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I generally recommend Lodgify. It's vacation rental management software that you can embed into your Squarespace website.

Here's another thread where this has been discussed:

 

Improve your online store with our extensions.
About: Squarespace Circle Leader since 2017. I value honesty, transparency, appreciation and great design ♥.
Work: Squarespace Developer and founder of SF Digital, building the features Squarespace didn't include™.
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