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The house and its upper terrace fit snugly against the rising hillside.

Sleeps: 4

An idyllic retreat for a couple or a small family, this stone house sits atop a wooded Umbrian hillside with sweeping views. With outdoor eating areas on two levels, a small panoramic pool and charming interiors, the house is perfect place to 'get away from it all'. And yet it is well placed to discover the medieval cities of Todi, Orvieto and Perugia or take in the lakeside delights of Lake Corbara.

7 nights from £727.00 / €765.00 / $934.00 View property Check availability
A great pleasure of Tuscan summers is the possibility of living and dining outdoors.

Sleeps: 7

In a hilltop village south of Siena and just a stroll away from a panoramic restaurant, Casalta is a beautifully appointed house where attention to detail is evident in its spacious interiors as well as in its well-tended gardens and furnished terraces. An excellent venue for a group of friends or a family of adults, the house serves as an excellent base for Tuscan excursions, while the extra catering, cleaning and transport services available mean that this could be a dream holiday where one's only task is discovery and enjoyment.

7 nights from £2280.00 / €2400.00 / $2928.00 View property Check availability
The houses in the Borgo include: a cottage for 2 at the top overlooking the pool, a studio apartment for 2 in the middle with the open loggia, and the large farmhouse to the left with from for 8 on the top two floors and 4 on the ground level.  The owner

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Sleeps: 16 (Multiple properties at this location)

For a family reunion, a workshop or a shared holiday of friends, Il Borgo is the ideal location. With spaces for everyone to dine together, inside and out, and accommodations distant enough to allow a bit of private space, this beautifully tended estate is an excellent base for discovering the treasures of Umbria. Having nurtured its 20 year restoration, the owner is a wonderful font of information on how to make this a holiday of a lifetime.

7 nights from £4370.00 / €4600.00 / $5612.00 View property Check availability
In the central piazza near the entrance a marble-topped table provides guests with an al fresco option for group meals.

Sleeps: 8 (Multiple properties at this location)

On two floors of a 18th century stone farmhouse, Casa Antica is a spacious holiday accommodation for a large family or a group of friends. At the heart of a beautifully tended Umbrian estate, it has four bedrooms, three bath or shower rooms, a large country kitchen and room for all to gather in its panoramic living room. With picturesque Umbrian and Tuscan towns in all directions and abundant markets and festivals in all seasons, this is a great base for a holiday.

7 nights from £1900.00 / €2000.00 / $2440.00 View property Check availability
At Terrazza's marble-topped table meals al fresco are definitely served with a view.

Sleeps: 4 (Multiple properties at this location)

Perfect for a small family or friends on holiday, Terrazza is named for its wide vine-covered terrace that looks onto rolling wooded hills and a medieval village. While two cosy bedrooms share a bathroom, the apartment has a spacious open plan living area with a kitchen and dining table ideal for people who are serious about good food. Situated on a beautiful Umbrian estate with a panoramic pool, Terrazza puts the famed sites of Umbria and Tuscany within easy reach.

7 nights from £950.00 / €1000.00 / $1220.00 View property Check availability
Sitting on Mulinetto's loggia one feels a bit removed from it all, yet still part of this beautifully tended estate.

Sleeps: 2 (Multiple properties at this location)

On the top floor of a 14th century olive mill, Mulinetto is a spacious studio apartment that has everything a couple might need, including a charming furnished loggia as well as a sunny patio. This romantic accommodation is well situated for savoring the quiet of the green Umbrian hills, but within easy reach of the markets, festivals and picturesque hill towns that have drawn visitors for centuries.

7 nights from £665.00 / €700.00 / $854.00 View property Check availability
Sitting at the top of the property, Casetta is a lovely two-story cottage that overlooks the pool.

Sleeps: 2 (Multiple properties at this location)

A two-story cottage on a beautifully tended Umbrian estate, Casetta is ideal for a romantic getaway or a quiet retreat from a busier life. With a private sunny patio for outdoor meals, an ensuite double bedroom and a panoramic living area overlooking the nearby property pool, this property guarantees a restful stay, yet has hill towns, festivals, shopping and Italy's 4th largest lake an easy drive away.

7 nights from £855.00 / €900.00 / $1098.00 View property Check availability
An aerial view of the Borgo features the owner's home, a large farmhouse comprising Casa Antica and Terrazza and Mulinetto.  Casetta is just beyond the large property pool.

Sleeps: 14 to 16 (Multiple properties at this location)

Settled in the folds of a green Umbrian hillside, Borgo Montecorona is a beautifully tended estate whose four apartments lend themselves to an idyllic retreat for couples or families, or, when taken together, a delightful place for a reunion of family and friends. With individual outdoor eating areas and a panoramic pool, the property is an easy drive from many of Umbria's most fascinating sites.

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The pleasure of having a portico just outside the kitchen is having breakfast overlooking the garden in any weather.

Sleeps: 8

Set in the wide Chiana valley, this newly renovated stone house is designed with family holidays in mind. With a large fenced garden and pool, bunk bedroom and an extra children's dining area, younger guests will be delighted. Yet panoramic living and dining areas inside and out and a modern kitchen that invites an Italian cooking lesson mean adults will also feel well placed for relaxing days at home as well as excursions that put Florence, Cortona and Arezzo at hand.

7 nights from £2327.00 / €2449.00 / $2988.00 View property Check availability
The Francigena  pool at the back of the house has spots both for sunning and for enjoying the view from under the arched loggia.

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Sleeps: 10

The perfect size for a family on holiday or a group of friends, this villa and its pool is off an ancient pilgrim's trail on a wine estate near San Gimignano. With five ensuite bedrooms, air-conditioning and the estate restaurant a pleasant walk away, this is a fine base from which to explore the medieval cities that dot the nearby landscape.

7 nights from £2356.00 / €2480.00 / $3026.00 View property Check availability
The wide facade of Pellegrino hints at the space one will find inside the front door.

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Sleeps: 15

This generous family home on a large wine and olive oil estate sits off the famous Via Francigena, the ancient route from France to Rome. With accommodations for up to 15, and places inside and out to get together, it is a wonderful place for family reunions or relaxed holiday workshops. With an estate restaurant in walking distance and the famous medieval towers of San Gimignano nearby, it is an excellent base for touring or a retreat from a faster pace.

7 nights from £3135.00 / €3300.00 / $4026.00 View property Check availability
The pleasure of staying in this village home is the wide panorama which waits at the end of the garden patio.

Sleeps: 6 to 8

This beautifully restored home sitting in the middle of a Tuscan hilltop village just about has it all - the convenience of shops and restaurants outside the front door, restful bedrooms and sitting rooms with panoramic views spread on four floors and an outdoor dining pergola, and refreshing plunge pool on a garden terrace with a stunning countryside panorama.

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The view from the dining pergola takes in the long facade of the historic convent.

Sleeps: 14

In the hills in which the Medici built their grand country villas, this former convent offers spacious bedroom suites and numerous gathering places to members of a family reunion, a workshop or couples on holiday together. With an in-house bar, billiards table and air-conditioning, it has all of the comforts and more, yet is in easy reach of fascinating Medieval and Renaissance sites.

7 nights from £5150.00 / €5421.00 / $6614.00 View property Check availability
While it is possible to enter the villa on the ground floor, the beautiful dual stairway also leads to a formal entrance on the first floor.

Sleeps: 12

This carefully restored country villa in the Arno valley, belonging to the same aristocratic family for centuries, offers its guests the gentle authenticity of earlier times. Ideal for a family reunion or a holidaying group of friends who are happy to explore the pleasures of relaxed country living, happily with all services only a kilometre away.

7 nights from £3288.00 / €3461.00 / $4222.00 View property Check availability
A very spacious main room with dining and living accommodation greets Aceronina guests who enter through wide double doors.

Sleeps: 6

With long panoramas from its pool and dining loggia, this spacious first floor apartment is a charming spot for a family or couples on holiday together. Set on an agricultural estate producing its own wine and olive oil, the property is in easy reach of historic spa and medieval market towns scattered in the hills of the stunning Val d'Orcia south of Siena.

7 nights from £760.00 / €800.00 / $976.00 View property Check availability
Easy entry to the villa's panoramic pool makes a daily swim possible for guests of all ages.

Sleeps: 11

With sweeping views of the valley below, this villa, beautifully refashioned from watchtower and farmhouse origins, along with its gracious guest cottage provide spacious accommodations for a large family gathering or a group of friends. Its position in the Chiana valley puts ancient spas, medieval market towns and cities perched on towering ridges but a short drive away.

7 nights from £2470.00 / €2600.00 / $3172.00 View property Check availability
Poolside cocktails and castle-studded views are certainly reasons to head down the terraced garden to its lowest level.

Sleeps: 9

This lovely villa, with accommodations on the ground and first floors, provides spacious and stylish living for a group of friends or a large family interested in exploring the famous vine-strewn hillsides outside Radda in Chianti. Beautifully planted terraced gardens lead down to a pool whose views take in the neighbouring castle that has been standing for 1,000 years, yet good roads have you off to the medieval villages between Florence and Siena which host events throughout a lively summer.

7 nights from £2565.00 / €2700.00 / $3294.00 View property Check availability
The generous proportions of the living room reflect the open-hearted hospitality of Docciole.

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Sleeps: 14

In walking distance to Radda in Chianti, Docciole is a great base for a large family holiday or a group of friends wishing to explore the famous Chianti hills. Set on large grounds with green vistas, the lovingly restored stone farmhouse has four independent bedroom suites on the ground floor and three bedrooms on the top floor along with a living room and kitchen of soaring proportions.

7 nights from £2432.00 / €2560.00 / $3123.00 View property Check availability
La Caserotta houses all of its guests in the two large structures facing each other - a converted olive mill and stone barn.

Sleeps: 22 (Multiple properties at this location)

La Caserotta offers ample and elegant accommodation for a large family reunion or a special event set in the Tuscan countryside. With five spacious apartments providing room for up to 22 guests, this hamlet has individual outdoor areas as well as wide terraces where a group can dine or party. Located just south of Florence and an easy drive from the famed villages of the Chianti, this is the perfect spot for celebration or simply savoring the best Tuscany has to offer.

7 nights from £8190.00 / €8621.00 / $10518.00 View property Check availability
At the end of the hamlet, Geranio is entered through doors off it wide outdoor terrace.

Sleeps: 4 (Multiple properties at this location)

The most spacious of the Borgo Caserotta accommodations, Geranio has terraces on two levels which take in views of the swimming pool and the wooded Chianti hills. A small family or holidaying couples will delight in the pleasure of living in this country hamlet and the ease with which they can reach the famed Chianti villages that lie between nearby Florence and Siena.

7 nights from £2063.00 / €2171.00 / $2649.00 View property Check availability