House holiday rentals in Wailea

A private lanai features a round table surrounded by a light-colored chair. A bottle of champagne and two glasses rest on the table, with flower petals artistically arranged nearby. Lush green grass extends to the beach beyond, complemented by tropical decor in the background.

4.98 out of 5 average rating, 45 reviews

Aloha Aku Bamboo Suite – Discover Beachfront Seren

Our luxury Beachfront estate has 4 beachfront one-bedroom suites and a garden view two-bedroom Ohana. Each suite has a private entrance, separate living room, full kitchen and is like having your own condo at the beach in Maui. This special place is hidden behind a private, double gated entrance, lined with 700 ft of lighted coconut palms that lure you into the feeling of leaving the world behind. But is still centrally placed in Kihei nearly all of the amenities you might desire. BBKM 2013/0002

LocationValueBiking

4.82 out of 5 average rating, 114 reviews

3B2B w/HotTub FamilyComfort HawaiianaCharm Central

True Hawaiiana charm, comfort, and convenience for your family vacation. Located in the heart of Maui, in historic Wailuku town, with easy access to all parts of the island for all your planned activities. Beaches within 10 minutes drive time in 3 directions and the beautiful West Maui mountains w/ Iao Valley National park behind. After a day of adventure come home to a restful time in the HOT TUB under the bright stars . Walk to boutiquey stores ,Coffee shops, First Friday party w/the locals

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A cozy living area features a blue sofa, a wooden coffee table, and two rattan chairs. A wall adorned with surf-inspired artwork complements the space. Natural light enters through glass doors that open to the outdoor area, enhancing the inviting atmosphere.

4.93 out of 5 average rating, 104 reviews

Cute Cottage-Large Outdoor Deck

Permit #STKM 2018/0006 Located on the south side of Maui in a quiet neighborhood close to the beach & the best shave ice, this intimate, one bedroom cottage with split AC system awaits! Whether you decide to dance to vintage vinyl, try a new recipe, or play the ukulele, this stylish indoor and outdoor space was thoughtfully designed to inspire you to be THERE & enjoy your time in paradise! For more pictures & tips, check out our blog at there maui dot com and our IG at @livetravelbe.there

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The kitchen features light-colored cabinetry paired with granite countertops and stainless steel appliances. A large refrigerator and microwave are visible, along with an oven and stove. A central island with a wooden top provides additional workspace. Soft lighting enhances the functional layout.

4.97 out of 5 average rating, 159 reviews

12 Minute Walk Kamaole Beach II-Quiet Private Easy

1 bedroom/1 bath suite is self contained, attached ohana (ADU) with private entry. Off street parking is 10 seconds from your door. A five minute drive to Kamaole Beach I, II and III. Ideal for longer stays! Convenient Location, Quiet and Private. Not a condo with condo noise. I am a SUPERHOST, see the 4.97 reviews and comments. INSTANT BOOK for a great stay. All fees and taxes are listed & collected when you book. There are no surprise or additional costs. Permit #BBKM 2O19/OOO2

LocationValueGetting around

A spacious single-story home is surrounded by lush palm trees and vibrant tropical plants. The well-maintained lawn features a mix of greenery, with the house's exterior displaying a neutral tone under a bright blue sky.

4.86 out of 5 average rating, 174 reviews

Cajudoy's Hale - STKM 2O13-OO18 / TA-081-709-8752-01

WONDERFUL! Three bedroom hale (home) in the Central Kihei area of Maui. Wood floors, lots of space, kitchen fully stocked, BBQ and so much more. Great for kids, elderly, and young at heart. This house is your home away from home. We have all of the necessary items for a home. If we do not have something please let us know and we will try our best to accommodated. Walking distance to the beach, shopping, park, public transportation, etc... You will not find a better place in Kihei.

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4.92 out of 5 average rating, 293 reviews

The Blue Door on Church Street | Vintage One Bedro

Stay in a restored 1929 plantation-style retreat at The Blue Door on Church Street in historic Wailuku. This private one-bedroom space features a king Helix bed, queen memory foam sleeper sofa, high ceilings, original wood details, kitchenette, rainfall shower, soaking tub, AC, fast WiFi, Smart TV, parking, and access to a shared infrared sauna. Walk to cafés, restaurants, shops, yoga, and the ʻĪao Theater, or drive minutes to ʻĪao Valley, beaches, hikes, and Maui adventures.

ValueFamilySleep quality

The covered private lanai is depicted, featuring seating areas with outdoor couches and ceiling fans. A well-maintained lawn leads up to the entrance. Bright blue skies and soft clouds frame the space, creating a serene outdoor environment for relaxation.

4.84 out of 5 average rating, 115 reviews

Modern Family Kihei Home by the Beach

Aloha! Welcome to one of the best located homes on the island! Located just under half a mile (or 5 minute walk) from the beach, surfing, park, restaurants, shops and stores. Our modern property offers complete relaxation for the perfect Maui vacation. Our home offers kid friendly amenities, A/C in ALL ROOMS, an espresso machine and Vitamix. Our calendar is always up to date. Please inquire with any questions, we will respond within 1 hour!

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4.96 out of 5 average rating, 469 reviews

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.

LocationFamilyBathroom

4.67 out of 5 average rating, 12 reviews

Walk-Out Kamaole Beach II | Sunset Lanai | Quiet

**NEW OWNER, SAME GREAT CONDO AND EXPERIENCE** Welcome to your serene Kihei oasis. Perfectly located between Kihei and Wailea, this stylish condo is walkable to beaches, sunsets, local eats, and the pool—yet tucked away on a quiet cul-de-sac with no street noise. Enjoy a bright, coastal space, fully stocked kitchen, beach gear, Roku, Bose speaker, and brand-new bedroom AC plus AC in the main living area. Relax, explore, repeat.

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The outdoor living area of the home features a covered patio with comfortable seating and a barbecue grill, surrounded by lush landscaping. The two-story structure is seen in the background, with soft evening lighting illuminating the yard.

5.0 out of 5 average rating, 43 reviews

4BR Kihei Retreat Walk to Beach A/C Family Ready

We are Experienced Hosts through other channels. See some of the GREAT 5 STAR reviews in the Property description. BOOK NOW AND ENJOY A 5 STAR HOME Our South Maui rental home accommodates up to eight guests, a comfortable space for your Tropical Hawaiian vacation. Four bedrooms and 2,400 square ft of living space and the beautiful outdoor living room to enjoy and relax after a day of sightseeing

LocationFamilySleep quality

A serene outdoor space features two light-toned chairs arranged on a tiled patio, overlooking a lush green lawn that leads to the ocean. Tall palm trees are visible, and the soft glow of the sunset casts a warm light across the scene.

4.94 out of 5 average rating, 113 reviews

Whales and sunsets, front row seats every day!

Charming three-bedroom home offers a private, "local" experience in one of Maui's rare oceanfront neighborhoods. Our charming and cozy home is complete with all you need and will make your transition from daily life into a vacation as seamless as possible. GE and TA taxes will be added after booking. Cleaning fee of $575. Amy Russell, reservations manager, and Jordan McEntire, property manager.

LocationFamilyBarbecue

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.

4.97 out of 5 average rating, 318 reviews

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 Wailea house rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

A private balcony features a wooden table surrounded by four chairs, with a serene view of lush greenery and palm trees. Bright sky and the distant buildings of the resort can be seen, suggesting a peaceful outdoor setting.

4.98 out of 5 average rating, 47 reviews

Stunning One Bd Partial ocean, AC, wifi,Pool C209

LocationValueSleep quality

5.0 out of 5 average rating, 10 reviews

South Maui • Pool • Hot Tubs• Beach • Ocean View

LocationWalkabilityHot tub

A bright living area is presented with large glass doors offering views of the ocean. A dining table made of wood is accompanied by light-colored chairs. A potted plant and a unique wood side table add natural elements, while pendant lights provide soft illumination.

4.75 out of 5 average rating, 55 reviews

Kihei 533- OceanView, 5 min drive to stores/food

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A refreshing swimming pool is surrounded by lounge chairs, set among tropical palm trees. The water's surface reflects the nearby buildings and sky, creating a serene atmosphere. The pool area is designed for relaxation and enjoyment.

4.97 out of 5 average rating, 73 reviews

Centrally located and steps to the beach!

ValueFamilyView

4.98 out of 5 average rating, 57 reviews

A relaxed living area features a blue sectional sofa with red and white decorative pillows. A coffee table sits in front, and a work desk is positioned near a glass sliding door that provides views of the ocean and surrounding palm trees.

Home in Maalaea

Maalaea Kai 307 - Maui Prime Oceanfront

ValueLocationSleep quality

A spacious living area features a comfortable grey sofa and a wooden coffee table. A dining table with four chairs is positioned nearby. Bright artwork depicting tropical leaves adorns the wall. The open kitchen includes modern appliances, illuminated by soft overhead lighting.

4.98 out of 5 average rating, 48 reviews

Kihei Ground Floor: AC, Steps to Pool & Beach

LocationFamilyAir conditioning

Two lounge chairs with bright green cushions are positioned next to a bubbling hot tub, surrounded by lush greenery and colorful plants. A green-and-white striped umbrella provides shade, enhancing the tranquil outdoor space.

4.89 out of 5 average rating, 27 reviews

Private home with Pool, Oceanview, Walk to Beach

ValueFamilyHospitality

A serene view features silhouetted palm trees against a colorful sunset sky, transitioning from orange to deep blue. The ocean horizon is visible in the background, with soft clouds hinting at the end of the day.

4.78 out of 5 average rating, 27 reviews

The Palms 1202 - The most expansive ocean views

ValueLocationAir conditioning

Weekly house rentals

A spacious living area showcases natural wooden elements, with a light-colored bamboo sofa and matching chairs. Large glass doors frame a stunning seaside view, allowing soft light to illuminate the room. A ceiling fan provides ventilation, complementing the relaxed ambiance of the space.

4.85 out of 5 average rating, 26 reviews

Beautiful Beachfront Townhouse !

LocationValueAir conditioning

4.95 out of 5 average rating, 65 reviews

Spectacular oceanfront Punahoa Beach Condo

FamilyValueBeach

A spacious bedroom is presented with a large bed, adorned with dark cushions and a green accent pillow. Tall windows with cascading green drapes allow natural light, highlighting the lush area rug. A potted plant adds a touch of greenery in the corner, enhancing the serene ambiance.

4.97 out of 5 average rating, 37 reviews

Kahili Suite - Historic charm meets Luxury

LocationValueParking

A charming plantation-style house is presented with a colorful turquoise exterior and a welcoming red front door. The facade features a simple staircase leading to the entrance, complemented by a well-maintained deck. Surrounding greenery enhances the home's inviting presence.

4.73 out of 5 average rating, 63 reviews

Vineyard Village Maui Ohana 2BR/1 Bathroom

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An outdoor seating area features a table surrounded by four metal chairs. Two cushioned chairs sit nearby, illuminated by string lights that add a touch of warmth to the evening setting. The space offers a private and relaxed atmosphere.

4.94 out of 5 average rating, 216 reviews

Spacious one bedroom, King bed, AC/WiFi,

FamilyValueHospitality

A dining area features a round wooden table surrounded by four wicker chairs. Large sliding glass doors provide access to an outdoor space with ocean views and natural light. The kitchen area is partially visible, showcasing wooden cabinetry and coastal décor.

4.97 out of 5 average rating, 70 reviews

Exclusive Beachfront Cottage, Ocean Views, WiFi/AC

LocationValueBackyard

The exterior of the beach cottage is shown, featuring a light blue facade and a sloped, gray roof. Lush greenery surrounds the property, and multiple window A/C units are visible. A gravel driveway leads to the entrance, which is highlighted by natural landscaping.

4.71 out of 5 average rating, 91 reviews

Private Cottage @ Keawakapu Beach Sleeps 6 - MMC2

LocationFamilyParking

A single-story home is surrounded by vibrant tropical gardens, featuring lush green grass and colorful flowering plants. Large windows invite natural light, while an outdoor seating area is visible on the patio, offering a space to relax amidst the lush landscape.

4.72 out of 5 average rating, 140 reviews

Bungalow w pickleball/tennis steps from beach

ValueLocationAir conditioning

Private house rentals

Maui Kamaole J214 Budget Luxury in a 2brm/2bath Ex

New place to stay

New Fall Special Ocean View AC 2 Bed Sleep 5

A serene beach is presented, featuring soft golden sands and clear turquoise waters gently lapping at the shore. A distant island is visible on the horizon under a bright blue sky, enhancing the peaceful coastal scenery.

exquisite condo in KKN #174

4.43 out of 5 average rating, 7 reviews

Central 3 bed 1 bath Cottage

ValueFamilyWalkability

1Bedroom Condo, Steps from Kamaole Beach/Kihei, HI

The exterior of a two-story cottage is visible, featuring a dark blue facade and white trim. A spacious balcony with decorative railings is positioned above the entryway. A covered area is located beneath the balcony, with concrete flooring and a few potted plants positioned nearby.

Home in Kahului

Brand New 2 Bed/ 1Bath Cottage

The kitchen and dining area feature modern appliances and a large wooden table surrounded by a built-in bench. Natural light enters through the window, illuminating the granite countertops and stylish cabinetry, while a beach-themed artwork complements the tropical surroundings.

4.88 out of 5 average rating, 120 reviews

Chic Villa 2 | Modern Vibes by the Ocean

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