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Holiday rentals with a pool in Kaanapali

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Kaanapali

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

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Top Guest favourite
A patio table is set with decorative plates, glasses, and a bottle of wine, accompanied by a vibrant flower. Lush green grass extends in the background, with palm trees and a cloudy sky completing the serene view.
Condo in Lahaina
4.98 out of 5 average rating, 139 reviews

Best Location in Kapalua, walk to beach, spacious

Best location spacious 1-bedroom 1-bath Kapalua Bay Villa, walk to Kapalua Bay Beach and Napili Bay -best for swimming and snorkeling. Ideal for families and couples. Modern interior with lots of natural light. Enjoy views and fresh island air from this ground-level unit with large bay windows and a walk-out patio. Walk to Montage, Ritz Carlton, Honolua Store, restaurants (Cane & Canoe, Merriman's, Taverna, Sansei, Seahouse), golf, and tennis. Free parking/wifi. Up to 4 people (including infants

Top Guest favourite
A private balcony features a cozy seating area with plush cushions, overlooking the ocean. The blue water extends into the horizon under a bright sky, while a bottle of wine and two glasses rest on a small table, inviting relaxation amid scenic views.
Condo in Lahaina
4.97 out of 5 average rating, 193 reviews

❤️Best Views on Maui! Perfect for Honeymooners!!❤️

*** NO RESORT FEES! *** Our Studio condo is Unit 1013, located in The Lanai Building at The Mahana. We recently had our roof replaced summer of 2024, so there will be no construction work in our building this year. Newly renovated 10th-floor OCEANFRONT studio condo with the best views on Maui! Drift to sleep on the new KING-sized memory foam mattress and awaken to the sounds of crashing waves. The Mahana on Kaanapali Beach offers a prime location near shops, restaurants, and the best beach!

Top Guest favourite
A private lanai features a dining table set for two, overlooking palm trees and the ocean. Fresh fruit and beverages are arranged on the table. The interior space, visible through open sliding glass doors, includes a smart TV and stylish furnishings.
Condo in Lahaina
4.97 out of 5 average rating, 245 reviews

Ka'anapali Oceanfront Dream-view Retreat with AC!

This serene oceanfront retreat is located along the Kaanapali coast, less than 50' from the beach and waves. The unit offers a whole lot of Aloha, with unobstructed views of an expansive crystal blue/green ocean, crashing waves, swaying palm trees, adjacent islands, starry skies and sea life (sea turtles and monk seals all year long, migrating humpback whales from late Dec through April). The interior is clean, nicely appointed, & has lots of amenities to make your stay comfortable & enjoyable.

Top Guest favourite
A lush outdoor garden area is visible, featuring vibrant green grass and tropical plants. A seating arrangement with a table and chairs can be seen under an overhang, framed by a flowering tree. The ocean glistens in the distance beneath a clear blue sky.
Townhouse in Lahaina
4.95 out of 5 average rating, 168 reviews

Amazing Kapalua ,Stay 7 nights, only pay for 6 !

Our place is close to 3 beautiful beaches, 2 spectacular golf courses, tennis garden, hiking trails, whales, zip line, shops, restaurants, pools, barbecue, and spas. You’ll love our place because of the incredible views from the outdoor garden. It is huge and we call it our living room on the lawn. You'll love the ambiance, neighborhood, people. You will love everything about the Ridge at Kapalua. Our place is good for couples, solo adventurers, business travelers, not suitable for children.

Top Guest favourite
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.
Condo in Lahaina
4.99 out of 5 average rating, 135 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.

Guest favourite
A dining table is set with plates and utensils, positioned on a lush green lawn. Palm trees surround the area, offering a tropical ambiance with the ocean visible in the background under a partly cloudy sky.
Condo in Lahaina
4.92 out of 5 average rating, 134 reviews

OCEAN FRONT Condo at Napili Bay, Near Kapalua!

Thank you for checking out my OCEAN FRONT condo located at the Charming Napili Shores resort. This recently renovated condo is in the high demand I building, which is the closest to the ocean in the complex. Imagine every morning you enjoy the brunch ordered from the famous Gazebo restaurant at your own Lanai right beside the ocean; Soak up the sunshine on the Napili beach steps away from the resort during the day, and come back in the evening to watch the stunning sunset in your room!

Top Guest favourite
A charming bungalow is surrounded by lush greenery and tropical landscaping, with tall palm trees framing the entrance. A dark blue SUV is parked in the driveway, positioned beside the front door. Bright sunlight highlights the vibrant plants and landscaping, creating a welcoming atmosphere.
Bungalow in Lahaina
4.99 out of 5 average rating, 203 reviews

Ka Hale Aloha (The Love Shack)

Escape and fall in love with “Ka Hale Aloha-The Love Shack” where paradise awaits you....This adventurous hideaway will leave you feeling refreshed, relaxed and more alive than ever before!! Experience all the life & Aloha the island of Maui has to offer in your private detached bungalow located on an old 8 acre fruit plantation turned condos, just steps from the ocean. This is a unique experience...there’s nothing quite like "Ka Hale Aloha" on island * Check us out on IG at @kahalealoha

Guest favourite
The living area showcases a spacious seating arrangement facing an unobstructed ocean view through large windows. A dining table is visible nearby, accompanied by a ceiling fan and modern decor. Natural light enhances the airy feel, while the tranquil ocean can be seen in the distance.
Condo in Lahaina
4.89 out of 5 average rating, 144 reviews

Absolutely Oceanfront - Corner Unit- Amazing Views

Absolutely Best Direct Ocean Front With Unobstructed Views if Molokai and Lanai Not from the side of a building or overlooking other units - Deluxe Corner High Floor Apartment - Additional Side Window - Plus Bedroom and Bathroom View Windows - Guests tell us the views from our high floor apartment is better than whale watching tours - Closest building to the Ocean on Maui - Memory Foam King Bed (not Queen) - No Bedbugs here/Bed Bug Protective King Mattress and pillow covers.

Top Guest favourite
Condo in Lahaina
4.97 out of 5 average rating, 127 reviews

Ocean's Edge Romance: Sunsets, Whales, Views!

Bask as you wake to the sound of the waves crashing below and the sight of pristine turquoise water and expansive rainbows. You may pinch yourself as you take it all in, thinking you are still dreaming. We are excited to be able to offer Maui Kai 807, a studio condo in the original beach front high-rise on Maui's west side. No other resort in Kaanapli will put you closer to the ocean's edge. Enjoy the sights of sunsets, turtles, dolphins, and whales (Dec-March) right from your lanai.

Guest favourite
A hallway leads to an outdoor area with views of the turquoise ocean and swaying palm trees. The scene is framed by a solid railing, showcasing the tropical coastal environment and vibrant colors of the water, with gentle waves visible in the distance.
Condo in Lahaina
4.89 out of 5 average rating, 329 reviews

TOP FLOOR!!!! Oceanfront, free Wi-Fi, free parking

Honokowai area. Fresh & clean island vibe on the top floor, one unit away from the end. Practically hanging over the water's edge. Beautiful views of Molokai out the screened front door, as well as Lanai off the lanai. Striking floor-ceiling mirrors capture ocean views from virtually anywhere inside. Location in building catches wonderful trade winds. Listen to the sounds of the waves, just steps away & enjoy the endless sea turtle traffic right under your nose.

Top Guest favourite
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.
Condo in Lahaina
4.98 out of 5 average rating, 187 reviews

Sunsets and Turtles and Whales, Oh My!

Spectacular ocean views Whales and turtles galore(whale season Nov-March) Great snorkeling Gorgeous landscaping Pool, grills, shuffleboard, laundry, and huge sundeck Pristine beaches, grocery stores and world class shopping nearby Sleek and modern Maui hale Chef's kitchen Stainless steel appliances Tv & wifi Cali King bed with luxury linens Beach toys Cooling trade winds Boutique building Elevator and luggage carts Free parking

Top Guest favourite
An outdoor lanai features a small table and two wicker chairs, offering a direct view of the expansive Pacific Ocean. The ocean's vibrant blue waters stretch toward the horizon under a partly cloudy sky, creating a serene and inviting area for relaxation.
Condo in Lahaina
4.98 out of 5 average rating, 199 reviews

DIRECT OCEAN FRONT STUDIO W OCEAN IS UR BACK YARD!

This is a hotel-zoned condo. It will not be affected by potential upcoming county regulations. Book with confidence!! Thank you for considering my direct ocean front studio condo in Kahana, my condo is located minutes outside of Lahaina , Kaanapali , Napili and Kapalua. You'll find the ocean view from my lanai/ room to be breathtaking and serene. This is truly an hidden gem on Maui.

Popular amenities for Kaanapali rentals with a pool

When is the best time to visit Kaanapali?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. price$629 AUD$652 AUD$692 AUD$689 AUD$612 AUD$793 AUD$809 AUD$803 AUD$612 AUD$497 AUD$523 AUD$620 AUD
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Quick stats about holiday rentals with a pool in Kaanapali

  • Total holiday rentals

    Explore 4,030 holiday rentals in Kaanapali

  • Verified guest reviews

    Over 40,850 verified reviews to help you choose

  • Family-friendly holiday rentals

    1,860 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 40 rentals that welcome pets

  • Rentals with dedicated workspaces

    2,600 properties have a dedicated workspace

  • Wi-Fi availability

    4,000 of Kaanapali holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wi-Fi and Pool across Kaanapali rentals

  • 4.8 Average rating

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

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