Holiday rentals with a pool in Lahaina

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Top-rated rentals with a pool in Lahaina

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

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Top Guest favourite
An open kitchen area features modern appliances, including a refrigerator and dishwasher, set against sleek cabinetry. A large island with countertop seating invites gatherings. Floor-to-ceiling windows present stunning ocean views, while natural light floods the space, enhancing a sense of openness and connection to the outdoors.
Condo in Lahaina
5 out of 5 average rating, 105 reviews

Luxury Mahana Studio-Great Views-WiFi-Free Park

Locally Owned and Operated Studio 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. Located on North Kaanapali Beach. Enjoy stunning views and the warm Maui sun inside while central AC keeps you cool and comfortable any time of day.

Top Guest favourite
Condo in Lahaina
4.94 out of 5 average rating, 201 reviews

Eldorado Beach Resort Ka’anapali - Whalers Village

Eldorado resort charges a one time $65 plus $22 per day resort fee at check in. Maui Eldorado resort # K110 is a beautiful remodeled studio suite with a privacy wall that sleeps 4 comfortably. K110 has a fully equipped kitchen, AC, new washer & dryer and remodeled bathroom suite. Eldorado's beach cabana provides everything needed for an amazing day at the beach and fronts the nicest stretch of beach in all of Ka'anapali. Whalers Village restaurants, shops and activities are a 5 minute walk,

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, 215 reviews

Peaceful Maui Bungalow | Ka Hale Aloha-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 @thoughtfulstays

Top Guest favourite
A spacious living area is furnished with a seven-piece sectional sofa and a comfortable twin daybed. A coffee table rests on a patterned area rug. Floor-to-ceiling windows provide garden views, while a ceiling fan adds comfort to the inviting ambiance.
Condo in Kapalua
4.99 out of 5 average rating, 150 reviews

NEWLY REMODELED OCEAN VIEW CONDO, STEPS FROM BEACH

Your next relaxing Lahaina escape awaits at this stunning 1-bedroom, 2-bath vacation rental condo - steps away from Kapalua Bay Beach & located next to The Resort at Kapalua Bay (formerly Montage). Your group of up to 6 guests will love returning to the comfort of this home, offering over 1,100 sq ft of living space. With easy access to championship golf courses, fine dining, walking/hiking paths, spas, & several bays/beaches for snorkeling, surfing, & relaxing, this is the perfect home base.

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 Kapalua
4.96 out of 5 average rating, 178 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
An inviting outdoor living area features wooden seating arrangements adorned with plush cushions. Lush greenery surrounds the space, and decorative string lights create a warm ambiance overhead. A shaded daybed offers a comfortable spot for relaxation amid the tropical landscape.
Cottage in Lahaina
4.93 out of 5 average rating, 147 reviews

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.

Top Guest favourite
Condo in Lahaina
4.95 out of 5 average rating, 151 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.

Guest favourite
Condo in Lahaina
4.93 out of 5 average rating, 131 reviews

Oceanfront 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

Top Guest favourite
The living room features comfortable seating with a light-colored sectional sofa and matching ottoman. A large wall-mounted TV displays a serene beach scene. Natural light streams in through expansive glass doors, offering views of the outdoors and creating an airy atmosphere.
Condo in Kapalua
4.99 out of 5 average rating, 155 reviews

Kapalua, luxe, ocean view, beach, spa, golf/tennis

KAPALUA - Best location! Welcome to the luxuriously Kapalua Bay Villa #37B1. Bright and airy, with comfortable furniture and modern appliances. Scenic ocean view, a 5-minute walk to Kapalua Bay, Montage Resort, tennis, golf, hiking, zip-lining, amazing restaurants, and a first-class spa. Kapalua Bay Villas is a low-density community within the Kapalua Resort—a 15-minute drive to Kaanapali, and a 40-minute drive to Central Maui to explore the island.

Top Guest favourite
A light-filled living area showcases a beige couch and two patterned chairs, positioned around a wooden coffee table. Floor-to-ceiling windows reveal expansive ocean views, allowing natural light to enhance the space. A ceiling fan adds to the comfort, while a mounted TV is visible on the sideboard.
Condo in Lahaina
4.96 out of 5 average rating, 154 reviews

Whales Watch: Lux Beachfront-180° Ocean views-AC!

Watch the Whales breach during their migration and boats sailing by while sitting up in your dreamy oceanfront bedroom with a cup of coffee! If you love the sound of the ocean, then this is the place for you. Luxuriously remodeled Island Oasis, just 15 feet from the ocean with unbeatable, 180 degrees ocean views. Super private, secluded corner unit located on the 5th floor of Valley Isle Resort in Kahana. Inside the Hotel Zone.

Guest favourite
Home in Wailea
4.96 out of 5 average rating, 455 reviews

Stunning ocean view, heated pool at home by Wailea

Ocean, sunset views, unique home reminiscent of a Victorian villa with heated private pool for guests in the villa, tropical gardens. Home renovated and maintained by designer. Cal King in main, second has twin beds. Pac n play and high chair are available. Open plan living with dining and relaxing on the lanai. Keawakapu beach, Wailea shops and restaurants 5 minutes drive. Your private view retreat. #BBMK 2016/0003

Top Guest favourite
A scenic view captures the sunset over a lush landscape, with a pool reflecting the colorful sky. Tall trees frame the scene, and the distant ocean is visible beneath the dramatic clouds. The vibrant greens of the surrounding vegetation provide a serene backdrop.
Cottage in Makawao
4.99 out of 5 average rating, 232 reviews

Rustic Upcountry retreat with breathtaking views!

Maui County Permits BBMP2019/0006 & SUP2 2019/0003 This is a BnB not a STRH Owners live on property At this time we are hosting to guests 12 or older. This property is terraced so not optimal for young children. This is a non smoking property. No smoking is allowed. Use of the pool, hot tub and dry sauna are private when reserved with our private calendar. Mahalo!

Popular amenities for Lahaina rentals with a pool

When is the best time to visit Lahaina?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. price$1,152 AUD$1,203 AUD$1,266 AUD$1,115 AUD$1,133 AUD$1,068 AUD$985 AUD$772 AUD$511 AUD$474 AUD$531 AUD$511 AUD
Avg. temp23°C23°C23°C24°C25°C26°C27°C27°C27°C26°C25°C24°C

Quick stats about holiday rentals with a pool in Lahaina

  • Total holiday rentals

    Explore 340 holiday rentals in Lahaina

  • Nightly prices starting at

    Lahaina holiday rentals start at $28 AUD per night before taxes and fees

  • Verified guest reviews

    Over 5,000 verified reviews to help you choose

  • Family-friendly holiday rentals

    190 properties offer extra space and kid-friendly amenities

  • Rentals with dedicated workspaces

    150 properties have a dedicated workspace

  • Wi-Fi availability

    330 of Lahaina holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Lahaina rentals

  • 4.8 Average rating

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

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