Kaanapali rentals with pool

Pick one of our 5,008 vacation 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 neighborhood, you’ll discover the ideal poolside property on Vrbo.

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, Vrbo has vacation rentals with a pool in Kaanapali for guests of all types.

When the day’s sightseeing is over, return to your vacation rental with a pool for a relaxing swim. The cherry on top? Some of these stays in Kaanapali also come with gorgeous beach views.

From making whirlpools with the kids to late-night swims under the stars, a vacation 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 vacation homes that come with this luxurious feature.

You’ll always have something fun to do with the family when you book into a vacation 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.

When you book a vacation rental with a pool with Vrbo, 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.