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Umbertide, Umbria

Casa Antica

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

Castiglion Fiorentino

Falconiere

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

Pancole, San Gimignano

Francigena

The Francigena  pool at the back of the house has spots both for sunning and for enjoying the view from under the arched loggia.

Save up to 15% on this property

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

Radda in Chianti

Lucumone

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

Trevinano, San Casciano dei Bagni

Villa San Rocco

Morning sun warms the earthern-hued stones of Villa San Rocco and makes it a good day to step out into the sun.

Sleeps: 9

A stone farmhouse, beautifully restored and with pools, furnished terraces and sweeping views of wooded hillsides and a village perched on a tufa cliff, Villa San Rocco has become a villa with a taste of luxury. With generous room for a family reunion or holidaying friends, it offers several places for the group to be together, but comfortable corners in which to retreat. It is well-positioned for easy reach of historic spa towns, medieval hilltop villages, protected parklands and cities that fill guidebooks.

7 nights from £2646.00 / €2786.00 / $3399.00 View property Check availability

Piazze, Cetona

Villa Vista Lunga

Though the panoramic pool at Villa Vista Lunga sits at a lower level to the house it is not far to go for a swim.

Sleeps: 10

Carefully restored to preserve its country heritage, Villa Vista Lunga is special place in which to spend a holiday. With generous space for up to 10 guests, it offers bedroom suites in which to retreat and various areas in which to come together, including a panoramic pool. Nearby medieval villages and history spa towns provide the chance to slip into Tuscan life, while the villa itself encourages one to relax into 'la bella vita'.

7 nights from £2918.00 / €3071.00 / $3747.00 View property Check availability

Piazze, Cetona

Radura

Whether from the french doors to the lower bedrooms or the upper level dining room the stroll to the pool is a short one.

Sleeps: 8

Set in a generous clearing on a wooded hillside, Radura is a charming farmhouse that follows the lay of the land, thus giving all of its floors access to the garden. With four ensuite bedrooms it is the perfect size for a family or a group of friends on holiday. Well situated between the medieval town of Cetona and San Casciano dei Bagni, historically famous for its thermal waters, it is an excellent base for exploration, but a comfortable place to savor the views.

7 nights from £2538.00 / €2671.00 / $3259.00 View property Check availability

Piazze, San Casciano dei Bagni

Villa Veduta

The dual staircases at the front of the villa lead directly to the sleeping quarters on the upper floor.

Save up to 25% on this property

Sleeps: 10

This restored country house, spacious enough for a family reunion, makes the most of its panoramic position on the slopes of Monte Cetona. With furnished patios and pergolas and a swimming pool dressed with sun beds and umbrellas, it is excellent for guests who enjoy outdoor living. Yet its air-conditioned bedrooms and comfortable interiors ensure similar ease once inside. Well placed for quick access to medieval spa towns, stately gardens and a motorway that delivers you to sites that fill guide books.

7 nights from £3325.00 / €3500.00 / $4270.00 View property Check availability

Trevinano, San Casciano dei Bagni

Rinnovato

The dining area is an eclectic mix of Italian design and recycled ecology, with a touch of whimsical nostalgia.

Save up to 15% on this property

Sleeps: 8 to 10

This large country house, a refashioned mix of Italian design and ancient origins, offers a comfortable family holiday home at the edge of Monte Rufeno National Park in southeastern Tuscany. With 2 hectares of garden and an endless panorama, the house has a relaxed open plan layout, generous spaces and windows that flood them with light. Well-positioned to explore ancient thermal spa villages, famed medieval hill towns and the mountains and lakes that have inspired artists and writers for centuries.

7 nights from £2646.00 / €2786.00 / $3399.00 View property Check availability

Montefollonico, Pienza

Podere Enea

A short stroll from the house, the pool area provides a salt-purified pool, a furnished pergola offering shade and a barbecue awaiting an outdoor chef.

Sleeps: 8

A sense of generous hospitality reigns in this carefully restored Tuscan farmstead. Set either side of a walled courtyard, the main farmhouse and annex provide accommodation for a family reunion or group of friends in 4 beautifully finished ensuite bedrooms. With sitting and dining areas both indoors and out, a gym and spa on premise, a furnished pool area and truffles in the nearby woods, this is both a place to linger and an excellent base from which to explore the beauty of the UNESCO acclaimed Val d'Orcia.

7 nights from £3610.00 / €3800.00 / $4636.00 View property Check availability

Sarteano, Val d'Orcia

Valdorcia

Valdorcia is a golden stone farmhouse sitting amongst greenery yet looking out on wide landscapes of a region whose name it bears.

Sleeps: 8

This classic Tuscan farmhouse sits on a beautifully landscaped hillside overlooking the wide Val d'Orcia region. With ample space for a large family or a group of friends, it offers a panoramic pool and tended gardens, yet is but few kms. from restaurants, shopping and summer concerts.

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Santa Colomba, Siena

Pastine for 10

Autumn has dressed the back of Pastine in vivid colour.

Sleeps: 10

In the verdant Montagnola hills close to Siena, Pastine is a beautifully restored country house that offers a large family or a group of friends the space needed for a relaxing holiday. With panoramic terraces, a spacious garden and a pool with a view, the house is also only 15 min. from the city, a gem of a Middle Ages.

7 nights from £2167.00 / €2492.00 / $2926.00 View property Check availability

Orgia, Siena

Cerreto for 8

Sun beds and pool towels are provided for those who enjoy a refreshing dip on a summer's day.

Sleeps: 8

A house in a glade that has been standing for centuries, Cerreto is surrounded in a loose embrace of holm oak, pines, cork trees and corbezzolo, yet is positioned to enjoy views of the valley below and the many horizons that lead to Mt. Amiata. An excellent place for family reunions and visitors of all ages, Cerreto abounds in places of quiet retreat and joyous get-togethers.

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Montaione, San Gimignano

Valdera

The villa sits high, overlooking the wide Valley of the Era river, a view also enjoyed from the pool.

Sleeps: 8

This villa for 8 combines a sense of luxury with a vast expanse of landscape, and better still is in walking distance to village restaurants. Halfway between the medieval hill towns of San Gimignano and Volterra, it is a lovely place for friends or a large family to sample Tuscan history in contemporary comfort.

7 nights from £3379.00 / €3557.00 / $4340.00 View property Check availability

Sarteano, Val d'Orcia

Casa del Pastore

Dappled clouds in a blue sky are seen overhead and on the watery surface.

Sleeps: 8

Riding the ridge of the Val d'Orcia in a UNESCO World Heritage site, this newly restored home of a Tuscan cheesemaker is perfect for a family reunion - spacious bedrooms with en suite shower rooms, large spaces for the group to gather and a pool whose infinity edge disappears into the rolling hills beyond.

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Barberino Val d'Elsa, Chianti, Florence

Dimora for 8

A palette of green dresses the countryside around Dimora, with rows of olive trees and grapevines and the bolder copse of oakwood.

Sleeps: 8

7 nights from £2084.00 / €2193.00 / $2676.00 View property Check availability

Arezzo

San Michele

San Michele, which sits just behind the church of the same name, was once the home of the neighborhood priest.

Sleeps: 8 to 10

With a layout ideal for friends holidaying together or for a family reunion, San Michele is a beautifully restored villa on a hilltop estate overlooking the medieval city of Arezzo. With a panoramic pool and jacuzzi and neighboring owners to cater dinners, cooking lessons or cellar tastings, this is a wonderful place to sample the best of Tuscan culture in restorative comfort.

7 nights from £2533.00 / €2667.00 / $3253.00 View property Check availability

Monte San Savino

Cuculo

The furnished courtyard and the refreshing pool are invitations to spend a relaxing time outdoors.

Sleeps: 8 to 9

This attractive stone farmhouse has been renovated with care and good taste, leaving spacious bedrooms and many gathering places for a group of friends or family members to relax in the Tuscan countryside. Whether around the pool or in the wide furnished courtyard, easy-going enjoyment is the order of the day. Yet the house is well placed for visits to Siena, Arezzo and medieval villages just down the road.

7 nights from £2321.00 / €2443.00 / $2980.00 View property Check availability

Radda in Chianti

Sassaia

The layout of the estate allows each house to enjoy its own privacy and the marvelous views.

Sleeps: 8 to 9 (Multiple properties at this location)

This ancient Chianti farming estate, now converted with style and country charm, has two stone cottages, each ideal for a small family or group of friends. On different levels and with private terraces that do not overlook one another, the view they share is of the olive groves, vineyards and wooded hillsides that have made this area famous.

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San Donato in Poggio, Chianti

Castellaccio

At Castellaccio there are three different living areas: the main house, a large converted barn and a limonaia overlooking the pool.

Sleeps: 8 to 9

The Classic Chianti country house, Castellaccio is surrounded by gently rising hills of green and the occasional distant villa. With its beautiful pool and generous accommodation this is an excellent place for a group of friends or a multi-generational family to find space for joyous gathering or tranquil retreat.

7 nights from £3019.00 / €3178.00 / $3878.00 View property Check availability