Family-friendly holiday rentals in Wailea

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

New 160K Renovation+Redecoration for a Hawaiian Beach Vibe.Wailea is one of the most sought after resort on Maui. Here you can relax in luxury of the beautiful grounds + refreshing swimming pool and spa. World Class Golf+Shopping. Ground floor condo with private lanai that overlooks the grass. King Master Bed with private bath,2 Uber deluxe pull out Queen bed couches.Short stroll to Keawakapu Beach from condo where you can snorkel+take long beach walks. EverythingProvidedBeach items+Yeti+ more

Indoor spacesKitchenBathroom

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

Unit #903 – Key Features Garden views, ground floor A/C (3 zones) Lanai seating Quiet Updated appliances; washer/dryer Primary: king bed Second: twins (convert to king) Sleeper sofa Kitchen TV, Wi-Fi Free U.S./Canada calls Amenities Beach chairs, umbrella, boards, cooler, towels Baby gear: Pack ’n Play Pool, hot tubs Location Wailea—near beaches, golf, shops, dining. Keawakapu Beach is a short walk. Guest Support On-island contact after booking. Parking Dedicated space + guest parking.

Indoor spacesFamilyHospitality

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.

Indoor spacesKitchenAir conditioning

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!

KitchenIndoor spacesAccess

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!

KitchenFamilyHeating

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.

KitchenIndoor spacesWalkability

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

Indoor spacesFamilyView

4.83 out of 5 average rating, 191 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.

Indoor spacesKitchenOutdoor spaces

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.

KitchenFamilyCheck-in

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.)

FamilyIndoor spacesValue

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 : )

KitchenIndoor spacesHospitality

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.

4.9 out of 5 average rating, 162 reviews

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

Experience the best of Wailea from this rare 3BR/2BA luxury villa, featuring breathtaking views of the Pacific Ocean, Wailea Blue Golf Course and majestic Haleakalā. Spacious enough for families or groups, this exceptional retreat offers all the comforts of home—just a short walk from world-famous beaches, luxury resorts, fine dining and premier shopping.

KitchenFamilyCheckout

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

4.97 out of 5 average rating, 116 reviews

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

FamilyKitchenAmenities

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

KitchenFamilyLong stay

4.98 out of 5 average rating, 195 reviews

Grand Champions 169 Beautiful 3 BR on the Fairway!

FamilyKitchenTV

Superhost

4.85 out of 5 average rating, 153 reviews

Kihei Condo: Steps from Beach & Yummy Eats!

FamilyIndoor spacesValue

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, 197 reviews

3BR spacious Condo with Ocean View in top location

Indoor spacesKitchenGetting around

4.95 out of 5 average rating, 168 reviews

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

KitchenFamilyLayout

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, 140 reviews

Spacious garden oasis next to Maui's best beaches!

Indoor spacesKitchenCleanliness

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

Indoor spacesFamilySolo travel

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

Indoor spacesFamilyComfort

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, 432 reviews

Ocean View Superior Deluxe - 200

FamilyKitchenAir conditioning

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.

KitchenFamilyCleanliness

Superhost

4.86 out of 5 average rating, 108 reviews

Sleeps 8 Ocean View 3bth Kamaole Beach HOT TUB

Indoor spacesKitchenAir conditioning

4.89 out of 5 average rating, 575 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

Indoor spacesFamilySolo travel

4.91 out of 5 average rating, 147 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!

Indoor spacesKitchenLaundry

Superhost

Home in Wailuku

3B2B w/HotTub FamilyComfort HawaiianaCharm Central

FamilyKitchenAccess

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

Indoor spacesKitchenCheckout

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!

FamilyKitchenBeach

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

Indoor spacesKitchenSleep quality

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

KitchenFamilyAccess

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

FamilyKitchenWalkability

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, 206 reviews

Groovy bright condo 2 bed / 2 bath South Kihei

KitchenFamilyAmenities

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

KitchenIndoor spacesNearby

4.96 out of 5 average rating, 469 reviews

Home in Wailea

Stunning ocean view Villa, Heated pool, Wailea

FamilyIndoor spacesComfort

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.