You might want to consider a palm tree. Depending on the area surrounding the pool. They have a small root ball so you won't have to worry about the roots invading your pool "wall". There are many varieties which have little or no debris. And they are great specimens remember that a lot of them are SLOW growers, but do indeed get VERY tall, but take years to get there!
Palm trees (buy advanced ones if you can't wait for them to grow), banana trees, umbrella trees, NOT hibiscus (flowers drop and turn mushy really fast), NOT pine (one night I might have to go next door and cut down the neighbours one- cursed pine needles), NOT eucalyptus (leaves fall all year round, so do branches, flowers, gumnuts and almost every other part of the tree), NOT box trees (same as eucalyptus but add the bark as well). NOT deciduous trees at all (everything falls off them). Look for large leafed, tropical, non-fruiting (NOT citrus, although the fruit floating around the pool looks interesting for a short while), evergreen, non-flowering or at least very short flowering. Succulents can look attractive around the pool, do not require much attention and are different to the tropical look.
I can tell you from experience a tree not to plant around a pool. That would be a pine tree. I have spent a numerous amount of time vacuuming pine needles out of the pool.
Silk Oaks are also not the tree to plant around a pool. Palms are the best and create a wonderful tropical retreat!
All deciduous or leaf bearing trees will lose their foliage in winter to some extent depending greatly on your geographical area, the colder it gets the more they lose. And for some deciduous and all coniferous or pine trees there is a constant loss and regrowth process, It depends on what you are willing to put up with. There are many colorful ornamental trees that in a temperate climate will not lose all their leaves such as the ornamental plum, and citrus trees, or maybe the magnolia which can add color and shade while not being all that dirty. But for ease of maintenance but not so much for shade the palm is the favorite.
Depending on where you live is what type of tree you should get period. Sometimes some trees do not do well in certain climates but if you do have a pool, I could assume that you live some where tropical. I would definitely recommend different types of palm trees, such as, Sago palm, a Travelers palm, some three headed Christmas palms are a great addition to any pool area. I have a few King Palms and couple coconut palms and they make a statement.
Sycamores are not a good choice. The leaves are so large that even commercial vacuums have a hard time getting the leaves out. You're looking at months of unswimable pool if the leaves get in. Trust me, I know.
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