House holiday rentals in Wailea

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.

4.92 out of 5 average rating, 146 reviews

Enjoy paradise living at the THERE Maui House!

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

ValueFamilyDecor

4.95 out of 5 average rating, 246 reviews

The Blue Door on Church Street | Spacious Two Bedr

Enjoy Haleakalā views from this spacious two-bedroom upstairs retreat at The Blue Door on Church Street, a restored 1930s plantation home in historic Wailuku. Features include a king Helix bed, queen Helix bed, full-size memory foam sleeper sofa, full kitchen, rainfall shower, AC, fast WiFi, Smart TV, parking for two vehicles, and a large private deck with outdoor dining and lounge seating. Walk to local cafés and restaurants, or drive minutes to ʻĪao Valley, beaches, hikes, and Maui attractions

LocationFamilyAccess

4.81 out of 5 average rating, 113 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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5.0 out of 5 average rating, 33 reviews

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

4 BEDROOMS, 2 FULL BATHROOMS - FULLY REMODELED HOME Located in central Kihei just two blocks from the beach, Starbucks, golf courses, Kalama park, restaurants, movie theater, food trucks, entertainment, Foodland, etc. This property is secured and fully fenced. The common area consists of a driveway, garden and 2 outdoor showers. A/C in all rooms + private outdoor BBQ and laundry. You will be staying in the main house of the property and will have your private parking spot with EV charger.

LocationFamilyCondition

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.

5.0 out of 5 average rating, 25 reviews

Beautiful Beachfront Townhouse !

OUR MAUI BEACH HOUSE... This is the perfect place for a family vacation and retreat!! And it is right on the beach! Many of our guests enjoy staying right on our property or on our beach -- no need to leave. A very large two bedroom, three bath - solar powered redwood townhouse we built in 1977 as a family retreat, with a fully-equipped kitchen and laundry. This is a comfortable beach house and we have done remodeling, refurnishing and updating. The master bedroom has huge ocean views.

FamilyValueKitchen

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, 172 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.

FamilyValueIndoor spaces

4.97 out of 5 average rating, 159 reviews

12 Minute Walk Kamaole Beach II-Quiet Private Easy

This 1 bedroom/1 bath suite is a self contained, attached ohana (ADU) with private entry. Off street parking is 10 seconds from your door. Located a 12 minute walk straight down to Kamaole Beach II. 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

LocationValueParking

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, 114 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!

FamilyLocationCondition

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.

ValueLocationAmenities

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

LocationFamilyLaundry

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, 316 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

ValueFamilyCheckout

4.97 out of 5 average rating, 33 reviews

Mermaid Bungalow, cozy and ready for action.

Come as guests, live like locals. Your private Maui home away from crowded condos — where the real island life happens. 🏝️🏡 🚗💨Cruise with Edward our white handsome Jeep, 🏄‍♂️🏄‍♀️ two surf boards, 🚴🚴‍♀️ e-bikes 🐠🤿and just bring your sense of adventure. This is where you’ll discover Maui the way locals do — genuine, unhurried, and absolutely unforgettable. 🌈

LocationValueWalkability

Popular amenities for Wailea house rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

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, 44 reviews

Aloha Aku Bamboo Suite – Discover Beachfront Seren

LocationValueAir conditioning

4.75 out of 5 average rating, 127 reviews

Oceanfront Stunner w/ Cruiser Bikes & Pickleball

LocationFamilyWalkability

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!

LocationValueWalkability

5.0 out of 5 average rating, 10 reviews

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

LocationPoolLong stay

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

FamilyLocationNearby

4.67 out of 5 average rating, 12 reviews

Walk-Out Kamaole Beach II | Sunset Lanai | Quiet

FamilyLocationWalkability

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, 46 reviews

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

ValueLocationPool

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

FamilyValueWalkability

Weekly house rentals

4.87 out of 5 average rating, 93 reviews

304 Punahoa Oceanfront Studio w/AC!

ValueFamilyAmenities

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

ValueLocationCondition

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

LocationFamilyNearby

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,

FamilyValueAir conditioning

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

LocationValueOutdoor spaces

5.0 out of 5 average rating, 10 reviews

Kamaole Sands 3104-Bright, Clean, and Fresh!

ValueLocationParking

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

FamilyValueIndoor spaces

A hot tub is situated in a lush, landscaped backyard, surrounded by tropical plants and trees. Lounge seating is available nearby, with a shaded area visible in the background. The house features a blend of modern and rustic design elements, creating a tranquil outdoor environment.

4.81 out of 5 average rating, 64 reviews

Kihei's Family Home Tropical Paradise BBQ, Hot Tub

LocationValueSleep quality

Private house rentals

4.64 out of 5 average rating, 284 reviews

Bare Feet Retreat 515B:Walk everywhere + Strong AC

ValueLocationNearby

A private lanai features a dining table surrounded by four chairs, offering views of swaying palm trees and the ocean beyond. The serene landscape showcases a clear blue sky and gentle waves.

4.6 out of 5 average rating, 45 reviews

Oceanfront Koa Lagoon Condo w/ Sunset Views

FamilyValueBeach

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

New place to stay

New Fall Special Ocean View AC 2 Bed Sleep 5

New place to stay

4.44 out of 5 average rating, 18 reviews

Unobstructed Oceanfront View | Turtles and Whales!

ValueLocationWalkability

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

LocationFamilyAccuracy