Holiday rentals with a pool in Wailuku

Find and book unique homes with a pool on Airbnb

Quick stats about holiday rentals with a pool in Wailuku

  • Total holiday rentals

    Explore 20 holiday rentals in Wailuku

  • Nightly prices starting at

    Wailuku holiday rentals start at $67 NZD per night before taxes and fees

  • Verified guest reviews

    Over 1,940 verified reviews to help you choose

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wi-Fi availability

    20 of Wailuku holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Wailuku rentals

  • 4.8 Average rating

    Wailuku stays are highly rated by guests—averaging 4.8 out of 5!

Top-rated rentals with a pool in Wailuku

Guests agree: These homes with a pool are highly rated for location, cleanliness and more.

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Guest favourite
The outdoor area features a large, inviting pool surrounded by a tiled deck. Comfortable lounge chairs are arranged around the pool, and vibrant potted plants add a touch of greenery. The main house, visible in the background, showcases spacious windows and a welcoming entrance.
Guest suite in Wailuku
4.83 out of 5 average rating, 520 reviews

Private Poolside Suite- Ocean Views

Escape to a relaxed tropical retreat in private villa-style suite featuring its own entrance, ensuite bathroom w/ natural stone shower, coffee station, mini fridge, & outdoor bistro seating. Guests also enjoy access to our lush shared pool area and shared kitchen spaces, creating a boutique island experience designed for comfort, connection, and relaxed Maui living. Centrally located & great for exploring all Maui has to offer. Great hikes and beaches nearby! Maui County Permit BBWK 2019/0003

Guest favourite
A tranquil beach scene is depicted, featuring soft sandy shores that gently meet the rolling waves. Lush greenery lines the coastline, while distant mountains provide a stunning backdrop under a partly cloudy sky.
Condo in Maalaea
4.91 out of 5 average rating, 252 reviews

Rare Beachfront Ground floor Oceanview from Lanai!

New kitchen appliances, complete bathroom renovation 2026. Enjoy a Romantic yet affordable BeachFront, Ground floor condo, partial ocean view from the Lanai. NOT ACROSS THE STREET FROM THE OCEAN! Located on gorgeous Sugar Beach, Maalaea, the LONGEST WALKING BEACH on the entire island. Humpback Whales (Nov-April), turtles are often seen in the waters. On a quiet non-through road, this is your own little neighborhood paradise! GE-210-827-7760-01 TA-210-827-7760-01 General Excise/Transient Tax

Top Guest favourite
A stunning sunset casts vibrant colors across the sky above the ocean. Silhouetted palm trees frame the scene, while distant mountains provide a scenic backdrop. The calm water reflects the hues of pink, orange, and purple, creating a serene atmosphere.
Condo in Maalaea
4.96 out of 5 average rating, 129 reviews

2BR 2Bath - Oceanfront Remodeled Condo!

Remodeled 2 Bedroom/2 Bath ocean front condo with A/C. Amazing ocean views with the best location in Central Maui. Enjoy the view of Maalaea Bay from your private Lanai . Watch the whales jumping and enjoy beautiful sunrises and sunsets without leaving your condo. The only thing between you and the ocean is the pool and grassy lawn. Let the waves lull you to sleep in the master bedroom king size bed and enjoy unobstructed views of the ocean from not only the living room but your bed as well!

Guest favourite
Home in Wailuku
4.83 out of 5 average rating, 111 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

Top Guest favourite
The modern kitchen features dark cabinetry and a large marble island with seating. Stainless steel appliances, including a refrigerator and microwave, are visible. A bowl of fresh fruit sits on the island, while natural light illuminates the space through ample windows and overhead pendant lighting.
Condo in Maalaea
4.98 out of 5 average rating, 190 reviews

Makani A Kai A5 beachfront, pool, a/c, w/d

Halerentals MAK A5 is a completely renovated beachfront condo, with high end materials throughout. RH furniture, cotton sheets, marble shower, gourmet kitchen, & a/c in every room-- just steps away from 3 miles of undeveloped beach! Bright spacious ground floor 1bed/1bath condo with fully stocked kitchen, and views of the beach, bay, & Haleakala volcano. King RH sofa bed in living room for up to 4 guests. Ideal for swimming, SUP, snorkeling, and surfing-- amazing value for families and couples.

Top Guest favourite
An open living area showcases a comfortable sofa and a textured area rug. A modern kitchen features stainless steel appliances and a granite countertop, complemented by two barstools. Soft lighting from pendant lamps and a nearby floor lamp enhances the inviting ambiance.
Condo in Maalaea
4.99 out of 5 average rating, 204 reviews

Beautiful Oceanfront Condo- Great View, A/C,Wi-Fi

The convenient location in Maalaea leaves you minutes away from beautiful beaches, restaurants, and all Maui destinations. An open layout consisting of 1 bedroom and 1 bath gives an expansive feel to this exquisite unit. Central A/C. Luxury upgrades include: luxury plank flooring, custom kitchen and bathroom cabinetry, granite counter-tops, new stainless appliances, stone flooring and stone/glass shower. Meticulously maintained grounds along with a refreshing swimming pool and grilling area.

Guest favourite
A bright living area features a turquoise accent wall and large windows, offering views of the ocean. A light-colored sofa is paired with a glass coffee table and rattan chairs around a dining table. Natural light enhances the inviting space, complemented by beach-themed decor.
Condo in Maalaea
4.86 out of 5 average rating, 138 reviews

Oceanfront Bliss Pool & Stunning Views Hono Kai C3

Kick back island style at this laid-back beachfront escape with a touch of luxury. Soak in epic ocean and Haleakala views right from your living room and lanai—perfect for whale and turtle watching or checking the waves. Fully stocked kitchen, comfy vibes, and all the essentials for easy living. Chill by the oceanfront pool, fire up the BBQ, or cruise down to stroll along the endless serene beach just steps away. Central spot close to Kahului, Kihei, Paia, and Kaanapali - surf, relax, repeat.

Top Guest favourite
A spacious living area features a light grey sofa and a wooden coffee table positioned on a natural fiber rug. Large glass doors open to a patio with ocean views, while a flat-screen TV sits atop a console. Neutral curtains frame the windows, creating an airy atmosphere.
Condo in Maalaea
4.98 out of 5 average rating, 123 reviews

Coastal Dream Oceanfront Condo!

Take a moment to unwind and appreciate the stunning views from the patio, where you can spot whales from Nov-April and catch a glimpse of surfers riding the "Freight Train" during mid-summer. Venture out for a leisurely walk to Maalaea Harbor Shops and the Maui Ocean Center, or explore with a drive to Lahaina (West), Hana (East), or Wailea (South tip). Enjoy delightful amenities including Heated Pool, Oceanfront BBQ station, and Lounge area on the lawn. Designated parking right out front.

Guest favourite
A modern kitchen features sleek cabinetry and stainless steel appliances, including a refrigerator and microwave. A light grey tile backsplash complements the white marble countertop, which hosts a built-in stove. Natural light enters through a small window, enhancing the airy space.
Apartment in Kihei
4.94 out of 5 average rating, 135 reviews

High-end, On Beach, View Balcony, with Pool & BBQ!

Free Parking. Building is right on the beach and under 3 min walk to small market and world famous Ululani's shave ice shop. This condo is on the second floor with balcony with ocean view! This World famous Sugar Beach is in the backyard w/ 10 miles of sand. Fully Remodeled with High End Finishings. TWO FULL BATH. One with Tub and One with Shower. KING ADJUSTABLE BED. Split System AC. One in Living Room and One in Bedroom. Super Quiet. TWO TV's. One in the Living Room and One in the Bedroom.

Top Guest favourite
A modern kitchen features sleek white cabinetry and a spacious island, with a view of the ocean visible through large glass sliding doors. Natural light fills the room, and tropical décor adds a welcoming touch, enhancing the seamless transition to the outdoor space.
Condo in Maalaea
4.95 out of 5 average rating, 114 reviews

Oceanfront Maui Escape for Two | Private Lanai

THERES NO PLACE LIKE MAUI! OCEANFRONT condo greets you with endless ocean views, open floor plan and the feeling you have just arrived in Heaven! Step out onto the private lanai and you are captivated by the soothing sound of the waves, warm sunny breezes and turtles everywhere! You deserve the BEST and this home offers it! Located in a perfect location far from the maddening crowd yet walking distance to restaurants, shopping, nightlife, and sightseeing tours. APN2380140110057000

Guest favourite
A scenic outdoor space features a table set for dining, overlooking a vibrant green lawn and an expansive ocean view. Nearby, comfortable seating invites relaxation. The kitchen area is equipped with modern appliances, while a stylish clock adorns the wall.
Condo in Maalaea
4.93 out of 5 average rating, 165 reviews

Oceanfront Getaway, Brand New, Steps To Beach

Enjoy the panoramic ocean view directly from the living room. This wonderful ground floor unit offers privacy and tranquility with expansive ocean views, where you can enjoy seasonal whale watching, paddle boarding, surfing, snorkeling as well as many other activities just outside your door. The unit is also adjacent to one of the longest beaches on Maui, Sugar Beach. And just down the road you will find great shopping, restaurants, nightlife and the Maui Ocean Center.

Top Guest favourite
A dining table set for two overlooks the ocean, featuring a pineapple centerpiece and plates arranged with utensils. The backdrop includes palm trees and scenic water views under a partly cloudy sky.
Condo in Maalaea
4.95 out of 5 average rating, 105 reviews

The Beach Hale

We are new to the vacation rentals and we are excited to host you at our 1 bedroom, 1 bath newly remodeled ocean front condo with spectacular panoramic ocean views. Enjoy your morning coffee with sunrise over Haleakala Crater. Green sea turtles rest almost every night on the beach in front of the condo. In winter months enjoy the breaching of the whales right in front of your eyes while enjoying your favorite beverage from the lanai (balcony).

Popular amenities for Wailuku rentals with a pool

When is the best time to visit Wailuku?

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Avg. price$265 NZD$244 NZD$207 NZD$211 NZD$206 NZD$194 NZD$189 NZD$177 NZD$177 NZD$167 NZD$192 NZD$212 NZD
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