Some assets can be valued significantly lower than their actual worth because of illiquidity and other factors.

Should I be looking at markets with a lower entry cost? 

Doesn't that help keep property taxes lower or the owner-occupants.If 5% of the properties are being bought by investment companies, that means 95% are not. 

Quote from @Chris Seveney: @Francisco AvancenaThere are specific lenders who will do land dealsBut of course not as many as traditional real estate.The key will be skin in the game - typically for land because it is less liquid than a home the lender will want to have a lower ltv on the deal I fund land flippers currently in  CO FLA WA ID MT NV AZ OR TX SC GA VA  one thing about land though LTV is lower and RATES are NOT the same as typical HML rates are higher for raw land but its a specialty niche and a business that I grew up in..

Is it to lower rate?

We will pay off a few more loans with smaller balances, even though they are lower interest than what we are getting on new acquisitions.

Lower income = lower rent.

Refinance offers a lower rate, longer term and a lower payment.

If you don't get a booking (views go up and down everyday) lower your nightly price a bit more. 

I don't know your specific market all that well but have you done some analysis on your ADR during the high season X your high season occupancy rate and determined whether taking lower priced slow season bookings vs letting your property stay vacant during the winter averages out in your favor?