Family-friendly vacation rentals in Kihei

4.99 out of 5 average rating, 196 reviews

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.

Condo in Wailea-Makena

Romantic, Luxury Retreat w/Ocean View-Couples Only

Luxury accommodations in the heart of Wailea, Maui. Our condo has lovely ocean views, views of the lush tropical gardens and the pool. Sunset views from the lanai are stunning. Gourmet kitchen. 2 HD TVs, Bose sound system, AC, washer/dryer in unit, complimentary assigned parking. 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 Our condo is not suitable for children or infants.

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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, 228 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, 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!

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Guest suite in Wailea-Makena

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.

4.99 out of 5 average rating, 142 reviews

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.

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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, 136 reviews

Spacious garden oasis next to 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/ a pull-out sleeper, and a pack and play for toddlers! Enjoy the essentials of modern connectivity, a fully stocked kitchen, with two full bathrooms. Soak in paradise on two garden patios!

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A modern living room is seen featuring a spacious blue sofa and two accent chairs. A round black coffee table is centered on a light area rug. A wall-mounted TV displays an ocean view, while an open concept kitchen and dining area are visible in the background.

4.94 out of 5 average rating, 108 reviews

5 Stars, Chic 2BR/2BA, Steps to Beach - AquaMaui

We are happy to invite you to our beautiful & stylish vacation condo - AquaMaui. Our family is grateful to have experienced the magic of Hawaiian living and we would love others to experience this. Our condo is a 3 minute walk to one of the most beautiful beaches in Maui - Charley Young Beach. The condo has been completely remodeled with luxury furnishings and comes with access to a pool & barbecue grill area. AquaMaui comes with all the amenities that you need to have a great vacation!

Indoor spacesFamilyView

The living area features a light-toned sofa adorned with decorative pillows, accompanied by a round coffee table. A view of the ocean is visible through floor-to-ceiling sliding glass doors, with tropical greenery framing the scene. A ceiling fan enhances the airy feel of the space.

4.97 out of 5 average rating, 176 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

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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, 167 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.

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A view from the balcony showcases swaying palm trees against a backdrop of the ocean and partly cloudy sky. Vibrant greenery and blooming flowers add color to the landscape, while parked vehicles are visible in the foreground.

4.93 out of 5 average rating, 258 reviews

Ocean View · King & Queen · Pool & Jacuzzi

Wake up to ocean views from your private balcony, then head down to the beach with chairs, umbrellas, and towels we provide. Back at the building, a heated pool and hot tub are waiting when you're ready to unwind. With a king bed in the private bedroom and a queen in the living area, there's comfortable space for the whole family — and a fully stocked kitchen so you're never scrambling for a meal. Downtown Kihei's shops and restaurants are just a 3-minute drive away.

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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.

4.93 out of 5 average rating, 192 reviews

3BR spacious Condo with Ocean View in top location

Enjoy ocean views and island living from this spacious 1,400 sq ft 3-bed/2-bath condo in the heart of Kihei. Located directly across the street from the beach, you can watch whales from the lanai or relax by the pool and BBQ area. Shores of Maui offers easy access to Kihei’s best beaches, shops, and restaurants, all within minutes. A perfect home base for families and groups looking for comfort, convenience, and the South Maui lifestyle.

Indoor spacesFamilyWalkability

A scenic view reveals the ocean with soft waves meeting sandy shores, framed by palm trees. In the foreground, tennis courts are visible against a backdrop of rolling hills, showcasing lush greenery under a clear blue sky.

4.97 out of 5 average rating, 118 reviews

Maui is Open - Come Support the Locals

This beautifully upgraded penthouse condo, with stunning ocean and majestic mountain views, is centrally located in Kihei, which is widely considered to have the best beaches and weather on Maui. World-class restaurants, trendy food truck parks, and favorite local haunts are just a stone's throw away. Do you take advantage of the unlimited number of close-by activities, or just relax on the lanai and enjoy the view? It's your call!

Indoor spacesFamilyWalkability

4.96 out of 5 average rating, 467 reviews

Home in Wailea-Makena

Stunning ocean view Villa, Heated pool, Wailea

Legendary Maui sunsets from your private lanai. Whales splashing offshore in season. A heated pool all your own, tucked into over half an acre of tropical gardens. This artist-designed Victorian-style villa is 5 minutes from Keawakapu Beach and the Shops at Wailea, and made for families, with shallow-end pool steps, a gated lanai, and baby gear ready on arrival. Boutique hotel attention, complete privacy. Your view retreat awaits.

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4.97 out of 5 average rating, 313 reviews

A charming guest house is presented with a wraparound deck, framed by palm trees and lush greenery. The exterior features light-colored siding and a sloped roof, with windows allowing natural light. A clear blue sky enhances the inviting setting of this private retreat.

Home in Wailea-Makena

South Maui Guesthouse

This air conditioned very exclusive, private 2-bedroom Guest House is surrounded with lush gardens on a ½ acre property, off the street located in an upscale very private neighborhood (Maui Meadows, above Wailea), yet minutes from the best beaches Maui has to offer. A real Hawaiiian retreat, where you wake up to the sound of birds, not traffic. Permit Number BBKM2018/xxx3 GETxxxxxxxx2801

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Popular amenities for Kihei family-friendly rentals

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Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

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

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A spacious living area features a comfortable gray sofa adorned with tropical-patterned cushions. A wooden coffee table is centered in the room. Large sliding glass doors provide views of palm trees and the ocean, allowing natural light to enhance the inviting atmosphere. A flat-screen TV is mounted on the wall.

4.95 out of 5 average rating, 222 reviews

Refined Oceanfront Vistas

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The sleeping area features a spacious bed with a light-colored quilt and decorative pillows. Large sliding glass doors provide an expansive view of the ocean and palm trees, with soft curtains framing the scenic backdrop.

4.85 out of 5 average rating, 569 reviews

Amazing views at Oceanfront Studio

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4.96 out of 5 average rating, 676 reviews

Condo in Wailea-Makena

Wailea Resort studio suite

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4.93 out of 5 average rating, 210 reviews

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.

Condo in Wailea-Makena

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

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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, 149 reviews

Very Comfortable Kamaole Sands Condo Sleeps 4

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An open and light-filled living area is featured, showcasing large glass sliding doors that offer views of lush tropical landscaping. A spacious gray sectional is complemented by a cozy chair, and a neutral area rug anchors the space. Decorative elements include the word "ALOHA" on the wall.

5.0 out of 5 average rating, 162 reviews

*Tropical luxury at South Maui Surf Shack*

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The living area features large sliding glass doors providing a view of the ocean and the outdoor lanai. A flat-screen TV is positioned on a wooden console, complemented by a cozy sofa. Light drapes frame the entrance, enhancing the bright ambiance.

4.83 out of 5 average rating, 108 reviews

Ocean View Condo at The Shores of Maui in Kihei

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Family- and pet-friendly home rentals

A stunning sunset is captured over the ocean, with a vibrant orange sun descending towards the horizon. Silhouetted palm trees frame the scene, their fronds gently swaying in the breeze. The calm waters reflect the warm colors of the sky, creating a serene coastal atmosphere.

4.88 out of 5 average rating, 416 reviews

Ocean View - Deluxe Unit #201

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4.92 out of 5 average rating, 144 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!

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Townhouse in Wailea-Makena

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.

4.97 out of 5 average rating, 144 reviews

Beautiful Wailea Ekolu Townhouse-Perfect Get-Away

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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

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The kitchen and dining area feature wooden cabinetry and modern appliances. A round glass table is surrounded by four rattan chairs. The space is well-lit with natural light from the overhead skylight, enhancing the inviting atmosphere of the room.

4.95 out of 5 average rating, 114 reviews

1BR Kihei Condo, Full Kitchen, Walk to Beach

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5.0 out of 5 average rating, 7 reviews

Surf Rider| Remodel • Ocean View • 350 steps Kam 1

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5.0 out of 5 average rating, 6 reviews

Home in Kihei

NEW! 1 bed | Walk to town/beach (S. Kihei)

KitchenDecorBeach

4.97 out of 5 average rating, 32 reviews

Home in Kihei

Mermaid Bungalow, cozy and ready for action.

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Family-friendly home rentals with a pool

4.94 out of 5 average rating, 134 reviews

A modern kitchen features sleek cabinetry and stainless steel appliances, including a refrigerator and microwave. A light grey tile backsplash complements the white marble countertop, which hosts a built-in stove. Natural light enters through a small window, enhancing the airy space.

Apartment in Kihei

High-end, On Beach, View Balcony, with Pool & BBQ!

Indoor spacesKitchenQuiet

4.96 out of 5 average rating, 113 reviews

A live-edge wooden table is positioned in a cozy nook, accompanied by a built-in bench with decorative pillows. A modern kitchen with stainless steel appliances and granite countertops is visible in the background, illuminated by natural light from a window.

Bungalow in Kihei

Walk to the Beach from a Modern Hideaway

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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, 147 reviews

Stylish Kihei Condo in Oceanfront Resort Complex

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Apartment in Wailea-Makena

The living area features large glass doors that open to a breathtaking ocean view, enhancing the spacious atmosphere. A comfortable sofa is complemented by two armchairs and a round coffee table. Elegant decor elements add to the modern aesthetic, accented by warm natural light.

4.97 out of 5 average rating, 104 reviews

A.R.A Retreats: Birds Eye View

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A bright living area is showcased with two patterned sofas draped in light blankets. A woven rug lies beneath a wooden coffee table, and wall art decorates the walls. Natural light filters through sheer curtains, creating a serene atmosphere.

4.93 out of 5 average rating, 184 reviews

A little beachy, bohemian slice of paradise

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An updated kitchen features wooden cabinets and a polished granite countertop. Stainless steel appliances, including a refrigerator, microwave, and oven, blend seamlessly. A double sink and coffee maker are visible, with a backsplash of small, iridescent tiles adding texture.

4.97 out of 5 average rating, 178 reviews

'E Komo Mai' ! 1 Bed/1 Bath in Tropical Gardens

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4.77 out of 5 average rating, 141 reviews

It's Always Sunny at Kihei Kai Nani!

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A light-filled living room features a designer sectional sofa and a wooden coffee table. Floor-to-ceiling glass doors offer unobstructed views of the ocean and balcony. A modern TV is positioned on a wooden console, enhancing the contemporary aesthetic of the space.