Family-friendly holiday rentals in Kihei

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, 124 reviews

Stylish garden oasis near Maui's top 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!

The image captures a serene view of a landscaped garden area with a central swimming pool. Surrounding palm trees provide shade, and sun loungers are arranged around the pool. The ocean is visible in the background, framed by a clear sky and gentle hills.

4.93 out of 5 average rating, 362 reviews

Oceanfront Kihei Condo Free SUP & Resort Pools!

This beautifully appointed 800 sq ft ground-floor condo features free paddleboard (a $50/day value) just 200 steps from sand. Enjoy resort-style amenities including a sparkling pool, soothing hot tub, kiddie pool, and pickleball courts nearby. Marvel at whale sightings (Dec-Apr) from your lanai or kitesurfing from shore. Stay productive with blazing 500 Mbps fiber WiFi and unlimited AC. We provide beach gear, parking, aon-site laundry. Our prime Kihei location offers the ultimate Maui escape

4.99 out of 5 average rating, 134 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 aerial view captures the coastal Menehune Shores complex, showcasing its resort-style architecture alongside the ocean. Lush green lawns extend towards the shore where gentle waves lap against the sandy beach. The backdrop features the expansive landscape of Maui, highlighting both land and sea.

4.99 out of 5 average rating, 137 reviews

Stylish Kihei Condo in Oceanfront Resort Complex

This 2 bed 2 bath home away from home offers everything you need for your Maui vacation and sleeps up to 6. Situated in the Hotel zoned oceanfront Menehune Shores complex, the condo is just steps to the beach and features an oceanfront pool, shuffleboard courts, and acres of grassy lawn. Snorkel with the turtles in the ancient Hawaiian fishpond fronting the property or watch whales while you BBQ on the rooftop deck at sunset. The centrally located condo will have you never wanting to leave.

A private rear deck features a shaded area with tropical foliage and bamboo fencing. Two surfboards and beach gear are neatly stored, along with a round table and colorful chairs for seating. A large black container sits in the corner, adding to the functional outdoor space.

4.92 out of 5 average rating, 371 reviews

•Maui BeachVilla• Parking @Your Own Private Entry•

Ground-floor, bottom corner unit across from Cove Beach — close to beach sunset, surf, food trucks and local stores. The only unit with a tandem parking stall right next to your wall and back deck entrance. Step out of your car, walk straight in to your smart lock security door on your own back deck. Fully upgraded with fast Wi-Fi, two AC units, new appliances and a lava rock shower with hot/strong pressure. Sleeps 4 with a master + studio, beach gear, well-stocked kitchen and fresh linens.

4.91 out of 5 average rating, 105 reviews

FABULOUS SPACIOUS CONDO ACROSS FROM BEACH

This spacious (1050 sq ft) condo is tastefully decorated with Hawaiian art and tropical style furniture for a sense of open space. Large windows in every room provide plenty of light and a partial view of Haleakalā. It is conveniently located 3 min walk away from family friendly Kamaole Beach III & II and at walking distance to restaurants and shops. Guests have access to a private condominium pool. Covered parking is located right below the building. Perfect location for family vacation.

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.

4.97 out of 5 average rating, 159 reviews

Stunning Ocean Views

Welcome to our slice of paradise in Maui and enjoy breathtaking 180° ocean views . Located just steps from the sandy Kamaole 1 Beach and a short stroll from vibrant restaurants and bars, our chic coastal-modern condo is the perfect spot for a beach getaway. Condo features all the amenities you need for a comfortable stay, including A/C in all rooms, a luxurious king bed, high-speed internet, fully equipped kitchen and a private lanai to watch sunsets. Your Maui adventure starts here

A scenic view showcases swaying palm trees against a vibrant blue sky, with a glimpse of the ocean in the background. Lush greenery frames a pool area, inviting relaxation, while the buildings provide a residential atmosphere. The beach appears just beyond the manicured lawns.

4.93 out of 5 average rating, 143 reviews

Lovely Oceanfront Condo with pool

Discover Paradise: Lovely Oceanfront Condo with Pool & Unforgettable Views Wake up to the symphony of waves and endless blue horizons in this stunning oceanfront condo, your ideal escape for relaxation, romance, or family adventures. Nestled right on the edge of the beach, this beautifully appointed retreat offers breathtaking panoramic ocean views from your private balcony—perfect for sipping morning coffee as the sun rises over the water or unwinding with a glass of wine at sunset.

A scenic beach scene showcases golden sand meeting turquoise waters under a clear blue sky. Lush green shrubbery line the shoreline, with palm trees swaying gently. A distant view of a mountain adds depth to the horizon, creating a tranquil coastal atmosphere.

4.85 out of 5 average rating, 140 reviews

Beautiful Resort Condo w/ AC @ Kam III Beach

Aloha from Maui. Our beautiful, spacious, Resort Condo is located at Kamaole III Beach Park...one of Maui's finest swimming and snorkeling beaches! The space is well equipped: with a full kitchen, washer/dryer, beach gear, comfy king bed, spacious private lanai, and new for 2024...A/C in the bedroom. Our resort features 2 pools, jacuzzi's, pickleball, exercise room, and convenient BBQ areas. A great selection of shops, restaurants, beaches and activities and all are nearby.

A dining setting is displayed on a balcony with a platter of fresh fruit, accompanied by glasses and a bottle of olive oil. Lush greenery and tropical plants surround the view, complemented by a bright blue sky and scattered clouds.

4.96 out of 5 average rating, 190 reviews

Newly Renovated Corner Unit w/ View at Maui Vista

Aloha - welcome to your Maui escape! Just steps from the iconic Charley Young and Kamaole I beaches, our newly remodeled condo offers comfort and convenience, with amazing dining and drink options a short walk away. Enjoy fresh seafood, tropical cocktails, and all the island vibes. Thoughtfully designed and continuously updated, our space has everything you need for a relaxing, unforgettable stay. Book your tropical getaway today—we’d love to host you! Mahalo, Dave & Neldie

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, 145 reviews

Very Comfortable Kamaole Sands Condo Sleeps 4

Very comfortable end unit 1 bedroom condo 2 bathrooms (818 sq ft) with views of the pool, partial ocean view, remodeled kitchen and bathrooms, recently painted, new flooring in living room and conveniently located to everything you need, unit is airy and bright with extra windows. The kitchen is well stocked with all the essentials and cooking utensils. A 5 mins walk to the beach and 10-15 mins leisurely stroll to nearby shops and stores. I take my own photos for my unit.

A spacious kitchen features modern white cabinetry and a large island with quartz countertops. Stainless steel appliances are visible, including an oven and refrigerator. The living area, partially seen in the background, includes a cozy couch and access to a balcony with views of lush greenery.

4.97 out of 5 average rating, 129 reviews

NEWLY remodeled Modern Maui condo across the beach

Enjoy a relaxing experience at this centrally-located Maui Vista condo, steps from popular Charley Young beach. Located in Building 2 with a nice breeze on the lanai overlooking lush lawn. Beautifully renovated (2021) modern design. This 1 bd 1 bath is located close to many shops and restaurants. Unit is on the 3rd floor (elevator access) w/luxury vinyl flooring. Stocked kitchen has everything you need w/ quartz countertops and large island. Stay cool with 2 AC units!

Popular amenities for Kihei family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.95 out of 5 average rating, 130 reviews

Kihei Garden Estates-Hidden Oasis, Steps to Beach!

A spacious sleeping area features a comfortable bed with a large white duvet. Framed botanical line drawings are displayed above the headboard. Soft light emanates from two bedside lamps, with a lush green plant positioned nearby, adding a touch of nature to the room.

4.91 out of 5 average rating, 141 reviews

Maui Poolside Villa at Kihei Bay Vista (B104)

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, 142 reviews

Newly Remodeled 1bed/1bath, Kihei/Wailea

4.96 out of 5 average rating, 172 reviews

Luxury Vacationing Modern Condo April Special $369

4.96 out of 5 average rating, 653 reviews

Wailea Resort studio suite

A bright living area features a large window that opens to a view of palm trees. A comfortable sofa adorned with various cushions is positioned around a round coffee table. A 65" Smart TV is mounted on a wooden console, complementing the bold teal accent wall.

4.95 out of 5 average rating, 148 reviews

Luxury Modern 2-Bedroom Condo, Amazing Ocean Views

The living area is filled with natural light from the large glass doors that open to a private balcony, providing views of the lush landscape and ocean. Modern furnishings include a spacious sectional sofa, a decorative coffee table, and a large flat-screen TV, offering a relaxed atmosphere.

4.97 out of 5 average rating, 144 reviews

Aloha Chic Penthouse Vistas

An aerial view showcases Kihei Garden Estates, highlighting its proximity to the beach, restaurants, and shopping areas. Lush greenery surrounds the complex, with the ocean visible in the background. Clear directional arrows indicate nearby amenities, enhancing the understanding of the location.

4.94 out of 5 average rating, 160 reviews

Close to the beach-2Bd/1Bath Condo-Great Location!

Family- and pet-friendly home rentals

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

4.97 out of 5 average rating, 136 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 living area is depicted with large sliding glass doors that open to a balcony view of the ocean and palm trees. A ceiling fan rotates gently above a comfortable seating arrangement that includes a light-colored sofa and two armchairs. A wooden coffee table is positioned in front.

4.93 out of 5 average rating, 30 reviews

High-Floor Island Surf | AC | Walk to Beach

5 out of 5 average rating, 13 reviews

A serene sunset is depicted over the ocean, with vibrant hues of orange and yellow radiating from the setting sun. Rays of light extend outward from the sun, casting a gentle glow across the water's surface, creating a tranquil coastal scene.

Cottage in Kihei

Grateful Casita

5 out of 5 average rating, 23 reviews

Home in Kihei

40% off monthly stay! 4 Bed Family Home (Kihei)

4.95 out of 5 average rating, 20 reviews

Luxury condo 20 steps from beach/pool/hot tub #103

4.88 out of 5 average rating, 255 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.

Flat in Wailuku

2B/2B Cottage/Cozy/Central/Private/Historic town

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, 96 reviews

Ocean View 3 bedroom 3bath Full AC Beach Access

Family-friendly home rentals with a pool

A comfortable living area features a sectional sofa and a coffee table, creating a relaxed atmosphere. Large sliding glass doors provide views of the ocean and open to the private lanai. A smart TV and a dining set with wicker chairs are also visible, enhancing the cozy space.

5 out of 5 average rating, 16 reviews

Stunning, Modern Oceanview! Beach, Pool, Hot Tub!

A cozy living room features a light blue sofa accompanied by a glass coffee table set on a patterned area rug. Two turtle-themed paintings adorn the wall above. Bright natural light streams in through large sliding glass doors, offering views of the greenery outside.

5 out of 5 average rating, 95 reviews

Maui Banyan 1bd/2ba, AC, quite, steps to the beach

A balcony offers a clear view of lush green grass leading to the ocean. A round glass table is accompanied by four black metal chairs. Tropical palm trees frame the scene, while mountains rise in the background under a partly cloudy sky.

4.78 out of 5 average rating, 23 reviews

Two Bd Ocean View, wifi, pool, hot tub D306

The living area features a comfortable sofa adorned with colorful pillows, flanked by a chair with a tropical design. Two lamps provide soft lighting beside the sofa. Wall art and a decorative table with a floral centerpiece enhance the inviting ambiance of the space.

4.98 out of 5 average rating, 96 reviews

Maui Vista 2304 Enjoy Your Island Hide Away

4.91 out of 5 average rating, 64 reviews

Tropical Newly Upgraded with CourtyardViews

5 out of 5 average rating, 13 reviews

Spread Aloha: Ocean Views, Artist Inspired Oasis

Superhost

Home in Kihei

5 out of 5 average rating, 3 reviews

Walk-Out Kamaole Beach II | Sunset Lanai | Quiet

An outdoor dining area is set up on a spacious lanai, showcasing a wooden table surrounded by six woven chairs. A vibrant bouquet of orange flowers adds a splash of color, while a panoramic view of the beach, palms, and ocean stretches into the distance.