Home rentals with a pool near Kaanapali Beach

The open-concept living space features a modern kitchen with sleek cabinetry and a bar top overlooking a sunlit living area. Floor-to-ceiling windows reveal panoramic ocean views and access to a comfortable seating area, inviting relaxation in a coastal setting.

4.99 out of 5 average rating, 158 reviews

Luxury Mahana 1bd/2ba-Great Views-Free Park/WiFi

Locally Owned and Operated 1BD/2BA condo with the best direct beachfront location, panoramic Ocean views, sunsets, and seasonal whale watching. The owner’s spared no expense in renovating this unit making it hand’s down one of the nicest units in all of the Mahana. Wake up to the cool tropical breeze and sounds of the shoreline just 50 feet away. Floor to ceiling windows in the living area and bedroom bring the stunning views and warm Maui sun inside while central AC keeps you cool inside.

4.93 out of 5 average rating, 150 reviews

Cottage in Kaanapali

Kaanapali Cottage ICC 29 Indoor/Outdoor Living

International Colony Club’s cottage 29 is located in the world-famous Kaanapali Beach area, and a five minute walk from one of Maui’s best beaches. Built in 1964, this community affords a spacious and mature landscape between 44 private cottages spread over 10 acres. Our Hawaiian plantation style cottage is reminiscent of homes built during the plantation era and conveniently located close to beaches, shopping and restaurants, but is secluded from the hustle and bustle of the big resorts.

A small outdoor dining set is positioned on a private lanai, featuring a round table flanked by two cushioned chairs. The backdrop showcases expansive views of the turquoise ocean and a clear blue sky, with gentle waves visible in the distance.

4.89 out of 5 average rating, 103 reviews

Rare 2 King Suites•Oceanfront•Watch Whales&Turtles

Wake up to whales, sea turtles, and breathtaking direct ocean views from our newly renovated ninth-floor retreat at Valley Isle Resort. Our rare one-of-a-kind condo features two spacious king suites—the only floor plan of its kind at the resort—making it ideal for romantic getaways, two couples, or families. Snorkel at Kahana Beach just steps away, watch unforgettable sunsets over Molokaʻi, and experience Maui from a home thoughtfully renovated by our family with comfort and aloha in mind.

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.

Maui Full Oceanfront Paradise

Indulge in the ultimate Maui getaway at our full oceanfront condo. The cozy balcony beckons you to unwind and marvel at the mesmerizing sea life. Sip on your morning coffee, or relish a sunset cocktail while you watch the ocean's playful inhabitants. For those warm tropical nights, rest easy knowing that the condo is equipped with air conditioning to ensure a comfortable night's sleep. The fully stocked kitchen provides all the essentials for cooking up a delightful island feast.

4.97 out of 5 average rating, 105 reviews

4.95 out of 5 average rating, 155 reviews

Kaanapali Fairway Vista - Legal STR Hotel Zoned

Escape to a Slice of Paradise – Where the Fairway Meets the Ocean. This beautifully appointed condo offers the best of Kaanapali living, featuring a prime golf course front position with serene, sweeping views and a sparkling partial ocean view that will take your breath away. Wake up to the sight of golfers setting off on the world-renowned Kaanapali Golf Courses. In the afternoon, relax on your private lanai and watch the sunset paint the Pacific Ocean in hues of gold and orange.

The lanai offers a table with a blue glass bottle as its centerpiece, surrounded by two comfortable chairs. Vibrant blue surfboards are positioned against the wall, while the ocean gently laps at the shore in the background, framed by swaying palm trees.

4.96 out of 5 average rating, 279 reviews

Soothing Waves with 180° View In Kahana, HI

Valley Isle Resort 306 We are located beachfront with an amazing view of the ocean and sunset. We can look right down into the water and watch the turtles swimming. We offer a full kitchen including poolside barbecue grills. Within a block of our Resort are several restaurants and bars. Our condo has a comfy queen-size wall bed along with a small sofa bed. We offer a well stocked kitchen. The ambiance is soothing and relaxing. Our place is good for couples and solo adventurers.

A spacious dining area includes a dark wooden table set for six, surrounded by woven chairs. The kitchen is visible in the background, featuring modern stainless steel appliances and warm wooden cabinetry. Large windows invite natural light, offering views of the lush outdoor landscape.

4.91 out of 5 average rating, 172 reviews

GORGEOUS Newly Remodeled Kaanapali Condo AVAIL !!!

Our NEWLY RENOVATED HOME is located in the prestigious community of Kaanapali, Maui in an exclusive gated community with pool and tennis. Overlooking Whaler's Village and the beautiful 16th fairway of Kaanapali Golf Resort. Our home is close to beach, restaurants, dining and family friendly activities. You'll love our home because of the neighborhood, the comfy bed, the coziness and the kitchen. Awesome for families, couples, solo adventurers and business travelers.

4.94 out of 5 average rating, 147 reviews

Condo in Lahaina

Beachfront Resort, Peaceful Mountain View Studio

Come stay at Lahaina Shores 506: - Oceanfront Building: Direct access to a sandy beach, pool, and hot tub just steps from the lobby - Mountain Views: Wake up to stunning sunrises from your 5th-floor lanai - Sunny & Clear: West Maui averages ~290 sunny days/year! - Amenities Nearby: Minutes drive to open spots like the Cannery Mall, Lahaina Gateway Center, & classic restaurants - West Maui: Only ~35 mins from the airport Note: Car recommended to explore the island

4.98 out of 5 average rating, 206 reviews

Kaanapali Shores - SUPER CLEAN! OceanView 1bd/1ba

A legal short term rental! 1 bedroom, 1 bath with open floor plan. This condominium has a comfortable Cal-King bed in the bedroom and sofa sleeper in the living-room. **Central A/C*Fully equipped kitchen w/ granite counters*refrigerator*stove top + oven*coffee maker* microwave* dishwasher* washer/dryer* Free in room WiFi** Onsite gym is managed by an outside contractor and charges $9/day for useage.

A spacious lanai offers a stunning ocean view, featuring a glass-top table with two wicker chairs. Bright blue beverages are placed on the table, while blue skies and gentle waves stretch out towards the horizon.

4.98 out of 5 average rating, 137 reviews

Stylish Love Hideaway, Maui Kaanapali Oceanfront

Oceanfront studio in one of a kind boutique condominium, on world famous Kaanapali Beach. Wake up to a breathtaking oceanview, take it all in from spacious lanai, fall asleep to the sound of the ocean every night Located on the 3rd floor with close touch to ocean breeze and fantastic views, easy access to world-class beaches, restaurants, shopping and golfing

4.8 out of 5 average rating, 116 reviews

A spacious outdoor area features a private pool with clear blue water, framed by stone landscaping. An arched structure offers shade near the pool, and a red bowl sculpture adds a pop of color. Lush greenery surrounds the space, enhancing the serene environment.

Villa in Kaanapali

Kaanapali Fairway Villa 3BR/3BA.

Welcome to this Kaanapali Golf course 3 bedroom 3 bath bed and breakfast. Permit number BBWMT 2021/0003-159 Halelo. This beautiful Mediterranean home is conveniently located on hole number 5 of the Kaanapali Golf Course with a private pool, swim up bar, and ocean view. Recently renovated with many added amenities and features, please see in description below.

4.84 out of 5 average rating, 157 reviews

Gorgeous 2bed/2bath Papakea Oceanview!

Our spacious, remodeled two bedroom/two bathroom condo on the 4th floor is fully air conditioned with separate AC controls in each room. With its vaulted ceilings and a gorgeous ocean view from a roomy lanai, this is the perfect home base for up to 6 people to relax and enjoy all that Maui has to offer. Everything you need to enjoy your vacation is provided.

Popular amenities for rentals with a pool near Kaanapali Beach

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a pool

4.92 out of 5 average rating, 147 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

4.93 out of 5 average rating, 620 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

4.94 out of 5 average rating, 108 reviews

A tranquil scene features lush greenery and palm trees framing a scenic view overlooking a valley. In the distance, mountains are visible against a colorful sunset sky, with soft clouds adding depth to the picturesque landscape.

Home in Makawao

Exceptional Upcountry Villa, breathtaking views!

4.93 out of 5 average rating, 420 reviews

A sunlit swimming pool is framed by lush green grass, leading to a well-designed single-story home with a distinct round roof. The expansive landscape stretches in the background, providing a view of the ocean and distant mountains under a clear blue sky.

Home in Kula

Kula Jewel - Pool, Hot Tub & Awesome Views!

4.87 out of 5 average rating, 123 reviews

Home in Kaanapali

Studio Kaanapali Beach, Beach Cabana, Jacuzzi, Gr

4.81 out of 5 average rating, 113 reviews

Home in Wailuku

3B2B w/HotTub FamilyComfort HawaiianaCharm Central

4.96 out of 5 average rating, 469 reviews

Home in Wailea

Stunning ocean view Villa, Heated pool, Wailea

4.88 out of 5 average rating, 120 reviews

The kitchen and dining area feature modern appliances and a large wooden table surrounded by a built-in bench. Natural light enters through the window, illuminating the granite countertops and stylish cabinetry, while a beach-themed artwork complements the tropical surroundings.

Home in Kihei

Chic Villa 2 | Modern Vibes by the Ocean

Condo rentals with a pool

4.91 out of 5 average rating, 169 reviews

Oceanfront Condo at Napili Bay | Newly Refreshed

4.98 out of 5 average rating, 130 reviews

Two plush, blue upholstered chairs are positioned beside a round glass-top table adorned with a vibrant floral arrangement. The backdrop features expansive floor-to-ceiling windows offering unobstructed views of the ocean and a clear sky.

Condo in Lahaina

Oceanfront Mahana Resort - Vacation West Maui

A serene resort pool is surrounded by tropical palm trees and lush greenery. The clear blue water reflects the bright sky, with lounge chairs positioned nearby for relaxation. Thatched-roof cabanas offer shaded areas for comfort alongside the pool's stone deck.

4.88 out of 5 average rating, 142 reviews

Luxury Condo Near Whalers Village

A lanai overlooks the ocean, featuring a glass railing and potted orchids on a table. The tranquil water is bordered by palm trees, creating a serene coastal scene. Comfortable lounge chairs are positioned to enjoy the view, enhancing the relaxing ambiance.

4.96 out of 5 average rating, 166 reviews

MAHANA 505 OCEAN FRONT W/ SPECTACULAR VIEWS

4.93 out of 5 average rating, 212 reviews

Eldorado Beach Resort Ka’anapali - Whalers Village

An outdoor dining area is presented on a private lanai, featuring a table set with two glasses and plates of food. In the background, palm trees sway against a clear blue sky, overlooking stunning ocean views that include distant islands.

4.99 out of 5 average rating, 211 reviews

Sunsets and Turtles and Whales, Oh My!

4.97 out of 5 average rating, 153 reviews

Oceanview Maui Condo, Turtles, Whales, Rainbows

4.99 out of 5 average rating, 189 reviews

Fresh Reno on 8th Floor Studio - Amazing Views

Other holiday rentals with a pool

4.97 out of 5 average rating, 127 reviews

A dining setup is presented on a patio table with bowls and turquoise glasses. A decorative pineapple stands at the center. The background features a stunning ocean view with clear blue waters and a line of greenery, under a bright sky with soft clouds.

Apartment in Kaanapali

Mahana at Kaanapali- Beachfront Walkout Jewel

5.0 out of 5 average rating, 3 reviews

Apartment in Kaanapali

Ocean View steps from beach, dining, shopping 723

4.96 out of 5 average rating, 53 reviews

2BR/2BA | @ Alii Beachfront Resort | Sleeps 8

5.0 out of 5 average rating, 23 reviews

Apartment in Kaanapali

Ocean View Condo with Beachfront Cabana for Guests

A bright interior space features a spacious bed adorned with decorative pillows, positioned beside large floor-to-ceiling windows offering sweeping ocean views. A dining table with two chairs is set near the window, complemented by a painting of tropical foliage on the wall.

4.73 out of 5 average rating, 111 reviews

Kaanapali Breeze and 180 degrees Ocean View!

5.0 out of 5 average rating, 14 reviews

Condo in Lahaina

Guest Favorite: Beachfront AC, Seals, Honu & Surf

5.0 out of 5 average rating, 18 reviews

Kahana Ocean View | Pool, Beach, Private Lanai

A view of the expansive ocean is framed by the sliding glass doors. A round dining table and four chairs are visible on the private lanai, with green palm trees gently swaying in the breeze. The distant mountains create a picturesque backdrop against the blue sky.