Family-friendly holiday rentals in Wailea

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, 104 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.

4.99 out of 5 average rating, 144 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 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, 233 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, on the border of Wailea and Kihei. Our condo is designed with a modern surf feel in mind, welcome to the beach! If you enjoy Wailea's 5 star resorts right down the beach, 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 PM in Maui, Tracy O'Reilly, to take amazing care of you!

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, 155 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 spacious living area features a gray sectional sofa arranged around a textured area rug. Two framed art pieces adorn the wall, and a large window offers views of the outside. A modern kitchen is visible in the background, accompanied by bar stools made of natural materials.

4.9 out of 5 average rating, 358 reviews

A.R.A Retreats: The Townhouse

Nicknamed “The Townhouse” this is a rare Townhouse in Wailea Ekolu Village. It has almost 1500 square feet and was completely renovated from top to bottom. While there are many things that make this unique from the view to the renovation the amazing townhouse layout is a rare treat for any guest in the area of Wailea. Steps from food, shopping, and some world class beaches. Sit and enjoy your drink whilst taking in our amazing views and when the sun goes down.

4.91 out of 5 average rating, 117 reviews

The spacious backyard features a resort-style pool complemented by a waterfall and grotto. Surrounding palm trees and tropical landscaping enhance the serene atmosphere, while lounge chairs and a shaded sitting area with an umbrella are positioned nearby. Soft lighting highlights the tranquil setting as dusk approaches.

Home in Wailea

Maui Meadows Retreat B&B-3 BR-Ocean Views-AC-Pool

Book with confidence, this gorgeous, newly remodeled, 3 bedroom, 2 bathroom home that has beautiful ocean views, a stunning backyard with a pool, hot tub, and tropical landscaping. THIS PROPERTY IS A PERMITTED BED & BREAKFAST (Permit #: BBKM20160005) LOCATED IN MAUI MEADOWS, AND IS MANAGED BY THE OWNER DAVID LAND. The house is in a great location in South Maui, close to beaches, restaurants, and the 5 star resorts of Wailea.

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.

4.95 out of 5 average rating, 200 reviews

Wailea Ekolu Village 2/2 with stunning ocean view!

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 Wailea Resort condo has received government approval to operate as a vacation rental for the next 5 years.

Luxe

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, 154 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, 192 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 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

Beautiful, fully remodeled Wailea Jewel! Peaceful and private location with expansive ocean views. Our newly renovated, one bedroom, 2 bathroom condo has everything you need to enjoy your Maui getaway. Located a short drive from the airport and just minutes away from some of the best beaches and dining in Hawaii. You will truly feel like you're in paradise during your stay.

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, 122 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

Wi-Fi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

A modern open-concept living area features a round wooden dining table in the foreground, surrounded by white chairs. In the background, a well-equipped kitchen displays sleek appliances. A cozy seating area with light-colored couches is visible, complemented by natural lighting from large sliding glass doors.

4.93 out of 5 average rating, 214 reviews

StunningReno*Palms in Wailea Condo-Beach*Golf*Pool

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, 151 reviews

Very Comfortable Kamaole Sands Condo Sleeps 4

4.88 out of 5 average rating, 173 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

4.97 out of 5 average rating, 116 reviews

Large 1BR, Palms at Wailea, Pool, Walk to Beach

4.89 out of 5 average rating, 103 reviews

Spacious 2 Bed+Sofabed in S. Kihei near Wailea!

4.95 out of 5 average rating, 168 reviews

Fairway-front 2BR, pool, walk to Wailea Beach

4.98 out of 5 average rating, 195 reviews

Grand Champions 169 Beautiful 3 BR on the Fairway!

Superhost

4.85 out of 5 average rating, 154 reviews

Kihei Condo: Steps from Beach & Yummy Eats!

Family- and pet-friendly home rentals

4.96 out of 5 average rating, 146 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 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, 433 reviews

Ocean View Superior Deluxe - 200

Superhost

4.86 out of 5 average rating, 108 reviews

Sleeps 8 Ocean View 3bth Kamaole Beach HOT TUB

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, 115 reviews

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

4.89 out of 5 average rating, 576 reviews

Guest suite in Wailuku

Oceanview, Banana Bread, Hot Tub & Sauna near OGG

4.91 out of 5 average rating, 148 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!

Superhost

Home in Wailuku

3B2B w/HotTub FamilyComfort HawaiianaCharm Central

4.82 out of 5 average rating, 114 reviews

4.98 out of 5 average rating, 59 reviews

Cottage in Wailea

Private Ocean View Cottage Near Wailea - Sunsets

Family-friendly home rentals with a pool

A private lanai features a round table with two high-backed chairs, offering panoramic views of the ocean and surrounding coastline. Lush palm trees and sandy beach are visible below, under a bright blue sky with scattered clouds.

4.96 out of 5 average rating, 143 reviews

Oceanfront Mana Kai Penthouse..Heaven meets Earth!

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, 106 reviews

Mana Kai Palms Oceanfront Condo: Keawakapu Beach

A well-appointed kitchen area features a spacious granite countertop with rich wooden cabinetry. Hanging red pendant lights provide soft illumination. Large windows offer views of lush greenery and the ocean, enhancing the inviting atmosphere of the space.

4.94 out of 5 average rating, 181 reviews

Gorgeous 2 Story Townhouse in Wailea w/ Ocean View

4.96 out of 5 average rating, 470 reviews

Home in Wailea

Stunning ocean view Villa, Heated pool, Wailea

A spacious living area is characterized by wood-paneled walls and natural light from large sliding glass doors. A comfortable queen-sized sleeper sofa and two accent chairs are arranged around a coffee table. A flat-screen smart television is mounted on the wall, adorned with complementary artwork.

4.91 out of 5 average rating, 119 reviews

Luxury Condo in Wailea Ekahi w/Direct Beach Access

4.98 out of 5 average rating, 52 reviews

Villa in Wailea

Luxury Oceanview Wailea Retreat with Sunset Views

A spacious bedroom features a wooden bed with plush bedding in soothing colors. Artwork is displayed above the bed, and large sliding glass doors open to a private lanai, showcasing tropical greenery. Natural light brightens the room, enhancing the tranquil atmosphere.

4.98 out of 5 average rating, 50 reviews

Tropical Escape to Wailea with Stunning Oceanview