
Vacation rentals with a pool in Wailea, Wailea-Makena
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Top-rated rentals with a pool in Wailea, Wailea-Makena
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Popular amenities for Wailea, 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

Centrally located and steps to the beach!
Mike and Ashley were incredibly amazing and helpful. They really went above and beyond for us. Really appreciated the special touch they left us for our anniversary and will recommend them to and friends and family that visit Maui. Their place is beautiful and it looks even better in pictures. It is perfectly homey, private, and quiet, which was very nice but also close to the beach with a three minute walk couldn’t recommend staying with Mike and Ashley more. Thanks for helping make our anniversary trip special!

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 was a fantastic host. She was responsive and so friendly. She truly loved the area and making guests feel at home. The space itself was such a dream. It had everything we needed and then some. The location and views were stunning. we sat on the porch almost every night just to take it all in. We loved staying at the Kula Jewel and would stay here again!

Aloha Aku Honu2 Suite – Relax by the Sea in Tranqu
Absolutely incredible stay. The suite was everything we needed and more. The beachfront porch was peaceful and private. There was gear for every beach activity you could ever want to do and it was so fun. We cannot wait to come back!

#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!!!

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!
Condo rentals with a pool

Gem near Keawakapu Beach - Privacy and Ocean Views
Amazing spot and stay

Oceanfront Getaway, Brand New, Steps To Beach
Gorgeous spot! The location is fabulous, close to fun restaurants and the harbor, but it still felt private. We would 100% stay here again!

Spectacular Ocean Front 1bd at Menehune Shores
A gem in Kihea High end remodeled kitchen and bathroom with thoughtful amenities / awesome host / beautiful full ocean view / easy parking and close to elevator. Winner!!

Wailea Elua 1101 - Beachfront Section - Ocean View
Beautiful location and setting. Very well organized and equipped. Especially nice bathroom and kitchen. She was also very thoughtful on the smaller details too, such as hooks to hang towels, clothes line in tub, non scented cleaning products . Also Very nice setup on the lanai

Newly Renovated Corner Unit w/ View at Maui Vista
Last minute booking for us and man did we get lucky finding this unit available! Nothing negative to say about it and sad to leave. We’ll be back!!

Gorgeous Condo in Wailea Ekahi Village!
We had the most lovely stay at this resort! Jordan’s place is exactly like the photos and is beautifully private. While you cannot exactly see the ocean from the condo—the trees and foliage has now grown too high—we loved opening the late sliding doors and listing to the ocean whenever we were at the home. The kitchen was wonderfully stocked and we loved having access to all of the coffee and appliances supplied. The walk to the beach is easy and the pool has all the amenities you can imagine. There a many places to eat, grab coffee, and activities in a close drive to the location. We did see a singular cockroach inside near where a screened window was ajar. Jordan was very responsive when we message him about this. We had absolutely no concerns about the cleanliness of the condo throughout the rest of our stay. Overall, this was a tropical luxury stay perfect for a honeymoon filled with privacy and easy access to all things one could want in Maui.

Wailea Resort studio suite
The place is excellent. I recommend it. The location is magnificent. We will definitely come back.

Wailea Ekahi Village | 12B
Great location with a view of the water though not necessarily the beach. The place has recently been updated and would be great for a couple. We liked the shaded patio and the cold AC. Ice machine worked well too in the fridge though as this is a studio I recommend you turn it off before going to bed. We didn’t cook at all but everything was there (except salt and pepper). Beach chairs were also provided and towels of course. Washer and dryer were newer and clean. We didn’ use them much. Lighting in the unit was nice, with dimmers throughout. This was useful when waking up or going to bed. A nice comfort addition that we appreciated. It’s a 4 minute walk to the beach and the pavilion. We went in October and the pool and beach were not too busy and the people were respectful. It was quiet and peaceful. The pool house is a great location to have a coffee or a beer at and watch sunset or listen to the waves. We would recommend this place. Great value and location.
Quick stats about vacation rentals with a pool in Wailea, Wailea-Makena
Total rentals
1.8K properties
Nightly prices starting at
ﺩ.ﺇ220 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
- Kaanapali Beach
- Kahului Beach
- Lahaina Beach
- Sandy Beach
- Kaipukaihina
- Laie
- Honolua Bay
- Spreckelsville Beach
- Kapalua Bay Beach
- Olowalu Beach
- Pahoa Beach
- Wailea Beach
- Manele Golf Course
- Hāmoa Beach
- Oneloa Beach
- Maui Ocean Center
- Mokulau Beach
- Wailea Golf Club
- Palauea Beach
- Old Lahaina Luau
- Wailau Valley
- Papaloa Beach
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