These people are pretty good http://www.ownersdirect.co.uk/italy.htm word you want is "villas" which will make googling easier.

Never stayed here, but it is one of the few Tuscan villas with a pool that I know of that is also walkable to a town. You can find reviews on line. The price may change in 2013, or vary from June to July, and may be negotiable. I don't know.

http://www.tenutedipecille.com/Appartamento.aspx?tenuta=Villa_Pecille&app=La_Limonaia&viewID=4&lang=it-IT

Try over at www.slowtrav.com they have a huge listing of reviewed villas etc...

Stayed here, LOVED IT! We will go back again and again.

Beautiful grounds, lovely and spacious villas, amazing hosts, incredible views, family friendly.

http://www.tripadvisor.com/Hotel_Review-g194833-d298890-Reviews-Sant_Antonio-Montepulciano_Tuscany.html

It is at best a 45 minute walk from the Sant'Antion apartments (above) to the center of the hilltown (Montepuliciano). Some of the walk is steep. I would not want to do it in hot sun, and there are no sidewalks on the road.

it is sometimes possible to find agriturismi near San Gimignano that are walking distance to the town, but you really need to use online maps like Google to calculate the distance from the address you are given to a real address or piazza inside the town. Don't rely on websites that tell you it is "two kilometers to town." That may only get you to the peripheral legal border of a Tuscan town, not to where restaurants and shops are located (uphill).

Sant'Antonio looks gorgeous. Rates are reasonable, too. Love the family-friendly aspect.
Thanks for the tip on the "walkability" to town. Definitely something to consider. I will be using Google map for sure before I book anything.

pizzocchieri is right!

Ooops.. I missed the "walking distance to town" part. Email Nico, the owner/host - he will be honest with you about walkability. We had a little car while we were there.

He will probably be happy to point you in the right direction, if his villas are not suitable.

Good luck, it sounds like an amazing trip

These may help:

http://www.tuscany-villas.com/villas-walk-into-town.html

http://slowtalk.com/groupee/forums/a/tpc/f/862600685/m/23810657021

The site above is a WEALTH of info!!

Oh dear, that thread from slowtalk is 7 years old..

This looks nice, but I have never been..

http://www.tripadvisor.com/VacationRentalReview-g187895-d1402987-Signorelli_Apartment_with_a_wonderful_terrace-Florence_Tuscany.html#review_138291638

Villa le Colline is located at Impruneta on the hills surrounding Florence, 10 minutes away from the city centre. It is a private villa with a huge park, usually rented from families with children studying at the near International School of Florence, but I know it can be rented per week as well.
And of course there is a pool!

http://www.villalecolline.com/

I have stayed at the Villa Pecille twice. (Pizzocchieri provided the link) It is exactly what you are looking for in terms of a pool and location. Villa Pecille is located at the edge of Panzano which is a lovely little town with wonderful restaurants and a world famous butcher. The restaurants and even the grocery store are within walking distance.
The views from Villa Pecille are breathtaking. It sits on the rim of the valley with the vineyard and olive groves going on and on below.

Get in touch with the manager, Gabriele. His replies are prompt. Hopefully the price will be right for you, as this place is beautiful!

You guys rule!!! Can't thank you enough. I have a full evening of surfing ahead of me. I am pretty settled on Sant'Antonio for a week. We will have a car so, although walking to town is a luxury, it is not a necessity. Nico and I have been emailing back and forth today.
So, onto our second week in Italy. Where should we go for week two with the kids before we fly off to Paris for our final week of travel bliss????

Wonderful! Nico is just terrific, isn't he? I adore him.

Nico has kids, so he may also be a great person to talk to about where to take the kids on week two.

If you stay at Sant'Antonio, make sure to go have pizza at Enzo's! I'm not sure what the name of the pizzaria is, but Nico recommended it and the guy who owns it is named Enzo. So much fun, great food, family friendly, and lovely guy.

I'll write more tomorrow, as I have a few more places you may enjoy out in that area.. I have to run off for a day after Thanksgiving dinner now!

Sant'Antonio is booked. We would love to visit Florence for a few days right after. Any ideas of places to stay? Family-friendly of course and priced around $200-$300US/nt. After that we are stuck: do we road trip up to Pairs and take our time? Or fly to Paris and spend a few days around the Loire?
So many decisions

Oh no, sorry to hear that Sant'Antonio is booked.

You have gotten a lot of great advice here for apartments in the Tuscan Hill towns above, so I will give you some help with Florence.

Also, what is your itinerary look like week to week? That will help. How long will you be in France? From what I can tell, 2 weeks Italy and the last week in France? How are you breaking it down? One week Tuscan villa/house, one week Florence, one week France? Or 10 days Tuscan villa/house, 4 days Florence, one week France?


Here are a few ideas for Florence:

Florence center apartment - The apartment in Florence offered by Nidi di Belforte is located in Florence's historical center, a few steps away from the Duomo. It has a kitchen, living room, two bedrooms and a small balcony.

http://www.anapartmentinflorence.com/apartment-guelfa.php

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Signoria Apartments - All apartments are very close to to main museums and attractions. They can host from two to seven persons and are perfect for families coming to Florence in any season. The accommodation are all recently restored and equipped with fully furnished kitchen, air conditioning system, wi-fi free internet connection.

http://www.signoriaapartments.com/

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Residence Palazzo Belfiore, the residence of an ancient Fourteenth century family, is situated in Florence near the Ponte Vecchio, the Uffizi Gallery, Palazzo Pitti, Boboli Gardens and Santo Spirito, in a quiet area in the city centre, in the heart of one of the traditional Florentine quarters rich in handicraft shops, antique shops and typical restaurants.

Apts: Clarice, Lorenzo il Magnifico, Leone X and Caterina dei Medici all have enough space/beds for your family

http://www.residencebelfiore.it/eng/appartamenti.htm

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Good luck!

Jinky, I meant I BOOKED IT!! It's all good.I will check out your Florence spots tomorrow - many thanks.
Here is how our 5 weeks break down:
Weeks 1-2: South of France near St. Remy. One week staying at a place my dad has rented, second weeks is a ???
Weeks 3 - Sant'Antonio
Weeks 4-5 - 4 nights in Florence and then EITHER fly to Paris and go for a few days in the Loire and then a week inParis or...make a road trip of it and drive from Florence to Paris. Last week in Paris.
You have been the biggest help!!! Any ideas are very happily accepted.