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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 £2207.00 / €2480.00 / $2753.00 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 £2937.00 / €3300.00 / $3663.00 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 £4825.00 / €5421.00 / $6017.00 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 £3080.00 / €3461.00 / $3842.00 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 £712.00 / €800.00 / $888.00 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 £2314.00 / €2600.00 / $2886.00 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 £2403.00 / €2700.00 / $2997.00 View property Check availability
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 £2278.00 / €2560.00 / $2842.00 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 £7673.00 / €8621.00 / $9569.00 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 £1932.00 / €2171.00 / $2410.00 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 £1698.00 / €1908.00 / $2118.00 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 £1031.00 / €1158.00 / $1285.00 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 £1932.00 / €2171.00 / $2410.00 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 £1932.00 / €2171.00 / $2410.00 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 £610.00 / €685.00 / $760.00 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 / €930.00 / $975.00 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 £2479.00 / €2786.00 / $3092.00 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 £2734.00 / €3071.00 / $3409.00 View property Check availability