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

Mahalo Pono @ Ka'anapali Royal
We had an amazing time. Amy & Jay were extremely responsive and the property was immaculate. Our family of 5 had everything we needed to be comfortable, enjoy the beach and be within 15 minutes of anything on the west side of Maui. We plan on returning soon!

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.

3BR/3BA Pualei Beach House
Ryan's place was truly exceptional and worth the price. The spaces matches the photos and description, the neighborhood was stunning with plants and flowers everywhere, and you can't get any better than being steps from the ocean. We will absolutely be staying here again! The AC worked great, the beds were comfortable, and they had good quality linens and towels. Something important to me is how comfortable the sitting area is, where people gather together. This living room was perfect! Couch was clean and comfortable, and the chairs next to it were too. It was easy to lounge in there with our family. We also really appreciated that there were so many great beach accessories we could use, like chairs, boogie board, sand castle buckets, etc. Ryan was easy to get a hold of and gracious. We did suggest that he put some grease on the bathroom door in the Ocean (master) bedroom because it gets quite loud when opening at night. He said they will get that fixed! Can't wait to come back!

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!

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

3BR Loft Beach Bungalow w/ Bikes & Pickleball gear
Prime location. House was equipped with beach necessities which made it really convenient for the family. A short walk across the highway and you're right at airport beach.

Aloha Aku Honu2 Suite – Relax by the Sea in Tranqu
My husband and I greatly enjoyed our stay at Aloha Aku. The place was amazing. Being able to walk out onto the patio, cross the yard, and go right onto the beach was amazing. We also really enjoyed the bikes and kayaks we were able to borrow from the property—it was both fun and saved us a ton of money since we didn’t have to rent those things. The place was neat and pristine and had everything we needed. If it wasn’t in our suite, we were able to find it in the common room. Gary and Char are great hosts and all of their staff were super friendly and helpful. They had great recommendations for places to go and things to see. I HIGHLY recommend Aloha Aku for your trip to Maui. You will not be disappointed! If we ever get the opportunity to visit Maui again, we will stay here, no second thought about it!

#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!!!
Condo rentals with a pool

Wailea Surf Shack: Golf, shopping & beaches!
Jes’s place was bright, open and had an amazing view. We were greeted with a gifts of fresh fruit, chocolates and hand written card. Her attention to detail with her condo was incredible and made our stay so comfortable. Everything you could want in a Airbnb . Would book this place again in a heartbeat! Quickly responded and accommodated us with an early check in. Pools and jacuzzi were great as well. Thank you Jes

Gem near Keawakapu Beach - Privacy and Ocean Views
Wir hatten eine wunderbare Zeit auf Maui und können unseren Aufenthalt in The Palms at Wailea, Apartment 1102, bei Elena nur wärmstens empfehlen. Die Wohnung war exakt so, wie beschrieben – sehr sauber, top ausgestattet und durchdacht eingerichtet. Man fühlt sich direkt wohl und findet sich sofort zurecht. Die Lage ist perfekt zwischen Wailea und Kihei, also ideal, um die Insel zu erkunden. Ein echtes Highlight war die Terrasse mit der ruhigen, nach hinten gelegenen Aussicht – morgens perfekt fürs Frühstück, abends traumhaft für den Sonnenuntergang. Es gibt sogar eine zweite Terrasse, auf der man am späten Nachmittag noch Sonne tanken kann. Auch der Poolbereich war sehr angenehm: sauber, gepflegt und entspannt. Trotz einiger Kinder war es nie laut – es wird darauf geachtet, dass die Atmosphäre ruhig bleibt. Alles in allem hat einfach alles gepasst – von der Kommunikation über die Ausstattung bis hin zur Lage. Vielen Dank an Elena für die tolle Unterkunft.

Renovated Condo | 3 Min Walk to Toes in the Sand!
Perfect condo. We were first time visitors to Hawaii and loved our stay. Walkable to 3 different beaches. Ice cream, restaurants and cafes all a short walk away. Close by rental car parking. Area felt very safe and clean. We came to Maui for a wedding hosted in the Wailea resort area. This was just a short drive away. Excellent spot if you want to be close to Wailea but not pay resort prices. The unit was clean and comfortable. Plenty of towels and beach chairs. Easy to find and nice keyless entry. Would stay again and recommend this rental.

Hot Deals! Limited Availability- Maui Getaway
Kalea’s was alway available to answer questions very quickly. The condo was very well taken care of and had everything we needed. Loved the location and area much different than Kanapali as it’s much closer to other areas of the Island to explore. The lights and fan can be tricky at times but remember your own Hawaiian time. Mahalo

Beachfront Wailea Condo with Private Lanai
Great location, allowed me to do an early check in and very quick at responding. Pool was private and grounds are beautiful. Quick walk to the beach, private patio, spacious living room, beautiful bathroom, comfortable bed, easy parking, a ton of stuff to do in area. Would book again without question !

Wailea Walk to Beach Spacious Lanai Full AC & Pool
Jill’s place was absolutely amazing. My husband and I loved this spacious unit. It was everything we needed and more. The location was so beautiful and we loved being a 10 minute walk to the most beautiful and private feeling beach. We highly recommend Jill’s place!

Spacious tropical oasis near gorgeous beaches!
Connie’s place was amazing. The condo is located in a convenient area close to the beach and local shops. The unit was equipped with all the beach gear you need so you don’t have to worry about renting on the island. The space was very cozy and we felt at home. The bed was amazingly comfortable. We loved the lanai and enjoyed relaxing there and taking in the lush gardens. The pools in the complex were perfect as well. We will be staying again. 🩷

New Listing | Maui Oasis at The Grand Champions
A perfect stay in paradise! We had such a lovely stay at this apartment. Everything was beautifully set up, perfectly clean, and fully functional. It truly felt like a home away from home. The hosts were incredibly responsive and caring throughout our stay, which made the experience even more special. Their hospitality was wonderful, and we absolutely fell in love with Maui. We’ll definitely be back. We are so grateful
Quick stats about vacation rentals with a pool in Wailea-Makena
Total rentals
1.8K properties
Nightly prices starting at
G$12,546 GYD 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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