I stayed at Tobago house for the month of October and loved it! This was my 2nd stay - my best friend rented the house for 6 weeks in the spring of 2012 - and it was even better than I remembered. The house is well appointed with all the things one needs to set up house for a few days or for several weeks.
The location is prime and provides easy access to Duval street and all the shops and restaurants. The walk to the 'action' end of Duval takes 15 minutes or so but there is so much to see and do along the way! I've been going to Key West for over 25 years and staying at Tobago house afforded me an opportunity to frequent places I sometimes don't get to.
The house is pet-friendly so my 10 year old lab accompanied me. She was very comfortable there and we took long walks every day, exploring side streets, strolling by the cemetery and going to Southernmost beach to watch the sun rise. We also visited the many pet-friendly establishments in Key West.