The first apartment Woody Allen’s character inhabits, in Manhattan – the one with the abundant bookshelves and the cast-iron[IIRC] spiral staircase. Also, the beachhouse from Interiors.
Most of the locations in Roman Polanski’s The Ninth Gate – especially the exquisitely ruined Portuguese villa and the luxuriously appointed office/library of the Paris collector. Also the Sanmartin compound outside of Paris… now, that’s serious real estate!
Pedro Almodovar’s Madrid – to take a tour of the locations and interiors in general. Everything would likely be very colorful and a bit over-the-top. Of course, I’d get around in the “Mambo Taxi” …
The Florence pensione from A Room With a View, preferably as a newlywed.
From The Empire Strikes Back, Yoda’s tiny home in the Degobah swamp. Taking Force lessons from the Master Jedi himself… it’s the ultimate sabbatical trip!
The ski chalet on top of a very big Swiss Alp, in On Her Majesty’s Secret Service. (Great views, but I don’t know what I’d do there, since I don’t know how to ski. Probably suffer ze altitude sickness and play ze shuffleboard.)
The English mansion in the detective-genre spoof Murder By Death, and the Transylvanian Gothic castle in Young Frankenstein – for their funhouse layouts and kitschy decor.
John Cusack’s Chicago apartment and store (“Championship Vinyl”) from High Fidelity. Just to, you know, hang out with Rob Gordon for a few hours… look through his personal record collection, admire the posters, go through the used bins, score a couple of rarities, chat about the music scene…
The run-down, rustic Penrith cottage from Withnail & I. Oddly enough, I read about three years ago that the cottage had recently come up for sale (and was still in the same condition it had been in the movie) and was attracting fans of the cult film from Sweden, Germany, the USA, Australia, Japan, Brazil,… all of them telling God-knows-what stories in order to get a tour. (Doubtless they were saying, “I’m not from London, you know.”) The real estate agent must’ve been going nuts!
“French Castle” from Monty Python & the Holy Grail. (This would be the ultimate geek tourist videocamera joke… go up to the top, lean your face over the wall, and let loose with a barrage of insults een zis out-RAG-ous akzent…) [Yes, I know the DVD has a locations tour and shows us armchair travellers what that castle is really like, and what it’s really called.]