
Holiday 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
A wonderfully comfortable Hawaiian cottage with plenty of room to spread out. It’s fully equipped with beach chairs, snorkel gear, pickle ball paddles and even a cooler. Van was so helpful and accommodating during our stay. Easy 10 minute walk down to the main beach access with a great boardwalk. Highly recommend this great little spot.

Summer Deals Book now Island Retreat Spacious 3B
This place was SO beautiful! The lana’i was exactly as described with breathtaking views. The pool is great for adults and kids; we had so much fun hanging out there. Bedrooms were spacious and kitchen was stocked. The best part is everything you can think of wanting at the beach is stocked in the garage. We were able to take tons of gear to the beach like pros. Thank you so much for the hospitality and we’d recommend this spot to everyone!

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.

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!
Staying at the Kula Jewel is nothing short of the perfect experience. Pamela made sure to personally welcome us, show us around and direct us to local shops. We should have just spent our entire time in Hawaii here, as the views and perfect design of the home gave us the experience of staying with a close friend. Stocked kitchen, great linens, pool and hot tub, bbq and all of the perfect details that make vacations special, Pamela really takes care in making her guests feel at home. The stunning interiors partner with the unique shape of the house, making the Maui landscape picturesque from sunrise to sunset. We will have a place to call our Maui spot when visiting from now on.
Apartment rentals with a pool

Kuleana Club #513-Oceanview -1 bd & 1 ba-3rd Floor
Amazing view! Will definitely be coming back here:)

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.

Valley Isle Resort #501 - Newly Remodeled w/ AC
We found the unit to be ideal for our trip. It was in a beautiful building on a nice beach, near a fantastic bar/restaurant that was right across the street, in a a safe, quiet neighborhood. There was wonderful Hawaiian music softly playing in the lobby at all times! Such a great thing! Parking was close and free and easy! Our unit's view was amazing. It is a corner unit and quite large. It was beautifully decorated. The Smart Tv was wonderful with all our apps already loaded.

Stunning! Oceanfront! Remodeled! Summer Specials!
I am a newlywed. We stayed at Lonelle’s place for our honeymoon last month. It’s beautiful, clean and has an amazing view of the ocean from the porch. Lonelle is swift in her responses and helpful with recommendations when needed.

Hot Deals! Limited Availability- Maui Getaway
Kalea’s was alway available to answer questions very quickly. The condo was very well taken care of and had everything we needed. Loved the location and area much different than Kanapali as it’s much closer to other areas of the Island to explore. The lights and fan can be tricky at times but remember your own Hawaiian time. Mahalo

Maui Resort Rentals: Honua Kai Konea 415
Pictures are exactly as is. Honua Kai is a great place for the family. This home met all our needs for our small family. We were already familiar with Kaanapali and this is a convenient location. The resort is big. Only suggestion would be a resort map (*I found via google) and a simple floor map to locate the elevators and garbage/recycle room. Not a big deal though; got familiar within 2 days of walking around. Thank you!

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!

Maui Beachfront Bliss |AC, Pool, Surf, Snorkel BBQ
Annie’s corner beachfront 9th floor condo is as advertised, AMAZING! If you like access to the beach and a peaceful place to stay, you’ll love this spot!
Quick stats about holiday rentals with a pool in Kaanapali
Total rentals
3.9K properties
Nightly prices starting at
₹1,731 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
- Sandy Beach
- Kaipukaihina
- Laie
- Honolua Bay
- Spreckelsville Beach
- Kapalua Bay Beach
- Olowalu Beach
- Kaupoa Beach
- Wailea Beach
- Manele Golf Course
- Hāmoa Beach
- Oneloa Beach
- Kalani Beach
- Maui Ocean Center
- Mokulau Beach
- Wailea Golf Club
- Palauea Beach
- Old Lahaina Luau
- Wailau Valley