
Vacation rentals with a pool in Wailea, Wailea-Makena
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Top-rated rentals with a pool in Wailea, 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, Wailea-Makena rentals with a pool
House rentals with a pool

Aloha Aku CoCoPalm Suite – Experience Tropical Bli
We had the most amazing time. All of the small touches were there, and we were constantly surprised by the high level of service and pride in the property. You cannot beat the view, and the hot tub is awesome! The unit was stocked with the nessesities, as well as delightful extras. The bed was incredibly comfortable, and the cherry on top was the ducks!! So charming. We cannot wait to come back!

Newly Remodeled Cottage
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.

ICC 20 Remodeled 2BD Hawaiian Cottage w Pool AC
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!

Luana Kai C209
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!

Oceanview Home with Private pool and hot tub
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!

Centrally located and steps to the beach!
Mike and Ashley’s place was perfect for our little getaway. It was one of our birthdays and they had a little balloon and card for us. They were very responsive when we needed a couple of things and I 10/10 recommend to stay here!

Stunning ocean view, heated pool at home by Wailea
We were so thankful to stay at Sandra's lovely place. The villa was clean, comfortable, and had everything we needed. We were able to make meals, including using the bbq, and ate most of our meals on the deck and a few out by the pool. The pool was nice and warm, and we loved the outdoor shower. The entire space was very private. Sandra was gracious and accommodating with a special, last minute request, we highly recommend this stay to other guests.

Oceanfront 2BR Condo w/ Pool Access & Sunset Views
Very highly recommend this listing! the views were stunning and with obstruction. The suite feels very private and the lanai is ideal for anyone looking to relax while looking out and watching the ocean. The unit is also very near attractions and beaches on West Maui with great parking access (included which is rare) and calm roads. Even during higher surf days, the sound proofing in the suite didn't disturb our sleep. we had a very enjoyable time!
Condo rentals with a pool

Condo-FULL AC-BEACH Kihei Maui
We had such great time during our short stay. The listing was just as described, with all the beach amenities provided, towels, chairs umbrella, etc. The location was right off the beach, yet very quiet during the night. Highly recommend staying here.

Discounted Rates! 305 Beautiful 2 bed/2 bath
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!

Luxurious Condo in South Kihei
Honestly, John’s place was fantastic. The fact that he had snorkeling gear, chairs, towels, and a beach with so many turtles so nearby was amazing. His place was immaculate, easy to get into, a parking spot so close by, his communication was on point and the place was just honestly one of the best Airbnbs I have ever been to is saying a lot. Thank you John for everything.

Luxury 2bd2bth Kihei Maui Condo Across from Beach
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!

Cozy Cute Condo | Maui Vista | Walk to The Beach
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.

Considered the Best Location Oceanfront on Maui
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.

1br remodeled ground floor condo near everything
Such a great location—we walked to dinner almost every night and there are several beaches a walk or quick drive away. Quiet, clean, and lots of beach friendly items for use like coolers, chairs, etc.

Front Row! 1 bd/2 ba with big ocean Views! Maui Ka
One of the few Airbnb owners that understand that guests want to be comfortable when they are hanging out in the unit. Highly recommend. Great views and close to everything. I will definitely be booking this unit again next time I'm in Maui.
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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