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Chianti Villas (42 properties found)

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The pleasure of roaming the Chianti is discovering a great winery or crenellated castle all on your own. Many of it’s┬ávillages merit a stop and almost everywhere you will find a good place to sample the wine or have a bite to go with it. We have villas, apartments and other accommodation throughout the region.

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 £2403.00 / €2700.00 / $3105.00 View property Check availability

Radda in Chianti

Docciole

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 / $2944.00 View property Check availability

San Casciano Val di Pesa, Chianti

La Caserotta

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 / $9914.00 View property Check availability

San Casciano Val di Pesa, Chianti

Geranio

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 / $2497.00 View property Check availability

San Casciano Val di Pesa, Chianti

Peonia

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 / $2194.00 View property Check availability

San Casciano Val di Pesa, Chianti

Glicine

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 / $1332.00 View property Check availability

San Casciano Val di Pesa, Chianti

Papavero

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 / $2497.00 View property Check availability

San Casciano Val di Pesa, Chianti

Girasole

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 / $2497.00 View property Check availability

San Casciano Val di Pesa, Chianti

Borgo Caserotta

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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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 £1952.00 / €2193.00 / $2522.00 View property Check availability

Radda in Chianti

Roccia

Draped with vines and buffered with greenery, Roccia is a charming stone cottage in the heart of the Chianti.

Sleeps: 4 (Multiple properties at this location)

A charming conversion of an ancient barn provides a small family or two couples with an excellent base for exploring the Chianti. With its own furnished panoramic terrace and a refreshing pool a stroll away, this stone cottage is only 5 minutes away from Castellina in Chianti and scarcely more from Radda, the unofficial capital of the famous wine region.

7 nights from £1351.00 / €1518.00 / $1745.00 View property Check availability

Radda in Chianti

Sasso

Sitting on one of Sasso's grassy terraces gives you a sweeping view of the property and its surroundings.

Sleeps: 4 to 5 (Multiple properties at this location)

A spacious stone cottage that follows the lay of the land and offers an ideal holiday location for a small family to enjoy their days in the famous Chianti region. With a panoramic pool nearby and grassy terraces on all sides, this house invites living outdoors as much as in. An short drive to Castellina in Chianti or Radda brings bustling village life, excellent restaurants and respected red wine within easy reach.

7 nights from £1460.00 / €1640.00 / $1886.00 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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Lornano, Castellina in Chianti

Canaiolo and Trebbiano

The two storey farmhouse off the former threshing floor contains the Canaiolo and Trebbiano apartments.

Sleeps: 6 to 7 (Multiple properties at this location)

A stone farmhouse on a renowned Chianti wine estate, consisting of two interconnecting apartments. This combination provides entrances from the central estate piazza as well as a private furnished lawn and garden.

7 nights from £923.00 / €1038.00 / $1193.00 View property Check availability

Greve, Chianti

Casolare

Surrounded by the green of the Chianti countryside, Casolare and its large pool

Sleeps: 22 (Multiple properties at this location)

7 nights from £6294.00 / €7071.00 / $8132.00 View property Check availability

San Casciano Val di Pesa, Chianti

Villa Oliveto

Villa Oliveto

Sleeps: 12 to 14 (Multiple properties at this location)

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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 £2829.00 / €3178.00 / $3655.00 View property Check availability

Lornano, Castellina in Chianti

Trebbiano

Sun chairs and and a table and chairs at the Trebbiano entrance provide privacy for outdoor meals or a place for enjoying the sun.

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

An intimate apartment on a wine estate, thanks to its private garden and delightful outdoor eating area, Trebbiano is a lovely retreat for a couple. For larger groups, this apartment can be easily combined with Caniolo.

7 nights from £454.00 / €510.00 / $586.00 View property Check availability

Monteriggioni, Siena

Cortile

The warm colors of the kitchen / dining area speak of hospitality and Tuscan tradition

Sleeps: 4 (Multiple properties at this location)

7 nights from £1068.00 / €1200.00 / $1380.00 View property Check availability

Barberino Val d'Elsa, Chianti, Florence

Dimora

Many enjoyable times at Dimora take place outdoors.

Sleeps: 11

In this sprawling ground-level house, whose every room opens onto the outside, you will never doubt that you are in the heart of Tuscany. Terracotta bricks and chestnut ceiling beams mix well with stylish colors and attractive fabrics of modern Italy and from every window there is the classic panorama of an ancient countryside.

7 nights from £2537.00 / €2851.00 / $3278.00 View property Check availability