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The Hunt Begins...Looking for a villa in Tuscany for next May for large group

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Whenever I have a travel inquiry I know I can turn to my fellow posters here at Fodors!

Here's the background:

4 years ago friends of mine celebrated their 5th anniversary by renting a villa in Tuscany (Gaiole in Chianti) and 20 of us went to help them celebrate. At that time it was bandied around that we would love to do it again for anniversary number 10.

Well, next year is anniversary 10 and just the other day everyone who went on the trip back in 2004 received an email from the anniversary couple asking if we'd be interested in doing a "Tuscan Two" trip.

Being the travel fanatic that I am I immediately responded in the positive! The wife of the anniversay couple (S) is pregnant with baby #2 and is due in October 2008 and this "Tuscany Two" trip would be the first week of May 2009, so being the trip planner that I am I shot off an email to S letting her know that if she would like my help in trip research I would be happy to do it.

I got an immediate response from her saying, "Yes", she would love my help doing villa research.

I have briefly started looking through the VRBO website and have already noted a couple possible villas that I will forward to S, but that got me thinking...are there any Fodorites out there who might have a personal recommendation they would share with me??

Here are some parameters we are looking at:

1. Tuscany region (Montepulciano is one area suggested), but we are open to just about any Tuscan location. We could also work with a northern Umbria location too.

2. We don't have a firm number yet, but the 2004 trip there were 20 of us, some couples, some individuals (who shared twin bedded room). We anticipate about the same number, so need a place that could sleep 20 (no children will be coming).

3. We had a pool at the villa on the last trip, but never used it (weather wasn't warm enough), so don't feel like a pool is needed this time around.

4. The price range we are looking at is $5000 for a week.

If any of you know of a villa or villa rental agency that you have worked with before and would recommend I would love to hear about it.

Thanks in advance for any information you can share!

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