
Holiday rentals with a pool in Wailea-Makena
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Top-rated rentals with a pool in Wailea-Makena
Guests agree: These homes with a pool are highly rated for location, cleanliness and more.
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Popular amenities for Wailea-Makena rentals with a pool
House rentals with a pool

Oceanview Home with Private pool and hot tub
Excellent location, beautiful view, house was well stocked and the communication was terrific from both homeowner Steve alongside the property manager Walker. Speedy responses to any questions we had. Our family had a blast in Maui and would rent from Steve again. Steve also had great recommendations for local eating alongside a picturesque sunset spot. For our family of five, Steve's home was a winner.

Maalaea Kai 307 - Maui Prime Oceanfront
We had the best time at this condo! It was quiet and clean and was exactly what we were hoping for! Don was incredibly responsive when I had questions or needed recommendations to rent baby gear! We had a great time and hope to Come back again

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.

#1 Kaanapali Beach Modern Condo C101 Maui Eldorado
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!!!

Aloha Aku Hula Suite – Find Peace by the Shore
This is really well situated. A hundred feet from the back door and you are on the beach. Wake to the sounds of the birds from the adjacent wildlife refuge. It's intimate, with only four rental units in the building. No big hotels in the area, so the beach is uncrowded, and has basking sea turtles! Beautiful sunsets. They could have had 5 units, but kindly equipped the middle unit as a common room where departing guests leave food, drinks, and supplies like sunscreen, bug spray, etc. Free snorkeling and beach supplies, bikes with lights/locks/helmets, boogie and paddleboards, an ocean kayak, TONS of movies, books, and CDs. Our unit was clean, the bed was comfortable, and the kitchen was equipped with everything except a dishwasher and a full-size oven (there is big high quality toaster oven). Note the toilet/shower area is open at the top. Gary and his team communicated clearly for entry and exit but otherwise left us alone unless we had a question. Would definitely stay again.

Maui direct ocean front . Super private
We absolutely LOVED our stay here. Originally, we were only supposed to stay 4 nights, but we loved it so much that we extended our stay 2 more nights! Jay made it so easy to extend our stay and make us feel welcomed. The location was close to various beaches and restaurants, yet it still felt private. It was calm, peaceful, and exactly what we wanted. The view was absolutely breathtaking and every night we slept with the slider open to hear the waves. We even saw turtles from the balcony!

Beautifully Remodeled 3 Bedrooms/2Bathrooms
Luan was a wonderful host, was available with any questions I had. The home was clean and felt cozy. A home away from home. The location was great and was walking distance from the gorgeous beach, shopping, and restaurants. I would definitely stay again and highly recommend.
Condo rentals with a pool

Maui Kihei Condo - Gem Steps from Ocean & Beach
Place was exactly as described. Laurie went above and beyond to give recommendations and instructions. We loved having the kitchen, in unit washer and dryer, beach chairs and cooler. Once we arrived we didn’t need a thing. Would definitely stay here again.

Beautiful Ocean Views and Aloha at Wailea Ekolu!
The pictures and description don’t do justice to this amazing place! We had the most wonderful time and our expectations were surpassed! The ocean view is much better in person, the lanai was perfect because our toddler could play outside while we enjoyed relaxing in the lanai! Perfect place and really kid friendly! :)

Newly Renovated Corner Unit w/ View at Maui Vista
David's place was perfect for my husband and I. Place was modern and clean, and there was a plethora of great quality beach equipment in the hall closet. Despite only the two window AC units, we appreciated the ceiling fans and small extra fans around the space. Being able to use the Dyson or Roomba to vacuum up grains of sand was a nice touch - felt like I was at home! David was proactive and touched base with us even when we didn't need anything. Location is great to be able to walk to restaurants and food trucks off S. Kihei Rd. Would definitely stay here again. Thanks for letting us stay in your home!

21A Grand Champions 1 Bed - Ulua & Mokapu beaches
Absolutely recommend Fiona’s place! Fiona as a host was responsive and very welcoming, and her Airbnb was perfect. Amazing location, well stocked with all beach supplies, and comfortable. We would stay here again in a heartbeat.

Maui Retreat Ekahi 50F -All YOU Need! 10% OFF WEEK
We’ve stayed in this complex a few times before and keep coming back because we always love it! Debra’s place is one of the best equipped ones we’ve stayed in! Kitchen made it easy to cook and beach equipment was appreciated. Being a second floor unit with high ceilings means it takes a while to cool down. Only one thing that could be improved: If you’re a person who likes to sleep with the ceiling fan on, the bedroom has one, but it really needs to be replaced — it’s very noisy (the one in the living room is silent in comparison). After a couple of nights with the noisy fan, we chose to keep it off and were reasonably comfortable with the AC unit. Otherwise we would stay again!

Modern Renovated Palms at Wailea Condo!
The condo featured everything we could hope for to enjoy the beaches and our vacation with a baby including full kitchen equipment, various baby chairs, toys, a bathtub and beach equipment (umbrellas, beach chairs, boogie boards, beachwaggon...). We really liked the interior design, it made us feel more at home.

Aloha Moon - The Honeymoon Hideaway
Wow! Let me start by saying… just book it! From the moment you walk in, you can feel the warmth and hospitality that Kate & Mark pour into this space. Every detail, from the thoughtful goodies to the stunning decor, is curated to perfection. The design is both aesthetically pleasing and inviting, instantly making you feel at home. We stayed at the Fairmont for the first part of our trip for business, and honestly, we both agreed—this place felt even more prestigious! My wife loved the bed sheets so much that she had to look them up, and they are now sitting in my Amazon cart, ready to purchase when we get back home. Another standout feature was the tablet they provide—it’s incredibly helpful and packed with all the information you could ever need to enhance your stay. Kate & Mark truly know what they’re doing, and we couldn’t have asked for a better experience. We hope to be back in the future!

Wailea Hidden Gem
We had a wonderful stay here for our daughter’s 1st birthday adventure! The place was perfect for our family of three. It was beautiful with an incredible amount of natural light. The place was super clean, and equipped with everything we needed, including a pack-and-play and a high chair for our baby girl. It was a great place to cool down and relax after days out exploring, and the location made it easy to get around. The home had everything we could have asked for and more. We had a great time making memories.
Quick stats about holiday rentals with a pool in Wailea-Makena
Total rentals
1.8K properties
Nightly prices starting at
$100 NZD before taxes and fees
Total number of reviews
45K reviews
Family-friendly rentals
1K properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
1K properties have a dedicated workspace
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- Maui
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