
Vacation 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

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!

Spacious 2BR Best Ocean Views -Kapalua Golf Villas
Very spacious place, well stocked and beautiful location. Host was very responsive and we felt it was good for the price. Would definitely come back again.

Oceanview Home with Private pool and hot tub
Steveās 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!

Luxury Panoramic Ocean Views!
Kapalua Ridge is an incredible development and Kevinās place was absolutely stunning. The entire setup gives all the resorts in the area a run for their money. The place itself was clean, well equipped, massive and luxurious. The views of the coast and islands was beautiful and we enjoyed stunning views everyday. Itās a short walk to the beach and few steps past the nearby beach gets you to Kapalua bay which is where the restaurants are. The bathrooms were very large and luxurious - which we loved. Our host Kevin was super responsive and was very helpful with recommendations and helping us find things in the airbnb. Will come back here if in Maui - amazing place.

Kapalua Ridge 622 Luxe Ocean and Coastal Views
Perfect location with beautiful beaches nearby. Not a lot of restaurants around but if you have a car - itās easy to navigate. The view from the bedroom and living room is brilliant š We really enjoyed the stay. Definitely recommend šš»

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.
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.

Beach Area Condo
Karen is an excellent Host. The Apartment is perfect, modern, great location, well equipped, there are plenty of restaurants in walking distance but yet the Apartment is in a peaceful location. There is a beautiful beach literally minutes away. Can't wait to come back.

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!

Incomparable Maui Sunset condo, includes all taxes
The owners were so welcoming and proactive. They went above and beyond to ensure our stay was wonderful. They had some uncontrollable maintenance issue arise that they handled immediately and it did not disrupt our trip at all. The building and amenities were perfect. Our son loved exploring the beach and chasing crabs. Our daughter spent the evenings in the pool after our daytime adventures. We will be back and are so grateful to have experienced this slice of paradise.

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.

Remodeled Kaanapali golf resort 1500ft condo w/AC
We loved this place. the complex is not crowded at all. Lots of bbq grills and multiple pools. The best part is the beach. They have chairs and towels that you can check out for free at the beach so you don't have to haul them down. Just call the front desk and they send a free golf cart to take you down to the beach. The beach was amazing. Not crowded at all and it was an amazing beach. I would definitely stay here again.

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 werenāt ready to go back home. We will definitely be back to Maui Sunset.
Quick stats about vacation rentals with a pool in Wailea-Makena
Total rentals
1.8K properties
Nightly prices starting at
$60 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
- Oneloa Beach
- HÄmoa Beach
- Manele Golf Course
- Maui Ocean Center
- Kaulana Beach
- Hallulu
- Paukukalo Beach
- Kailiili
- Mokulau Beach
- Pahoa Beach
- Ka'anapali Golf Courses
- Honukanaenae
- Puu Olai Beach
- Oneuli Beach
- Kalepolepo
- PÅhakukÄŹ»anapali
- Kalua
- KaŹ»Åpala
- Slaughterhouse Beach
- Wailau Valley
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