This months issue of Smart Money Magazine has a 4 page article on villa rentals. The real focus of the article is on the inspections that some villa rental companies carry out to check on their properties.
According to the article, Anthony Lassman, founder of high-end guidebooks Nota Bene, stated that subpar rentals are "endemic" to the villa industry. So the article recommends finding a rental agent that you trust.
The author visits several villas on St Barths, accompanying a villa inspector from one of the villa rental agencies. The tours produce an interesting mixed bag of results; one villa has low flying aircraft, another has tired furniture and a third has nearby construction - some of which the inspector can fix and others that are beyond their control.
The article lists 5 villa rental companies, who each perform varying levels of inspections. The best company - Homebase Abroad - has a ratio of one inspector for every twelve villas, but rentals average $20,000 per week.
If you're renting a villa we recommend you ask how often the villas are inspected, ask for current photos and look on google maps to check the location and how close or faraway other villas and amenities really are.
If you typically travel in a large group or with extended family and friends only once a year or less, then one off villa rentals are the way to go. As recommended above find a good agency and ask them the right questions.
If you travel with family and friends a couple of times a year or more then look at destination clubs. The clubs provide a wide selection of homes around the world and maintain their homes to a very high level. What's more they offer a very high level of services and provide local concierge staff.
If you have a favorite location that you like to visit over and over, consider a luxury fractional or private residence club.