List your home
Apply filters
£ to

Holiday homes 35

Reset search

Show results on map

Filter your search

Price per night

Price per night

£ to per night

Bedrooms

Location

  • Italy Clear
  • Tuscany Clear
  • Province of Siena Clear
  • Castelnuovo Berardenga Clear

Location

  • All locations
  • Monteaperti (3)
  • Ponte a Bozzone (1)
  • San Gusme (6)
  • Vagliagli (4)

more +

less -

Also consider

Coastal Cottages
222 properties
Apartments Sardinia
478 properties
Apartments Tuscany
3181 properties
Apartments Lake Garda Area
103 properties
Apartments Lake Como Area
494 properties
Apartments Sicily
634 properties
Vagliagli
27 properties
San Gusme
22 properties
Pianella
6 properties

Filters applied: Villa (35)

Payment Protection
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
35 Results   |  
24 Photos

Castelnuovo Berardenga / Vagliagli

Villa / 8 Bedrooms / sleeps 14

7 Nights min stay

Add to shortlist

from £230 / night

£1606 - £2920 / week

View

Key info:

  • Nearest beach 40 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Pets welcome
  • Private garden
The Piaggione of Serravalle is like a gateway entrance that protects an uncontaminated hill that seems lost in time and where nature apparently undisturbed articulates its own natural rhythms. Located on one of the highest summits of Chianti, in between Siena and Flore  …see more

20 Photos

Province of Siena / Castelnuovo Berardenga

Villa / 3 Bedrooms / sleeps 6

7 Nights min stay

Add to shortlist

from £100 / night

£694 - £1380 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Pets welcome
  • Private garden
The Piaggione of Serravalle is like a gateway entrance that protects an uncontaminated hill that seems lost in time and where nature apparently undisturbed articulates its own natural rhythms. Located on one of the highest summits of Chianti, in between Siena and Floren  …see more

Excellent 5/5 

24 Photos

Province of Siena / Castelnuovo Berardenga

Villa / 9 Bedrooms / sleeps 20

Excellent 5/5 

Min stay varies

Add to shortlist

from £263 / night

£1839 - £2868 / week

View

Key info:

  • Nearest beach 90 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Pets welcome
  • Private garden
Poggio Lungo is set amid the rolling green hills of Tuscany, in a peaceful setting where you can enjoy total relax during your stay. It has two kitchens, a dining room, a lounge with satellite tv, there are 9 bedrooms and a further double bedroom in an annexe.  …see more


31 Dec 2013

5/5

"We spent our holidays in this beautiful Villa"

We spent two weeks in Poggio long. The Villa is very well kept. Ms. Marcella was always available when we needed something. The rooms are spacious, very clean and the view from the windows is wonderfu… More


17 Jul 2014

5/5

"una casa da sogno!!!"

Siamo stati in questo agriturismo i primi di giugno, eravamo 18 persone. Piscina con acqua salata..fantastica!!! Arredamento di alto livello e casa veramente bella e pulita!! Siccome eravamo un gruppo… More

See all reviews Continue

Featured properties

Excellent 5/5 

23 Photos

Province of Siena / Castelnuovo Berardenga

Villa / 6 Bedrooms / sleeps 11

Excellent 5/5 

1 night min stay

Add to shortlist

from £400 / night

£2795 - £3015 / week

View

Key info:

  • Nearest beach 60 km
  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Pets welcome
  • Private garden
Villa in Chianti/Siena, Tuscany, Italy On top of a Hill with Private Pool and Large Terrace A Haven of Peace and Quietness, 20 Minutes from Siena Sleeps 11 (6 Bedrooms with en suite bathrooms) For parties of 2 or 4 people the villa will be shared , unless the guests are  …see more


21 Sep 2013

5/5

"A phenomenal villa, with exceptional views in the true heart of Chianti"

We have been traveling to Italy for some time and have found the perfect spot for our recent and future vacations. This well appointed villa has great views, loads of herbs and fruit on site and is lo… More


19 May 2013

5/5

"A villa with a view"

The view is amazing. From every window of the house you can see the rolling hills of Chianti with its famed vines, woods and castles. The property is set in an old wine yard that surrounds a landscape… More


5 May 2013

5/5

"very nice place in tuscany"

The ancient residence immersed in the Tuscan countryside, is a special and beautifull place, surrounded by an incredible landscape with vineyards and olive trees, there is also a nice pool. The house… More

See all reviews Continue

8 Photos

Province of Siena / Castelnuovo Berardenga

Villa / 2 Bedrooms / sleeps 4

3 Nights min stay

Add to shortlist

from £127 / night

£883 - £1030 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Pets welcome
  • Private garden
The estate has a swimming pool, tennis court, bocce ball court, laundry facilities and private garden areas. Enjoy the independence of a self-catering villa with all the advantages of a concierge's assistance.  …see more

7 Photos

Province of Siena / Castelnuovo Berardenga

Villa / 4 Bedrooms / sleeps 8

3 Nights min stay

Add to shortlist

from £253 / night

£1765 - £2059 / week

View

Key info:

  • Great for children of all ages
  • Car essential
  • Some pets are welcome - please contact the owner
The estate has a swimming pool, tennis court, bocce ball court, laundry facilities and private garden areas. Enjoy the independence of a self-catering villa with all the advantages of a concierge's assistance.  …see more

8 Photos

Province of Siena / Castelnuovo Berardenga

Villa / 6 Bedrooms / sleeps 12

Min stay varies

Add to shortlist

from £368 / night

£2574 / week

View

Key info:

  • Swimming pool
  • Not suitable for children
  • No pets allowed
  • Private garden
Villa dell'800 in perfette condizioni. Rustica ma familiare ed elegante. Incredibile affaccio sul Chianti. Vicina sia a Firenze che Siena. Possibilità di vivere a contatto con la produzione vitivinicola. Mervigliosi boschi dove passeggiare. Chef ad hoc a disposizione  …see more

63 Photos

Castelnuovo Berardenga / Vagliagli

Villa / 5 Bedrooms / sleeps 12

3 Nights min stay

Add to shortlist

from £316 / night

£2206 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Some pets are welcome - please contact the owner
  • Private garden
The 13th century villa has been recently renovated, maintaining its original characteristics joined with modern comfort. The bathrooms are all with shower or tub, sink, toilet and bidet. Its wooden beamed ceilings and bricked floors keep the typical features intact. The  …see more

14 Photos

Castelnuovo Berardenga / Monteaperti

Villa / 5 Bedrooms / sleeps 9

7 Nights min stay

Add to shortlist

from £110 / night

£767 - £1716 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • Some pets are welcome - please contact the owner
  • Private garden
prova 2 Piscina privata di 8x4 m con doccia calda. La piscina può essere utilizzata dal 1 / 5 a 30 / 9  …see more

20 Photos

Castelnuovo Berardenga / San Gusme

Villa / 3 Bedrooms / sleeps 8

7 Nights min stay

Add to shortlist

from £143 / night

£1000 - £1600 / week

View

Key info:

  • Nearest beach 90 km
  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Pets welcome
  • Private garden
Private viila and swimming pool deeped in nature and quiet.We rent out the whole house,so you could enjoy your holiday without any disturb.  …see more

10 Photos

Province of Siena / Castelnuovo Berardenga

Villa / 2 Bedrooms / sleeps 4

7 Nights min stay

Add to shortlist

from £53 / night

£365 / week

View

Key info:

  • Nearest beach 100 km
  • Not suitable for children
  • No pets allowed
  • Private garden
per altre informazioni visitate il sito: www.lafattoriamontalcinello.it sezione CASAVACANZE CHIANTI.  …see more

Very Good 4/5 

16 Photos

Castelnuovo Berardenga / San Gusme

Villa / 2 Bedrooms / sleeps 4

Very Good 4/5 

7 Nights min stay

Add to shortlist

from £157 / night

£1096 - £1464 / week

View

Key info:

  • Nearest beach 115 km
  • Swimming pool
  • Great for children of all ages
  • Car essential
  • No pets allowed
  • Private garden
San Donato is an exquisite gem set in rolling Chianti vineyards with views that stretch 360 degrees past a nearby 13th century hill town to Siena and into infinity.  …see more


8 Aug 2014

4/5

"wonderful and peaceful place"

San Donato is very quiet, a very beautiful place, the garden and all the Villa Arceno aera are amazing, the house is simple but comfortable, and with a soul, as if you ever know this place, I will ret… More

See all reviews Continue

Excellent 5/5 

22 Photos

Castelnuovo Berardenga / San Gusme

Villa / 2 Bedrooms / sleeps 6

Excellent 5/5 

7 Nights min stay

Add to shortlist

from £122 / night

£849 - £1187 / week

View

Key info:

  • Nearest beach 185 km
  • Swimming pool
  • Not suitable for children
  • Car essential
  • Pets welcome
Colonica Gigli is a portion of a typical Tuscan farmhouse immersed in the green Chianti hills covered with vineyards and olive groves. Recently restored the original stone building stands in a well tended green lawn. The large private garden is totally fenced ensuring  …see more


17 Nov 2014

5/5

"A tuscan country dream"

There are several things that, to us, make for a special home rental. The location, for sure. The ambiance of the area. The graciousness of the hosts. And, certainly the cleanliness, character, and c… More

See all reviews Continue

Excellent 5/5 

16 Photos

Castelnuovo Berardenga / San Gusme

Villa / 2 Bedrooms / sleeps 4

Excellent 5/5 

7 Nights min stay

Add to shortlist

from £156 / night

£1088 - £1453 / week

View

Key info:

  • Nearest beach 185 km
  • Swimming pool
  • Not suitable for children
  • Car essential
  • No pets allowed
San Donato di Villa Arceno is an exquisite gem set in rolling Chianti vineyards with views that stretch 360 degrees past a nearby 13th century hill town to Siena and into infinity. Part of the original estate of Villa Arceno, San Donato di Villa Arceno has a history th  …see more


11 Feb 2012

5/5

"Lovely villa; perfect location"

My husband and our sister and brother-in-law stayed at this lovely villa in situated between the tiny, but magic little towns of San Gusme and Castelnuovo Bernardena. The interior of the villa was co… More


23 Jun 2011

5/5

"Amazing"

My husband and our 2 grown children enjoyed this rental very much. We think about it all the time and will go back again. Very beautiful and the loft was unique and very comfortable. All the necessiti… More


22 Jun 2011

5/5

"Everything we had hoped for and more"

Manola, Firstly a big thank you for making the whole process of booking and staying at San Donato Villa so easy. Your relaxed and efficient manner was really apparent and much appreciated. As for t… More

See all reviews Continue

22 Photos

Castelnuovo Berardenga / San Gusme

Villa / 2 Bedrooms / sleeps 6

7 Nights min stay

Add to shortlist

from £123 / night

£856 - £1195 / week

View

Key info:

  • Nearest beach 115 km
  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Some pets are welcome - please contact the owner
  • Private garden
Colonica Gigli is a portion of a typical Tuscan farmhouse immersed in the green Chianti hills covered with vineyards and olive groves. Recently restored the original stone building stands in a well tended green lawn.  …see more

20 Photos

Castelnuovo Berardenga / Vagliagli

Villa / 7 Bedrooms / sleeps 14

2 Nights min stay

Add to shortlist

from £264 / night

£1843 - £3072 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Some pets are welcome - please contact the owner
Villa Solara is a beautiful, modern villa, offering spectacular views of the surrounding countryside. Set within well-kept, private grounds and with easy access to local amenities, the villa is a perfect place for family or cultural holidays.  …see more

19 Photos

Province of Siena / Castelnuovo Berardenga

Villa / 3 Bedrooms / sleeps 6

2 Nights min stay

Add to shortlist

from £254 / night

£1773 - £1927 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • No pets allowed
  • Private garden
The enchanting Villa Terrazzeria is a adorable villa set in the stunning Tuscany countryside.  …see more

17 Photos

Castelnuovo Berardenga / Monteaperti

Villa / 5 Bedrooms / sleeps 10

7 Nights min stay

Add to shortlist

from £728 / night

£5095 - £7416 / week

View

Key info:

  • Ask owner if suitable for children
  • Some pets are welcome - please contact the owner
Enjoy the best of Tuscan country and city life at Il Roseto. Set on a hilltop on a private farming estate just outside Siena, the five-bedroom villa is surrounded by olive groves. Its stone walls and tile roof evoke traditional Tuscan style, but the elegant interiors ha  …see more

Very Good 4.5/5 

34 Photos

Castelnuovo Berardenga / Ponte a Bozzone

Villa / 6 Bedrooms / sleeps 10

Very Good 4.5/5 

4 Nights min stay

Add to shortlist

from £224 / night

£1562 - £3381 / week

View

Key info:

  • Ask owner if suitable for children
  • Car not necessary
  • Some pets are welcome - please contact the owner
Set in the green outskirts of the medieval city of Siena, Fienile is wonderfully located to take in the countryside, for apart from the hospital seen on the horizon all else is olive groves, cultivated fields, and large distant villas which sit where the land rises. Whi  …see more


22 Sep 2012

5/5

"Lovely villa, excellent location"

We stayed at Fienile for a week with extended family (including 3 children between 1-3). Very relaxing environment, well appointed, spacious villa with good facilities (internet (which did drop out a … More


27 Sep 2011

5/5

"very relaxed & comfortable"

Il Fienile is a very well equipped house, lovely location, pool and gardens very well maintained and attractive. Helpful owner, all round a perfectly relaxing place to stay. We would definitely reco… More


15 Jul 2011

5/5

"A beautiful house, perfect for relaxation"

The house is lovely, very comfortable, clean and well-appointed. The pool is clean, close to the house and a good size for proper swimming as well as playing, though would not be suitable for very sm… More

See all reviews Continue

20 Photos

Province of Siena / Castelnuovo Berardenga

Villa / 9 Bedrooms / sleeps 18

7 Nights min stay

Add to shortlist

from £872 / night

£6103 - £6765 / week

View

Key info:

  • Nearest beach 0 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
Relais Chianti is a typical Tuscan homestead from the early 1800s located in the unmistakable Chianti Classico countryside, in the renowned vine-growing and wine-making region.  …see more

19 Photos

Province of Siena / Castelnuovo Berardenga

Villa / 3 Bedrooms / sleeps 6

7 Nights min stay

Add to shortlist

from £125 / night

£869 - £1599 / week

View

Key info:

  • Nearest beach 50 km
  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Pets welcome
  • Private garden
The Piaggione of Serravalle is like a gateway entrance that protects an uncontaminated hill that seems lost in time and where nature apparently undisturbed articulates its own natural rhythms. Located on one of the highest summits of Chianti, in between Siena and Floren  …see more

8 Photos

Province of Siena / Castelnuovo Berardenga

Villa / 2 Bedrooms / sleeps 4

3 Nights min stay

Add to shortlist

from £127 / night

£883 - £1030 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Some pets are welcome - please contact the owner
The estate has a swimming pool, tennis court, bocce ball court, laundry facilities and private garden areas. Enjoy the independence of a self-catering villa with all the advantages of a concierge's assistance.  …see more

10 Photos

Province of Siena / Castelnuovo Berardenga

Villa / 2 Bedrooms / sleeps 4

3 Nights min stay

Add to shortlist

from £127 / night

£883 - £1030 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Pets welcome
  • Private garden
The estate has a swimming pool, tennis court, bocce ball court, laundry facilities and private garden areas. Enjoy the independence of a self-catering villa with all the advantages of a concierge's assistance.  …see more

8 Photos

Province of Siena / Castelnuovo Berardenga

Villa / 1 Bedroom / sleeps 2

3 Nights min stay

Add to shortlist

from £69 / night

£478 - £552 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Pets welcome
  • Private garden
The estate has a swimming pool, tennis court, bocce ball court, laundry facilities and private garden areas. Enjoy the independence of a self-catering villa with all the advantages of a concierge's assistance.  …see more

9 Photos

Province of Siena / Castelnuovo Berardenga

Villa / 2 Bedrooms / sleeps 4

3 Nights min stay

Add to shortlist

from £127 / night

£883 - £1030 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Some pets are welcome - please contact the owner
The estate has a swimming pool, tennis court, bocce ball court, laundry facilities and private garden areas. Enjoy the independence of a self-catering villa with all the advantages of a concierge's assistance.  …see more

8 Photos

Province of Siena / Castelnuovo Berardenga

Villa / 1 Bedroom / sleeps 2

3 Nights min stay

Add to shortlist

from £69 / night

£478 - £552 / week

View

Key info:

  • Swimming pool
  • Ask owner if suitable for children
  • Car essential
  • Some pets are welcome - please contact the owner
The estate has a swimming pool, tennis court, bocce ball court, laundry facilities and private garden areas. Enjoy the independence of a self-catering villa with all the advantages of a concierge's assistance.  …see more

7 Photos

Province of Siena / Castelnuovo Berardenga

Villa / 1 Bedroom / sleeps 2

3 Nights min stay

Add to shortlist

from £69 / night

£478 - £552 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Some pets are welcome - please contact the owner
  • Private garden
The estate has a swimming pool, tennis court, bocce ball court, laundry facilities and private garden areas. Enjoy the independence of a self-catering villa with all the advantages of a concierge's assistance.  …see more

9 Photos

Province of Siena / Castelnuovo Berardenga

Villa / 3 Bedrooms / sleeps 6

3 Nights min stay

Add to shortlist

from £190 / night

£1324 - £1545 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Pets welcome
  • Private garden
The estate has a swimming pool, tennis court, bocce ball court, laundry facilities and private garden areas. Enjoy the independence of a self-catering villa with all the advantages of a concierge's assistance.  …see more

8 Photos

Province of Siena / Castelnuovo Berardenga

Villa / 3 Bedrooms / sleeps 6

3 Nights min stay

Add to shortlist

from £190 / night

£1324 - £1545 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Some pets are welcome - please contact the owner
  • Private garden
Montalto Castle has a rich past dating back over one thousand years. Much of the castle is from medieval times, with extensive restorations performed in the 16th century and again in the 19th century.  …see more

36 Photos

Province of Siena / Castelnuovo Berardenga

Villa / 8 Bedrooms / sleeps 16

4 Nights min stay

Add to shortlist

from £506 / night

£3536 - £9233 / week

View

Key info:

  • Swimming pool
  • Not suitable for children
  • Pets welcome
In the gently rolling hills of the Sienese Chianti region stands Torreantica, whose origins date back to the 13th century when it was a watchtower dominating over the streets and possessions of the lords of the valley. Centuries have passed but the beauty of the landsca  …see more

24 Photos

Castelnuovo Berardenga / Vagliagli

Villa / 3 Bedrooms / sleeps 6

7 Nights min stay

Add to shortlist

from £145 / night

£1009 - £1753 / week

View

Key info:

  • Nearest beach 0 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
Lovely house in the heart of the Chianti area, just 15 km from Siena. Situated in peaceful position, even though a secondary road passes 50 m away. The property is partly fenced-in and the swimming pool, just below the house ground, has a lovely view over the ...  …see more

19 Photos

Castelnuovo Berardenga / San Gusme

Villa / 6 Bedrooms / sleeps 12

7 Nights min stay

Add to shortlist

from £313 / night

£2190 - £3154 / week

View

Key info:

  • Swimming pool
  • Not suitable for children
  • Some pets are welcome - please contact the owner
This amazing villa is suitable for a party of up to twelve people to enjoy a holiday today in Tuscany. Two bedrooms are located on the ground floor, while the remaining rooms lead off from the living room which you’ll find on the first floor. This amazing villa is sui  …see more

20 Photos

Castelnuovo Berardenga / Monteaperti

Villa / 6 Bedrooms / sleeps 12

7 Nights min stay

Add to shortlist

from £376 / night

£2628 - £4205 / week

View

Key info:

  • Not suitable for children
  • Some pets are welcome - please contact the owner
If a villa holiday in Tuscany is calling to you, take a closer look at Villa Magna. This property provides ample room for twelve guests, offering six beautiful bedrooms and a variety of other features you’ll fall in love with on first sight. If a villa holiday in Tusc  …see more

48 Photos

Province of Siena / Castelnuovo Berardenga

Villa / 9 Bedrooms / sleeps 18

1 night min stay

Add to shortlist

from £861 / night

£6022 - £6665 / week

View

Key info:

  • Nearest beach 117 km
  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • No pets allowed
This villa is large and boasts a wonderful and typical Tuscan style. It sleeps up to 18 people, and it affords all the modern comforts and facilities needed for a perfect stay. It can also be rented for weddings and other events.  …see more

48 Photos

Province of Siena / Castelnuovo Berardenga

Villa / 8 Bedrooms / sleeps 16

1 night min stay

Add to shortlist

from £365 / night

£2555 - £3285 / week

View

Key info:

  • Nearest beach 75 km
  • Swimming pool
  • Great for children of all ages
  • No pets allowed
This villa offers 8 bedrooms to accommodate up to two people each. They all have their own en-suite bathroom, and they share a beautiful dining room, two living areas, kitchen, covered patio and a fabulous garden with swimming pool.  …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