List your home
Apply filters
£ to

Holiday homes 40

Reset search

Show results on map

Also consider

Coastal Cottages
222 properties
Sardinia
478 properties
Tuscany
3,181 properties
Lake Garda Area
103 properties
Lake Como Area
494 properties
Sicily
634 properties
To book this holiday home you need to pay through the Holiday Lettings website. We can’t protect your payment if you don’t pay through us. Learn more
40 Results   |  

from £43 / night

£300 - £515 / week

View

Excellent 5/5 

24 Photos

Province of Siena / Radda in Chianti

Farmhouse / 2 Bedrooms / sleeps 4

Excellent 5/5 

4 Nights min stay

Add to shortlist

from £43 / night

£300 - £515 / week

View

Key info:

  • Beach / lakeside relaxation
  • Great for children of all ages
  • Pets welcome
  • Private garden
In our farm only  …see more

from £33 / night

£229 - £350 / week

View

Excellent 5/5 

19 Photos

Province of Siena / Radda in Chianti

Farmhouse / 2 Bedrooms / sleeps 3

Excellent 5/5 

4 Nights min stay

Add to shortlist

from £33 / night

£229 - £350 / week

View

Key info:

  • Not suitable for children
  • No pets allowed
  • Private garden
A holiday in Tuscany at Podere Tegline Farmhouse to enjoy and get to know life in Chianti Classico wine territory.You can live in an ancient house of 1500 to offer the authenticity of the past with an old charm in a virgin natural Oasis where you are WELCOME. Our house is in a central position between art cities as Florence, Siena, S.Gimignano, Lucca, Pisa, Arezzo.  …see more

from £50 / night

£350 / week

View

Excellent 5/5 

16 Photos

Province of Siena / Radda in Chianti

Apartment / 1 Bedroom / sleeps 3

Excellent 5/5 

4 Nights min stay

Add to shortlist

from £50 / night

£350 / week

View

Key info:

  • Great for children of all ages
  • Car essential
  • Some pets are welcome - please contact the owner
A very comfortable one bedroom apartment in a farmhouse whose origins go back 1000 years, immersed in the heart of the Chianti countryside, ideal for complete relaxation, pleasant walks and visits to the cultural cities and nearby villages.  …see more

Featured properties

from £41 / night

£286 - £425 / week

View

Excellent 5/5 

26 Photos

Province of Siena / Radda in Chianti

Farmhouse / 2 Bedrooms / sleeps 3

Excellent 5/5 

3 Nights min stay

Add to shortlist

from £41 / night

£286 - £425 / week

View

Key info:

  • Great for children of all ages
  • Pets welcome
  • Private garden
A holiday in Tuscany at Podere Tegline Farmhouse to enjoy and get to know life in Chianti Classico wine territory.You can live in an ancient house of 1500 to offer the authenticity of the past with an old charm in a virgin natural Oasis where you are WELCOME. Our house is in a central position between art cities as Florence, Siena, S.Gimignano, Lucca, Pisa, Arezzo.  …see more

from £93 / night

£648 - £1727 / week

View

Very Good 4/5 

24 Photos

Province of Siena / Radda in Chianti

Villa / 3 Bedrooms / sleeps 7

Very Good 4/5 

4 Nights min stay

Add to shortlist

from £93 / night

£648 - £1727 / week

View

Late Deal: save up to €458 (approx. £329)

Key info:

  • Nearest beach 110 km
  • Swimming pool
  • Great for children of all ages
  • Car essential
  • No pets allowed
  • Private garden
What makes a holiday at LisiDor an unforgettable memory? the people you will meet ... * our Chef * our lovely housekeeper * our professional tennis teacher * our local guide * our 'PERSONAL DAILY HOLIDAY PLANNER' !! ... EXPERIENCE REAL TUSCANY ... Self-catering villa stunning view over hills Private pool. tennis court wifi  …see more

from £123 / night

£859 - £2367 / week

View

Excellent 5/5 

23 Photos

Province of Siena / Radda in Chianti

Villa / 4 Bedrooms / sleeps 8

Excellent 5/5 

4 Nights min stay

Add to shortlist

from £123 / night

£859 - £2367 / week

View

Key info:

  • Nearest beach 110 km
  • Swimming pool
  • Great for children of all ages
  • Car essential
  • No pets allowed
  • Private garden
What makes a holiday at LisiDor an unforgettable memory? the people you will meet ... * our Chef * our lovely housekeeper * our professional tennis teacher * our local guide * our 'PERSONAL DAILY HOLIDAY PLANNER' !! ... EXPERIENCE THE REAL TUSCANY Typical Tuscany stone house. private villa private swimming pool fenced garden tennis court wifi  …see more

from £37 / night

£258 - £322 / week

View

Excellent 5/5 

24 Photos

Province of Siena / Radda in Chianti

Farmhouse / 1 Bedroom / sleeps 2

Excellent 5/5 

4 Nights min stay

Add to shortlist

from £37 / night

£258 - £322 / week

View

Key info:

  • Nearest beach 130 km
  • Great for children of all ages
  • Car essential
  • Pets welcome
  • Private garden
A holiday in Tuscany at Podere Tegline Farmhouse to enjoy and get to know life in Chianti Classico wine territory.You can live in an ancient house of 1500 restored to offer the authenticity of the past with an old charm in a virgin natural Oasis here you are WELCOME Our house is in a central position between art cities as Florence, Siena, S.Gimignano, Lucca, Pisa, Arezzo.  …see more

from £65 / night

£454 - £605 / week

View

Excellent 5/5 

24 Photos

Province of Siena / Radda in Chianti

Barn / 2 Bedrooms / sleeps 5

Excellent 5/5 

4 Nights min stay

Add to shortlist

from £65 / night

£454 - £605 / week

View

Key info:

  • Great for children of all ages
  • Pets welcome
  • Private garden
Casa ben restaurata e arredata con senso sia estetico che pratico con vista unica sulla valle nel cuore del Chianti Classico. Ideale per chi vuole visitare le città d'arte della Toscana e avere anche delle giornate di relax in un ambiente tranquillo e confortevole.  …see more

from £144 / night

£1008 - £1295 / week

View

Excellent 5/5 

13 Photos

Province of Siena / Radda in Chianti

Apartment / 2 Bedrooms / sleeps 4

Excellent 5/5 

3 Nights min stay

Add to shortlist

from £144 / night

£1008 - £1295 / week

View

Key info:

  • Swimming pool
  • Not suitable for children
  • Air conditioning
  • No pets allowed
Charming Apartment in the heart of the Chianti countryside with the Hotel Services.  …see more

from £57 / night

£393 / week

View

Excellent 5/5 

18 Photos

Province of Siena / Radda in Chianti

Farmhouse / 1 Bedroom / sleeps 2

Excellent 5/5 

2 Nights min stay

Add to shortlist

from £57 / night

£393 / week

View

Key info:

  • Great for children of all ages
  • No pets allowed
  • Private garden
Massimo, Florentine and Rebecca, Scottish, live in the farmhouse offering suggestions of day trips, restaurants and local attractions. Massimo runs cooking lessons and for an extra cost will cook you a meal of local specialities served on your own private terrace. Remember a do it yourself breakfast if provided for you so you can get up when you please.  …see more

from £137 / night

£955 - £1444 / week

View

43 Photos

Province of Siena / Radda in Chianti

House / 5 Bedrooms / sleeps 12

Short stays welcome

Add to shortlist

from £137 / night

£955 - £1444 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car not necessary
  • Pets welcome
  • Private garden
6-room semi-detached house 180 m2 on 2 levels. Rustic and cosy furnishings: living/dining room with satellite TV. Exit to the loggia. Kitchen (4 hot plates, oven, microwave, freezer, electric coffee machine). Upper floor: 1 double bedroom with 1 bed, 1 double bed and sh  …see more

from £350 / night

£2447 - £3454 / week

View

17 Photos

Province of Siena / Radda in Chianti

Villa / 5 Bedrooms / sleeps 10

7 Nights min stay

Add to shortlist

from £350 / night

£2447 - £3454 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Some pets are welcome - please contact the owner
  • Private garden
Cosoli is located in Chianti Classico, conveniently half way from Florence and Siena. The villa overlooks a massive olive grove but yet surrounded by a great view of surrounding vineyards and small cities in the distance. 3 hours weekly housekeeping is included as well as the complete house cleaning after leaving.  …see more

from £65 / night

£454 - £864 / week

View

10 Photos

Province of Siena / Radda in Chianti

Apartment / 2 Bedrooms / sleeps 4

3 Nights min stay

Add to shortlist

from £65 / night

£454 - £864 / week

View

Key info:

  • Nearest beach 100 km
  • Great for children of all ages
  • Car essential
  • Air conditioning
  • Some pets are welcome - please contact the owner
  • Private garden
We are situated in the historical heart of Tuscany and Chianti, half way between Siena and Firenze, on a hill overlooking a green and striking valley.The apartments are located in a picturesque hamlet that has been completely ristored- chianti full immersion, wine, food, striking landscape and culture  …see more

from £108 / night

£756 - £907 / week

View

4 Photos

Province of Siena / Radda in Chianti

Apartment / 2 Bedrooms / sleeps 4

3 Nights min stay

Add to shortlist

from £108 / night

£756 - £907 / week

View

Key info:

  • Suitable for children over 5
  • Air conditioning
  • Some pets are welcome - please contact the owner
  • Private garden
Thanks to the “Self-catering Formula” our guests will feel like they're at home, the equipments of every flat are really complete. The position in the heart of Chianti makes Resort Olmo a privileged starting point to explore Tuscany.  …see more

from £83 / night

£576 - £864 / week

View

13 Photos

Province of Siena / Radda in Chianti

House / 4 Bedrooms / sleeps 10

7 Nights min stay

Add to shortlist

from £83 / night

£576 - £864 / week

View

Key info:

  • Great for children of all ages
  • No pets allowed
  • Private garden
Very confortable countryhouse, in the heart of Chianti hills, ideal for family or groups who wants to visit the best of Tuscany and relax in the country. Four large bedrooms, two bathrooms, large livingroom with fireplace, kitchen, big garden, internet wifi.  …see more

from £68 / night

£471 - £638 / week

View

24 Photos

Province of Siena / Radda in Chianti

House / 2 Bedrooms / sleeps 4

Short stays welcome

Add to shortlist

from £68 / night

£471 - £638 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car not necessary
  • Pets welcome
  • Private garden
3-room house 55 m2, on the ground floor. Fully renovated, rustic and cosy furnishings: living/dining room with open-hearth fireplace. Exit to the terrace. 1 double bedroom with shower/bidet/WC. 1 double bedroom with shower/bidet/WC. Kitchenette (4 hot plates, oven, elec  …see more

from £1028 / night

£7195 - £8274 / week

View

18 Photos

Province of Siena / Radda in Chianti

Villa / 8 Bedrooms / sleeps 14

7 Nights min stay

Add to shortlist

from £1028 / night

£7195 - £8274 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Some pets are welcome - please contact the owner
  • Private garden
Between the two small towns of Radda and Gaiole in Chianti, two historical sites for the production of Chianti Classico, right in the heart of Tuscany, there lies Fattoria of Villa Divina, a large farm of approx 500 acres  …see more

from £114 / night

£793 / week

View

21 Photos

Province of Siena / Radda in Chianti

Farmhouse / 3 Bedrooms / sleeps 8

1 night min stay

Add to shortlist

from £114 / night

£793 / week

View

Key info:

  • Great for children of all ages
  • No pets allowed
  • Private garden
Stunning apartments in the heart of Tuscany. Beautiful old, stone farmhouse , cool in the summer and warm in the winter. Private patio and Terrace, eat 'Al Fresco' listening to the crickets or under the stars sipping your chianti wine. Massimo, Italian and from the area, and Rebecca, Scottish, your hosts, will be on hand to help you.  …see more

from £82 / night

£572 - £715 / week

View

19 Photos

Province of Siena / Radda in Chianti

Farmhouse / 3 Bedrooms / sleeps 7

7 Nights min stay

Add to shortlist

from £82 / night

£572 - £715 / week

View

Key info:

  • Great for children of all ages
  • Pets welcome
  • Private garden
Casale in pietra nel cuore del Chianti Classico, immerso nella fantastica campagna Toscana. Struttura rustica ma confortevole, arredata con gusto, ideale per vacanza all'insegna di relax, tranquillità, contatto con la natura, buona gastronomia e visite a città d'arte.  …see more

from £57 / night

£393 / week

View

18 Photos

Province of Siena / Radda in Chianti

Farmhouse / 1 Bedroom / sleeps 2

1 night min stay

Add to shortlist

from £57 / night

£393 / week

View

Key info:

  • Great for children of all ages
  • No pets allowed
  • Private garden
Massimo, Florentine and Rebecca, Scottish, live in the farmhouse offering suggestions of day trips, restaurants and local attractions. Massimo runs cooking lessons and for an extra cost will cook you a meal of local specialities served on your own private terrace. Remember a do it yourself breakfast if provided for you so you can get up when you please.  …see more

from £52 / night

£360 / week

View

20 Photos

Province of Siena / Radda in Chianti

House / 1 Bedroom / sleeps 2

1 night min stay

Add to shortlist

from £52 / night

£360 / week

View

Key info:

  • Not suitable for children
  • No pets allowed
Un gioiello di casa ristrutturata nei minimi particolari. E' proprio nella piazzetta del paese, con le finestre che affacciano proprio sul castello in pietra risalente al 1200...Piccola ma con tutti i comfort, disposta su due livelli. Adatta a coppie in cerca di privacy Raggiungibile solo con l'automobile.  …see more

from £73 / night

£508 / week

View

17 Photos

Province of Siena / Radda in Chianti

Apartment / 1 Bedroom / sleeps 4

1 night min stay

Add to shortlist

from £73 / night

£508 / week

View

Key info:

  • Great for children of all ages
  • No pets allowed
  • Private garden
La Pruneta is in a fantastic location in the centre of Tuscany 15 minutes drive from the medieval town of Radda in Chianti. Beautiful views, tranquility and a friendly welcome from the owners who are always on hand to help and offer advice. Remember a do it yourself breakfast if provided for you so you can get up when you please.  …see more

from £40 / night

£277 - £328 / week

View

11 Photos

Province of Siena / Radda in Chianti

Guest house / 1 Bedroom / sleeps 2

1 night min stay

Add to shortlist

from £40 / night

£277 - £328 / week

View

Key info:

  • Great for children of all ages
  • No pets allowed
Il Ristoro a Lucarelli, Bar, Ristorante e B&B Camere nel Chianti, Toscana  …see more

from £88 / night

£612 - £648 / week

View

25 Photos

Province of Siena / Radda in Chianti

Tower / 2 Bedrooms / sleeps 4

3 Nights min stay

Add to shortlist

from £88 / night

£612 - £648 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Pets welcome
  • Private garden
Torre Romantic View Lake Vineyards Olive Grouth Swimming Pool Wine Relax Families Childrens Peacefull The Torre is 1,5 km from Radda enjoing all the facilities of a charming small village. Full of Activities!  …see more

from £42 / night

£288 / week

View

20 Photos

Province of Siena / Radda in Chianti

B&B / 1 Bedroom / sleeps 2

1 night min stay

Add to shortlist

from £42 / night

£288 / week

View

Key info:

  • Not suitable for children
  • No pets allowed
  • Private garden
bed and breakfast nel cuore el chianti  …see more

from £54 / night

£378 - £1000 / week

View

Excellent 5/5 

24 Photos

Province of Siena / Radda in Chianti

Villa / 2 Bedrooms / sleeps 5

Excellent 5/5 

7 Nights min stay

Add to shortlist

from £54 / night

£378 - £1000 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Some pets are welcome - please contact the owner
Sitting on a ridge overlooking the fabulous Tuscan countryside with its olive groves and vineyards, is the undiscovered Hamlet of Montebuoni. This cluster of privately owned villas and apartments sit amongst olive groves, beautiful planted gardens and courtyards.  …see more

from £162 / night

£1130 - £1882 / week

View

Very Good 4/5 

24 Photos

Province of Siena / Radda in Chianti

Villa / 3 Bedrooms / sleeps 6

Very Good 4/5 

7 Nights min stay

Add to shortlist

from £162 / night

£1130 - £1882 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • No pets allowed
Adine is a fantastic, private villa situated in a typical Tuscan hamlet of private homes. It is a few minutes drive from the quaint village of Lecchi in Chianti . There are breathtaking views from the windows, terraces and pool area.  …see more

from £308 / night

£2152 - £5749 / week

View

20 Photos

Province of Siena / Radda in Chianti

Farmhouse / 6 Bedrooms / sleeps 10

7 Nights min stay

Add to shortlist

from £308 / night

£2152 - £5749 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Some pets are welcome - please contact the owner
  • Private garden
Breathtaking views over the Chianti Classico valleys. Very tastefully restored and lovely furnished. Attractive and panoramic swimming pool area.  …see more

from £201 / night

£1403 - £2713 / week

View

Excellent 5/5 

24 Photos

Province of Siena / Radda in Chianti

Villa / 7 Bedrooms / sleeps 14

Excellent 5/5 

7 Nights min stay

Add to shortlist

from £201 / night

£1403 - £2713 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
A splendid home in one of the most beautiful areas of Tuscany. This lovely farmhouse is situated in the heart of the Chianti region on a wine producing estate with a breathtaking view of the private vineyards just 1km from the characteristic borgo of Radda in Chianti.  …see more

from £48 / night

£331 - £601 / week

View

Excellent 5/5 

24 Photos

Province of Siena / Radda in Chianti

Villa / 1 Bedroom / sleeps 3

Excellent 5/5 

7 Nights min stay

Add to shortlist

from £48 / night

£331 - £601 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Air conditioning
  • Some pets are welcome - please contact the owner
  • Private garden
Within easy reach of Florence, Siena and San Gimignano this lovely one bedroomed villa makes for a romantic getaway with its two private terraces with spectacular views over the Tuscan countryside.  …see more

from £353 / night

£2470 - £3250 / week

View

20 Photos

Province of Siena / Radda in Chianti

Apartment / 3 Bedrooms / sleeps 8

7 Nights min stay

Add to shortlist

from £353 / night

£2470 - £3250 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • No pets allowed
  • Private garden
Villa Calpurnia is a charming two-story historical villa situated in the heart of the Tuscan countryside. It sleeps eight people. From Villa Calpurnia you will enjoy a spellbinding view of the Chianti hills and of the vineyards  …see more

from £247 / night

£1727 - £2806 / week

View

15 Photos

Province of Siena / Radda in Chianti

House / 3 Bedrooms / sleeps 6

7 Nights min stay

Add to shortlist

from £247 / night

£1727 - £2806 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • No pets allowed
Located in the Volpaia hamlet (Chianti region) with local restaurant. Private and panoramic position. Tennis court on the estate.  …see more

from £411 / night

£2872 - £3811 / week

View

14 Photos

Province of Siena / Radda in Chianti

Farmhouse / 5 Bedrooms / sleeps 9

7 Nights min stay

Add to shortlist

from £411 / night

£2872 - £3811 / week

View

Key info:

  • Swimming pool
  • Not suitable for children
  • Some pets are welcome - please contact the owner
Villa in Radda In Chianti with 5 bedrooms sleeps 9  …see more

from £76 / night

£532 - £944 / week

View

6 Photos

Province of Siena / Radda in Chianti

Apartment / 2 Bedrooms / sleeps 5

7 Nights min stay

Add to shortlist

from £76 / night

£532 - £944 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car not necessary
  • Pets welcome
  • Private garden
Apartment for 5 persons, with swimming pool , in Chianti  …see more

from £308 / night

£2152 - £4310 / week

View

20 Photos

Province of Siena / Radda in Chianti

Farmhouse / 6 Bedrooms / sleeps 11

7 Nights min stay

Add to shortlist

from £308 / night

£2152 - £4310 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • No pets allowed
Located in the Volpaia hamlet (Chianti region) with local restaurant. Renowned local wine produced on estate. Private and panoramic position. Tennis court on the estate.  …see more

from £279 / night

£1952 - £3839 / week

View

13 Photos

Province of Siena / Radda in Chianti

Farmhouse / 6 Bedrooms / sleeps 12

7 Nights min stay

Add to shortlist

from £279 / night

£1952 - £3839 / week

View

Key info:

  • Swimming pool
  • Not suitable for children
  • Some pets are welcome - please contact the owner
Villa in Volpaia with 6 bedrooms sleeps 12  …see more

from £246 / night

£1721 - £3448 / week

View

11 Photos

Province of Siena / Radda in Chianti

Farmhouse / 6 Bedrooms / sleeps 11

7 Nights min stay

Add to shortlist

from £246 / night

£1721 - £3448 / week

View

Key info:

  • Swimming pool
  • Not suitable for children
  • Some pets are welcome - please contact the owner
Villa in Volpaia with 6 bedrooms sleeps 11  …see more

from £427 / night

£2986 - £4677 / week

View

18 Photos

Province of Siena / Radda in Chianti

Farmhouse / 5 Bedrooms / sleeps 9

7 Nights min stay

Add to shortlist

from £427 / night

£2986 - £4677 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • No pets allowed
  • Private garden
In the heart of Chianti Classico. Very close to the village of Radda. Furnished in refined country style.  …see more

from £338 / night

£2361 - £4427 / week

View

24 Photos

Province of Siena / Radda in Chianti

Villa / 5 Bedrooms / sleeps 12

7 Nights min stay

Add to shortlist

from £338 / night

£2361 - £4427 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car not necessary
  • Pets welcome
  • Private garden
Holiday house for 12 persons, with swimming pool , in Chianti  …see more

from £340 / night

£2375 - £4677 / week

View

20 Photos

Province of Siena / Radda in Chianti

House / 6 Bedrooms / sleeps 12

7 Nights min stay

Add to shortlist

from £340 / night

£2375 - £4677 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • No pets allowed
Peaceful position for a holiday of total relax in Chianti. Fenced pool. Very panoramic outdoor eating area. Tennis court on the estate.  …see more

Don’t let an old browser slow down your holiday

Your browser is out of date and might not work well with our website. Download the latest version to speed up your hunt for the perfect holiday home.

Just click on the icons to get to the download page