Vacation rentals with a pool in Kaanapali

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Popular amenities for Kaanapali rentals with a pool

House rentals with a pool

Top guest favorite
A serene sandy beach is shown with gentle waves lapping against the shore. Sunbathers are positioned leisurely on the sand, and a few umbrellas provide shade nearby. Lush palm trees line the back of the beach, creating a tranquil atmosphere under a clear blue sky.
Home in Lahaina
5 out of 5 average rating, 21 reviews

Newly Remodeled Cottage

SusanRating, 5 stars1 week ago
Look no more!! Vans place is absolutely stunning. We stayed here with our four kids & we cannot wait to return. The location is so peaceful and extremely spacious. Thank you Van for hosting our stay. We look forward to staying here again.
Superhost
Home in Lahaina
4.93 out of 5 average rating, 30 reviews

ICC 20 Remodeled 2BD Hawaiian Cottage w Pool AC

NeekaRating, 5 stars4 months ago
Beautiful property with a great deck. Was perfect for a family vacation. So close to all the resorts and the beach. Great location to get around Maui. Would highly recommend!
Guest favorite
A private balcony features a wooden table surrounded by four chairs, with a serene view of lush greenery and palm trees. Bright sky and the distant buildings of the resort can be seen, suggesting a peaceful outdoor setting.
Home in Kihei
4.95 out of 5 average rating, 22 reviews

Luana Kai C209

ShriyaRating, 5 stars6 months ago
Beautiful condo in Kihei with every possible amenity to make you feel right at home. Private and peaceful with a pool, beach access. Perfect for getting around to snorkeling which was nearby. Access to stores too. Great place from which to visit Haleakala as well!
Guest favorite
A clear view of the private pool is presented, surrounded by lush greenery and palm trees. An orange umbrella offers shade over poolside loungers, enhancing the outdoor relaxation space. The ocean and mountains create a scenic backdrop under a bright blue sky.
Home in Kihei
4.93 out of 5 average rating, 30 reviews

Oceanview Home with Private pool and hot tub

JennieRating, 5 stars1 week ago
Steve’s place is great and he is an excellent communicator and very invested in ensuring his guests have a great experience. We loved watching the sunset from the deck and the pool and game room were both so fun for our family. Lots of pantry staples on hand as well as some yummy snacks to greet us. The location is private and peaceful and we loved all the beautiful Hawaiian plants and geckos in the yard. Thanks for a great stay!
Guest favorite
A spacious living area features natural light from large windows, complemented by a comfortable seating arrangement. A stylish television is mounted on the wall, and an open kitchen with modern appliances is visible in the background. Decorative elements bring a touch of warmth to the space.
Home in Lahaina
5 out of 5 average rating, 6 reviews

Luxury Panoramic Ocean Views!

ShrijitRating, 5 stars6 months ago
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.
Guest favorite
A spacious lanai features a round dining table with four chairs, overlooking lush greenery and sweeping ocean views. The tranquil setting is bathed in natural light, presenting an ideal space for outdoor dining or relaxation amid the picturesque coastal landscape.
Home in Lahaina
5 out of 5 average rating, 12 reviews

Kapalua Ridge 622 Luxe Ocean and Coastal Views

AdilbekRating, 5 stars5 months ago
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 🙌🏻
Superhost
A panoramic view of a sandy beach is offered, with gentle waves lapping at the shore. Clear turquoise waters meet a bright blue sky, dotted with fluffy white clouds. Lush greenery fringes the beach, enhancing the natural beauty of the idyllic setting.
Home in Kaanapali
4.89 out of 5 average rating, 108 reviews

#1 Kaanapali Beach Modern Condo C101 Maui Eldorado

JesseRating, 5 stars7 months ago
Very beautiful location to stay at in Kaanapali! Has a gym with just enough equipment, grills and pools, and an included private golf cart upon request to the beautiful Kaanapali beaches. Also towel service available until 5:30pm! So wonderful! AC and other amenities were great, did not have a single issue or complaint my entire stay here. Had a great time here, will hopefully be back!!!
Guest favorite
Home in Maui
4.97 out of 5 average rating, 232 reviews

Private Hot Tub + Pool Access + AC - Star Lookout

AndreiRating, 5 stars2 weeks ago
We had the best time at the Star Lookout during our short stay in Maui. The private location, and amenities like the spacious hot tub, outdoor shower, and pool (which we never saw anybody else at) were above and beyond what was described. The location on the road to Hana is very convenient and near the twin falls and many other notable stops. The views from the cliff walk are one of a kind and this property is an absolute treasure. The communication from the host and the entire staff / team on property was outstanding and we felt very welcomed and right at home. We won’t be staying anywhere else when we’re on the Island as this place seriously has it all. Thank you for the best Maui experience! :)

Condo rentals with a pool

Superhost
A large outdoor pool is surrounded by lounge chairs and tables, inviting relaxation. The condo building features multiple floors with balconies visible above the pool area. Lush greenery and palm trees frame the scene, enhancing the tropical feel of the space.
Condo in Kihei
4.77 out of 5 average rating, 263 reviews

Condo-FULL AC-BEACH Kihei Maui

JeffRating, 5 stars2 weeks ago
We loved staying in Rebecca's place. The location was perfect, the condo was clean and we'll cared for. Dena stopped by to help us with the internet and she was very friendly and helpful. Our family of 6 for perfectly. They had chairs and pool noodles for us. We used the cooler and boogie boards(3) every day. We'd stay here again and hope to be back someday.
Superhost
A pool area is displayed, featuring a hot tub with bubbling water and a swimming pool beyond. Paved tiles surround the area, with two children sitting on the edge of the pool, enjoying the sunny day. Lush plants are visible in the background.
Condo in Kihei
4.91 out of 5 average rating, 151 reviews

Beach Area Condo

ManojRating, 5 stars2 weeks ago
Karen is an excellent Host. The Apartment is perfect, modern, great location, well equipped, there are plenty of restaurants in walking distance but yet the Apartment is in a peaceful location. There is a beautiful beach literally minutes away. Can't wait to come back.
Superhost
A private lanai presents an unobstructed ocean view, framed by wooden siding. A glass-top table with a round design is paired with two white chairs. A bright terracotta vase filled with red flowers adds a touch of color to the serene coastal setting.
Condo in Lahaina
4.86 out of 5 average rating, 36 reviews

Discounted Rates! 305 Beautiful 2 bed/2 bath

AubrieRating, 5 stars1 month ago
Great places to stay! Amazing views of the water where you can sit out and watch the whales and turtles. Host was amazing, we had a problem with a light (it turns out it was user error) but she sent the handyman out right away and he was very helpful. Highly recommend!
Top guest favorite
Condo in Kihei
4.89 out of 5 average rating, 132 reviews

Incomparable Maui Sunset condo, includes all taxes

TahneeRating, 5 stars1 month ago
The owners were so welcoming and proactive. They went above and beyond to ensure our stay was wonderful. They had some uncontrollable maintenance issue arise that they handled immediately and it did not disrupt our trip at all. The building and amenities were perfect. Our son loved exploring the beach and chasing crabs. Our daughter spent the evenings in the pool after our daytime adventures. We will be back and are so grateful to have experienced this slice of paradise.
Superhost
The outdoor pool area is surrounded by lounge chairs and tropical landscaping. The three-story building looms in the background, featuring multiple balconies and green awnings. The clear blue water of the pool reflects the sunny sky, creating a refreshing atmosphere.
Condo in Kihei
4.8 out of 5 average rating, 178 reviews

Luxury 2bd2bth Kihei Maui Condo Across from Beach

BrookeRating, 5 stars3 weeks ago
We were so happy with our stay. The location is great- right across the street from a nice beach area, close to fun restaurants and centrally located to everything we wanted to do in Maui. It was so nice having access to the beach chairs/umbrellas/beach toys and having everything we needed provided with the rental. Rebecca was great about giving us clear information and instructions, and responded quickly when we needed a response. We felt right at home and will definitely consider booking here again if we ever make it to Maui again!
Superhost
A circular pool is surrounded by a paved area, featuring multiple lounge chairs positioned around it. Lush greenery and flowering plants create a vibrant backdrop, with palm trees offering shade. A small building with a red roof is visible, along with colorful floats near the water's edge.
Condo in Kihei
4.84 out of 5 average rating, 253 reviews

Cozy Cute Condo | Maui Vista | Walk to The Beach

BradleyRating, 5 stars1 month ago
This place is a great find as it is close to the beach and restaurants. The only thing was interacting with the security to get a parking pass. He was an older man who acted very unprofessionally towards me as I was asking for a parking pass. He would give unnecessary comments like: "Put this pass in your car. We live in America, so the driver's side will be on your left." Luckily, I don't get offended easily, but this is just a heads up. Juliana and the location is great though! So the rating is still high and the security does not effect this rating.
Superhost
Condo in Lahaina
4.89 out of 5 average rating, 112 reviews

Remodeled Kaanapali golf resort 1500ft condo w/AC

SpencerRating, 5 stars2 weeks ago
We loved this place. the complex is not crowded at all. Lots of bbq grills and multiple pools. The best part is the beach. They have chairs and towels that you can check out for free at the beach so you don't have to haul them down. Just call the front desk and they send a free golf cart to take you down to the beach. The beach was amazing. Not crowded at all and it was an amazing beach. I would definitely stay here again.
Superhost
An open living area is presented with a light-colored sofa, wicker furniture, and a ceiling fan. A dining table and chairs are seen near the kitchen, which is equipped with wood cabinetry. Natural light is invited in through a large window, enhancing the inviting space.
Condo in Kihei
4.83 out of 5 average rating, 29 reviews

Considered the Best Location Oceanfront on Maui

AmandaRating, 5 stars1 month ago
This place was so beautiful! The condo had everything we needed and being right next to the pool was an awesome bonus. It was clean and perfect for our family of four. We loved the courtyard and the easy access to the beach. We loved our stay so much and weren’t ready to go back home. We will definitely be back to Maui Sunset.

Quick stats about vacation rentals with a pool in Kaanapali

  • Total rentals

    3.9K properties

  • Nightly prices starting at

    $20 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

Destinations to explore

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  6. Rentals with pools