
Vacation rentals with a pool in Wailea-Makena
Find and book unique homes with a pool on Airbnb
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

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!

Island-Inspired 2BD Oceanfront ~ Quam Properties
We stayed in two units at Hololani. This one was my fav. More spacious. Wonderful lanai. Unit is comfortable and we felt at home. Made some great dinners and enjoyed the view. This is a neighborhood condo not the high end resort. Pool amazing. 90 degrees! We loved our stay! Note units are Not air conditioned. Fans adequate. A couple of big box fans would have gone a long way to making us more comfortable.

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!

Maalaea Kai 307 - Maui Prime Oceanfront
This was a fantastic place to spend our week in Maui. The condo was amazing and spacious with all the amenities you would need to enjoy your time. The location is perfect, relatively close to the airport and well situated next to route 30 so you could go everywhere on the island quite easily. The view from the condo is second to none, from the patio you can easily see the Haleakalā mountain and from the front door is a great sight of the western Maui mountains. And on top of everything this condo was much more peaceful than the huge resort areas. There were not too many people around, and even when we did go to the beach we were able to find a spot easily. I’d recommend this condo for anyone who wants to spend a week or a few days in Maui - the price is quite good compared to the normal resorts, you get a great view and anything you don’t pick up on your way from the airport you can grab on a 20 minute drive to Kihei. This place was perfect for us.

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!

Maui direct ocean front . Super private
Wow! What a place! I’m not the best writer so I’ll keep it short. Jay was great and his place was beautiful. We were there in early March and could see whales breaching, slapping tails and find, and more EVERY morning day and night. Turtles constantly in the ocean near the sea wall. And just overall a fantastic place. You are plenty close to Kaanapali or Kapalu yet remote enough you feel you’re at your own home away from home. Great walkable food options, and just everything was amazing. Bed is SUPER comfortable!! Jay provides everything you need. Thank you Jay, mahalo!

Kahana Villas: Oceanview 2BR Condo w/ AC & Pool
Great location with a beautiful view.
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.

Renovated 2BD/2BA | 3 Min Walk to Beach | A/C
This was a lovely apartment with a fantastic host. Dimitry catered for everything that he possibly could and when certain aspects such as early check in/ late check out were not available, Dimitry did everything he could to offer alternative suggestions. The apartment was clean and comfortable and we well catered for. I’d recommend this Airbnb to anyone.

Relaxing Kihei Condo right on the Beach in Maui
We loved our stay here! Beautiful property and beach. Everything we needed was available. It was so helpful to have access to beach chairs, towels, snorkel gear, etc.

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.

NEW Ocean View 1 Bedroom Condo with Common Hot Tub
Super clean, amazing ocean front Condo with everything we needed! Communication with Dan was outstanding, he provides all the information you need to find the place and access it without any problems. The Condo is beautiful, very comfy bed, equiped with everything you can think of and great view! We are looking forward to be back in December!

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.
Quick stats about vacation rentals with a pool in 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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- Sandy Beach
- Kaipukaihina
- Laie
- Wailea Beach
- Hāmoa Beach
- Manele Golf Course
- Oneloa Beach
- Pahoa Beach
- Maui Ocean Center
- Kailiili
- Mokulau Beach
- Kaulana Beach
- Hallulu
- Paukukalo Beach
- Ka'anapali Golf Courses
- Pepeiaolepo Beach
- Kahemanō
- Halepalaoa Beach
- Maluaka Beach
- Waipu
- Changs Beach
- Oneuli Beach
- Honukanaenae
- Maui Golf & Sports Park
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