Photo by Stephanie Moraca

Winter Springs rentals with pool

We found 15,256 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 Winter Springs?
Stay in one of our 15,256 holiday rentals with a pool in Winter Springs and get ready for cannonball competitions. Goldenrod, Aloma and Alafaya Woods are among this city's most popular areas to stay.
How much does it cost to stay in a holiday rental with a pool in Winter Springs?
It doesn't get better than a holiday rental with a pool, and it doesn't have to break the bank with Stayz. While a range of things will determine how much you'll pay for your getaway in Winter Springs, our filters will help you find the best deal, every time. Choose 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 beck and call, you'll probably want to stick around longer anyway!
When is the best time to book a holiday rental with a pool in Winter Springs?
Consider booking your poolside escape to Winter Springs in March, when the average temperature ranges between 15ºC and 25ºC. This is the most popular time of year for Stayz guests to get a holiday rental with a pool in this destination, which is located in North Orlando.
What holiday rentals with a pool in Winter Springs have nice views?
Use the "Location" filter to find a holiday rental with a pool and the views you'd love to wake up to. Start by entering the dates you plan to visit Winter Springs, then narrow your search based on the sort of area you'd rather stay in. All that's left is to pack your swim gear and you're all set for a splashing good time.
Are there holiday rentals with a private pool in Winter Springs?
In Winter Springs, you won't find any holiday rentals with a private pool, but we do have some amazing properties we know will tempt you. From standard amenities like separate bedrooms to perks like hot tubs, our accommodation come with a range of features to cater to every preference and budget. And the best thing about our holiday rentals? You and whoever you're holidaying with will get the entire place to yourselves.
What are the top things to do in Winter Springs?
Central Florida Zoo & Botanical Gardens, Kia Centre and Dr. Phillips Centre for the Performing Arts are popular attractions that'll keep the whole family occupied in Winter Springs. There's nothing like travel to bring everyone together, so browse our holiday home rentals in this exciting destination.
Why should I book my holiday rental with a pool with Stayz?
No sharing your space, no uncomfortable encounters with people you don't know. When you choose a Stayz holiday rental with a pool, you'll have the whole place to yourself to splish splash around. Need to alter or cancel your plans? Our flexible cancellation policies mean you're able to book your rental house with total peace of mind.