Vacation rentals with a pool in Wailuku

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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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Top guest favorite
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 Wailuku
4.98 out of 5 average rating, 162 reviews

Makani A Kai A5 beachfront, pool, a/c, w/d, 2 sups

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 favorite
A lanai space features a table and chairs with a view of the ocean and distant islands. Tropical foliage decorates the foreground, including palm trees. The backdrop includes a clear sky with scattered clouds and a parking area adjacent to the property.
Condo in Wailuku
4.95 out of 5 average rating, 166 reviews

Cozy Retreat With Ocean Views & Luxury Amenities!

Welcome to a convenient Maui adventure base that is cozy, comfortable and modern! This Premier Vacation Condo in the harbor town known as Maalaea Village and located just 20 minutes from Kahului airport. Island Sands, a resort where you can enjoy a refreshing pool and barbecue grilling while overlooking stunning ocean and mountain viewing. Your tropical paradise includes opportunities to view turtles on a small beach, steps from the condo! This escape truly provides an unforgettable stay!

Superhost
A modern living area features a comfortable sofa and a round coffee table. A wall-mounted TV is positioned across from the seating area. Natural light fills the space, highlighting bamboo flooring. A dining area with wooden chairs is visible, along with a kitchen in the background.
Condo in Wailuku
4.81 out of 5 average rating, 107 reviews

Modern 1 Bedroom Suite with Spacious Lanai

Relax in this calm, stylish space in Maalaea. It has everything you need to make this your homebase to explore Maui. Suite features a large private lanai surrounded by tropical plants & trees. New queen bed plus double sofabed. Kitchen with fridge, stovetop, convention microwave and dishwasher. Quiet A/C keeps the suite cool. Located on the 2.5 mile long Sugar Beach. Stroll the beach and enjoy the views across Maalaea Bay. 20 mins from the airport, 13 mins to Kihei, 26 minutes to Lahaina.

Guest favorite
A wooden sign displaying the name 'Kihei Bay Vista' stands along the roadside, surrounded by green grass. The ocean can be seen in the background, along with distant mountains and a clear blue sky.
Condo in Kihei
4.9 out of 5 average rating, 209 reviews

Newly Updated Clean Condo w/AC! <2min to beach!

Aloha and welcome to Kihei Bay Vista! Enjoy the scenic ambiance in this newly updated 1 bed 1 bath condo located on the peaceful, quiet side of the resort. This gorgeous condo is steps away from Kalepolepo Beach and Turtle Sanctuary! Walk right out of your accommodations and stroll down the beach, watch the gorgeous sunset every evening & enjoy the whales during season. Great proximity to Kalepolepo Beach, Keaka Beach, Waipuilani Park, shopping, restaurants, Maui Nui Golf Club, and more!

Guest favorite
A sunlit balcony features a bar-height table and one chair, overlooking the ocean. The living area includes a comfortable seating arrangement with a lamp and artwork on the walls. The kitchen showcases modern appliances and a neutral color palette, enhancing the inviting space.
Condo in Wailuku
4.98 out of 5 average rating, 103 reviews

Oceanfront Panorama: Newly Refreshed 3rd Floor Gem

Welcome to our newly renovated 1b1b 3rd-floor oceanfront condo at Maalaea Banyan, a very popular destination! Steps from the sea, enjoy grand ocean vistas and island breezes. Nestled in Ma'alaea, our harbor town is known for snorkeling cruises and fishing delights. Explore Haycraft Park, Maui Ocean Center, or amble along Sugar Beach. Ideal for whale and turtle sightings. Enjoy a king bed, workspace, living room & bedroom a/c, free parking, pool, & hot tub. Your dream Maui retreat awaits!

Top guest favorite
A light-filled living room features a designer sectional sofa and a wooden coffee table. Floor-to-ceiling glass doors offer unobstructed views of the ocean and balcony. A modern TV is positioned on a wooden console, enhancing the contemporary aesthetic of the space.
Condo in Kihei
4.99 out of 5 average rating, 237 reviews

Luxury condo • 180° Ocean Views • Steps to Beach

Enjoy panoramic ocean, mountain, beach & sunset views year round at Hale Meli (short for "Hale Mahina Meli" or “Honeymoon House” in Hawaiian), a top floor condo with exquisite designer interiors and high-end amenities. Ideally located in Kihei, the condo is right across the street from one of the best beaches on Maui and is walking distance to restaurants, shops and grocery stores. It is also your perfect home base for exploring the rest of Maui, being centrally located on the island.

Top guest favorite
A collection of colorful canoes is positioned along the shore, framed by swaying palm trees. The ocean waves glisten under a moody sky, transitioning to sunset hues, while soft clouds add texture to the backdrop.
Guest suite in Kihei
4.98 out of 5 average rating, 391 reviews

"Dancing Turtle's "Guest Suite"

CHECK-IN WINDOW IS: 3-8PM. GIVE US AN HOUR WINDOW FOR CHECK-IN TIME AT LEAST 1 DAY BEFORE ARRIVAL; we need to adjust our schedule to make sure we can welcome you. We will try to accommodate your arrival time (e.g. later flight) as much as possible. NO EARLY CHECK IN or BAG DROP OFF. You will be in our private. Guest Apt. with fully equipped kitchen. We live upstairs. We are a licensed "B&B" , which is the Maui County destination to operate legally in an “owner occupied residence”.

Guest favorite
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 Wailuku
4.94 out of 5 average rating, 131 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 favorite
A modern loft interior features a spacious living area with a light grey sectional sofa adorned with various blue and white throw pillows. A simple wooden dining table with teal seating is visible alongside a kitchen with a white island. Large windows allow natural light, and a decorative wall clock adds charm.
Condo in Kihei
4.98 out of 5 average rating, 178 reviews

Live, Love, Loft in Beautiful Maui

Experience the beautiful island of Maui and all its wonder in this modern loft in Central Kihei. You’re just minutes away from stunning beaches, local markets, and some of the best food on island. Nothing feels like you’ve arrived in Maui like the welcoming sand and warm waters of Charlie Young Beach, just across the street. Head down to The Cove to surf or paddle board with the locals. Or simply relax, put on a classic record and enjoy the sunset from the balcony.

Top guest favorite
A dining table set for four is positioned on the private lanai, surrounded by lush greenery. A bottle of wine sits center stage, accompanied by a plate of fresh fruit and pastries. Bright blue skies provide a serene backdrop.
Condo in Wailea
4.96 out of 5 average rating, 208 reviews

Top 5% Home with King Bed + Steps to Beach & Shops

Exquisitely remodeled top floor condo in one of the most desirable condo complexes in South Maui. Enjoy sunsets and peekaboo ocean views from your private lanai, walk to some of the finest beaches, shops & restaurants and lounge in the multiple pools & hot tubs on property with this perfect Hawaiian oasis! Everything (and we mean everything) is fully remodeled. From a peaceful island getaway to your next Hawaiian adventure, Makana Condo is ready for your enjoyment!

Superhost
The living area features a modern couch in front of an art piece depicting maps on three canvases. Two chairs are positioned around a coffee table atop a blue area rug. Soft lighting is provided by two lamps on each side of the couch.
Condo in Kihei
4.86 out of 5 average rating, 233 reviews

Walk to Beach XL 1 Bedroom w/Pool & Jacuzzi

This is your perfect getaway place right across the beach! 1 b1 b condo includes fully set up kitchen, dining area and living room, Cal King size bed, full size washer and dryer in the unit(+laundry detergent), TV, beach chairs and cooler, wifi internet, shared jacuzzi and pool. Located in North Kihei across the street from Kalepolepo Beach Park and Turtle Sanctuary. 5 minute drive to stores and shopping. Building is secluded from the road and traffic.

Guest favorite
A serene beach scene unfolds with gentle waves lapping at the shoreline. A tall palm tree stands prominently, overlooking the golden sand. Lush greenery frames the foreground, while the distant island can be seen beneath a partly cloudy sky and vibrant blue ocean.
Condo in Kihei
4.85 out of 5 average rating, 112 reviews

Paradise awaits!

E Komo Mai to our beautiful top of the line condo on the South Shore of Maui. This condo comes loaded and fully stocked with everything you need from your home away from home. Beautiful lanai to sit and have your coffee or afternoon spirits and watch the sunset. Beach towels, chairs, umbrella, cooler & boogie board. Beach (200 steps or less) from your door to capture spectacular sunsets. RB-21667 Holo Imua Properties Hallie Walker

Popular amenities for Wailuku rentals with a pool

When is the best time to visit Wailuku?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$27,956 GYDG$30,042 GYDG$25,244 GYDG$22,531 GYDG$23,157 GYDG$21,697 GYDG$23,366 GYDG$21,906 GYDG$21,906 GYDG$25,661 GYDG$26,078 GYDG$28,373 GYD
Avg. temp23°C23°C23°C24°C25°C26°C27°C27°C27°C26°C25°C24°C

Quick stats about vacation rentals with a pool in Wailuku

  • Total vacation rentals

    Explore 20 vacation rentals in Wailuku

  • Nightly prices starting at

    Wailuku vacation rentals start at G$8,345 GYD per night before taxes and fees

  • Verified guest reviews

    Over 1,760 verified reviews to help you choose

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wi-Fi availability

    20 of Wailuku vacation 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!

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