Our Favorite Region of Tuscany

Tuscany’s Val d’Orcia may well be the most perfect slice of the most perfect part of Italy. Lying just south of Siena, this ancient valley of gently rolling hills and scenic villages can feel blissfully timeless, its rich history and natural splendor exquisitely preserved. “You go back to paintings from the Renaissance or the 18th century, and the landscapes you see depicted tell you that the Val d’Orcia is an uncontaminated place,” says Gelasio Gaetani d’Aragona Lovatelli, a wine consultant whose family has owned land in the region for centuries. “It has not been destroyed.”

The valley was made a World Heritage site by UNESCO in 2004 and has long been an idyllic getaway for Italians and foreign travelers alike, though it is not flooded with tourists during the summer like Chianti.  They come for the relaxed sophistication found in and around the towns of Montalcino, Pienza, and Montepulciano, for the renowned cuisine and wine, and for the area’s convenience to Florence and Rome (both are less than a two-hour drive away). Autumn always shows the valley at its best: As the tourist season winds down, vineyards turn to russet and gold, and harvest festivals abound. And now visitors have more options than ever, thanks to a new generation of hoteliers and restaurateurs.

This is the perfect place for the Italian villa experience, and we have a wonderful selection of beuatiful properties to entice you. We just did our inspection trip to this area in Autumn of 2016 and would like to especially reccomend a number of properties, whose owners are doing a wonderful job.

For the best in contemporary Tuscan design, take a look at Villa La Torre. The design and facilities are unsurpassed, and the views to die for. The demonstartion kitchen is fantastic, and the cook Marcella has authored a number of cookbooks. Her cooking is the highpoint of any trip. Her lasagna is simply the best in the world.. Three hundred meters up the hill, Villa Bella is owned by the same designer/architect and is equally wonderful. Two smaller properties within a kilometer, Bella Vista and Villa D'Orcia are also great examples of Tuscan design, offer all staff and facilities and have wonderful views of the whole valley. If your tastes in design style are more grandiose and traditional, the noble villa, Palazzo Chiusi might be to your taste. Millions of Euro were spent restoring this show place. It is probably the prettiest villa for rent in Tuscany, though might be a little fussy for some. All services are on offer, including a chef who has worked in Michelin establishments. La Casa Vigna is a house owned and operated by the most renowned vintner in the valley. A wonderful English speaking staff is available, and while there you can chekout the wine making facilities and vineyards, as well as the organic animal farm, from where your meals will come. Casa Vista is a brand new property on the market this year. Very close to the wonderful renaissance town of Pienza , it features beautiful contemporary Tuscan design and furnishings, and offers all staff and services. Another attractive new property on the market, which might be especially nice for off season rentals, as it features an indoor pool and wellness features is Poderosa.

Anway, this region is our specialty and we have many more enchanting properties listed, all unique in their own right.  Browse our selections and contact us with any questions or recommendations.

Villa 16

Villa Dimora

Tuscany-Southeast/Val D'Orcia

Gorgeous 6 bedroom villa with spectacular views of the Val D'Orcia, and especially beautiful outside areas for lounging and dining. Set up well for families with children, can sleep up to 16.

Villa 18


Tuscany-Southeast/Val D'Orcia

A charming 9 bedroom villa with spectacular views of Pienza. This luxury villa comes complete with its own chef and staff. From $21,000 per week

Villa 8

Villa Bagni

Tuscany-Southeast/Val D'Orcia

A 4 bedroom, 5 bathroom luxurious Tuscan farmhouse overlooking the stunning Val d'Orcia landscape, within a 20 minute walk of village.

Villa 9

Palazzo Montepulciano

Tuscany-Southeast/Val D'Orcia

Beautifully restored 4 bedroom noble palazzo in downtown Montepulciano

Villa 4

Art House

Tuscany-Southeast/Val D'Orcia

A very unique and design forward 2 bedroom accommodation. From $3,200 per week

Villa 2


Tuscany-Southeast/Val D'Orcia

2 bedroom villa with pool in the Val D'Orcia. From $1,607 per week

Villa 8

Villa Montalcino

Tuscany-Southeast/Val D'Orcia

Stylish 4 bedroom villa with beautiful views and outdoor spaces only a short 7 minute walk to the wine town of Montalcino. From $9,900 per week

Villa 22


Tuscany-Southeast/Val D'Orcia

Well restored 11 Bedroom historic castle on 1,500 acre estate. From $27,000 per week

Villa 10

Via Fonte Antese

Tuscany-Southeast/Val D'Orcia

Very well done 5 bedroom home, just a 15 minute walk to the village of Radicofoni in the beautiful UNESCO Work Heritage site of Val d'Orcia. From $6,550 per week

Villa 15

Villa La Vittoria

Tuscany-Southeast/Val D'Orcia

Beautiful, newly refurbished 7 bedroom villa in the Unesco designated Val d'Orcia, just a 20 minute walk from the village of Contignano. From $16,950 per week

Villa 12

Villa Pienza

Tuscany-Southeast/Val D'Orcia

Very pretty and well furnished luxury 6 bedroom villa near Pienza. From $5,398 per week