Holiday rentals with a pool in Wailuku

4.83 out of 5 average rating, 520 reviews

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

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

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.

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

4.83 out of 5 average rating, 111 reviews

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

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.

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.

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.

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!

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.

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.

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.

4.95 out of 5 average rating, 180 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!

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.

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.

4.99 out of 5 average rating, 196 reviews

A stunning beach scene captures vibrant sunset colors reflecting off wet sand. Rocky outcrops frame the tranquil waters, while palm trees sway gently in the foreground. Wispy clouds stretch across the sky, adding depth to the evening landscape.

Condo in Wailea-Makena

Romantic, Luxury Retreat w/Ocean View-Couples Only

Luxury accommodations in the heart of Wailea, Maui. Our condo has lovely ocean views, views of the lush tropical gardens and the pool. Sunset views from the lanai are stunning. Gourmet kitchen. 2 HD TVs, Bose sound system, AC, washer/dryer in unit, complimentary assigned parking. If our condo is not available during the days of your travel, please check availability at our other Wailea Palms condo at https://www.airbnb.com/rooms/1728525 Our condo is not suitable for children or infants.

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.

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

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.

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.

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.

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

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.97 out of 5 average rating, 116 reviews

Home in Kihei

Oceanview Townhome • Modern • 2 Min Walk to Beach!

4.93 out of 5 average rating, 619 reviews

The spacious studio features a comfortable bed and a seating area with colorful cushions. Large glass doors provide access to a private balcony with stunning ocean views. A flat-screen TV and a ceiling fan are visible, alongside a wooden dresser and a coffee table.

Home in Napili-Honokowai

Maui direct ocean front . Super private

4.96 out of 5 average rating, 469 reviews

Home in Wailea-Makena

Stunning ocean view Villa, Heated pool, Wailea

4.87 out of 5 average rating, 180 reviews

Two hanging chairs are positioned on a private balcony, surrounded by lush greenery and an ocean view. The chairs are adorned with floral accents, inviting relaxation while enjoying the scenic landscape and coastal horizon.

Home in Napili-Honokowai

Oceanfront Paradise with Pickleball gear!

4.92 out of 5 average rating, 145 reviews

A wide sandy beach extends along the shoreline, meeting clear blue waters. Guests are seen relaxing under umbrellas, while others stroll along the water's edge. Lush palm trees provide shade in the background, contributing to a serene island atmosphere.

Home in Kaanapali

Beautifully Remodeled 3 Bedrooms/2Bathrooms

4.88 out of 5 average rating, 119 reviews

A spacious living area features comfortable seating arrangements with a sectional sofa and wicker chairs. A large mirror enhances the sense of openness. Two televisions are positioned on opposite walls, and the tiled floor is complemented by natural lighting from multiple windows.

Home in Wailea

Condo in Kihei 2 BR - 2 bath Condo

4.87 out of 5 average rating, 122 reviews

Home in Kaanapali

Studio Kaanapali Beach, Beach Cabana, Jacuzzi, Gr

4.88 out of 5 average rating, 42 reviews

A tropical outdoor area features lounge chairs beside a heated swimming pool. Palm trees sway in the gentle breeze, with a shaded seating area visible under a pergola. The expansive ocean view is framed by lush landscaping, creating a serene atmosphere for relaxation.

Home in Lahaina

Serene and Peaceful with Heated Pool

Condo rentals with a pool

A serene view of the ocean is captured from the lanai, framed by the silhouettes of palm trees. An outdoor table and chairs are positioned for relaxation, with a glimpse of a pool area and lush greenery below.

4.83 out of 5 average rating, 326 reviews

Hello View!

A panoramic view of the ocean is framed by lush palm trees, with gentle waves lapping at the shore. The sky is filled with scattered clouds, casting soft shadows on the tranquil water. A railing borders the view, enhancing the sense of openness.

4.99 out of 5 average rating, 109 reviews

Oceanfront Maui - 2 King Suites, AC & Lanai

4.96 out of 5 average rating, 183 reviews

A modern kitchen and dining area are visible, featuring a round table set for four with woven placemats and plates. Stainless steel appliances are arranged in the sleek kitchen design, while large sliding glass doors open to reveal views of lush gardens and the ocean beyond.

Condo in Wailea-Makena

A.R.A Retreats: Big Blue Pacific

The living room features a comfortable brown sofa and a cozy hanging chair beside a large window that frames ocean views. A round coffee table sits on a woven area rug, and decorative lighting adds a stylish touch to the space.

4.95 out of 5 average rating, 133 reviews

All New Beachy Chic Remodel, Ocean front with AC

4.85 out of 5 average rating, 569 reviews

The sleeping area features a spacious bed with a light-colored quilt and decorative pillows. Large sliding glass doors provide an expansive view of the ocean and palm trees, with soft curtains framing the scenic backdrop.

Condo in Kihei

Amazing views at Oceanfront Studio

A spacious lanai features a round table with a decorative centerpiece, surrounded by comfortable chairs. Lush palm trees sway gently in the breeze, while the vast ocean and distant shoreline are visible through the railing, under a partly cloudy sky.

4.97 out of 5 average rating, 190 reviews

Turtle Cove Oceanfront Views Island Sands Resort

A lanai offers a scenic view of the ocean, framed by palm trees swaying in the breeze. A round dining table with four chairs is set on the patio, surrounded by manicured greenery, while the glistening water is visible in the distance.

4.81 out of 5 average rating, 172 reviews

Ocean front! Listen to the waves all day and night

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.

4.97 out of 5 average rating, 129 reviews

Oceanfront Panorama: Newly Refreshed 3rd Floor Gem

Other holiday rentals with a pool

4.95 out of 5 average rating, 104 reviews

Apartment in Maalaea

Maalaea Beachfront Resort

4.89 out of 5 average rating, 247 reviews

Apartment in Maalaea

Breathtaking, FRONT ROW seat to the azure Pacific

4.93 out of 5 average rating, 149 reviews

Cottage in Kaanapali

Kaanapali Cottage ICC 29 Indoor/Outdoor Living

4.96 out of 5 average rating, 236 reviews

Townhouse in Kapalua

Spectacular views, prime location Kapalua, Maui.

4.94 out of 5 average rating, 136 reviews

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

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

Apartment in Napili-Honokowai

A spacious balcony features a simple dining table surrounded by two chairs, offering an unobstructed view of the ocean. Palm trees frame the scene, while a bottle and glass sit on the table, reflecting the bright blue sky above and the serene water below.

4.97 out of 5 average rating, 103 reviews

Maui Full Oceanfront Paradise

4.97 out of 5 average rating, 427 reviews

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

"Dancing Turtle's "Guest Suite"

A cozy living area features a plush brown sofa adorned with leafy pillows, accompanied by a textured coffee table. A pair of wicker chairs sits nearby. A colorful artwork hangs on the wall, and warm lighting enhances the inviting atmosphere.