Make Your Next Trip Extraordinary

Rent A Villa In Italy For the Whole Family

by Wendy Perrin | September 22, 2016
Poolside and deck view.
Poolside and deck view. Photo: Homebase Abroad
countryside view
Countryside view. Photo: Homebase Abroad
outdoor side view
Outdoor side view. Photo: Homebase Abroad
dining room
Dining room. Photo: Homebase Abroad
Master suite sitting area
Master suite sitting area. Photo: Homebase Abroad
outdoor cooking
outdoor dining
Outdoor dining. Photo: Homebase Abroad
Dining Pergola
Dining pergola. Photo: Homebase Abroad
Cantina detail
Cantina detail. Photo: Homebase Abroad
Cinema night
Cinema night. Photo: Homebase Abroad
cinema seating
Cinema seating. Photo: Homebase Abroad
Bellavista suite detail
Bellavista suite detail. Photo: Homebase Abroad
Brunello suite sitting room
Brunello suite sitting room. Photo: Homebase Abroad
Brunello suite sitting room
Brunello suite sitting room. Photo: Homebase Abroad
Living room view
Living room view. Photo: Homebase Abroad
interior view Ca di Pesa Italy villa
Interior view. Photo: Homebase Abroad
breakfast nook Ca di Pesa Italy villa
Breakfast nook. Photo: Homebase Abroad
children's TV room Ca di Pesa Italy villa
Children's TV room. Photo: Homebase Abroad
Italy villa ca di pesa jungle room
Jungle room. Photo: Homebase Abroad
countryside view
Countryside view. Photo: Homebase Abroad


Hi Wendy,

I’m looking for a really special villa in Tuscany for a family reunion for my mom and dad’s 40th wedding anniversary. There will be 18 of us, ranging in age from three years old to 82. We want a great setting with fabulous views, and also a good base for making day trips to the hill towns. Can you suggest a village or villa for us—or a good resource for securing a rental?
Thanks for any help you can offer,



You’ve got a challenge, Margaret: The dreamiest villas in Tuscany tend to be restored farmhouses or castles filled with things that can be treacherous to toddlers or grandmas or both: slippery centuries-old stone steps, open-hearth fireplaces, wobbly antique furniture, spiky medieval-style door latches, etc. I know this from personal experience, having rented an ancient Italian farmhouse with my own mom and kids. I went to sleep every night worried my two-year-old was going to trip over an antique, go flying into a door latch, catapult down the stairs, and end up in the fireplace.

But I do, in fact, have a place in mind for you. Several years ago, when I was in Tuscany I was shown a rambling property called Ca di Pesa that is actually an historic borgo (medieval village). I’ve remembered it since because it struck that unusual note of being sophisticated enough for adults (it’s got a wine cellar where you can dine by candelight, for instance, not to mention a cinema and a bocce court), while also kid-friendly enough for tots (it’s got plenty of flat lawn and a freshwater pool with a child-friendly gate). It’s in an ideal central location amid the vineyards and olive groves of Chianti, near the charming town of Panzano, halfway between Florence and Siena. And it fits 18.

Two caveats: First, a lot of people who rent homes in Tuscany like to be able to walk into town, and while it’s only a five-minute drive to town, it’s a 3.6-mile walk—and not on a charming country path but just on the regular road. Second, the price tag is high, so it helps if you can fill the house. (Maybe you can scrounge up two more family members to make your group 20?) The price in May is $22,500 for the week—which sounds exorbitant until you do the math and realize it translates to $161 per person per night and includes a concierge and a welcome dinner.

So it’s a splurge, for sure, but then again, you did ask for “really special.” And, to this day, whenever I fantasize about the Tuscan villa vacation I desperately need, I think back to Ca di Pesa and look through the photos above. My favorite touch in the house? The jungle fresco in one of the bedrooms.



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  1. Skip

    We stayed at Ca di Pesa with a group and even picked grapes. Going to the hen house to retrieve fresh eggs each morning is still vivid in my mind. The property is exquisite , the ambience spectacular, the food and service like a 5 star Relais and Gourmand. Close enough to make a day trip to Florence or Sienna. Did I mention the wines of Ca di Pesa? They have won awards . I could go on but I’ll summarize . One of the best vacations ever.

  2. Cacinda Maloney

    One of the most amazing places I have stayed at in Tuscany is Villa Pipistrelli, not too far from Siena. The Donati Family owns 2500 acres, where they have restored each of the old farmhouses into a small town of luxury villas. It is quite stunning to say the least:

  3. Jody

    I have rented a villa from Parker Villas. They do only Italy and have great properties for a large crowd. They operate out of MA and I was able to go into there office and talk to them about our needs. It was for our Honeymoon. They are very knowledgeable and may know which of their properties are more kid friendly. I’d take a look at their site.

  4. Susie

    We’ve stayed at Ca di Pesa, several times with a small (4people) and a large group and it’s a complete delight. The rooms are lovely, the view is spactular and dining either indoor or out is special. There is even a grill and a hedge of rosemary, so you can pick your own and the pizza oven is amazing. Their own olive oil is the best. What a treat!

  5. Amy Sittler

    I have stayed at this villa and can’t imagine a better place to spend a relaxing, food and wine filled holiday. The grounds and views are amazing, the surrounding towns and villages are fun to explore and the house is perfect. It’s not too fancy but is instead comfortable. Having pizza baked in the centuries old pizza oven is a rare treat. Highly recommend this for families or groups of friends

  6. Kathy McCabe, Dream of Italy

    Congrats on the new site! This villa looks exquisite and you are so right about most people wanting to be able to walk into town from their villa rental but they’re happy to give that up for a very special villa. We have a free Italy villa rental guide over at that may be of interest to your readers.

    Kathy McCabe

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