
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

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
A wonderfully comfortable Hawaiian cottage with plenty of room to spread out. It’s fully equipped with beach chairs, snorkel gear, pickle ball paddles and even a cooler. Van was so helpful and accommodating during our stay. Easy 10 minute walk down to the main beach access with a great boardwalk. Highly recommend this great little spot.

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
Leslie’s place was a gem! If we are ever back to Maui, we would love to stay here again. The location was perfect for snorkeling, and Leslie’s local recommendations were awesome. The check in and out was very easy to follow. The place has beach chairs, boogie board, beach towels and so many more! We also appreciated the hot jacuzzi in the condo and the beach in the front.

Spacious 2BR Best Ocean Views -Kapalua Golf Villas
Place was so so beautiful and peaceful. we loved it. The check-in was not very comfortable. The management was very adamant about check-in only after 4:00 PM even when there was no one at the property. we had little kids and we got there at 2 and we had to just sit in the car for 2 hours with little kids even after requesting the host. but other than that property was very clean and very nice. i would book it again. it was very spacious. it was exactly like how its mentioned on the booking site.

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!

3BR/3BA Pualei Beach House
Ryan's place was exactly as pictured. The neighborhood and townhouse was very quiet and family friendly. Ryan was very responsive to the small things that can sometimes come up when traveling. Lahaina is still in process of rebuilding but even so there was more than enough to stay busy. Would highly recommend.

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 - it’s easy to navigate. The view from the bedroom and living room is brilliant 😍 We really enjoyed the stay. Definitely recommend 🙌🏻
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.

Tropical Resort Centrally Located
Lily's place is just as described. Comfortable and had everything our family of 5 needed for 1-week stay. Kitchen was well stocked and we appreciated that all the beach stuff was provided. Lily was very communicative. Close to many beaches, restaurants, and stores.

Kaanapali Shores - SUPER CLEAN! OceanView 1bd/1ba
Wish we could have stayed longer. Place was so clean, convenient location in the building and easy in and out access to explore the surrounding areas. We felt right at home. Loved the balcony views. Washer and dryer are big and nice, perfect for us between stops on different islands. Kelly was super nice, communicative and responsive! Would absolutely come back.

Sea Views entire 1 Bedroom Apartment Poolside
Very nice apartment in a very good location. South Maui Gardens are very near and highly recommended. Carolyn was also very friendly and easy to reach.

Incomparable Maui Sunset condo, includes all taxes
First and foremost was the excellent, prompt communication with the host. Kyra always responded to any questions, and offered suggestions that encouraged us to explore the beautiful island. The condo itself has everything one would expect, from a very comfortable bed, to a fully equipped kitchen, BBQ's cleaned daily in the beautifully maintained grounds, and a short walk to the beach. Also, with a security guard present, one feels very safe. Definitely recommend!

Cozy Cute Condo | Maui Vista | Walk to The Beach
Juliana was great-super helpful and communicative. Her place was very conveniently located. Would stay again!

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.
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
Destinations to explore
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