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Orgia, Siena

Cerreto for 8

The light of late summer brings out Nature's colours and the stones of this sturdy farmhouse.

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


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 £2228.00 / €2943.00 / $3296.00 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

Simple, yet delicious, ingredients add to whatever will be brought to the table from Dimora's nearby kitchen.

Sleeps: 8

7 nights from £1660.00 / €2193.00 / $2457.00 View property Check availability


San Michele

The estate that sits hilltop overlooking Arezzo includes the owner's home and San Michele, a lovely rental property behind the church.

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 £1968.00 / €2600.00 / $2912.00 View property Check availability

Pomaia, Livorno

Dipinta di Blu

Three shades of blue greet guests on a sunny day.

Sleeps: 8 to 10

A spacious family home with an air of celebration, Dipinta di Blu has all the elements for a delightful holiday: generous spaces in which to gather - the biggest of them all an incredible furnished portico - charming bedrooms in which to retreat and a large pool that mitigates the Tuscan sun. With a village 3 minutes away and the Mediterranean on the distant horizon, this is an easy place to be.

7 nights from £2488.00 / €3286.00 / $3681.00 View property Check availability

Laveno, Lake Maggiore

Villa Labiena

The pool in the garden can be seen from all of the large terraces at Villa Labiena

Save up to 10% on this property

Sleeps: 10

Villa Labiena sits high on a hill overlooking Lake Maggiore, yet its extensive grounds extend to the water's edge. An excellent place for a family reunion or a holiday with friends, the property offers spacious accommodation, furnished terraces and a large pool - all with lake views. In walking distance to a lively lakeside village and a ferry away from charming towns and the gardens and elegant villas for which the lake is famous.

7 nights from £3536.00 / €4671.00 / $5232.00 View property Check availability

Moltrasio, Lago di Como

Riva del Lago

This quintessential Italian villa dips its toes into the lake's shimmering waters.

Sleeps: 8 to 9

This three-story villa on the western leg of Lake Como combines luxury, generous space and an easy welcome to guests who would like their own terrace on the water. Ideal for a group of friends or a family reunion, it has bedrooms that face the lake or the long furnished garden and a private dock for effortless lake access.

7 nights from £4980.00 / €6579.00 / $7368.00 View property Check availability

Monte San Savino


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 £1849.00 / €2443.00 / $2736.00 View property Check availability

Radda in Chianti


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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Varenna, Lake Como


Situated at the entrance of the estate, Rubino has two balconies from which to enjoy mountain-rimmed lake views.

Sleeps: 8 to 10 (Multiple properties at this location)

A spacious house for 8, Rubino is situated at the entrance of the Varenna Estate. With beautiful views of Lake Como from its balcony terrace and a garden with a private pool, it is a short distance from the village of Varenna and the ferries that provide transport to charming lakefront venues.

7 nights from £2889.00 / €3816.00 / $4274.00 View property Check availability

Meina, Lake Maggiore


This modern house with lawned garden and private swimming pool is the perfect family holiday destination.

Sleeps: 8

This stylish villa with a panoramic terrace with views of the west shore of Lake Maggiore, is a very comfortable place for a family holiday. With a swimming pool and bedroom air-conditioning to take the edge off the summer sun, it is within easy reach of all services.

7 nights from £2142.00 / €2829.00 / $3168.00 View property Check availability

Castiglion Fiorentino, Cortona


The stone loggia marks the welcoming entry to this comfortable two storey family house.

Sleeps: 8 to 10

This two-storey home set in three fenced hectares has comforts inside and out that encourage an easy-going family vacation. With a pool and BBQ at hand and panoramic views over the Valdichiana, Avventuriero is a short drive from the lively Castiglion Fiorentino and the beautiful Etruscan Cortona, brought to the screen in "Under the Tuscan Sun".

7 nights from £865.00 / €1143.00 / $1280.00 View property Check availability

Zanego, Montemarcello

Pian della Chiesa

Dolina from Dolinetta

Sleeps: 10

Set in a cultivated dell within a National Park, surrounded by woods and under dappled shadow, Pian della Chiesa is an small agricultural estate with 2 carefully converted homes, both facing a wide lawn, bordered by woods and vines.

7 nights from £1533.00 / €2177.00 / $2377.00 View property Check availability

Magliano in Toscana


With dappled shade and a BBQ/pizza oven close at hand stands Morellino, named for the grapes growing nearby.

Sleeps: 8

Morellino, a rosy-hued summer home, named for the wine produced in this area, is well positioned to enjoy both its proximity to the coast as well as the surrounding bounty of a gently rolling countryside and offers a comfortable setting for an easy-going family holiday.

7 nights from £1568.00 / €2071.00 / $2320.00 View property Check availability


Villa Piera

Villa Piera sits high over the village against the bright skies of summer

Sleeps: 8

This 18th century villa and its extensive grounds stretch out above a small village and is an excellent venue for groups of 8, 10 or 12. Suited out with all the features that make a holiday comfortable and the extra services that make it enjoyable, the villa and its pool are ideal for family reunions or a gathering of friends.

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Sovicille, Siena

Casa Gaia

Gaia loggia

Sleeps: 10 (Multiple properties at this location)

This large 1st floor apartment in a country villa offers accommodation for 10 in mid and low seasons. With a wide furnished loggia to shelter from the heat and a large Tuscan fireplace for when the spring or autumn evenings require, this is a wonderful location for a country holiday just 20 minutes from the medieval beauties of Siena.

7 nights from £1577.00 / €2083.00 / $2333.00 View property Check availability

San Donato in Poggio, Chianti


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 £2406.00 / €3178.00 / $3560.00 View property Check availability

Ville di Corsano, Siena

Podere Le Mandrie

With its panoramic pool a short distance below the main house, Podere Le Mandrie sits high to enjoy its gardens and a wide Tuscan sky.

Sleeps: 8

A large farmhouse in the wooded outskirts of the Crete Senese has undergone a luxurious transformation and here visitors are surrounded by the bounty of the land yet enjoy great comfort and the beauty of a tastefully designed home. With discreet staff on hand Monday - Friday mornings, this is a house that will pamper you, yet leave you to enjoy the natural splendour of a Tuscan hilltop.

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Orgia, Siena

Cava di Calbello

Sunbeds and the privacy afforded by walls and a generous garden mean sunbathing in complete privacy.

Sleeps: 8

At the base of a Montagnola hillside near Siena is a tribute to relaxed well-being and excellence in gardening. A former stone quarry has been lovingly transformed and the comfortable rooms of the sprawling home all access its gracious gardens. The arrangement of the sleeping accommodations make this the ideal choice for extended family holidays where different generations can retreat to private quarters yet still meet in large common areas.

7 nights from £2487.00 / €3286.00 / $3680.00 View property Check availability