Hello, Pool Diva ~ Sounds as if you need a reputable drainage and paving company in your area. Where are you? Check Angie's List for contractors in your area who specialize in this type of work.
If a swimming pool is involved, you also need a pool contractor. Many people think it's a good idea to drain their in-ground pools in winter, because they're not using them. Usually it's a very bad idea. The weight of the water maintains the integrity of the lining of the pool, so that it's not as susceptible to cracking when the ground underneath and around it goes through expansion and contraction, depending on the season. It's much less expensive to give the pool a professional cleaning before swim season, than to have to repair or resurface the pool.