Family-friendly holiday rentals in Kihei

The living room features a stylish sofa with soft cushions, complemented by decorative pillows. A light wood table sits in front of the sofa, while a modern floor lamp adds illumination. Artwork hangs on the wall above, and a textured area rug anchors the space.

4.98 out of 5 average rating, 128 reviews

Ground Floor | Building 1 | Across the Best Beach

❖ Bldg 1 closest to ocean of 3 resort buildings ( 2-3 minutes walking) ❖ Newly remodeled the entire condo ❖ Sparking new & clean bathroom ❖ all NEW furnitures, New strong 2 AC ❖ Ground Floor, no stairs ❖ all tiles flooring , clean and germ-free ❖ 1 FREE parking ❖ washer & dryer in unit ❖ 300+mbps Wifi ❖ beach chairs, cooler, beach umbrella ❖ all photos were taken by IPHONE (photo shows what you will see). ❖ 24/7 response during your stay! Hosted directly by the home owner than 3rd party/agent!

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, 215 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.

A light-filled living area is shown with a gray sofa and a yellow accent chair against a decorative wall featuring a leaf pattern. In the background, a tranquil ocean view and sandy beach are visible through large windows. A cozy bedroom corner displays a spacious bed with patterned bedding and soft blue curtains.

4.82 out of 5 average rating, 201 reviews

STEPS TO THE BEACH! Newly Renovated Condo in Kihei

NEWLY RENOVATED, STEPS TO THE BEACH/SHOPS/RESTAURANTS! Welcome to our newly renovated 1bed/1bath unit located across from Cove Beach Park in Kihei. Our space is relaxing and comfortable, exactly what you would come to expect in Maui. It can be enjoyed by up to four people - 2 beds! - 1 bedroom with NEW KING SIZE Mattress - Queen Sleeper Sofa - 55" Smart TV - Air Conditioning - Full Kitchen (+ New Keurig) - Private Lanai - Community pool/BBQ/laundry - FAST WiFi - Beach Chairs/Cooler & Snorkels

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, 113 reviews

Spacious tropical oasis near beautiful beaches!

Aloha! Welcome to our beautiful home at Maui Kamaole, an upscale complex located across Kamaole 3 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!

A light-filled living area features a comfortable, neutral-colored sofa adorned with a mix of decorative pillows. A wooden surfboard hangs artfully on the wall, while a low coffee table displays books and magazines, complemented by soft lighting from nearby lamps.

4.88 out of 5 average rating, 340 reviews

Everything you need to enjoy true paradise!

After spending a month in Kihei, we didn't want to leave... we also wanted a place to invite other people to island living! Welcome to our Hawaii oasis. Steps away from food, drinks, the pool and the beach, what more could you ask for? Central to downtown Kihei and Wailea, it's the perfect location to explore Maui from. Walking distance to perfect sunsets, amazing eats, and Kihei's finest beaches our unit is tucked at the end of the cul de sac - serene, quiet, and away from any street noise.

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.

4.94 out of 5 average rating, 179 reviews

Groovy bright condo 2 bed / 2 bath South Kihei

Enjoy our home away from home! Bright Groovy Beach Condo offers you a naturally lit and engaging space to relax with two bedrooms each with their own en suite bathrooms (4th bed is the pull out sofa bed in the living room). Enjoy your morning coffee on the lanai and listen to the birds. Haleakala Shores is located 300 meters from world famous Kamaole Beach III. You are also located within a casual stroll (or snorkel or paddle board) north to Kamaole Beach II, I and finally Charley Young Beach.

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, 185 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 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, 135 reviews

Newly Remodeled 1bed/1bath, Kihei/Wailea

Aloha, welcome to Hale Kamaole, a beautiful quiet resort across the street from one of Maui's most popular beaches. Only a 3-minute walk to Kamaole park. A place that you can enjoy the incredible sunset. Newly owned one bed/one bath, sleeps up to 4 people w/ a queen-size pull-out couch. Pool/jacuzzi/tennis court and BBQ for family gatherings are available. Cable/WiFi/landline also available. This newly remodeled condo has A/C in the living room and a bedroom to help you stay cool.

A modern loft interior features a spacious living area with a light grey sectional sofa adorned with various blue and white throw pillows. A simple wooden dining table with teal seating is visible alongside a kitchen with a white island. Large windows allow natural light, and a decorative wall clock adds charm.

4.98 out of 5 average rating, 178 reviews

Live, Love, Loft in Beautiful Maui

Experience the beautiful island of Maui and all its wonder in this modern loft in Central Kihei. You’re just minutes away from stunning beaches, local markets, and some of the best food on island. Nothing feels like you’ve arrived in Maui like the welcoming sand and warm waters of Charlie Young Beach, just across the street. Head down to The Cove to surf or paddle board with the locals. Or simply relax, put on a classic record and enjoy the sunset from the balcony.

A dining table set for four is positioned on the private lanai, surrounded by lush greenery. A bottle of wine sits center stage, accompanied by a plate of fresh fruit and pastries. Bright blue skies provide a serene backdrop.

4.96 out of 5 average rating, 208 reviews

Top 5% Home with King Bed + Steps to Beach & Shops

Exquisitely remodeled top floor condo in one of the most desirable condo complexes in South Maui. Enjoy sunsets and peekaboo ocean views from your private lanai, walk to some of the finest beaches, shops & restaurants and lounge in the multiple pools & hot tubs on property with this perfect Hawaiian oasis! Everything (and we mean everything) is fully remodeled. From a peaceful island getaway to your next Hawaiian adventure, Makana Condo is ready for your enjoyment!

The living area features a modern couch in front of an art piece depicting maps on three canvases. Two chairs are positioned around a coffee table atop a blue area rug. Soft lighting is provided by two lamps on each side of the couch.

4.86 out of 5 average rating, 233 reviews

Walk to Beach XL 1 Bedroom w/Pool & Jacuzzi

This is your perfect getaway place right across the beach! 1 b1 b condo includes fully set up kitchen, dining area and living room, Cal King size bed, full size washer and dryer in the unit(+laundry detergent), TV, beach chairs and cooler, wifi internet, shared jacuzzi and pool. Located in North Kihei across the street from Kalepolepo Beach Park and Turtle Sanctuary. 5 minute drive to stores and shopping. Building is secluded from the road and traffic.

A well-lit living area is visible, featuring a spacious bed with a grey blanket and decorative pillows. A comfortable sofa sits adjacent, complemented by a patterned area rug. A round mirror reflects light, enhancing the sense of space. The open design creates a welcoming environment.

4.87 out of 5 average rating, 202 reviews

Your Island Home - KBS

Newly remodeled! This corner unit is conveniently located across Kalepolepo Beach Park, & the Humpback Whale Sanctuary. Ideal for couples, a small family or a group of friends. The condo has a queen bed, queen sleeper sofa, full kitchen, bath & walk-in shower. You are minutes away from restaurants, shopping & groceries. Parking is located in front of the condo, air conditioned, and free wifi. Kick back, relax & enjoy what the Valley Isle has to offer.

Popular amenities for Kihei family-friendly rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

A swimming pool is surrounded by a spacious deck featuring lounge chairs. Palm trees and lush greenery reflect in the crystal-clear water, which is framed by a light tile border. The sky above showcases soft clouds and hints of blue.

4.79 out of 5 average rating, 549 reviews

Cozy Surf Suite

4.89 out of 5 average rating, 114 reviews

Kihei Condo: Steps from Beach & Yummy Eats!

A person stands in the ocean water, silhouetted against a vibrant sunset with shades of orange and gold. Gentle waves lap at the shore, reflecting the warm colors of the sky, while clouds drift above, adding texture to the scene.

4.9 out of 5 average rating, 137 reviews

Incomparable Maui Sunset condo, includes all taxes

A bright and airy living space features vaulted wooden ceilings and large sliding glass doors, opening to a balcony with a garden view. A comfortable seating area is adorned with blue and white accents, while a dining table surrounded by six chairs is visible in the foreground.

4.95 out of 5 average rating, 109 reviews

Maui Kamaole Retreat Modern Remodel, Close 2 Beach

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.

4.98 out of 5 average rating, 105 reviews

Maui is Open - Come Support the Locals

A modern living area features comfortable seating, with a large dining table positioned nearby. Floor-to-ceiling sliding glass doors provide views of the lush garden outside. Coastal decor is present, with a vibrant orange ceiling fan and artwork enhancing the airy ambiance.

4.95 out of 5 average rating, 222 reviews

As Seen on HGTV I Koa Resort 1G

A private lanai features a table set for two with chairs, overlooking landscaped grounds and palm trees. The Pacific Ocean is visible in the distance, along with a glimpse of the resort building.

4.9 out of 5 average rating, 112 reviews

Sugar Beach Renovated 10% Discnt on 7 days Booking

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, 135 reviews

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

Family- and pet-friendly home rentals

4.98 out of 5 average rating, 117 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

4.98 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, 129 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

An aerial view of the Island Surf Building in Kihei, highlighting its convenient location near the ocean and Kalama Park. Lush greenery surrounds the building, and various vehicles are parked nearby, indicating a bustling environment. The coastline and blue waters stretch into the distance.

4.93 out of 5 average rating, 30 reviews

High-Floor Island Surf | AC | Walk to Beach

A cozy studio condo includes two double beds covered with white bedding and a blue accent thrown. Large glass doors lead to a private patio, offering natural light. A small seating area and a TV are visible, adding to the comfort of the space.

4.85 out of 5 average rating, 130 reviews

Resort 2-Bed Studio- Steps to Beach/Shops/Dining

A private lanai is showcased with woven seating and a wooden table, offering a view of vibrant green grass that leads to the ocean. Palm trees frame the scene against a clear blue sky, enhancing the relaxing beachside atmosphere.

5 out of 5 average rating, 5 reviews

Breathtaking Location-Sugar Beach #129

4.88 out of 5 average rating, 251 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.

Apartment in Wailuku

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

A modern living area features a comfortable sofa and a chair, with a flat-screen TV situated on a wooden media console. Large sliding glass doors provide access to a private lanai, with views of palm trees and the ocean in the background.

4.99 out of 5 average rating, 67 reviews

Oceanfront renovated luxury-best location! SBR 404

Family-friendly home rentals with a pool

4.83 out of 5 average rating, 570 reviews

A spacious studio features a queen bed adorned with a tropical-patterned quilt, complemented by wooden furniture. Large sliding glass doors open to a private outdoor area, while framed artworks add an island touch. Light from the lamps provides a cozy ambiance.

Apartment in Kihei

Hawaiian Paradise Escape Across Street from Beach

The lanai features a small round wooden table surrounded by two wooden chairs. Lush greenery and palm trees are visible, along with glimpses of the ocean and surrounding buildings. The sky above is partly cloudy, creating a serene outdoor space.

4.82 out of 5 average rating, 153 reviews

200 yards from one of the best beaches on Maui.

4.83 out of 5 average rating, 262 reviews

A coastal scene features rocky shoreline transitioning into gentle waves. Lush greenery and palm trees are visible along the land, contrasting with the blue ocean. The horizon reflects warm light, suggesting a serene atmosphere at sunset. The natural landscape provides a tranquil environment.

Apartment in Kihei

Quiet Studio, Great location across from beach

A serene bedroom is visible, featuring a spacious bed with white linens and a teal accent blanket. A piece of wall art depicting ocean waves enhances the decor. Natural light flows in through a window, and a ceiling fan provides ventilation.

4.98 out of 5 average rating, 154 reviews

Chic Maui Condo Steps From Beach & Ocean

A view of the lush green lawn from the lanai features a seating area with a small table holding drinks. The ocean is visible in the distance, framed by trees and palm trees under a bright blue sky with fluffy clouds.

4.9 out of 5 average rating, 146 reviews

Kamaole Sands, King Bed, Ocean View, Kamaole Beach

A serene pool is set amid palm trees and lounge chairs under umbrellas. The water reflects the clear blue sky, creating a calm and inviting atmosphere. The surrounding area includes tropical greenery and well-maintained landscaping.

4.92 out of 5 average rating, 100 reviews

Condo w/FREE AC, great location - steps to ocean!

A spacious lawn area features several lounge chairs and tables, surrounded by palm trees. Red umbrellas provide shade over some seating, while the ocean is visible in the background. The shoreline is framed by gentle waves under a bright blue sky.

4.87 out of 5 average rating, 428 reviews

Can be 2 Units! Modern On Beach Ocean View Balcony

A small studio space features a queen bed with gray bedding, accented by a wooden headboard. A ceiling fan and bedside lamp provide light. The room includes a window with light blue curtains and a colorful wall art piece above the bed, while a kitchenette is visible in the background.