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.

4.91 out of 5 average rating, 139 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

4.81 out of 5 average rating, 101 reviews

A comfortable living area features a sectional sofa in a deep blue hue, paired with a wooden coffee table. Natural light pours in through multiple windows, illuminating the space. A framed artwork of a woman adds a pop of color to the wall, enhancing the room's inviting charm.

Home in Wailuku

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

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 out of 5 average rating, 23 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 custom 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 recently. The master bedroom has huge ocean views.

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, 168 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.

4.79 out of 5 average rating, 129 reviews

An open living area features a comfortable seating arrangement with green sofas and orange accent pillows. A wooden coffee table is placed on a patterned rug. The kitchen, displaying wooden cabinetry and modern appliances, is visible in the background. Light fills the space from large windows.

Home in Paia

Ocean Views – AC – Minutes to Town and Beaches

Your Tranquil Maui Retreat STPH20150002 Paia Ko is a serene and charming 3-bedroom, 2.5-bath home featuring beautiful ocean views and central air conditioning. Nestled against an old sugar cane field, this lovely property offers peace and tranquility while being conveniently close to the vibrant town of Paia. Enjoy the convenience of a ten-minute walk to downtown Paia and its beautiful beaches Within just a two-minute stroll you can reach Island Fresh Cafe and Maui Yoga studio

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, 158 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. 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

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, 111 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!

4.88 out of 5 average rating, 169 reviews

The exterior of a charming home is highlighted, featuring a distinctive turret and surrounded by lush greenery. Palm trees and flowering plants add to the tropical ambiance. The welcoming porch is framed by columns, inviting guests to enjoy the natural surroundings.

Home in Paia

Villa Parthenope in Paia bnb #3 *****

Permit n. : BBPH (PHONE NUMBER HIDDEN) (for the permit nuber look at the pics) Prices are inclusive of taxes. Lovely and Romantic home with private bath in Paia, about 7/8 min. walking distance from the beaches and all the services in town.Private entrance. Kitchen corner with hot plates, coffee machine, mini oven, microwave,fridge, blender, and all that you need to cook at home. We DON’T accept kids to this property.

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.

4.93 out of 5 average rating, 105 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.

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, 304 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

An outdoor lanai features a wooden deck with a table and four chairs, surrounded by vibrant tropical plants and blooming bougainvillea. Sunlight filters through the greenery, creating a welcoming space for relaxation or dining outdoors.

4.91 out of 5 average rating, 100 reviews

One Block to the Beach! Cozy Beach House in Kihei

Welcome to Chez Maui, a 3 Bedroom, 1 Bath unique, cozy, relaxed, clean and comfortable beach house located one block from the beach. Centrally located in the heart of Kihei. Perfect for Guests looking for that local Hawaii experience. Great for longer-term rentals as well. *Make sure to turn on your notifications for Airbnb Messaging.*

An outdoor view showcases a private pool surrounded by tropical landscaping. A spacious home with a wrap-around deck overlooks the ocean, while the blue sky and scattered clouds enhance the serene setting. Lounge chairs are positioned beside the pool for relaxation.

4.93 out of 5 average rating, 43 reviews

Oceanview Home with Private pool and hot tub

Come stay with me here in sunny south Maui at this beautiful, lovingly remodeled ocean view home with private pool. There are amazing ocean views from almost all rooms in the house and the wrap around covered deck is perfect for indoor/outdoor style island living. STRH Permit # STKM 2013/0004

Popular amenities for house rentals in Wailea

Kitchen

Wifi

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, 42 reviews

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

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, 72 reviews

Centrally located and steps to the beach!

4.98 out of 5 average rating, 53 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

4.88 out of 5 average rating, 8 reviews

Walk-Out Kamaole Beach II | Sunset Lanai | Quiet

5 out of 5 average rating, 6 reviews

A201a-The closest Maui Banyan studio to the beach

Lush green lawns are framed by tall palm trees, leading to an unobstructed view of the ocean in the distance. A serene pond is visible among the greenery, enhancing the natural beauty of the landscape.

5 out of 5 average rating, 6 reviews

Kamaole Sands FRONT ROW OCEAN Unit 116

5 out of 5 average rating, 10 reviews

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

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.

4.86 out of 5 average rating, 22 reviews

Private home with Pool, Oceanview, Walk to Beach

Weekly house rentals

An aerial view captures the layout of the complex, featuring red-roofed buildings surrounded by lush greenery and palm trees. The turquoise pool glistens under the sun, with a nearby open lawn area. A scenic ocean view stretches into the horizon, enhancing the natural beauty of the location.

S. Kihei 2br/2ba - 650' to Ocean

New place to stay

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

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.

4.58 out of 5 average rating, 43 reviews

Oceanfront Koa Lagoon Condo w/ Sunset Views

4.93 out of 5 average rating, 185 reviews

Home in Paia

PAIA HALE Walk to beach and town

Home in Wailuku

4.67 out of 5 average rating, 3 reviews

Central 3 bed 1 bath Cottage

4.73 out of 5 average rating, 11 reviews

Oceanfront 2BR w/AC - Walk out to Beach!

New place to stay

Kamaole Sands 3104-Bright, Clean, and Fresh!

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

Private house rentals

A serene outdoor area includes smooth stone dipping pools and a Jacuzzi with sunset views. Tropical plants are situated in decorative pots, complementing the landscape. The setting is enhanced by tiki torches, and a lush lawn extends towards the horizon under a soft evening sky.

5 out of 5 average rating, 4 reviews

Aloha Aku CoCoPalm Suite – Experience Tropical Bli

An open-concept kitchen and living area features a counter with seating for four, complemented by a wooden dining table for four. Sunlight floods through large sliding glass doors, illuminating stylish furnishings and a lush green lawn visible through the patio area.

4.91 out of 5 average rating, 93 reviews

Maui Sunset Resort A102 - Aloha Mai, Remodel, Grou

The beachfront estate is presented from a distance, showcasing its two-level structure surrounded by lush greenery. Large glass doors reveal the inviting spaces within, while a spacious lawn leads to the sandy beach. Solar panels are visible on the roof, emphasizing sustainability.

5 out of 5 average rating, 7 reviews

Aloha Aku Hula2 Suite – Beachfront Bliss

An outdoor lanai features a wooden table with two matching chairs, offering a view of manicured lawns and tennis courts. Lush greenery and palm trees frame the scene, while the ocean can be seen in the distance under a clear blue sky.

4.8 out of 5 average rating, 10 reviews

Remodeled One BD Ocean, AC,wifi, pool D202

A shaded outdoor lounge area features comfortable seating arranged around a stone fireplace. Large windows provide views of the palm trees and sunset, while a spacious pool glimmers nearby. The space is adorned with modern light fixtures and surrounded by lush greenery.

4.86 out of 5 average rating, 86 reviews

1 Bedroom Villa with Ocean Views, Steps to Beach

A patio area features a round table with two chairs, decorated with a small potted orchid and a box of treats. Beyond the table, a lush green lawn stretches toward the ocean, with a striking weathered tree adding character to the peaceful view.

4.93 out of 5 average rating, 27 reviews

Aloha Aku Hula Suite – Find Peace by the Shore

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, 42 reviews

Aloha Aku Bamboo Suite – Discover Beachfront Seren

A balcony table is adorned with a glass vase filled with colorful flowers, offering a vibrant contrast to the wooden surface. In the background, sweeping views of the ocean and lush palm trees are visible against a backdrop of distant mountains.