Family-friendly holiday rentals in Wailea

A picturesque view captures a beach at sunset with vibrant orange and purple hues in the sky. Swaying palm trees line the shoreline, where beachgoers can be seen enjoying the golden sand and gently lapping waves. The grassy area near the beach is dotted with lounge chairs.

4.97 out of 5 average rating, 105 reviews

Mana Kai Palms Oceanfront Condo: Keawakapu Beach

Welcome to Mana Kai Palms Our luxurious, newly renovated condominium is located on Keawakapu Beach, named Maui's best for its pristine sand, clear waters, and abundant marine life. The Mana Kai Resort offers a wide range of amenities and with only 100 units, provides a warm, family feel. We are conveniently located minutes from all South Maui has to offer. Hosted by Tracy O'Reilly, a Superhost and #1 rated rental agent on Maui. Do as much as you want or as little as you desire at Mana Kai Palms

An aerial view highlights the expansive grounds of Ekahi Village, featuring lush greenery and walking paths. The ocean glistens in the background, creating a coastal ambiance. The unit's location is marked, showcasing proximity to amenities and nearby beach access.

4.95 out of 5 average rating, 103 reviews

Ekahi 22C Toes in the Sand in Under 2 Minutes

Ideal location in Wailea's Ekahi Village. Less than 2 minutes till your toes are in the sand of south Maui's best beach. Private partial ocean view 2 bedroom, 2 bath 1,505 sf recently updated condo. Ground floor unit, main lanai spills onto green belt. Ekahi's amenities of pools, pickleball, and pavilion are mere steps away. Fully equipped kitchen, 3 HDTVs, & 3-zone AC. Beach chairs, cooler, and beach towels provided. Easy access with zero steps from parking lot to unit. Owned by Ekahi 22C, LLC.

An open dining area features a round table made of natural wood, surrounded by woven chairs. A well-equipped kitchen with stainless steel appliances and quartz countertops is visible in the background. Large sliding glass doors provide unobstructed views of the ocean and nearby palm trees.

4.94 out of 5 average rating, 333 reviews

A.R.A Retreats: The Molokini

FULLY Renovated Summer 2023! Nicknamed “Molokini” this condo has stunning ocean view front and center of Molokini, you can witness multiple humpbacks jumping and playing during whale season from the comfort of your own private lanai. This condo is located in Wailea Ekolu in the well-known luxury resort community of Wailea. It offers a beautiful 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

The living area is arranged with comfortable seating over a textured carpet. A low coffee table holds decorative elements, while art adorns the wall and a modern kitchen with stainless steel appliances is visible in the background, enhancing the open layout.

4.97 out of 5 average rating, 167 reviews

Hawaiian Reno on Wailea Blue Golf *Ocean View*Pool

Stunning Full Renovation and Hawaiian Styled Contemporary Decor. Located right on Wailea Blue Golf course in the Grand Champions at Wailea with incredible ocean views from the lanai.We are perfectly located just down from Money Pod+across from The Wailea Village popular with all the best restaurants. The Shops of Wailea with all of the exclusive brands is a short walk down the hill. Resort style amenities with 2 pools. Everything provided from Beach towels, Boogie Board, Yeti cooler and more.

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, 232 reviews

Mana Kai 608: Oceanfront Remod- February 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, 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 Manager in Maui, Tracy O'Reilly to take amazing care of you!

4.99 out of 5 average rating, 143 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.

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, 154 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!

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.

4.99 out of 5 average rating, 151 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

4.83 out of 5 average rating, 189 reviews

Last Minute Deal! Wailea Condo Oceanfront Complex

Step into your own private tropical oasis in this fabulous Wailea condo! This adorable 792 square foot, ground floor unit is walking distance to one of the most incredible beaches on Maui with tantalizing turquoise blue waters of the Pacific! This lavish condo boasts an open and airy living space you will love with AC throughout. Relax on the remarkable lanais with a table with seating for four.

A large swimming pool is surrounded by lounge chairs and tropical landscaping, offering views of palm trees and the ocean. The area features a sun deck, umbrellas, and a shaded seating spot, contributing to a relaxed resort environment.

4.92 out of 5 average rating, 170 reviews

Spacious comfy unit Netflix & huge pool Maui Hill

Welcome to Aston Maui Hill Resort in the heart of Kihei right next to Wailea. We offer you the entire place with kitchen ,two bathrooms, one bedroom ,a living room with a queen bed. You’ll have the entire place, Its a real garden style resort close to beaches and restaurants. We always value our guests recommendations to improved and if there’s anything you we could do we are here to help.

4.98 out of 5 average rating, 208 reviews

Ocean/Golf Course Views, Tropical Resort in Wailea

Breathe in and exhale slowly while gazing at the beautiful ocean, serene greenery and misty mountaintops. Make the most of a country-club setting by lounging on sun decks and swimming in heated pools. Retreat to an updated condo to unwind and fall asleep in a comfy bed. (This unit is suitable for a maximum of four (4) guests. Infants of any age are counted as guests.)

A modern living area features a large television set on a dark wooden console. Bright natural light illuminates the space through expansive sliding glass doors, leading to a small outdoor seating area. A decorative rug enhances the floor, complemented by a cozy sofa adorned with various cushions.

4.93 out of 5 average rating, 120 reviews

Maui Wailea Brand New Modern Spacious Condo

Beautifully designed, modern, and brand new vacation condo is situated on the Wailea Blue golf course and the Wailea tennis club. Walk to Shops at Wailea and 3 min drive to Keawakapu Beach. Brand new kitchen, spa like bathroom with walk in shower, in-unit laundry. Relax with friends and families at this peaceful place to stay. Book your vacation today : )

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 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.

4.99 out of 5 average rating, 139 reviews

Spacious garden oasis next to Maui's best beaches!

4.88 out of 5 average rating, 172 reviews

A spacious living area features a large sectional sofa adorned with various throw pillows. A wooden coffee table sits in front of the sofa, while built-in shelves display decorative items and a flat-screen TV is positioned for easy viewing.

Apartment in Wailea

Go Golfing from a Peaceful Apartment in a Beach Community

A clear view of a swimming pool is presented, surrounded by lounge chairs and tropical greenery. Palm trees frame the scene, with the ocean visible in the background under a bright blue sky dotted with clouds.

4.92 out of 5 average rating, 194 reviews

3BR spacious Condo with Ocean View in top location

Superhost

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.

4.88 out of 5 average rating, 136 reviews

Grand Champions - King Bed - Close to Wailea Beach

4.98 out of 5 average rating, 195 reviews

Grand Champions 169 Beautiful 3 BR on the Fairway!

The kitchen area features warm wood cabinetry, a stainless steel refrigerator, and a modern microwave. A spacious countertop provides ample room for meal preparation. Sunflowers are arranged in a vase on the counter. Two wooden stools are positioned at the breakfast bar, adjacent to a round dining table.

4.95 out of 5 average rating, 128 reviews

Luxurious Condo in South Kihei

A sandy beach stretches along the coastline, framed by tall palm trees swaying gently. Gentle waves lap against the shore, creating a serene atmosphere. In the distance, lush green hills rise under a partly cloudy blue sky, enhancing the natural beauty of the location.

4.99 out of 5 average rating, 150 reviews

Very Comfortable Kamaole Sands Condo Sleeps 4

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, 197 reviews

Romantic, Luxury Retreat w/Ocean View-Couples Only

Family- and pet-friendly home rentals

4.97 out of 5 average rating, 145 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 bright living area is showcased with large glass doors offering access to an outdoor space. Comfortable seating is provided by a gray sofa and wicker chairs, accented with blue and patterned cushions. A glass coffee table is placed centrally, complemented by a mounted flat-screen TV.

4.86 out of 5 average rating, 107 reviews

Sleeps 8 Ocean View 3bth Kamaole Beach HOT TUB

A serene beach scene at sunset showcases soft hues of orange, pink, and purple in the sky. Silhouetted figures walk along the shoreline, while a tall palm tree stands nearby, framing the tranquil landscape and creating a sense of calm.

4.84 out of 5 average rating, 431 reviews

Ocean View Superior Deluxe - 200

A private lanai features a round glass-top table surrounded by colorful cushioned chairs. Lush tropical plants and palm trees create a serene garden view, while a clear blue sky adds brightness to the scene.

4.95 out of 5 average rating, 114 reviews

Walk to Kam Beach! King Bed, Pools, Pet Friendly.

4.92 out of 5 average rating, 146 reviews

A cozy outdoor deck is showcased, featuring two wicker chairs and a small table, inviting relaxation. The inviting turquoise door stands adjacent to a wall with the word 'Aloha' elegantly displayed. String lights add a warm touch above, surrounded by tropical greenery.

Home in Kihei

Enjoy paradise living at the THERE Maui House!

4.89 out of 5 average rating, 569 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

Superhost

Home in Wailuku

3B2B w/HotTub FamilyComfort HawaiianaCharm Central

4.81 out of 5 average rating, 113 reviews

4.98 out of 5 average rating, 58 reviews

Cottage in Wailea

Private Ocean View Cottage Near Wailea - Sunsets

Family-friendly home rentals with a pool

4.99 out of 5 average rating, 134 reviews

Beachfront Oceanview Wailea Ekahi 16B Studio W/AC

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, 197 reviews

Wailea Ekolu Village 2/2 with stunning ocean view!

The image captures a vibrant sunset over the ocean, with hues of orange, pink, and purple reflected across the water. Silhouetted palm trees line the foreground, adding a tropical feel. The landscape features rocky shorelines and gentle waves under the colorful sky.

4.96 out of 5 average rating, 142 reviews

Oceanfront Mana Kai Penthouse..Heaven meets Earth!

4.96 out of 5 average rating, 469 reviews

Home in Wailea

Stunning ocean view Villa, Heated pool, Wailea

A vintage toy van is positioned on a sandy beach, facing a vibrant sunset over the ocean. Warm golden light reflects off the waves, creating a serene scene. The gentle surf adds a sense of calm to the atmosphere, with small ripples lapping at the shore.

4.93 out of 5 average rating, 205 reviews

Groovy bright condo 2 bed / 2 bath South Kihei

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.

4.96 out of 5 average rating, 202 reviews

Wailea Gem-Remodeled Ocean View

4.86 out of 5 average rating, 139 reviews

The oceanfront pool area is surrounded by swaying palm trees, providing a serene setting. Lounge chairs are arranged around the pool, which features a curved shape, complemented by a tiled deck. The expansive ocean view is framed by a cloudy sky.

Townhouse in Wailea

Wailea Villa with Oceanfront Pool