Wailea rentals with pool

We found 1,301 rentals with pool — enter your dates for availability

  • 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 Wailea?
You can select from 1,301 holiday rentals with a pool in Wailea. Whether you're thinking of staying in Halama Street or another popular neighbourhood, we'll help you find an ideal poolside escape where you can enjoy a dip when you like.
How much does it cost to stay in a holiday rental with a pool in Wailea?
It doesn't get much better than a holiday rental with a pool, and it doesn't have to cost a lot with Stayz. While a range of things will determine how much you'll pay for your Wailea escape, our filters will help you find an amazing deal. Set your budget and take advantage of our "Discounts" filter to look for properties that offer savings if you stay longer. With an enticing pool at your disposal, you'll probably want to stick around longer anyway!
When is the best time to book a holiday rental with a pool in Wailea?
August is when the majority of Stayz guests book a holiday rental with a pool in Wailea, which is in Kihei. On average, temperatures range from 25ºC to 27ºC during this month.
What holiday rentals with a pool in Wailea have nice views?
Relaxing comes easy at Stayz's holiday rentals with a pool in Wailea. Splash around in the water or simply marvel at the vistas. Tailor your search by "Recommended" or "Guest rating" to find exceptional properties where you can lose yourself in the incredible scenery as your worries float away.
Are there holiday rentals with a private pool in Wailea?
From poolside gatherings to midnight swims under the stars, a holiday rental with a private pool offers plenty of possibilities for relaxation and fun. If you're travelling to Wailea, use our "Private pool" filter to find accommodation that come with this premium perk.
What are the top things to do in Wailea?
Wailea Beach, Maui Ocean Centre and Kamaole Beach Park are top-rated attractions that'll keep the whole crew entertained in Wailea. There's nothing like a fun getaway to bring everyone together, so check out our holiday home rentals in this exciting destination.
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 typical hotel experience — think a private space with a place to relax by the water. You're also covered by our Book with Confidence Guarantee. This means we're here to guarantee a stress-free stay throughout your entire getaway. Have an unexpected change to the itinerary? Check out our cancellation policies to find out if you are eligible for a complete refund.