Wailea-Makena rentals with pool

We found 4,434 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, 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 Wailea-Makena?
Wailea-Makena has 4,434 holiday rentals with a pool in Makena and other renowned destinations. Whether for an early morning swim or evening dip, you can jump into the water whenever it suits you at these Vrbo properties.
How much does it cost to stay in a holiday rental with a pool in Wailea-Makena?
It doesn't get much better than a holiday rental with a pool, and it doesn't have to be costly with Vrbo. While a range of things will influence how much you'll pay for your escape in Wailea-Makena, our filters will help you find the best deal. Choose your budget and use our "Discounts" filter to look for properties that offer savings for longer stays. With an enticing pool at your disposal, you'll be tempted to stick around longer anyway!
When is the best time to book a holiday rental with a pool in Wailea-Makena?
March is when most Vrbo guests splash out on a holiday rental with a pool in Wailea-Makena. Expect average temperatures of between 21ºC (70ºF) and 24ºC (75ºF) if you plan your trip during this month.
What holiday rentals with a pool in Wailea-Makena have nice views?
If you want to splash around after a busy day of exploring, check out our holiday rentals with a pool in Wailea-Makena that boast picturesque vistas like beach views.
Are there holiday rentals with a private pool in Wailea-Makena?
Morning, noon or evening, enjoy a swim whenever you please when you book a holiday rental with a private pool in Wailea-Makena. To find stays that'll boost the fun factor during your holiday, use our "Private pool" filter.
What are the top things to do in Wailea-Makena?
There are lots of memorable experiences to be had when you book a holiday home rental in Wailea-Makena. The kind of things you're interested in and the people you travel with will help you decide what to do and see, so do a little research before you leave home.
Why should I book my holiday rental with a pool with Vrbo?
Vrbo promises attentive customer support from the minute you book until you're back home, so every aspect of your holiday is enjoyable and worry-free. It's all part of our Book with Confidence Guarantee, which also includes deposit and payment protection and flexible cancellation policies. Plus, with our rewards programme, One Key™, you'll earn OneKeyCash™* on eligible bookings on Vrbo. Whether you want a pet-friendly space or an oceanside getaway for the family, we've got holiday rentals with a pool that match your exact style and needs. *OneKeyCash disclaimer - OneKeyCash is not redeemable for cash and can only be used on Vrbo.