Family-friendly holiday rentals in Kihei

A bright living space is highlighted by a large smart TV displaying vibrant fish. Light wood furniture complements a comfortable blue couch, while a wooden dresser and artwork adorn the walls. A cool ceiling fan enhances the modern decor, creating a relaxed atmosphere.

4.92 out of 5 average rating, 146 reviews

Modern Kihei Studio Steps to Beach *Private Lanai*

Welcome to our newly remodeled condo centrally located in South Kihei! We are a licensed property in a Hotel Zoned community, unaffected by the short term rental ban passed by the Maui Council in Bill 9. Book with confidence! Look forward to rolling out of the comfy king sized bed and loading up our beach wagon with some chairs and a cooler for a short walk to the beach. Later on, enjoy some shaded outdoors time in our beautiful private lanai space. Peace, relaxation. You’re going to love Maui!

The bedroom features a plank headboard with a spacious bed dressed in soothing seafoam colors. Soft accent pillows adorn the bed, including one that reads 'aloha', while a bedside lamp provides gentle illumination.

4.98 out of 5 average rating, 142 reviews

Tropical Kihei Resort | 3 Min Walk to Beach | A/C

NEW kitchen remodel, new floors & paint! Professionally CLEANED. Plush King size Sealy bed, all new kitchen and bathroom cabinets, stainless steel appliances, full size washer dryer, tile & LV floors throughout. Beautiful furniture, artwork throughout, granite countertops, high end linens, Queen sofa sleeper with 5" FOAM mattress. After the beach relax and enjoy sipping a beverage and lounging on your private lanai overlooking the tropical grounds. A/C units in BOTH the living area & bedroom.

A clear blue pool is surrounded by palm trees, creating a relaxing atmosphere. Lounge chairs are positioned along the deck, offering spots for sunbathing. Umbrellas provide shade for outdoor dining tables nearby, all with a scenic view of the ocean in the background.

4.95 out of 5 average rating, 218 reviews

Maui's Best - Wailea Ekahi 47A

Ekahi says it all. Don't come all the way to Maui to stay in a bargain space. Unit 47A is a one bedroom (with sleeper sofa), two-bath renovated on the ground floor. This means a larger lanai than upper units. It also means that when you step off that lanai, you step onto A LOT of grass. Our condo is a 5-minute (barefoot) walk to the most wonderful of all Maui beaches; a ten-minute walk to the shops at Wailea. Restaurants nearby. Convenient yet without the road noise.2067153903 Privacy and peace.

4.98 out of 5 average rating, 109 reviews

A spacious living area features a light grey sofa and a wooden coffee table positioned on a natural fiber rug. Large glass doors open to a patio with ocean views, while a flat-screen TV sits atop a console. Neutral curtains frame the windows, creating an airy atmosphere.

Apartment in Wailuku

Coastal Dream Oceanfront Condo!

Take a moment to unwind and appreciate the stunning views from the patio, where you can spot whales from Nov-April and catch a glimpse of surfers riding the "Freight Train" during mid-summer. Venture out for a leisurely walk to Maalaea Harbor Shops and the Maui Ocean Center, or explore with a drive to Lahaina (West), Hana (East), or Wailea (South tip). Enjoy delightful amenities including Heated Pool, Oceanfront BBQ station, and Lounge area on the lawn. Designated parking right out front.

A comfortable living area features a large sofa adorned with decorative cushions, paired with an accent chair and a coffee table. A surfboard is mounted on the wall, while the kitchen area is visible in the background, showcasing modern appliances and bar seating.

4.83 out of 5 average rating, 157 reviews

Beautiful Maui Beach Condo Steps from the Shore!

Live like a local during your stay at Kihei Bay Vista unit D110. This ground floor unit features a large lanai overlooking the tropical green lawn, mere moments from the sparkling shore! Our private oasis provides you a home away from home with a king sized bed, full bathroom, full kitchen, full size in-unit washer & dryer with a living area that includes a queen size pull out couch for up to 2 extra guests. Prime location near the best beaches and for easily exploring other parts of Maui.

A modern living space is showcased with a grey sofa and wooden coffee table, complemented by a dining area featuring a rectangular table and high-backed chairs. Large mirrors create a sense of openness, while a kitchen is visible in the background, enhancing the comfortable atmosphere.

4.87 out of 5 average rating, 118 reviews

Great Location! Walk to Everything in South Kihei!

If you want to be close to it all - best beaches, best snorkeling, only surf spot in Kihei, SUP, kayaking, snorkel tours, dinner cruises, shopping, restaurants, nightlife - our recently updated, owner-managed (no dealing with unresponsive property managers) condo is the perfect home away from home for you! Watch humpback whales (Nov-Apr), swim with giant sea turtles, or witness world-famous Maui sunset from 1 of the most beautiful beaches in all of Maui - only 3 1/2 mins from your doorstep!

A modern kitchen is shown with sleek gray cabinetry and stainless steel appliances. An island seating area with two wooden stools is present, topped with a decorative tray and two cups. Pendant lights with blue shades illuminate the space, enhancing the open and functional layout.

4.96 out of 5 average rating, 192 reviews

Renovated Condo | 3 Min Walk to Toes in the Sand!

Welcome to Pacific Pearl — your serene Maui escape just steps from golden-sand Kamaole Beach Park II. Set in the lush, resort-style Maui Banyan complex, this fully remodeled ground-floor condo offers peaceful garden views, a walkable location near dining and shops, and all the comforts of home. Spend your mornings snorkeling, your afternoons lounging by the pool, and your evenings with sunset walks on the shore. Perfect for couples, families, or friends seeking the effortless Maui getaway.

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, 156 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 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, 189 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 bright sleeping area features a spacious bed adorned with quality linens. Beach-themed decor enhances the atmosphere, with a fan overhead and large windows providing views of the private lanai surrounded by lush greenery. A wooden dresser adds functionality to the space.

4.95 out of 5 average rating, 107 reviews

Steps to Beach, Updated Studio + Pools & Hot Tubs

Walk to Kamaole Beach II in just 3 minutes from this freshly renovated, beachy studio in the heart of Kihei. Enjoy tropical resort vibes with 2 pools, hot tubs, BBQ grills, and tennis courts — all just steps from sand, surf, and sunsets. Relax on your private lanai, stroll to cafés and shops, and enjoy thoughtful touches like A/C, fast Wi-Fi, beach gear, and a king bed. Ideal for couples, solo travelers, or small families seeking comfort and convenience.

4.84 out of 5 average rating, 216 reviews

The first image captures a serene sky at sunset, framed by swaying palm trees. The second image showcases a pool area surrounded by a well-maintained landscape and the accommodations in the background. The third image highlights a spacious living area featuring modern furnishings, large windows allowing natural light, and a view of the pool.

Flat in Wailea

*Last Minute Deal! Beautiful by TOP Swimming Beach

Nestled steps from stunning sunsets and moonrises, this 778 sq ft partial ocean view unit is an ideal island getaway. Revel in its bright ambiance and spacious kitchen. Unwind on the private lanai, overlooking the pool or savor views of waves and playful whales off Maui's coast. Perfectly situated across from Kam III beach, this family-friendly condo is your gateway to a memorable Maui experience.

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 out of 5 average rating, 136 reviews

*Tropical luxury at South Maui Surf Shack*

South Maui Surf Shack is a beautifully renovated (Feb 2022) 1-bedroom, 2-bath condo in Maui Kamaole with over 1,050 sq ft of beach-style living. Features include a king bed, queen Murphy bed, and fully stocked kitchen. Located on the Kihei–Wailea border, you’re minutes from Maui’s best beaches, golf, dining, and activities. We’re happy to help make your stay memorable, relaxing, and fun!

Popular amenities for Kihei family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

A view from the second floor displays lush tropical landscaping with palm trees and vibrant greenery. The ocean is visible in the background, framed by a clear blue sky. The scene offers a serene outdoor ambiance typical of Wailea.

4.88 out of 5 average rating, 120 reviews

Luxury Condo w/wide Ocean View (Palms at Wailea)!

A living area is presented with a comfortable gray sofa, two reclining chairs, and a coffee table. Soft lighting from two side tables creates a welcoming ambience. The space features a ceiling fan and a large window with dark curtains, allowing for natural light to enter.

4.81 out of 5 average rating, 228 reviews

Tropical Oasis 2 bed/1 bath next to Ocean/Beach

The oceanfront view captures gentle waves rolling onto a sandy beach, with vibrant shades of turquoise blending into deeper blue hues. A coastal landscape in the background features distant hills under a canvas of partly cloudy skies.

4.99 out of 5 average rating, 137 reviews

Beach/Oceanfront Property, Sleeps 5, Kihei Maui

A spacious living area is highlighted by large sliding glass doors that provide ocean views and natural light. Comfortable seating is arranged around a wooden coffee table, with decorative cushions enhancing the space. A wall-mounted television offers entertainment options against a neutral backdrop.

4.97 out of 5 average rating, 132 reviews

Modern & Polished Oceanfront Vistas

A modern kitchen is presented with sleek white cabinetry and quartz countertops. Stainless steel appliances, including a refrigerator, oven, and dishwasher, are installed. Two wooden stools with dark woven seats are positioned at an island, offering a space for casual dining or preparation.

4.88 out of 5 average rating, 218 reviews

Maui Banyan 1BR With View Across from Beach

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.

4.95 out of 5 average rating, 231 reviews

Ocean View, Remodeled, XL condo w/ Pool & Jacuzzi!

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, 120 reviews

Stylish garden oasis near Maui's top beaches!

4.98 out of 5 average rating, 109 reviews

A sunlit balcony features a bar-height table and one chair, overlooking the ocean. The living area includes a comfortable seating arrangement with a lamp and artwork on the walls. The kitchen showcases modern appliances and a neutral color palette, enhancing the inviting space.

Apartment in Wailuku

Oceanfront Panorama: Newly Refreshed 3rd Floor Gem

Family- and pet-friendly home rentals

4.98 out of 5 average rating, 121 reviews

The exterior of a spacious home is framed by lush tropical plants and trees. A charming pathway leads to a welcoming front deck illuminated by soft lighting. Large sliding doors enhance visibility into the interior, where comfortable seating is visible in a cozy living space.

Home in Wailea

Mana Hale Vacation Rental

4.89 out of 5 average rating, 9 reviews

The living room features a comfortable sofa, accent chairs, and a coffee table. Two upholstered ottomans offer additional seating. A large flat-screen TV is mounted on the wall. Sliding glass doors open to outdoor seating, allowing natural light to fill the space.

Flat in Wailea

Paradise! Ground Floor 1BR AC Kamaole lll beach

5 out of 5 average rating, 41 reviews

Guest house in Kihei

Sunflower Suite

4.97 out of 5 average rating, 134 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

4.85 out of 5 average rating, 131 reviews

Resort Studio-Walk to Beach, 2 Beds, AC & WIFI

5 out of 5 average rating, 20 reviews

Home in Kihei

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

4.92 out of 5 average rating, 61 reviews

A comfortable living area features a neutral-colored sofa and a light-toned ottoman. A dining table with turquoise chairs is positioned nearby, and a flat-screen TV is mounted on the wall. The open layout allows for easy movement between the kitchen and seating areas.

Flat in Kihei

A New Piece of Paradise in Kihei # BBKM20150003

Family-friendly home rentals with a pool

4.99 out of 5 average rating, 74 reviews

A modern living area showcases a comfortable gray sofa with decorative pillows, complemented by a round coffee table. A vibrant piece of wall art featuring a whale hangs above the sofa. Two table lamps with blue bases provide soft lighting, enhancing the serene ambiance.

Flat in Kihei

Kihei Maui Getaway

5 out of 5 average rating, 30 reviews

Stylish Retreat in South Maui

A private lanai offers a breathtaking view of the ocean and sandy beach. Two light-colored chairs with striped cushions are positioned around a small round table, accompanied by two glasses of water. Lush greenery and palm trees frame the serene setting.

5 out of 5 average rating, 184 reviews

Sugar Beach Resort Beach / Ocean Front Unit 426

A serene ocean view is showcased at sunset, featuring calm waters reflecting warm hues of orange and pink. In the foreground, palm trees gently sway, enhancing the tranquil seascape. The distant landmass reveals a soft silhouette against the colorful sky, creating a peaceful atmosphere.

5 out of 5 average rating, 214 reviews

Cozy Beach Condo Ocean & Mountain View’s

A coastal view features calm turquoise waters alongside a sandy beach. Palm trees are seen in the foreground, with rolling hills and distant buildings framing the landscape. The sky is partly cloudy, allowing for ample natural light over the serene shoreline.

4.95 out of 5 average rating, 149 reviews

Penthouse Island Surf Shack -AC in BR & Living Room

4.98 out of 5 average rating, 51 reviews

Across From Kam Beach, Big Lux 2 BDRM 2 Bath Condo

4.96 out of 5 average rating, 114 reviews

Aloha. Ground floor, A little different. AC. W/D.

A spacious living room is highlighted by a comfortable sofa and a round coffee table. A ceiling fan circulates air above. A dining area with four chairs is set near a large window that offers views of the outdoors. A decorative painting and a flat-screen TV add to the ambiance.