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

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.

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

Aloha Aku Honu2 Suite – 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!

Kamaole Sands FRONT ROW OCEAN Unit 116
Stayed just over 3 weeks in this spectacular unit. Well appointed, incredible views, so clean! It was fully stocked with anything and everything you could possibly need. Full size toiletries in bathrooms, tons of clean linens, soap, detergent, cleaning supplies, and toilet paper to cover our entire stay. We felt right at home. Andre was responsive and immediately assisted when we had an issue with the AC unit in the second bedroom upon arrival. There is ongoing construction in the complex, but it didn't affect our building or interrupt our stay at all. Parking is open season during this construction period, which turned out great because we could choose any open spot - super convenient and tons of availability. Kamaole Sands is our fav complex in Kihei and we are already planning our return visit. Will definitely stay in this unit over and over again.

Beautiful One bd Ocean AC,wifi,pool A102
We had a lovely 2 weeks at Luana Kai. Our condo was clean and had everything we needed for our time there. There was plenty to do right in Kihei and we had a great time.

CLOUD 9 BEACH HOUSE, Maui Family Owned and Managed
We loved this home. Whether it was having dinner with a Maui Sunset or enjoying the first morning cup on the front patio with the blue Pacific as a backdrop or just enjoying the home and beautifully kept landscaping, with pool, we have nothing but positive things to say about this experience. The owner was very responsive to our questions. Truly felt like we were guests not customers. I was traveling with my Niece and her teen age and adult children and we all loved it. Lots of snorkeling and beach gear. Restaurants, beaches and shopping all very convenient. Several good swimming and snorkeling beaches minutes away. From first contact through checkout, this was my best experience with Airbnb. Mahalo, Joe

Romantic Oceanview Condo Steps to Beach
Wonderful stay, right by a nice beach and walkable to restaurants!
Condo rentals with a pool

Oceanfront Getaway, Brand New, Steps To Beach
Gorgeous spot! The location is fabulous, close to fun restaurants and the harbor, but it still felt private. We would 100% stay here again!

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.

Amazing Ocean Views at Wailea Ekolu Village!
I had an excellent stay here with my girlfriend. The Airbnb is very spacious, and also is in a beautiful, peaceful neighborhood. Laurie has the Airbnb well stocked with supplies. I would definitely recommend staying here!

Wailea Ekahi Village | 12B
Great location with a view of the water though not necessarily the beach. The place has recently been updated and would be great for a couple. We liked the shaded patio and the cold AC. Ice machine worked well too in the fridge though as this is a studio I recommend you turn it off before going to bed. We didn’t cook at all but everything was there (except salt and pepper). Beach chairs were also provided and towels of course. Washer and dryer were newer and clean. We didn’ use them much. Lighting in the unit was nice, with dimmers throughout. This was useful when waking up or going to bed. A nice comfort addition that we appreciated. It’s a 4 minute walk to the beach and the pavilion. We went in October and the pool and beach were not too busy and the people were respectful. It was quiet and peaceful. The pool house is a great location to have a coffee or a beer at and watch sunset or listen to the waves. We would recommend this place. Great value and location.

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.

*Fully Remodeled* Modern Island Style*
Beautiful Airbnb. As described. Clean. Good location. Well stocked. There are rules on label maker in your face everywhere (ie no smoking, don’t slam door, etc), but assuming positive intent, the labeling of light switches, fans, etc is very helpful. Would stay here again and recommend without hesitation.

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

Aloha Moon - The Honeymoon Hideaway
Wow! Let me start by saying… just book it! From the moment you walk in, you can feel the warmth and hospitality that Kate & Mark pour into this space. Every detail, from the thoughtful goodies to the stunning decor, is curated to perfection. The design is both aesthetically pleasing and inviting, instantly making you feel at home. We stayed at the Fairmont for the first part of our trip for business, and honestly, we both agreed—this place felt even more prestigious! My wife loved the bed sheets so much that she had to look them up, and they are now sitting in my Amazon cart, ready to purchase when we get back home. Another standout feature was the tablet they provide—it’s incredibly helpful and packed with all the information you could ever need to enhance your stay. Kate & Mark truly know what they’re doing, and we couldn’t have asked for a better experience. We hope to be back in the future!
Quick stats about vacation rentals with a pool in Wailea, Wailea-Makena
Total rentals
1.8K properties
Nightly prices starting at
G$12,553 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
- Kaanapali Beach
- Kahului Beach
- Lahaina Beach
- Sandy Beach
- Kaipukaihina
- Laie
- Honolua Bay
- Spreckelsville Beach
- Kapalua Bay Beach
- Olowalu Beach
- Pahoa Beach
- Wailea Beach
- Manele Golf Course
- Hāmoa Beach
- Oneloa Beach
- Maui Ocean Center
- Palauea Beach
- Old Lahaina Luau
- Wailau Valley
- Papaloa Beach
- Mokulau Beach
- Kaulahao Beach
- Wailea Golf Club