The first thing I want to point out is that it may be wise, in your thinking, to separate the property itself from the STR business that's being run from the property.In the old days (as recent as 10 years ago), people buy a vacation home to enjoy, and they leave it empty when not in use. 

Key points include:Security Deposits: In Indiana, there’s no legal cap on security deposits, but you must return the deposit (minus any valid deductions) within 45 days of the tenant vacating the property.Evictions: Follow the formal process carefully.

Hot tubs can be a major revenue booster for STRs, especially in colder climates or vacation destinations.

I do well, at least enough to go on vacations as a family, put money into high yield savings accounts, max out the ROTHs and add to investments when I can with money saved in savings and checking accounts.

Without knowing all of your specifics, I'd say that it's only worth holding on to if you can reasonably expect to have some really good appreciation in the near future (like 5 yrs)....Or, in the case where it would run well as a vacation rental, you could switch the usage, maybe?

Quote from @Ryan DeRobertis: Quote from @Marc Rice: Quote from @Ryan DeRobertis: I am considering my first rental/vacation property and would like it to be in Puerto Rico for a few reasons:--1. 

Sure it does. but depending on who the celebrity is/was.....That's why so many little hotels, boarding houses, vacation rentals, etc..... feature this in their advertising.And in some cases, you will not get more money, but you will get more guests.A little while ago, I went to Tombstone AZ and stayed in 'The first boarding house in Tombstone'....really cool place but kinda small and, well....old feeling.

They will have 48 hours to vacate and if not gone, constables come a knocking.

Were you investing with a vacation loan / 10% down?

Out of curiosity would anyone be willing to share any experience with non-paying renters who've vacated the property prematurely?