Holiday 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

Superhost
Home in Kihei
5 out of 5 average rating, 3 reviews

Aloha Aku CoCoPalm Suite – Experience Tropical Bli

AshleyRating, 5 stars74 months ago
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!
Top Guest favourite
Home in Lahaina
5 out of 5 average rating, 23 reviews

Newly Remodeled Cottage

KrystalRating, 5 stars3 days ago
We had a wonderful week long stay here with the kids and grandparents. The house was spacious and exactly as described in the listing. I really appreciated how responsive Van was the few times we reached out. It was also a big bonus that they had a great selection of beach toys, good quality beach chairs, a boogey board and noodles that we could use. The house was well stocked with everything needed for our stay. The walk to the beach was a bit far for our small kids (all under 5), but it would be an easy walk for big kids and adults.
Guest favourite
Home in Kihei
4.96 out of 5 average rating, 23 reviews

Luana Kai C209

ShriyaRating, 5 stars6 months ago
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!
Guest favourite
Home in Kihei
4.93 out of 5 average rating, 30 reviews

Oceanview Home with Private pool and hot tub

JennieRating, 5 stars3 weeks ago
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!
Guest favourite
Home in Lahaina
5 out of 5 average rating, 6 reviews

Luxury Panoramic Ocean Views!

ShrijitRating, 5 stars6 months ago
Kapalua Ridge is an incredible development and Kevin’s 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. It’s 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.
Guest favourite
Home in Lahaina
5 out of 5 average rating, 12 reviews

Kapalua Ridge 622 Luxe Ocean and Coastal Views

AdilbekRating, 5 stars5 months ago
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 🙌🏻
Guest favourite
Home in Kihei
4.96 out of 5 average rating, 427 reviews

Stunning ocean view, heated pool at home by Wailea

JonathanRating, 5 stars3 weeks ago
The property grounds are manicured and gorgeous. The villa itself was spotless with the perfect balcony view for sunsets and our morning coffee. We were fortunate to meet Sandra who is a delight and full of local recommendations. The location is privately tucked away from the busier areas but still close enough to everything you need. The photos and description are accurate. The space was perfect for our small family of 3.
Superhost
Home in Kaanapali
4.88 out of 5 average rating, 109 reviews

#1 Kaanapali Beach Modern Condo C101 Maui Eldorado

JesseRating, 5 stars7 months ago
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

Superhost
Condo in Kihei
4.77 out of 5 average rating, 267 reviews

Condo-FULL AC-BEACH Kihei Maui

ElenaRating, 5 stars2 weeks ago
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.
Guest favourite
Condo in Kihei
4.91 out of 5 average rating, 151 reviews

Beach Area Condo

ManojRating, 5 stars4 weeks ago
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.
Superhost
Condo in Lahaina
4.86 out of 5 average rating, 36 reviews

Discounted Rates! 305 Beautiful 2 bed/2 bath

AubrieRating, 5 stars2 months ago
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!
Guest favourite
Condo in Kihei
4.89 out of 5 average rating, 132 reviews

Incomparable Maui Sunset condo, includes all taxes

TahneeRating, 5 stars1 month ago
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.
Superhost
Condo in Kihei
4.8 out of 5 average rating, 179 reviews

Luxury 2bd2bth Kihei Maui Condo Across from Beach

RonaldRating, 5 stars1 month ago
verry nice place and close to beach to watch the sunset👍
Superhost
Condo in Kihei
4.84 out of 5 average rating, 253 reviews

Cozy Cute Condo | Maui Vista | Walk to The Beach

BradleyRating, 5 stars1 month ago
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.
Superhost
Condo in Lahaina
4.89 out of 5 average rating, 113 reviews

Remodeled Kaanapali golf resort 1500ft condo w/AC

SpencerRating, 5 stars3 weeks ago
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.
Superhost
Condo in Kihei
4.83 out of 5 average rating, 29 reviews

Considered the Best Location Oceanfront on Maui

AmandaRating, 5 stars2 months ago
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 weren’t ready to go back home. We will definitely be back to Maui Sunset.

Quick stats about holiday rentals with a pool in Wailea-Makena

  • Total rentals

    1.8K properties

  • Nightly prices starting at

    $92 AUD 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

  1. Airbnb
  2. United States
  3. Hawaii
  4. Maui County
  5. Wailea-Makena
  6. Rentals with pools