Vacation rentals with a pool in Kaanapali Beach

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Kaanapali Beach

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

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Top guest favorite

Condo in Wailea-Makena

4.97 out of 5 average rating, 119 reviews

Grand Island Paradise on Golf Course w/Ocean Views

🌅 Enjoy sunset ocean views every night! 🏖️ <1 mile from Wailea Beach! Inside are 3 bedrooms w/ a King, Queen, 4 Twin, and 2 trundle beds! There are 2 private balconies, private laundry, and it's ground level- NO STAIRS! The complex has 2 POOLS and Parking for 2+ cars. Close to Wailea, Makena, Keawakapu! This property will be transitioning to another Superhost. If you would like to make a reservation beyond August 18th 2025, please do so via the new listing at http://airbnb.com/h/hoku-hale.

Guest favorite

Condo in Kihei

4.93 out of 5 average rating, 120 reviews

Luxe Oceanview 2B2B Escape w/AC Near Beach & Shops

Location and Quality! You will feel the relaxed beach vibes from the very first step walking into this tastefully updated & beach luxe unit. Directly sit across the famous Cove surf spot & in the middle of all, you will be memorized by the ocean waves along with surfers, paddlers and the breathtaking sunset views, and the incredible walk distance to everything Kihei has to offer including activities, shopping, dining, nightlife and more! Experience the best of Maui from our Luxe-design condo!

Top guest favorite

A sunlit swimming pool is framed by lush green grass, leading to a well-designed single-story home with a distinct round roof. The expansive landscape stretches in the background, providing a view of the ocean and distant mountains under a clear blue sky.

Home in Kula

4.92 out of 5 average rating, 335 reviews

Kula Jewel - Pool, Hot Tub & Awesome Views!

Pamela has been hosting two fully permitted listings for the last 11 years with over 1,000 five star reviews. BUT this one, Kula Jewel, burned to the ground in the Maui wildfires in 2023. We have recently completed building the NEW Jewel, and it is GORGEOUS! We just had our first guests stay, and this was their review: "Pamela’s place is extraordinary! The views are stunning! The design and decor are fabulous in every detail! I’ve stayed in many Air B&Bs; I give her place my highest rating!"

Guest favorite

A serene outdoor area features well-maintained green grass and several lounge chairs positioned to face the ocean. A table with decorative items is visible in the foreground, while palm trees sway gently in the breeze against a clear blue sky, providing a view of the distant mountains.

Condo in Wailuku

4.89 out of 5 average rating, 119 reviews

Oceanfront Condo with Pool and Jacuzzi

Relax in this peaceful gem on Maui. Located on the ground floor, you can walk into the ocean from your back porch. You'll see Turtles on our little secluded beach, amazing sunrises and sunsets over Maalaea Bay, and Whales during whale season! Maalaea Banyan is the only property in the area that includes a pool and jacuzzi. Just 1/4 mile away is Maalaea Harbor featuring snorkel, SCUBA, and sunset boat trips, the world famous Maui Ocean Center aquarium, restaurants and gift shops!

Superhost

A private pool area features a vibrant blue swimming pool surrounded by a spacious deck. Sun loungers are positioned around the pool, inviting relaxation. Lush greenery and tropical plants frame the area, contributing to a serene outdoor environment with a communal building visible in the background.

Condo in Kihei

4.82 out of 5 average rating, 131 reviews

Cozy 2 Bedroom Condo with pool near beach

Popular Vacation Rental near Kihei's best beaches! This highly sought after 2 bedroom, 1 bath corner unit at Kalama Terrace is close to Charley Young, Kamaole One, and The Cove beach parks. Located on the top floor, you'll enjoy ocean, Lanai and West Maui Mountain views. This condo is perfect for couples and families with a comfortable King bed and a Queen bed. note: The nightly pricing includes taxes like General Excise Tax 0f 4.712% and Transient Accommodations Tax of 10.25%.

Superhost

A serene pool area is surrounded by lush tropical landscaping, with sun loungers positioned along the water's edge. Palm trees provide shade, and vibrant flowers add color to the scene. The pool's clear blue water reflects the sky, enhancing the tranquil ambiance.

Condo in Wailea

4.83 out of 5 average rating, 146 reviews

Beautiful Palms At Wailea #608-April/May Discount

Beautiful Palms At Wailea ,2BR/2BA,Condo, located in the heart of Wailea. 5* location. Vinyl wood flooring & Split Air-Cond. system in hallway & in master-B/R. Fans through-out. Immaculately clean & comfortable. Walking distance to shops, hotels, restaurants, beaches.1200 sq. ft., wide open floor plan ,2nd. fl.unit. Low rise complex. Very private. Large lanai . Barbecue grills located near entryway of complex. Views from the Club House & Pool.The best place to stay!

Superhost

A clear swimming pool is surrounded by white lounge chairs placed on a sun-kissed patio. Lush green foliage provides privacy on one side, while a building is visible in the background under a bright blue sky with scattered clouds.

Condo in Lahaina

4.82 out of 5 average rating, 162 reviews

Whale Season Special! T-046-692-0448-02

We love to host! Listing was paused to help fire families! Read our 5*reviews! Directly across from a State Beach Park with morning sea turtles and the best Maui Sunsets. Food Trucks,Grocery store, Badass coffee, Miso Phat Sushi all in walking distance and give it a neighborhood feel. Onsite BBQ, Newly Updated Pool and Free Parking! 10 min to Kaanapali / Napili. Beach towels/Chairs provided. Clean, comfortable unit with lots of privacy and a great local vibe!

Superhost

The image depicts a serene swimming pool surrounded by a paved deck with multiple lounge chairs. Lush palm trees sway in the gentle breeze, and the ocean can be seen in the background under a partly cloudy sky.

Condo in Kihei

4.7 out of 5 average rating, 264 reviews

Oceanview Surfrider

Scenic unobstructed sea views, steps away from the pool. Remodeled August 2021. We are across the street from Cove Beach and Kalama Park. Ideal location for paddleboarders, beginner surfers, wave rider rentals next door. Convenient short blocks to restaurants, bars and entertainment, Foodland and convenience market. New sofa and queen mattress July 2022. King Cool Gel Bed. There is no dedicated work space. Island in the kitchen with 3 stools.

Top guest favorite

The outdoor pool area features a large, inviting pool surrounded by palm trees and lush tropical plants. Comfortable lounge chairs are positioned around the pool deck. A small waterfall adds a serene touch to the setting, with sunny skies illuminating the landscape.

Condo in Lahaina

4.98 out of 5 average rating, 184 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.

Superhost

An expansive green lawn extends towards the ocean, lined with lounge chairs for relaxation. Gentle waves roll onto the rocky shoreline, while the vibrant blue water is accented by wispy clouds in the clear sky. The view captures a serene coastal atmosphere.

Condo in Lahaina

4.86 out of 5 average rating, 102 reviews

Top Floor Stunner! Highly Upgraded! Summer Special

"The Kaleialoha" #414 Maui is open and ready for your arrival! Please come help us rebuild our community! This TOP FLOOR unit has unobstructed Ocean and outer island Views! This beautiful completely remodeled unit will take your breath away! New AC unit in living area! New High end sofa sleeper in living room! Cal King Bed and second TV in bedroom. Bosch Washer and dryer in unit.

Guest favorite

A large swimming pool is surrounded by palm trees, with clear blue water under a partly cloudy sky. A hot tub is situated on the left, and a green bridge spans the pool area, connecting both sides. Lush landscaping enhances the tranquil setting.

Condo in Kihei

4.92 out of 5 average rating, 175 reviews

Koa Resort Unit 5C - 1 BR Garden View

Back on Airbnb after 1 year rental by fire displaced Lahaina resident 1 Bedroom Garden view, ground floor condo on 5.5 acres across from beach in central Kihei. Close to all of the Kihei beaches, restaurants, shopping. Short drive to Wailea, Makena, Sugar Beach. Unit is 750 sq ft, with air conditioner in the bedroom and a 200 sq ft lanai with outdoor dining area.

Guest favorite

A clear blue pool is surrounded by tropical landscaping and palm trees, offering a relaxing atmosphere. A heated spa is located adjacent to the pool, with steps leading into both water areas. A bridge crosses over part of the pool, adding to the scenic view.

Condo in Kihei

4.87 out of 5 average rating, 107 reviews

Tropical Paradise Close to Everything

Aloha Aloha, if you are looking for the perfect place to call home in Maui, you just found it! Located on 5 acres of lush tropical grounds, with open grassy spaces and private walk paths, one of the only heated pools on Maui, private tennis courts, bocci ball court, ping pong, and the ocean directly across the street, Koa Resort is a private oasis in central Kihei.

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What guests are saying

Great Listing and Price!

4.88 out of 5 average rating, 52 reviews3 months ago

Mrs. Barbara was very good at giving us her time every time we had a question about something regarding the condominium. The truth is that my family's stay there was very pleasant. Thanks to her being very kind the whole time. This is something very important that I want to mention. I had to return the unit at 11am, but our flight was not until 4:30 and she allowed us to leave our luggage there for a few more hours. I really appreciate this because our luggage was safe the whole time we were gone.

Condo in Wailuku

What guests are saying

Maui Ocean and beach front Great views Lahaina

4.91 out of 5 average rating, 32 reviews3 months ago

Great place, with an ocean view. I'm not a fan of big resorts, this stay is in an unpretentious condo building which is right up my alley for vacation. Just a heads up, parking spaces in Maui are tight, I 2ouldnt have rented the jeep I did I knew how tight it was.

Condo in Lahaina

What guests are saying

Oceanview updated condo w/AC @ beachfront resort

5 out of 5 average rating, 5 reviews3 weeks ago

Nothing else to say. It was great. Good WiFi was important for me because I’ve been on Maui for work. Good WiFi was available. The back of the building was less than 50’ from the ocean. Great place to relax after work and to enjoy the sunset. Any appliances worked. Clean rooms and bathrooms. Nothing to complain.

Apartment in Kihei

What guests are saying

Resort Stay Entire 1Bdr Villa Kaanapali Beachfront

5 out of 5 average rating, 4 reviews14 months ago

Had an amazing vacation to Maui. Dee Dee made everything easy right from the start to the end. We even rented her own vehicle and she was so great to pick us up and drop us off at the airport. I highly recommend Dee Dee’s accommodations. Amazing host, responded so quickly to anything we needed, super friendly, always a cheerful hello and chat when she would see us at the pool or near by. I cannot wait to come back to Maui and will definitely book with Dee Dee again. Don’t question it, just book it!!!

Condo in Lahaina

What guests are saying

Ideal For Two Couples Travelling Together

4.77 out of 5 average rating, 35 reviews11 months ago

We spent 8 days with our 2 boys at Steven's place and we were all crying when we left. It has been home since day one, the location is very peaceful, the garden is simply amazing and the pool was the highlight for all of us. We met friendly neighbours and the location was perfect for discover a new piece of Maui every day. We had everything we need in the apartment, literally everything. Thanks again Steven

Condo in Kihei

What guests are saying

$149 a night May/June. Book Now. Pool and Ocean at

4.85 out of 5 average rating, 59 reviews4 months ago

This is just the perfect place to stay in Maui. We’re a few steps away from the beach and the house was well stocked with everything you need (beach chairs, snorkel gear, etc.). The property itself is very well maintained and Martha is a wonderful host.

Condo in Kihei

What guests are saying

Out Standing Value Surrounded by Palm Trees New AC

4.71 out of 5 average rating, 78 reviews1 month ago

My husband and I were very comfortable in this condo. We really appreciated how quiet the building is. Even though it is an older building, it is well maintained. The newer air conditioning was quiet and efficient. The lanai is large with a lovely view of the yard area. The kitchen is well equipped for a bit of cooking and the beach towels and chairs are handy. Fabulous washer and dryer. It might be good to have a spotlight or something to show Building C a bit easier when you arrive in the dark. Overall, we loved our stay. Thanks! Angus and Isabel

Condo in Kihei

What guests are saying

Koa Resort 1F 4 Bedrm,3ba 1800sf townhome

4.76 out of 5 average rating, 62 reviews2 months ago

This place was perfect for our families to enjoy our time together. Spacious and especially enjoyed the patio table for our meals outdoors. Bedrooms were also spacious and offered private quiet time. Kids loved the pool!! Our only regret was not staying longer.

Apartment in Kihei

What guests are saying

60%OFF APRIL-JUNE/25! Ocean views! Air Conditioned

4.97 out of 5 average rating, 114 reviews1 month ago

Dee’s condo was everything my husband and I could have asked for! It was fully stocked with everything we needed—sunscreen, ocean gear like chairs, boogie boards, and coolers, plus plenty of games and every kitchen item imaginable. There were also more than enough towels, along with condiments and spices, which made our stay even more convenient. Beyond the amenities, the condo itself was beautifully updated and decorated—so much so that neighbors in other units commented that they wished they had booked Dee’s place instead! We stayed for eight nights and had zero complaints. Even though we’re usually picky about beds that aren’t ours, this one was incredibly comfortable. To top it all off, Dee was so helpful and friendly throughout the entire process, making sure we had everything we needed for a perfect stay. If you’re looking for the best spot in Papakea, **this is it!** We would absolutely stay here again.

Condo in Lahaina

What guests are saying

Ideal location, 2 lanais, family friendly

4.92 out of 5 average rating, 93 reviews3 weeks ago

what an amazing place! So clean and so much included. The hot tub and pool were stunning and made paradise even more "paradise ". Julisa was very responsive and really cared about our stay and excellent communication. 10 🌟 🤩 ⭐️ stay!!! Very grateful to find this place!

Condo in Kihei