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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The Hunt Begins...Looking for a villa in Tuscany for next May for large group
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Trip Ideas
Give this site a try:
www.initaly.com
They are based in the States and have very unique accommodations.
We found Palazzo Niccolini thru this site and I found them to be very efficient and I would book thru them again if a property interested me.
Have a lovely journey!
You might look at Parker Villas.
http://www.parkervillas.com/
I think they have some large (and lovely) villas in Tuscany.
Byrd
Tiff and Byrd...
Thanks for the links. I'll check them out!
Parker villas is a great place to do your search. Caveat.... some of the villas they rent can be rented from other sites at a substantial amount less.
We've stayed at La Rimbecca in Greve twice. This villa was advertised by Parker but we booked through another agency for about 75% of what Parker wanted.
It has been 5 years since we've been there but you may want to look at La Foce (www.lafoce.com).
We rented 2 houses with 5 other couples but I seem to remember a villa that had several smaller apartments. Something like that may work for your group. We loved our stay there and the owners were a joy to deal with.
La Foce would be great.
Here is a place I have wanted to visit for years:
http://www.luxurylink.com/luxury-hotels/villa-of-il-borro-il-borro.html?productId=109596
or
http://www.ilborro.it/welcome.asp
http://www.ilborro.it/accomodations.asp
This shows the different accomodations available.
I rented from www.italyrentals.com The company is Gira the owner is a American woman called Susan. She was a delight to work with. We ended renting a villa that was divided into 3 apartments. we had a total of 8 bedrooms and 7 full baths. The rental property was called Sodi. It was in Castellina in Chianti. It was in a vineyard.The property was incredible, better than the pictures and descriptions. We had a beautiful pool and lovely outdoor eating areas We were about a 10 minute drive to the nearest village. We loved everything about the property. If the amount of bedrooms works check this out. She also may have larger propertires. Good luck in your search.
As always, if it is about Tuscany rentals start at slowtrav.com for personal references by location in Tuscany. And,location should be your top criteria. The boutique rental agencies above will cost you 20% more.
Thank you all for the recommendations! I haven't had a chance to look at all the links yet, but I will.
I don't think $5,000 is a reasonable amount for a place that will accommodate 20 people for a week. I think you need to increase your budget.
That price sounds very low to me for so many people in May. But I did find this; note that electric and heat are not included:
http://www.parkervillas.com/villas/villadetails.cfm?sid=15074920080528073807&villa_ID=5686&occ=20&year=-1#priceChart
My daughter and 4 other couples(all with children) stayed at this villa:
http://www.vrbo.com/20378
It is within your price range, has 10 bedrooms, 2 pools (1 inside and 1 outside), etc. It is located near Todi. Easy access to Montepulciano, Florence, Assisi, Orvieto, etc. They did day trips to many places. She said the villa is FABULOUS. We are trying to get a family reunion planned and will book this for our family.
Thanks everyone for sharing your information. I've got some great starting places now!
I rented a villa in Tuscany 35km south of Florence, high above the Arno Valley, in a very untourist town, Pian di Sco. I rented it for a month and had from 8 to 20 people their during the four weeks.
The villa and apartments would more than accommodate your group, and while the dollar is worth much less than 3 years ago, I'm pretty sure you would be able to hit very close to your $5,000.00 budget.
It is an agritoursimo, and the family that runs it are incrediable people. If requested they will make an incrediable dinner for your group. The food was amazing. The family has vineyards, and olive trees, so it is a real working farm.
The villa has a great kitchen, pool and vistas.
La Capitata, the villa is called La Focolare
http://www.agriturismolacapitata.com/focolare_eng.htm
Note that the house near Todi in Umbria is 5000 Euro a week, so about 7500 USD.
We just came back from Italy on May 18th. There were 28 of us. We stayed at Todi Castle Estate and the surrounding villas. Check out their website: todicastle.com. Mario was a gem. Think about this place. It is beautiful.
Thanks JoanNH...La Focolare looks like it may be a good fit. I've included it in our choices.

ekscrunchy...thanks for the heads-up on price. While doing my research I've found some places that are above the stated price range, but I am including them for review by the anniversary couple, especially if they look really good. And who knows, the budget may increase!
DosGatos...thanks for link to the Todi castle estate, it looks good too!
try www.craigslist.org click on Italy as your country then choose Florence/Tuscany or any other region, there is a ton of listings. also try www.casaspinelli.com i stayed there a year ago it was a very afforable vacation apartment in Florence.
Hello LowCountryIslander, I am familar with the area where LaFocolare is located as I have Italian friends in Florence that have a second home on the outskirts of Reggello where I have stayed and personally I find that area paradise. For someone who has never been to Italy before it would probably be to quiet so to speak but from what you have said I think if your group decided on LaFocolare you would be most happy staying there.
lilybud...thanks for the information I will check out craigslist, I hadn't thought to look there.

LoveItaly...thanks for the personal recommendation. I'm not too worried about being in a more "off the beaten path" location. This group has been to Tuscany before at least once (some more then once) and this trip will be more of a relax and enjoy the wine and food vacation instead of trying to see every site in Tuscany.
www.villaeurope.com;
Suzanne Cohen is the owner, based in Maine. We rented a fabulous villa
near Castellina in Chianti, which unfortunately is no longer available.
We were able to speak with Suzanne and her staff several times; she had stayed in the villa herself and answered all of our questions, as well as getting a rental car for us, arranging a special birthday dinner, and recommending local tour guides.
Hi Lowcountry,
Instead of one villa give thought to a property like this http://www.chiantinet.it/leselvole/
eng.html. We stay here every year and have booked the whole place for larger groups. They have 4 two bedroom aptmts and 2 one bedroom apartments... 20 people all told. The grounds are beautiful.. 12 acres fenced, large pool, 500 olive trees, flowers everywhere and great fun for a crowd. Le Selvole is about a mile from Radda in Chianti, which of course is close to Gaiole so you might have been there.
In May the 2 bedrooms rent for about 700 euros. If you rent the whole place it is not out of line to ask Francesca for a discount.
sammy123 and jnjfraz...
Thanks for the information both accommodations look like what we have in mind.
I am going to Tuscany with 16 friends and family in just over a week. We booked a villa through TuscanyNow.com. It is called le Celle and is located in Lecchi in Chianti near Radda and can accommodate up to 20 people. The villa has a main house as well as some small cottages and a pool. The photos look gorgeous. The villa is 20 minutes from Sienna and an hour from Florence. Lecchi is a small village with a few amenities and is in the heart of Chianti wine country. The company will send you a catalogue of their villas if you are interested.
Joana...
Thanks for the information, I will check it out.
Have a great time in Tuscany!