
Vacation rentals with a pool in Kaanapali
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Top-rated rentals with a pool in Kaanapali
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Popular amenities for Kaanapali rentals with a pool
House rentals with a pool

Mahalo Pono @ Ka 'anapali Royal
We had an amazing time. Amy & Jay were extremely responsive and the property was immaculate. Our family of 5 had everything we needed to be comfortable, enjoy the beach and be within 15 minutes of anything on the west side of Maui. We plan on returning soon!

Newly Remodeled Cottage
Van was kind and friendly. The home was great. Loved that there was mini split ac units in every bedroom. Right across the street from the best beach on the island. Would highly recommend.

Luxury Panoramic Ocean Views!
Kapalua Ridge is an incredible development and Kevin’s place was absolutely stunning. The entire setup gives all the resorts in the area a run for their money. The place itself was clean, well equipped, massive and luxurious. The views of the coast and islands was beautiful and we enjoyed stunning views everyday. It’s a short walk to the beach and few steps past the nearby beach gets you to Kapalua bay which is where the restaurants are. The bathrooms were very large and luxurious - which we loved. Our host Kevin was super responsive and was very helpful with recommendations and helping us find things in the airbnb. Will come back here if in Maui - amazing place.

ICC 13 Beautifully Furnish Kaanapali Cottage
We had a wonderful stay at Maui Paradise Properties! The location is unbeatable and the space is well-lit, roomy, and well-decorated. I loved the open space kitchen and patio. We will definitely come back to Maui Paradise Properties on our next visit!

Kapalua Ridge 622 Luxe Ocean and Coastal Views
Perfect location with beautiful beaches nearby. Not a lot of restaurants around but if you have a car - it’s easy to navigate. The view from the bedroom and living room is brilliant 😍 We really enjoyed the stay. Definitely recommend 🙌🏻

Stunning ocean view, heated pool at home by Wailea
Sandra was very nice. The house was clean and exactly what we expected. She offered great suggestions when we asked for recommendations on places to visit. I would definitely recommend staying here.

Best Studio Ocean Views at Honua Kai -Hokulani 719
We, a small family, recently stayed in Kaanapali Maui and couldn’t have been happier with the experience. From the moment we arrived, everything exceeded our expectations. The unit was spotless, beautifully decorated, and fully stocked with all the essentials — from kitchenware including a blender and all of the beach necessities. After going around the island and picking up some fresh fruit, it was a nice afternoon treat to be able to make our own smoothies! Highly recommend it. The view from the lanai (balcony) was absolutely stunning. Every morning we enjoyed our coffee while watching the sunrise over the ocean, and in the evenings we were treated to the most spectacular sunsets. The sound of the waves crashing was the perfect background to a truly relaxing vacation. The location was ideal just a short walk to the beach, shops, and great local restaurants. We loved being close to snorkeling spots and whale watching opportunities. The complex also had a pool, hot tub, and BBQ grill

Kula Jewel - Pool, Hot Tub & Awesome Views!
Pamela’s place is amazing! As a host Pamela was very welcoming and gave a great tour of her place. The view is beautiful and the pool and hot tub are perfect! We would definitely stay here again. Thank you Pamela!
Condo rentals with a pool

Ocean View steps from beach, dining, shopping 961
Very clean and wonderful place! Walkable to shops and to the beach. Restaurants nearby as well. Would come back!

Kuleana Club #513-Oceanview -1 bd & 1 ba-3rd Floor
AMAZING VIEW.!!! Wonderful place to stay in, LOVED LOVED

Oceanfront Penthouse Maui Kaanapali, Aloha Getaway
This was definitely a 5 star stay. I’ve stayed at plenty of nice Airbnbs and I think this was my favorite. It’s very easy, in a good location, very safe and extremely clean. Usually you can expect some sand on the ground or on the furniture at a beach stay even after it’s been cleaned, but not here. The entire place was spotless. The hosts were very responsive and kind. The beach is right out front and great for snorkeling and sea turtles. However, the best part was definitely the stunning view. The pictures online don’t do it justice. It’s beautiful. We laid in bed every day listening to the waves and watching the sunset. We woke up to the sunrise each morning. We also spent a good bit of time, especially in the morning, just watching the water. Every time we looked out the lanai we saw at least 3-4 sea turtles and one morning we even saw a sea lion swimming next to the shore. We never turned on the TV. I cannot recommend this stay enough. It’s easily worth the money.

Turtles & Tales: Luxe Beachfront w/AC & Ocean view
We loved our stay, would highly recommend! The condo is beautiful and had everything we needed. I wouldn’t hesitate to stay here again!

Premier Oceanfront Retreat in Lahaina
Hawaii Life thought of everything. The condo was spotless. The views and lanai made it worth every penny. The host was always available to answer questions, even helping me to remove fabric stains and helping with business paperwork. This was above and beyond. The amenities were superb but the personal touch with food and activities recommendations, nice beach chairs, wagon, coolers, sunscreen, shampoo, coffee maker, keurig, and espresso machines made things seem like at home. We didn’t need to purchase a lot of extras just to throw away after 8 days. We love to travel and I would by far say this is the best place we have stayed. Not only the location and cleanliness but the personal touch in every detail! We will be telling our friends about this location.

OCEAN FRONT CONDO IN KAHANA NEAR SELECTED! ,KAPALUA
Everything was exactly as described. You can see the sunset from the balcony and the views did not disappoint. Bin's recommendations were on point and perfect. The snorkeling at Honolua Bay was by far the best suggestion he had. Loved the place and environment. The ABC store down the street has everything you need and a deli, you gotta try the garlic mashed potatoes.

Beachfront on Kaanapali The Mahana 1106!
This condo on the 11th floor in Kaanapali was an absolute dream! From the moment we walked in, we were greeted by floor-to-ceiling windows that opened up to a jaw-dropping panoramic view of the ocean. The balcony became our favorite hangout—we spotted dolphins dancing in the waves and sea turtles gliding near the shore. And the best part? The beach is literally right in front of the building—just a few steps from the lobby to the sand. Inside, the condo had everything you could possibly need for a perfect stay. Every detail felt intentional, from a fully stocked kitchen to beach gear and thoughtful touches that made it feel like home (but better). The owners were incredibly responsive and clearly care about their guests’ experience—they were kind, attentive, and made sure we had everything we needed. This wasn’t just a place to stay—it was an experience we’ll never forget. Five stars doesn’t feel like enough. If you're coming to Maui, this is the place you want to be.

Modern + Serene Oceanfront Napili Getaway w/ AC
The condo and location were even better than we could have imagined! Snorkeling with sea turtles was right out the door and a gorgeous sandy beach was a short and fun walk away. The ocean views and sunsets were incredible. It’s a really nice and comfortable condo with everything you could possibly need for an amazing trip. Don and Nandi were quick to communicate and graciously offered their assistance throughout our stay. We will absolutely stay there again! Mahalo to Don and Nandi!
Quick stats about vacation rentals with a pool in Kaanapali
Total rentals
3.9K properties
Nightly prices starting at
G$4,182 GYD before taxes and fees
Total number of reviews
38K reviews
Family-friendly rentals
1.8K properties are a good fit for families
Pet-friendly rentals
30 properties allow pets
Rentals with dedicated workspaces
2.3K properties have a dedicated workspace
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- Maui
- Kaanapali Beach
- Kahului Beach
- Kepuhi Beach
- Lahaina Beach
- Kaipukaihina
- Laie
- Honolua Bay
- Spreckelsville Beach
- Kapalua Bay Beach
- Olowalu Beach
- Kaupoa Beach
- Wailea Beach
- Manele Golf Course
- Hāmoa Beach
- Kapua
- Oneloa Beach
- Kalani Beach
- Maui Ocean Center
- Wailea Golf Club
- Palauea Beach
- Old Lahaina Luau
- Kaulahao Beach
- Hale or Lono Beach