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The generous proportions of the living room reflect the open-hearted hospitality of Docciole.

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 £2365.00 / €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 £7966.00 / €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 £2006.00 / €2171.00 / $2649.00 View property Check availability
With its back to the rest of the Borgo, Peonia's outdoor eating area faces the wooded Chianti hills on the horizon.

Sleeps: 4 (Multiple properties at this location)

With an outdoor patio that puts the green Chianti hills on the horizon, this hamlet apartment is particularly spacious for a small family or two couples. Smart bedrooms and a generous kitchen set the stage for a restful and delicious holiday that makes the most of the gentle countryside and fresh Tuscan ingredients on offer just south of Florence.

7 nights from £1763.00 / €1908.00 / $2328.00 View property Check availability
Lacing the apartment with Tuscan light, the double doors lead to a private garden furnished with divans and a dining table.

Sleeps: 2 (Multiple properties at this location)

This stone annex to an ancient olive mill has become a beautifully converted cottage for two. With a private furnished garden space and the estate pool a short stroll away, Glicine offers considered comfort in quintessentially Tuscan surroundings. Within easy reach of Florence and a short drive away from famed Chianti villages, this is a base from which to explore a countryside that appears unchanged in Renaissance paintings.

7 nights from £1070.00 / €1158.00 / $1413.00 View property Check availability
Papavero's entrance is the middle door in the large building on the left

Sleeps: 6 (Multiple properties at this location)

Set in countryside once dotted with the summer palaces of Florentine nobility and now famed for its Chianti wines, this estate apartment in a converted olive mill is a comfortable option for a small family or group or group of friends. With a large pool at hand and bicycles to explore the country roads, guests of all ages will find the days pass delightful ease.

7 nights from £2006.00 / €2171.00 / $2649.00 View property Check availability
The Girasole entrance is through wide double doors that look onto the Borgo's stylish outdoor living area, whereas the area to the right behind the gate is their own private outdoor area.

Sleeps: 6 (Multiple properties at this location)

This olive mill conversion on a Chianti estate provides a wonderful holiday accommodation for a small family or group of friends. Sharing the spacious estate grounds and large swimming pool, the apartment is in walking distance to the nearest town and a short drive to Chianti towns and vineyards. Easily reached from Florence, it is ideally set to explore the rolling countryside between Renaissance Florence and Medieval Siena.

7 nights from £2006.00 / €2171.00 / $2649.00 View property Check availability
Oil mill and barn

Sleeps: 22 (Multiple properties at this location)

The ancient olive oil mill and stone barn of a neighboring aristocratic villa in the Chianti hills have been sensitively converted into five tasteful apartments. Taken individually for groups of 2, 4 or 6, or rented together for a group of up to 22, they are in walking distance to an ancient market town and an easy drive to famed Chianti villages.

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The doors open onto the top of the stairs.

Sleeps: 4

Frantoio is on the top floor of a renovated olive oil mill at the entrance to the medieval village of Montemarcello, on the border of Liguria and Tuscany. It is a delightful apartment, with a spacious living/dining area and beautiful views towards the Apennine mountains, across the Magra valley.

7 nights from £633.00 / €685.00 / $836.00 View property Check availability
What draws people to Tuscany is here on the covered terrace at La Senese - a beautiful landscape, a glass of good wine, and the leisure to enjoy them both.

Sleeps: 6 to 7

Backed by the oak and chestnut woods of the Sienese countryside, this charmingly refurbished country house is a restful place for a group of friends or a small family. With a panoramic terrace perfect for meals al fresco and easy access to the quaint villages and medieval cities of central Tuscany, La Senese is both a holiday haven and a base for exploration.

7 nights from £750.00 / €975.00 / $1125.00 View property Check availability
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 £2574.00 / €2786.00 / $3399.00 View property Check availability
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 £2838.00 / €3071.00 / $3747.00 View property Check availability
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 £2468.00 / €2671.00 / $3259.00 View property Check availability
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 £1122.00 / €1214.00 / $1481.00 View property Check availability
The dual staircases at the front of the villa lead directly to the sleeping quarters on the upper floor.

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 £2904.00 / €3143.00 / $3834.00 View property Check availability
The dining area is an eclectic mix of Italian design and recycled ecology, with a touch of whimsical nostalgia.

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 £2218.00 / €2400.00 / $2928.00 View property Check availability
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 £2112.00 / €2286.00 / $2789.00 View property Check availability
An inviting garden room under the pergola is the heart of the home in warmer months.

Sleeps: 4

With the winning combination of being a private property within walking distance of a Tuscan town, close to the beach and with a small pool in the garden, Rosaio is a wonderful house for a carefree or even car-free family holiday.

7 nights from £1016.00 / €1100.00 / $1342.00 View property Check availability
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 £1690.00 / €1829.00 / $2231.00 View property Check availability
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 £628.00 / €680.00 / $830.00 View property Check availability