
Holiday 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

Brand Newly Remodeled Luxury 2 BR - Kapalua Golf
We loved our stay at this place. The location in Kapalua and the beautiful grounds were unbeatable. There were just a few hiccups initially but they were resolved within 24 hours. Firstly the AC was not working which was hard with 2 young kids and the warm climate. The company was going to send a tech but he wouldn't be in until the next day so luckily my husband was able to fix it in the meantime. Secondly, we had ordered and paid for a pack and play which was supposed to be in the unit on arrival but did not arrive until 9 pm (already after my child needed to go to sleep). I was told this would be refunded by the lovely manager Scott who came to deliver the pack and play. He was also kind enough to lend us his binoculars for whale watching :) The unit itself is beautiful. Very new and clean and exactly as the photos. We would 100% rebook if staying back in Kapalua, Maui.

Luana Kai C209
Leslieās 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 Leslieās 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.

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!

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

Kula Jewel - Pool, Hot Tub & Awesome Views!
The new Kula Jewel is an amazing property with an incredible panoramic view of the island with an exceptionally cozy and spacious interior and a lovely porch. The main living area and kitchen were beautifully designed and highly functional which made us feel at home. The master bedrooom was so relaxing with a great mattress and was made even better when opening the windows at night and listening to the gentle rhythm of raindrops falling. The master bathroom design was brilliant. Pamela and the property manager Jim made sure our young daughter was well taken care of by setting up a comfortable pullout twin size bed in the Master so she could stay in the same room with us and not be scared. The other two bedrooms were spacious and well equipped, we just didnt need to use them. Pamela is the best host we have ever had the pleasure of working with on Airbnb. Her commnication was superb, recommendations for what to do and where to eat on the island spot on, and we cant wait to come back!

Aloha Aku Honu2 Suite ā Relax by the Sea in Tranqu
Absolutely incredible stay. The suite was everything we needed and more. The beachfront porch was peaceful and private. There was gear for every beach activity you could ever want to do and it was so fun. We cannot wait to come back!

#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!!!

Maui direct ocean front . Super private
The view was absolutely beautiful! This was a very peaceful and private oasis in Maui! I would love to come back and stay here again. The place was clean and the amenities were super nice! I stayed here with my boyfriend and it was the perfect space for us two.
Apartment rentals with a pool

Wailea Surf Shack: Golf, shopping & beaches!
We thoroughly enjoyed our stay! Great communication and instructions with the host! This unit includes everything you need to enjoy your vacation. My husband particularly liked how everything is well labeled :) This is a great location in Mauiā¦close to beach, golf, shopping, restaurants and more! If we could give it more than 5 stars we would. 100% would stay here again!

Gem near Keawakapu Beach - Privacy and Ocean Views
Amazing spot and stay

Ohe'o || Wailea Ekahi Unit 28B || Lowered Rates
This condo worked well for us. We were traveling with family who had rented other units in this complex. We liked ours best, due to its updated/well-stocked kitchen, paper/toiletry supplies, two bathrooms, wide lanai, convenient parking, comfortable bed, generous square footage, and beach/snorkeling gear. We enjoyed the absolute quiet (this unit is away from the road), but found lots to do, especially in the excellent main pool area and on the relatively-wide beach, with easy snorkeling and walking options (Wailea luxury resorts to the left; natural beauty to the right). If you're looking for family-friendly green space and don't mind a longish walk to the main pool/beach, consider this property. If you have mobility issues that make walking difficult or need onsite restaurants, high-end furnishings and spa-like baths, you might not be happy here. We found it very comfortable. It was evident to us that Jazlyn has put a lot of thought into meeting her guests' needs. Highly recommend.

Maui Retreat Ekahi 50F -All YOU Need! 10% OFF WEEK
Weāve stayed in this complex a few times before and keep coming back because we always love it! Debraās place is one of the best equipped ones weāve stayed in! Kitchen made it easy to cook and beach equipment was appreciated. Being a second floor unit with high ceilings means it takes a while to cool down. Only one thing that could be improved: If youāre a person who likes to sleep with the ceiling fan on, the bedroom has one, but it really needs to be replaced ā itās very noisy (the one in the living room is silent in comparison). After a couple of nights with the noisy fan, we chose to keep it off and were reasonably comfortable with the AC unit. Otherwise we would stay again!

Modern Renovated Palms at Wailea Condo!
The condo featured everything we could hope for to enjoy the beaches and our vacation with a baby including full kitchen equipment, various baby chairs, toys, a bathtub and beach equipment (umbrellas, beach chairs, boogie boards, beachwaggon...). We really liked the interior design, it made us feel more at home.

Romantic Beach Retreat, New King Bed & A+ Wi-fi
Sara is a fantastic host! She is very easy to communicate with, responds quickly and gives great recommendations. The condo is well situated across from Kamaole III (we watched the sunset there every night) and in close walking distance/short drive to other great beaches. Saraās condo was a great home base and had everything we needed (beach chairs, umbrellas, beach towels etc.). We definitely would not hesitate to stay again!

Spacious S. Kihei Suite New A/C across from Kam 3
Quick responses. Did not need to communicate much since the place was wonderful!

Wailea Ekolu Village | 1205
Enjoyed everything about this place. Love how close it was to walk to the mall and several restaurants. The beach was 4-5 min drive. The unit itself was spacious and felt very peaceful. Full kitchen and laundry in unit
Quick stats about holiday rentals with a pool in Wailea-Makena
Total rentals
1.8K properties
Nightly prices starting at
ā¹5,138 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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