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South of Siena Villas (31 properties found)

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Montisi, Siena


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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San Casciano dei Bagni


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

San Casciano dei Bagni

Villa Frescollina

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

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


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

Celle sul Rigo, San Casciano dei Bagni


Only a few steps separate the sweet Cellevista cottage from its refreshing private pool.

Sleeps: 4

Whether for a small family or a couple wanting a relaxing romantic retreat, Cellevista is ideally situated. The panoramic view from the front portico is all countryside, with the property's pool set in a generous lawn, yet a short walk of 100 m. has guests in the heart of the ancient village of Celle sul Rigo where there are small shops and restaurants. Nearby is the attractive town of San Casciano dei Bagni, whose history is entwined with its famous hot springs and elegant spa, yet this is only the beginning. Roads through a beautiful landscape easily deliver one to medieval towns their guidebooks will praise.

7 nights from £1154.00 / €1214.00 / $1481.00 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

Cetona, Sarteano

Dama di Campagna

Dama di Campagna is a charming Tuscan farmhouse only 2 km from the nearest village.

Sleeps: 6

Near the medieval town of Cetona, this charming stone house is a perfect location for a small family or couples on holiday. Carefully restored and furnished with warmth and good taste, it offers a pool set in a fenced garden and pergolas and porticos dressed for outdoor dining. Drives through the rolling landscape lead to nearby and varied destinations: ancient spa towns, historic gardens holding summer concerts, a Pope's ideal Renaissance city, outlet shopping or a motorway entrance that has you in Tuscan and Umbrian capitals for a relaxing day out.

7 nights from £2511.00 / €2643.00 / $3224.00 View property Check availability

Ciciano, Massa Marittima

Il Monte

The generous pool (8 x 20 m) with an infinity edge has more than enough room to allow all guests to enjoy the view.

Sleeps: 11 to 15 (Multiple properties at this location)

A restored hay barn and the ground floor of a large farmhouse provide hilltop accommodation for a family reunion that will revel in spacious grounds, a large panoramic pool, and the fresh food that the owners' garden and rich woodlands have to offer. Three apartments and an extra bedroom suite provide some private areas, while wide terracotta patios and a large common room ensure areas to sit down together for meals. In easy driving distance to small villages with restaurants and historic medieval cities that merit pages in guide books.

7 nights from £2318.00 / €2440.00 / $2977.00 View property Check availability

Ciciano, Massa Marittima


Leccio's main room includes a well-furnished kitchen with a dining table and nearby sofa.

Sleeps: 3 to 4 (Multiple properties at this location)

Leccio, the largest and best equipped of three farmhouse apartments, sits on wide lawns atop a tree-covered hill midway between Siena and the coast. Not far from the historic San Galgano Abbey, a splendid concert venue, it is the perfect size for a small family who will enjoy local activities - biking, gathering mushrooms or chestnuts, or simply enjoying the property's large panoramic pool - or venture out and discover the medieval towns and villages on other hilltops.

7 nights from £752.00 / €791.00 / $966.00 View property Check availability

Ciciano, Massa Marittima


Just outside the Quercia window is a furnished area for the guests' private use.

Sleeps: 2 to 3 (Multiple properties at this location)

Perfect for a couple who wants to get away from the city and enjoy the pleasures of a 'green' Tuscan farmhouse, Quercia offers fresh vegetables from the owner's garden, inspiring views from the shared pool and short drives to the medieval cities of Massa Marittima and Siena.

7 nights from £573.00 / €603.00 / $735.00 View property Check availability

Ciciano, Massa Marittima


The former hay barn now hosts the upper Faggio apartment and the ground floor Common room which opens to a generous furnished patio.

Sleeps: 4 (Multiple properties at this location)

The upper floor of a restored hay barn is now a panoramic accommodation for a small family or two couples ready to explore the rolling hills between Siena and the seacoast. Independent from the farmhouse containing two other apartments on the Tuscan estate, Faggio looks out to the large property pool and surrounding hilltop villages.

7 nights from £917.00 / €966.00 / $1178.00 View property Check availability

Ciciano, Massa Marittima

Monte del Bosco

On its own Tuscan hilltop Monte del Bosco apartments are surrounded by wide lawns for children to play and overlook an infinity pool in which to enjoy the view.

Sleeps: 11 to 15 (Multiple properties at this location)

A farmstead with more than a century under its belt, Monte del Bosco is now in the hands of young owners who are generous hosts to couples, small families or a family reunion come to enjoy their hilltop. Located near ancient abbeys, medieval towns of all sizes and only 40 km from the sea, this farm-based accommodation has three apartments, each with its own private outdoor dining area, a large pool and a spacious Common Room that provides both WiFi and a spot to meet and eat together.

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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 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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Arbia, Siena


Quintessentially Tuscan, especially around Siena, is a large farmhouse surrounded by olive groves and rolling hills in the Crete

Sleeps: 5 to 6

This first floor farmhouse apartment set in the middle of the picturesque 'Crete Senese', the gently rolling clay hills outside Siena, is all about peaceful space. Ideal for a couple or a small family, it offers generous interior space that reflects the beautiful landscape just outside the front door.

7 nights from £823.00 / €867.00 / $1057.00 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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Roccatederighi, Maremma


Belvedere's terrace has a 360 degree view that takes in a lovely pond and a panoramic green valley leading to the sea.

Sleeps: 4 (Multiple properties at this location)

Belvedere is aptly named for from the furnished terrace with its 360-degree view and the large living room window of this first floor apartment there are panoramic views of wide green valley leading to the sea.

7 nights from £923.00 / €971.00 / $1185.00 View property Check availability

Roccatederighi, Maremma

San Genziano

San Genziano's living room opens out to its own small terrace.

Sleeps: 2 (Multiple properties at this location)

A junior suite ideal for short stays, San Genziano has a private furnished patio which leads into a large open plan room with sofa, double bed, an ensuite shower room, and a self-catering breakfast/snack corner.

7 nights from £543.00 / €571.00 / $697.00 View property Check availability