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House holiday rentals in Wailea

Find and book unique houses on Airbnb

Top-rated house rentals in Wailea

Guests agree: these houses are highly rated for location, cleanliness and more.

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Guest favourite
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.
Home in Kihei
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

Superhost
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
4.81 out of 5 average rating, 101 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

Guest favourite
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.
Home in Kihei
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.

Superhost
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
4.79 out of 5 average rating, 129 reviews

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

Top guest favourite
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.
Home in Kihei
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

Superhost
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
4.88 out of 5 average rating, 169 reviews

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.

Top guest favourite
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.
Home in Kihei
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.

Top guest favourite
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.
Home in Kihei
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 œ 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

Guest favourite
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.
Home in Kihei
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.*

Guest favourite
Home in Paia
4.87 out of 5 average rating, 120 reviews

Green Turtle House by all North Shore beaches

Comfortable two bedroom house in the middle of all the North Shore beaches, less than one mile to Paia town in a quiet neighborhood off the road but close to everything. Great for family, honeymoon, sports vacations, get aways. Home away from home. Full kitchen, up to four beds. Permit number STRH2017/0001

Guest favourite
Home in Kihei
4.92 out of 5 average rating, 151 reviews

Go for an Ocean Swim From a Fun Beach Villa

Wake up to the soft sounds of waves in this wonderful bungalow. Walk atop the hardwood floors while floor-to-ceiling windows let in plenty of sunlight. Lounge by the communal pool and enjoy a warm evening out on the private lanai.

Top guest favourite
An outdoor living area features comfortable seating arranged around a coffee table on a patterned rug, surrounded by tropical foliage. A grill and picnic table are visible in the background, enhancing the inviting space for relaxation and social gatherings.
Home in Kihei
4.98 out of 5 average rating, 137 reviews

Family-Friendly House-Hot Tub/Games/Yard, Walkable

“So comfortable for our family of 8!” Guests love the spacious layout, luxury beds, and amazing outdoor space. Pack light—this home has it all, from beach gear to baby essentials, plus a private hot tub and fully stocked kitchen.

Popular amenities for house rentals in Wailea

When is the best time to visit Wailea?

MonthJanFebMarAprMayJunJulAugSeptOctNovDec
Avg. price$687 SGD$751 SGD$653 SGD$686 SGD$617 SGD$632 SGD$632 SGD$512 SGD$513 SGD$568 SGD$568 SGD$632 SGD
Avg. temp16°C16°C16°C17°C18°C18°C19°C20°C19°C19°C18°C17°C

Quick stats about house rentals in Wailea

  • Total holiday rentals

    Explore 50 holiday rentals in Wailea

  • Nightly prices starting at

    Wailea holiday rentals start at $89 SGD per night before taxes and fees

  • Verified guest reviews

    Over 1,970 verified reviews to help you choose

  • Family-friendly holiday rentals

    40 properties offer extra space & child-friendly amenities

  • Holiday rentals with a pool

    30 properties feature pools

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wifi availability

    50 of Wailea holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Wailea rentals

  • 4.9 Average rating

    Wailea stays are highly rated by guests – averaging 4.9 out of 5!

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