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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:

 

About me: I've been a SQSP User for 18 yrs. I was invited to join the Circle when it launched in 2016. I have been a Circle Leader since 2017. I don't work for Squarespace. I value honesty, transparency, diversity and good design ♥.
Work: I founded and run SF.DIGITAL, building Squarespace Extensions to supercharge your commerce website. 
Content: Views and opinions are my own. Links in my posts may refer to SF.DIGITAL products or may be affiliate links.
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