If you want a second home/holiday home or a Furnished Holiday Letting on the Isle of Wight you'll need to consider a few things. This is certainly not a comprehensive list, it's more of a splurge of thoughts which might help guide someone in the right direction.
Most of this applies all over the UK but I'll throw in some local place names to keep it interesting.
Please note, I'm not an accountant and the bits which mention tax should be seen as a vague pointing in the right direction rather than up to date or water tight advice.
The Second Homes Issue
A second home just for friends and family
Locations and leases
Hiring out your second home as a Furnished Holiday Let
Ferry discounts for second home owners
Insurance on second homes
Isle of Wight Guru's Blog