Vacation rentals with a pool in Kaanapali

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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 favorite
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 Lahaina
4.97 out of 5 average rating, 108 reviews

Mahana at Kaanapali- Beachfront Walkout Jewel

Maui Gov’t Approved Short Term Rental - Hotel District- Direct beach access with ground floor spacious lanai. Unreal views from this one bedroom, one sofa bed ground level entry, beachfront condo located directly on Kaanapali Beach. Central AC with LR and BR providing separate direct walkout to the lanai and 15 steps away is the beach! 75" TV, Sonos system, Apple TV, washer/dryer etc. Stocked kitchen includes coffee makers and supplies to get yourself ready for romantic dinners with the sunset!

Top guest favorite
A tranquil pool area is surrounded by lush tropical vegetation, with a mix of vibrant flowers and palm trees. Relaxing lounge chairs are positioned near the water, offering scenic views of distant mountains and the ocean. The sky is clear, enhancing the inviting atmosphere.
Condo in Lahaina
4.88 out of 5 average rating, 196 reviews

MKV Resort - Last Minute Cancellation Sweet Deal

Note.. MKV charges $35 per day resort fee due at check in. Beautifully updated spacious studio with an ocean view. Amazing sunsets and whale watching are found here. Features new modern furniture, fresh paint and new decor throughout. MKV has direct beach access, two swimming pools, hot tubs, spa, gym, shuffleboard, outdoor BBQ's and Castaway's ocean front bar & grill. Parking is super convenient & free. Free trolly rides to Whalers village and Ka'anapali restaurants, markets and golf courses.

Top guest favorite
Condo in Lahaina
4.94 out of 5 average rating, 200 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 favorite
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, 149 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 & centrally located next to the Montage Resort. 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, shopping, spas, & several bays/beaches great for snorkeling, surfing, & relaxing, this is the perfect home base.

Top guest favorite
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 favorite
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, 144 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.

Top guest favorite
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 favorite
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, 341 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.

Guest favorite
A dining table set for two is positioned on a private lanai, overlooking the ocean. Two glasses of orange juice and a colorful fruit platter are arranged on the table. Palm trees sway gently in the foreground, framing a picturesque view of the blue water and distant landscape.
Condo in Lahaina
4.94 out of 5 average rating, 105 reviews

Perfect Romantic Getaway - Right on the Ocean!

You can't beat our little corner of paradise. This is truly our HAPPY PLACE! Relax on the lanai with your favorite beverage, and allow yourself to be serenaded by the crashing of waves and the refreshing salt water breeze. Our expansive ocean view is amazing every day and even better during prime whale watching season, which falls during the winter months. Stay put and enjoy or go out & explore the island of Maui.

Guest favorite
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.
Condo in Lahaina
4.87 out of 5 average rating, 132 reviews

Luxury Condo Near Whalers Village

Luxury + location at an unbeatable rate. Located in the heart of Ka'anapali on the golf course behind Whalers Village. Enjoy a 10-minute walk to world-famous Ka'anapali beach or relax at the resort’s pool and BBQ area. This spacious 1,800 sqft suite features 2 bedrooms, central A/C, and elegant travertine floors. (Please note: $160 parking fee is not included in the Airbnb rate and must be paid at check-in.)

Top guest favorite
Condo in Lahaina
4.97 out of 5 average rating, 197 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.

Guest favorite
A spacious living area is furnished with a soft gray sofa adorned with decorative pillows, complemented by a wooden coffee table with glass top. A vibrant ocean view is framed by large windows, and a cozy dining set is positioned on the lanai, enhancing the inviting space.
Condo in Lahaina
4.97 out of 5 average rating, 115 reviews

Direct Waterfront, Air conditioned, Amazing Views!

Stunning views! There is nothing better than sitting on your Lanai and listening to the waves! It is not unusual to spot whales and sea turtles while sitting on our Lanai. One of the nicest, if not THE nicest units at Papakea. Truly deluxe! Ocean front with full ocean view, just 30 feet from the ocean. If you are looking for multiple units, we are also owners of G104.

Popular amenities for Kaanapali rentals with a pool

When is the best time to visit Kaanapali?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$86,018 GYDG$89,157 GYDG$94,598 GYDG$94,180 GYDG$83,715 GYDG$108,411 GYDG$110,714 GYDG$109,876 GYDG$83,715 GYDG$81,413 GYDG$84,553 GYDG$101,086 GYD
Avg. temp23°C23°C23°C24°C25°C26°C27°C27°C27°C26°C25°C24°C

Quick stats about vacation rentals with a pool in Kaanapali

  • Total vacation rentals

    Explore 4,230 vacation rentals in Kaanapali

  • Nightly prices starting at

    Kaanapali vacation rentals start at G$2,093 GYD per night before taxes and fees

  • Verified guest reviews

    Over 42,900 verified reviews to help you choose

  • Family-friendly vacation rentals

    2,090 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 30 rentals that welcome pets

  • Rentals with dedicated workspaces

    2,770 properties have a dedicated workspace

  • Wi-Fi availability

    4,220 of Kaanapali vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, 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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