Windermere rentals with pool

We found 32,995 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 Windermere?
Book one of our 32,995 holiday rentals with a pool and start making plans for your trip to Windermere. Whether you'd like to stay in Bay Hill, Metro West, Windhover or another popular neighbourhood, you'll find the ideal poolside property on Bookabach.
How much does it cost to stay in a holiday rental with a pool in Windermere?
A number of factors will influence the price of a holiday rental with a pool in Windermere, such as the size of the property and when and how long you're staying. All you need to do is enter your travel dates and any preferences to find a house where you can have some poolside fun.
When is the best time to book a holiday rental with a pool in Windermere?
Our holiday rentals with a pool in Windermere are in peak demand in February. You can expect average temperatures that range between 14ºC and 23ºC if you choose to explore this corner of Orlando then. If there's limited availability in February, explore possibilities in the months prior or following.
What holiday rentals with a pool in Windermere have nice views?
Relaxing is effortless at our holiday rentals with a pool in Windermere. Go for a swim or simply admire the views. Filter your search by "Recommended" or "Guest rating" to see the very best stays where you can soak up the incredible scenery as your worries float away.
Are there holiday rentals with a private pool in Windermere?
Pick a holiday rental with a private pool in Windermere and enjoy a refreshing morning swim or late-night dip — or anytime you want! You'll be able to keep your little ones easily amused, and you won't have to worry about sharing with other guests. Use our "Private pool" filter to find your ideal stay.
What are the top things to do in Windermere?
There's always something cool to do with the crew when you stay at a holiday home rental with a pool in Windermere. Get out and explore major sights like Universal Studios Florida, Magic Kingdom® Park and Disney's Animal Kingdom® Theme Park, then come back to unwind and recharge by the water.
Why should I book my holiday rental with a pool with Bookabach?
We provide attentive customer support from the minute you book until you've returned home, so every step 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. Another good thing about us? You can use our filters to fine-tune your search by budget, location, amenities and more. Whether you're looking for a pet-friendly pad or a beachside getaway for the family, we've got holiday rentals with a pool that fit your exact style and needs.