Photo by Karen Alvarez

Kaanapali rentals with pool

We found 5,179 rentals with pool — enter your dates for availability

Find spaces that suit your style

  • Peace of mind

    Our Book with Confidence Guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Frequently asked questions

Are there any holiday rentals with a pool in Kaanapali?
Pick one of our 5,179 holiday rentals with a pool and make a start on planning your Kaanapali trip. Whether you want to be in Napili, Plantation Estates, Launiupoko or another much-visited neighbourhood, you'll discover the ideal poolside property on Stayz.
How much does it cost to stay in a holiday rental with a pool in Kaanapali?
Prices vary depending on length of stay, season and specific location, so enter your travel details to find a property offering a splashing good time. Whatever your budget or plans, Stayz has holiday rentals with a pool in Kaanapali for guests of all types.
What holiday rentals with a pool in Kaanapali have nice views?
When the day's sightseeing is over, return to your holiday rental with a pool for a relaxing swim. The cherry on top? Some of these stays in Kaanapali also come with gorgeous beach views.
Are there holiday rentals with a private pool in Kaanapali?
From making whirlpools with the kids to late-night swims under the stars, a holiday rental with a private pool offers plenty of possibilities for fun and relaxation. If you're on your way to Kaanapali, use our "Private pool" filter to look for holiday homes that come with this luxurious feature.
What are the top things to do in Kaanapali?
You'll always have something fun to do with the family when you book into a holiday home rental with a pool in Kaanapali. Get out and visit leading attractions like Kaanapali Beach, Kapalua Golf Club Plantation Course and Iao Valley State Park, then return to lounge and relax poolside.
Why should I book my holiday rental with a pool with Stayz?
When you book a holiday rental with a pool with Stayz, you'll enjoy more than the standard hotel experience — think a private pad with a place to relax by the water. You're also covered by our Book with Confidence Guarantee. This means we're here to make sure everything goes smoothly throughout your entire break. Have an unforeseen change of plans? Check out our cancellation policies to see if you are eligible for a full refund.