Kihei vacation rentals with pools

We found 187 vacation rentals waiting for you.

Find your ultimate splash pad

From plunge pools for a quick dip to infinity pools with a view, here are the Kihei vacation homes where you can dive in, cool off, and catch some sun.

Top-rated Kihei rentals with pools

Our guests have spoken. Explore their favorite and top-rated homes in Kihei with refreshing pools, sun-splashed decks, and poolside seating.

Explore All Vacation Rentals With Pools

Recent guest reviews

Condo

I stayed at Wailea Grand Champions Unit 58 last week, and it was truly one of the best vacation stays I’ve ever had. The condo was spotless, comfortable, and beautifully maintained—everything felt fresh, welcoming, and well cared for. The view from the lanai is absolutely breathtaking. If you love watching sunsets, this is the perfect place. Every evening felt like a private show, and it really made our time in Maui unforgettable. One of the biggest perks was all the extras the condo provided. There were beach chairs, boogie boards, and other gear available for us to use, which made our beach days effortless and so much more fun. It was a huge convenience and really enhanced our enjoyment on vacation. The location in Wailea is perfect—peaceful, beautifully landscaped, and close to amazing beaches, shops, and restaurants. We felt relaxed the entire time, and coming “home” to this condo each night was just as wonderful as exploring the island. I would absolutely stay here again and highly recommend Unit 58 to anyone visiting Wailea. It made our trip truly special.
Jacob OG L. | Dec 2025

Condo

Nice place!
Martha Susan A. | Dec 2025

Condo

I loved the ocean front. Parking is very close. The cleanliness.
Judith G. | Dec 2025

Condo

The view was incredible. Great room. Spacious king rooms. Small kitchen but it worked for us. We made bacon and eggs every morning. Washer Dryer was nice to have available. Pool was amazing! Right on the beach.
Joel R. | Dec 2025
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FAQ

Our vacation rentals offer both private and shared pools. Each property’s listing description will specify whether the pool offered is private or shared.

Every home is stocked with plenty of towels. However, the availability of pool towels varies by property.

Some pools are heated, and there may be an additional fee for this service. You can find more information about heating fees in the property description.

Yes, pool maintenance is included during your stay. We ensure that pools and hot tubs are regularly cleaned and maintained to provide an optimal experience. If you encounter any issues with the pool during your stay, contact our Guest Experience team immediately.

Many of our properties include lounge chairs, umbrellas, or shaded areas by the pool, but this can vary. Check the property details and listing photos for specific details.

Generally, food and drinks are allowed by—but not in—the pool. However, to be safe, it’s best not to use glass or china in the pool area.

Pool toys, floaties, or inflatables are typically not provided. You may want to bring your own, if needed.

Some properties include a poolside grill or outdoor kitchen area, but this is not standard across all rentals. Check the property listing for details.

We have a good neighbor policy that includes quiet hours from 10 p.m. to 8 a.m. In addition, certain communities have noise policies in place. Unauthorized parties are not allowed, and excessive noise can lead to intervention and removal from a property.

If you encounter any issues with the pool during your stay, contact our Guest Experience team immediately. Your local Vacasa team will work to resolve the problem as quickly as possible.

Not all pools are open all year round. Some pools—depending on the destination—are seasonal only. Read the listing description for specific operating times for the pool.

More ways to stay in Kihei

Dog-friendly
Hot tub
Internet
Electric vehicle charger
Ocean view
Oceanfront
Sound view
Soundfront

Nearby destinations

Maui
Haleakalā National Park
South Maui
Maalaea Bay
Sugar Beach Resort
Maui Kamaole - Kihei, HI
Kihei Akahi
Mana Kai Maui Resort - Kihei, HI
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