stylish garden oasis nearby Maui's best beaches

Aloha! Welcome to our beautiful home at Maui Kamaole, an upscale complex located next to Keawakapu 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.

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, 151 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.

4.96 out of 5 average rating, 134 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, 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!

A view from the second floor displays lush tropical landscaping with palm trees and vibrant greenery. The ocean is visible in the background, framed by a clear blue sky. The scene offers a serene outdoor ambiance typical of Wailea.

4.89 out of 5 average rating, 114 reviews

Luxury Condo w/wide Ocean View (Palms at Wailea)!

There is no better location than Wailea to experience your Maui vacation! This quiet and spacious condo has every amenity you could want to make your Maui vacation truly unforgettable. This condo is only a short walk to one of the best beaches (Keawakapu) on Maui and is also in close proximity to the Shops at Wailea. We spared no expenses in stocking this condo with everything you need to make your Maui experience memorable and luxurious.

4.96 out of 5 average rating, 443 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

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, 136 reviews

Newly Remodeled 1bed/1bath, Kihei/Wailea

A patio area is framed by lush palm trees, featuring a round table surrounded by four chairs. Soft sunlight illuminates the scene, highlighting views of the ocean beyond the greenery.

4.97 out of 5 average rating, 100 reviews

*Maui Kamaole Amazing Ocean Views Fab Front Row

4.98 out of 5 average rating, 295 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

4.96 out of 5 average rating, 164 reviews

Luxury Vacationing Modern Condo Dec. Specials $249

A bright and airy living space features vaulted wooden ceilings and large sliding glass doors, opening to a balcony with a garden view. A comfortable seating area is adorned with blue and white accents, while a dining table surrounded by six chairs is visible in the foreground.

4.95 out of 5 average rating, 110 reviews

Maui Kamaole Retreat Modern Remodel, Close 2 Beach

A modern kitchen and dining area is featured, with light-colored cabinetry and a spacious countertop. Pendant lights illuminate the space. A vibrant mural depicts tropical foliage on the wall. Large glass doors provide views of the lush outdoor area, enhancing the bright atmosphere.

4.94 out of 5 average rating, 111 reviews

☀Very Desirable South Kihei | Enlivening Getaway ☀

4.97 out of 5 average rating, 94 reviews

Modern Renovated Palms at Wailea Condo!

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!

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, 68 reviews

Oceanfront renovated luxury-best location! SBR 404

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, 144 reviews

Stunning Ocean Views

5 out of 5 average rating, 12 reviews

Apartment in Wailea

Wailea Escape/Golf Views, Beaches & Family Comfort

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 spacious bedroom features a comfortable bed with a light-colored, art-inspired bedspread. A wooden dresser stands opposite a corner television. Large windows provide views of the surrounding tropical landscape, while soft lighting enhances the serene atmosphere.

4.93 out of 5 average rating, 80 reviews

Wailea Elua 1101 - Beachfront Section - 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, 63 reviews

Gorgeous Condo in Wailea Ekahi Village!

4.98 out of 5 average rating, 41 reviews

A dining table with two chairs is positioned on a balcony, offering views of the ocean and lush palm trees. A decorative lantern and glassware decorate the table, enhancing the inviting dining setting against a backdrop of greenery and blue water.

Apartment in Wailea

Wailea Ocean View Escape

4.93 out of 5 average rating, 137 reviews

A bright living area features a comfortable sofa and armchairs, complemented by a coffee table. Large windows offer stunning ocean views, while a dining table and chairs are positioned nearby. A TV sits on a wooden unit, and vibrant artwork adorns the wall.

Apartment in Kihei

Maui Oceanfront Penthouse at Nani Kai Hale (609)

A spacious living room is presented with comfortable seating options, including a sofa and decorative chairs. Natural light floods the area through large windows, highlighting the neutral color palette. A wooden coffee table is centered on a textured rug, offering a cozy gathering space.