Maternity Leave Vacation Suggestions - near pool/lake/beach in Sept

Baby #2 is coming in June.  My  husband and I are overlapping our maternity and paternity leaves at the end and would like to take a vacation with our daughter (age 3.5 at the time) and infant (3 months or so) in September.  Our thinking is that if we having to be feeding the baby every three hours, we may as well do it someplace warm where we can swim and relax in between.  Likely to bring a set of grandparents with us.  We will be flying out of SFO.  Europe is too far for us.  Any other suggestions of great places for a 3.5 year old and a baby in late September?  Many thanks!

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I would go to an all-inclusive resort in Mexico.  We went to Puerto Vallarta with our then 2 and 6 year olds and it was fabulous - no having to figure out meals/restaurants as they were all on site and almost always open, pool right there (find one with a large shallow area), ocean right there, beautiful, warm, lots of different room/suite options, nightly entertainment that turned out not to be awful.  Flight is only 4-5 hours.  I thought I would hate all-inclusive but we went to the Melia, which was mostly Mexican nationals on vacation along with a smattering of people from other countries (very few Americans), and it was simply awesome.

I would highly recommend Chatham, MA in Cape Cod. When our kids were younger we rented houses there several summers. It was an easy place to go with young children. The beaches are nice, and there is no rough surf, so you don’t have to worry about waves crashing down on toddlers. The kids would play for hours on the beach, and then we would head home and have a relaxing evening. You pay more for a house near the beach and within walking distance to Main Street, which were worth it to us. It depends on what you want. The rates drop after Labor Day. September would probably be a great time to go. Good luck.

We did something similar (our oldest was only 2 at the time though) and considered East Coast (Maine, Outer Banks), Canada, Europe. Ultimately we decided we probably wouldn't actually see much of the place we were visiting so we opted to stay close. We rented a beautiful house in Sonoma for a week. It had a pool, an extra room for friends/parents to stay and visit, and we got to enjoy good food and wine, and amazing weather. Tahoe may be another similar option. We're big travelers so it felt hard to not choose a new and far destination but we ended having the best time with minimal stress. Good luck and enjoy!! 

So many possibilities! Hawaii would be at the top of my list. But you might also want to consider  San Diego, Tahoe or Florida.