List your home
Apply filters
£ to

Holiday homes 1,200

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

Location

  • All locations
  • Abbadia San Salvatore (1)
  • Asciano (38)
  • Bagni di San Filippo (1)
  • Bagno Vignoni (4)
  • Brenna (1)
  • Buonconvento (15)
  • Campiglia d'Orcia (2)
  • Casciano (2)
  • Casole d'Elsa (49)
  • Castellina In Chianti (47)
  • Castelmuzio (7)
  • Castelnuovo Berardenga (64)
  • Castiglione D'Orcia (14)
  • Cetona (21)
  • Chianciano Terme (17)
  • Chiusdino (7)
  • Chiusi (14)
  • Colle di Val d'Elsa (53)
  • Gaiole in Chianti (49)
  • Le Piazze (1)
  • Lucarelli (2)
  • Montalcino (35)
  • Montepulciano (70)
  • Monteriggioni (23)
  • Monteroni d'Arbia (16)
  • Monticiano (12)
  • Montisi (12)
  • Murlo (13)
  • Palazzone (5)
  • Piancastagnaio (6)
  • Pienza (24)
  • Pievasciata (1)
  • Pievescola (2)
  • Poggibonsi (46)
  • Radda in Chianti (25)
  • Radicofani (19)
  • Radicondoli (56)
  • Rapolano Terme (27)
  • Rosia (1)
  • San Casciano dei Bagni (13)
  • San Gimignano (140)
  • San Giovanni d'Asso (10)
  • San Quirico d'Orcia (7)
  • Sarteano (14)
  • Siena (121)
  • Sinalunga (30)
  • Sovicille (32)
  • Torrita di Siena (20)
  • Trequanda (3)
  • Ville di Corsano (7)

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
Villas Siena
422 properties
Villas San Gimignano
410 properties
Villas Montepulciano
238 properties
Gaiole in Chianti
178 properties
Villas Castelnuovo Berardenga
173 properties
Villas Casole d'Elsa
172 properties
Villas Castellina In Chianti
155 properties
Villas Poggibonsi
151 properties
Villas Pienza
141 properties
Villas Sinalunga
138 properties
Asciano
137 properties
Apartments Colle di Val d'Elsa
129 properties
Villas Montalcino
126 properties
Sovicille
92 properties

Filters applied: Balcony or terrace (1,200)

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
1,200 Results   |  
25 Photos

Province of Siena / Colle di Val d'Elsa

Villa / 5 Bedrooms / sleeps 10

7 Nights min stay

Add to shortlist

from £833 / night

£5825 - £9208 / week

View

Key info:

  • Ask owner if suitable for children
  • Some pets are welcome - please contact the owner
Set on a hilltop on a wine-producing estate near Siena, villa Le Porciglia offers stunning vistas inside and out. The lush grounds feature an infinity-edge pool, herb garden and dining and lounging areas, while the magazine-worthy, fully restored interiors mix modern an  …see more

21 Photos

Province of Siena / San Quirico d'Orcia

Villa / 8 Bedrooms / sleeps 16

7 Nights min stay

Add to shortlist

from £1192 / night

£8339 - £10424 / week

View

Key info:

  • Ask owner if suitable for children
  • Some pets are welcome - please contact the owner
Villa Valente is an elegant country house with an annex, located in the magical Val d’Orcia whose typical undulating hills and golden fields inspired, and still do, many artists. Val d’Orcia has been recognized a UNESCO World Heritage Site in 2004 for its beauty and  …see more

24 Photos

Province of Siena / Montalcino

Villa / 7 Bedrooms / sleeps 14

7 Nights min stay

Add to shortlist

from £1189 / night

£8319 - £9412 / week

View

Key info:

  • Ask owner if suitable for children
  • Air conditioning
  • Some pets are welcome - please contact the owner
Sitting on a spectacular 25-acre estate and boasting stunning views of the hills of Montalcino, Villa Leopolda is a true gem of Tuscany's countryside. This remarkable 7-bedroom 7-bathroom property has been recently restored and tastefully furnished with a fine selection  …see more

Featured properties

24 Photos

Montepulciano / Sant'Albino

Villa / 5 Bedrooms / sleeps 10

7 Nights min stay

Add to shortlist

from £197 / night

£1377 - £2464 / week

View

Key info:

  • Nearest beach 115 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • Some pets are welcome - please contact the owner
  • Private garden
Villa Croce, recently restored, is situated on one of the most beautiful and panoramic hills around Montepulciano. The villa can accommodate 10 persons in 5 bedrooms private en suite bathrooms. Private and panoramic swimming pool.  …see more

23 Photos

Montepulciano / Sant'Albino

Villa / 7 Bedrooms / sleeps 14

7 Nights min stay

Add to shortlist

from £259 / night

£1812 - £4348 / week

View

Key info:

  • Nearest beach 115 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
Podere Sant'Albino is a 16th century farmhouse built on Roman foundations, nestled between woods and olive groves. It can accommodate 14 persons in 7 bedrooms with private bathroom. Private swimming pool available in the garden of the property.  …see more

24 Photos

Castelnuovo Berardenga / Guistrigona

Apartment / 2 Bedrooms / sleeps 6

6 Nights min stay

Add to shortlist

from £56 / night

£389 - £561 / week

View

Key info:

  • Great for children of all ages
  • Pets welcome
  • Private garden
2 bedroom, 2 bath, sleeps 6 with a kitchen and wifi. Located in Siena, Italy  …see more

100 Photos

Province of Siena / Colle di Val d'Elsa

Apartment / 3 Bedrooms / sleeps 8

Short stays welcome

Add to shortlist

from £89 / night

£621 - £1454 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car not necessary
  • Pets welcome
"La Corte", 5-room apartment 180 m2 on 1st floor: large living/dining room with 1 sofabed and TV. Lounge with 2 beds. 1 double bedroom. 1 double bedroom with 1 bed. 1 room with 2 beds. Kitchen-/living room (4 hot plates, oven, dishwasher, freezer). Bath/bidet/WC, shower  …see more

10 Photos

Province of Siena / San Casciano dei Bagni

House / 6 Bedrooms / sleeps 12

7 Nights min stay

Add to shortlist

from £125 / night

£870 - £1740 / week

View

Key info:

  • Swimming pool
  • Not suitable for children
  • Some pets are welcome - please contact the owner
Six Bedroom Private Villa Southern Tuscany Villa Loren is a beautifully restored stone country house situated on a large farming estate with wonderful views of rolling Tuscan hills for miles around. This totally unspoilt panorama is particularly enjoyed from the gard  …see more

8 Photos

Province of Siena / Monteriggioni

House / 3 Bedrooms / sleeps 6

7 Nights min stay

Add to shortlist

from £151 / night

£1051 - £1595 / week

View

Key info:

  • Swimming pool
  • Not suitable for children
  • Some pets are welcome - please contact the owner
Three Bedroom Detached Private Villa Monteriggioni near Siena Villa Francis is a superb detached villa in a fantastic position close to Siena. Completely private the villa has its own swimming pool and garden both enjoying with wonderful views of the countryside. The v  …see more

14 Photos

Province of Siena / Castellina In Chianti

House / 6 Bedrooms / sleeps 14

7 Nights min stay

Add to shortlist

from £11 / night

£73 - £3008 / week

View

Key info:

  • Swimming pool
  • Not suitable for children
  • Some pets are welcome - please contact the owner
Six Bedroom Private Villa Chianti Villa Mulino is a charming country house immersed in the wonderful unspoilt countryside deep in the famous Chianti Classico region of Tuscany. Originally a mill this beautiful property has been lovingly restored and is surrounded by it  …see more

14 Photos

Province of Siena / Castellina In Chianti

House / 4 Bedrooms / sleeps 9

7 Nights min stay

Add to shortlist

from £11 / night

£73 - £2283 / week

View

Key info:

  • Swimming pool
  • Not suitable for children
  • Some pets are welcome - please contact the owner
Four Bedroom Private Villa Chianti Villa Mulino is a charming country house immersed in the wonderful unspoilt countryside deep in the famous Chianti Classico region of Tuscany. Originally a mill this beautiful property has been lovingly restored and is surrounded by i  …see more

55 Photos

Montalcino / Poggio alle Mura

Villa / 5 Bedrooms / sleeps 16

7 Nights min stay

Add to shortlist

from £727 / night

£5085 - £8377 / week

View

Key info:

  • Not suitable for children
  • No pets allowed
Fontanelle is without doubt one of our loveliest Tuscan properties. It is located to the west of Montalcino, an area renowned for its beauty and for its wines, especially the famous Brunello di Montalcino. The property is in a spectacular position, surrounded by vineyar  …see more

12 Photos

Province of Siena / San Casciano dei Bagni

Villa / 6 Bedrooms / sleeps 12

7 Nights min stay

Add to shortlist

from £1061 / night

£7422 - £9277 / week

View

Key info:

  • Not suitable for children
  • No pets allowed
Villa Mimmi is located in the Val D'Orcia area, an unspoiled region of Tuscany, in the southern part of Siena. The property was designed with the new millennium in mind, combining spiritual relaxation, harmonious surroundings and modern amenities. The impeccable interio  …see more

31 Photos

Province of Siena / Casole d'Elsa

Villa / 6 Bedrooms / sleeps 12

7 Nights min stay

Add to shortlist

from £993 / night

£6949 - £12962 / week

View

Key info:

  • Not suitable for children
  • No pets allowed
This magnificent property is located in a beautiful position with a 360 degree view over the surrounding countryside, close to the village of Casole d'Elsa. Decorated with exceptional taste and attention to details, it has been completely restored in the last few years  …see more

24 Photos

Province of Siena / Castelmuzio

Villa / 5 Bedrooms / sleeps 10

7 Nights min stay

Add to shortlist

from £363 / night

£2537 - £3443 / week

View

Key info:

  • Nearest beach 100 km
  • Swimming pool
  • Great for children of all ages
  • Car not necessary
  • No pets allowed
  • Private garden
Casa Oliveto is the guest villa, and sits at the end of an olive grove known for producing one of Italy's premier extra virgin olive oils. The villa, the pool & the gardens are totally private - separated from the main house by a large expanse of olive grove.  …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

20 Photos

Province of Siena / San Gimignano

Villa / 6 Bedrooms / sleeps 12

2 Nights min stay

Add to shortlist

from £301 / night

£2106 - £4000 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • No pets allowed
  • Private garden
Villa Toiano is a quaint, lovingly decorated property. The stones and the old ceiling beams have been incorporated into a beautifully-finished new country home that oozes personality and charm.  …see more

Excellent 5/5 

20 Photos

Province of Siena / Cetona

Apartment / 2 Bedrooms / sleeps 5

Excellent 5/5 

4 Nights min stay

Add to shortlist

from £58 / night

£400 - £700 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • No pets allowed
Tuscan style apartment with pool, ideally situated on the outskirts of the medieval town of Cetona, with panoramic views. Two minute walk from local amenities. Perfect for exploring cultural Tuscany.  …see more


11 Jul 2014

5/5

"Great Apt & charming wee village - not too touristy"

Delightful apt. with great views over the surrounding countryside & over olive groves. We were met by the lovely Marina & were very grateful to the owner Sophia who both, at short notice were able to … More


1 Mar 2014

5/5

"Excellent Accomadations"

Stayed with my wife and daughter for one week, and found it was the perfect location to discover Tuscany and Umbria. The apartment is beautiful and only within minutes of town Center. The booking proc… More


8 Sep 2013

5/5

"Being in Cetona is like stepping back in time!"

Our holiday in Cetona was wonderful. We stayed at La Madonna for 2 weeks having flown into Rome and spending 24 hours in Rome sightseeing. The drive from Rome took about 2 hours and was quite easy. Th… More

See all reviews Continue

Very Good 4.5/5 

24 Photos

Province of Siena / Gaiole in Chianti

Villa / 3 Bedrooms / sleeps 8

Very Good 4.5/5 

Short stays welcome

Add to shortlist

from £75 / night

£519 - £1183 / week

View

Key info:

  • Nearest beach 107 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • Pets welcome
  • Private garden
Located within walking distance of the village of Gaiole in Chianti, the villa offers the perfect setting to explore the Chianti Classico region, enjoy the breathtaking views of the vineyards and olive groves, and experience the charming Tuscan lifestyle. Beautiful vill  …see more


9 Jul 2013

5/5

"Amazing holiday in gorgeous Gaiole"

We had a wonderful 10 day stay in Villa Gaiole. The villa is located in a small residential area, a short stroll from the main hub of the quaint village of Gaiole. The town itself is well located to e… More


20 Jul 2014

4/5

"Aangename vakantie"

We hadden een fijne vakantie met 6 volwassenen in Villa Gaiole. Het is een erg gezellig dorpje met een goede uitvalsbasis voor bezoeken aan bv Siena, San Gimignano,... Een héél groot pluspunt was v… More


20 Aug 2012

4/5

"TRES BELLES PRESTATIONS !"

Maison très agréable à vivre, bien équipée. Piscine agréable et partagée uniquement avec 3 autres logements. Petits points d'attention : chiens et voisins un peu bruyants A revoir : Complé… More

Bonjour, et merci pour votre feed-back sur vos vacances dans notre villa, il est toujours un grand plaisir de savoir que les invités ont eu un agréable séjour. Un grand merci aussi pour nous avoir fait connaître le problem avec le parapluie sous le porche, de cette façon, nous avons été en mesure de le corriger pour les prochains clients. Nous avons hâte de vous revoir à l'avenir!

See all reviews Continue

Excellent 5/5 

10 Photos

Province of Siena / San Gimignano

Apartment / 1 Bedroom / sleeps 2

Excellent 5/5 

3 Nights min stay

Add to shortlist

from £32 / night

£219 - £271 / week

View

Key info:

  • Nearest beach 72 km
  • Great for children of all ages
  • Car essential
  • No pets allowed
  • Private garden
The Podere Magione is immersed in the San Gimignano countryside, amidst hills covered with olive trees and vineyards. From its ideal position it is possible to quickly reach the most beautiful, historical and artistic towns of Tuscany. Podere Magione is a farm house; we  …see more


16 Aug 2012

5/5

"An all round fantastic experience...we have great memories..."

My partner and I stayed here for a week in July, and count ourselves lucky to have discovered this place. About 8kms from San Gimignano (an easy jaunt in a car, the latter being vital), we felt li… More


30 Jun 2012

5/5

"Podere Magione - "a must stay place in the Chianti Hills""

We stayed for 10 days and the apartment is so comfortable. Large open windows, all screened and shuttered, and doors opening to a very large terrace, looking straight out to San Gimignano. All kitchen… More


30 Oct 2014

5/5

"Ein Paradies im Herzen der Toskana"

Wir haben unsere 9 Tage in diesem wundervollen Appartment jede Sekunde genossen. Sehr saubere und stilvolle Unterkunft in ruhiger Lage mit traumhaftem Blick auf San Gimignano und die toskanische Lands… More

See all reviews Continue

Very Good 4.5/5 

15 Photos

Province of Siena / San Gimignano

Apartment / 2 Bedrooms / sleeps 4

Very Good 4.5/5 

3 Nights min stay

Add to shortlist

from £61 / night

£424 - £526 / week

View

Key info:

  • Nearest beach 72 km
  • Great for children of all ages
  • Car essential
  • No pets allowed
  • Private garden
This apartment is situated on one of the most ancient routes of the pilgrims, just a few kilometres from San Gimignano. All the windows offer a beautiful view of the neighbouring villages and hills. Podere Magione is a farm house we produce Chianti wine, White wine and  …see more


26 Oct 2013

5/5

"Hidden Gem and Centrally Located In Tuscany Wine Region"

We stayed in July 2013 for 3 nights. Located on top of a hill near Ugando,, this lovely villa is part of a working vineyard and farm owned by Jianna and her family. My husband and his parents stayed i… More


4 Jul 2013

5/5

"Very relaxing holiday in a beautiful place!"

We stayed for a week at Olive e Acacia Apartment which is part of a farmhouse on a family run farm. Giana made us very welcome and we enjoyed the home produced wine & olive oil. The view from the gard… More


9 Aug 2012

5/5

"great place"

my husband and i stayed for 3 nights at podere magione at july 2012. the location is on the hill with amazing views, peaceful. the apartment is spacious, clean and very comfortable, cool and pleasant … More

See all reviews Continue

Excellent 5/5 

20 Photos

Province of Siena / Gaiole in Chianti

Apartment / 1 Bedroom / sleeps 3

Excellent 5/5 

7 Nights min stay

Add to shortlist

from £42 / night

£289 - £530 / week

View

Key info:

  • Nearest beach 105 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • Some pets are welcome - please contact the owner
  • Private garden
Ideal location for couples and families, set within walking distance of Gaiole in Chianti with the typical Tuscan lifestyle at your doorstep. Perfect place to unwind and come back to after a cycle, a walk, or discovering the artistic and historic cities of Tuscany. Gaio  …see more


21 Mar 2014

5/5

"Lovely place in heart of Chianti"

We stayed several weeks in Franco's wonderful Casa Giardino. Unlike many one bedroom apartments, there is plenty of room to move here. The bedroom is large, the living room is truly separate from the … More

See all reviews Continue

16 Photos

Montalcino / Val d'Orcia

Farmhouse / 5 Bedrooms / sleeps 12

3 Nights min stay

Add to shortlist

from £240 / night

£1679 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
Tuscany farmhouse with swimming pool in Pienza, Siena in a magnificent part of Italy. Farmhouse Podere Pienza is located in an area of Southern Tuscany that is still untouched by tourists with a private swimming pool.  …see more

12 Photos

Province of Siena / Montepulciano

Apartment / 2 Bedrooms / sleeps 4

7 Nights min stay

Add to shortlist

from £60 / night

£417 - £592 / week

View

Key info:

  • Not suitable for children
  • No pets allowed
  • Private garden
A rental apartment with private garden in Montepulciano. A unique opportunity for 2-4 people to live the real Italian life.  …see more

Very Good 4.5/5 

23 Photos

Province of Siena / Gaiole in Chianti

Apartment / 2 Bedrooms / sleeps 6

Very Good 4.5/5 

Short stays welcome

Add to shortlist

from £108 / night

£750 - £850 / week

View

Key info:

  • Nearest beach 0 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
Apartment with spectacular views in the heart of the Chianti Region in Tuscany. A €150 deposit for air con payable on arrival usage will be calculated and refund given.€1.50 p/n local tax  …see more


27 Jul 2014

5/5

"Great family break"

Stay for a week and had a great time. Apartment was ideal for the pool, handy for our children to nip in and out. 2 nice size bedrooms, galley kitchen and a good size lounge/dining room was great for … More


23 Aug 2013

5/5

"Absolutely idyllic"

Stayed at this charming apartment mid July with my wife and three small children. The apartment was ideally situated right beside the sun terrace and the swimming pool which was so convenient, not onl… More


24 Apr 2013

5/5

"Peaceful taste of Tuscany!!!!"

Stayed here for a lovely, idyllic, December week. Amazing apartment with all home comforts. Loved walking through the village, stopping for pizza and fine wines :-) The views over the hills and vineya… More

See all reviews Continue

17 Photos

Province of Siena / San Gimignano

Villa / 3 Bedrooms / sleeps 6

7 Nights min stay

Add to shortlist

from £178 / night

£1240 - £2165 / week

View

Key info:

  • Swimming pool
  • Ask owner if suitable for children
  • Some pets are welcome - please contact the owner
Villa Fienile is a beautifully presented converted barn, located just 1.2km from the village of Monticiano. The villa is private and surrounded by a lovely garden with salt-water swimming pool.  …see more

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 £164 / night

£1146 - £1909 / 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


30 Jan 2015

4/5

"A lovely villa in a quiet setting"

Lovely accomodation for large family group despite slightly unusual room layout.Great outside space for dining .Bit of a steep treck to pool but nicely secluded. We were bothered by flies but probabl… More

See all reviews Continue

Very Good 4/5 

24 Photos

Gaiole in Chianti / Lecchi

Villa / 3 Bedrooms / sleeps 8

Very Good 4/5 

7 Nights min stay

Add to shortlist

from £134 / night

£935 - £1563 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
Vignale is a small hamlet that has a total of 6 private homes. It is located on top of a Chianti hill that gives it the luxury of a stunning view all around. Within a short drive there are three of the five famous Chianti towns.  …see more


16 Jan 2014

4/5

"Lovely villa in a stunning location"

The villa occupies a beautiful hilltop location in a small hamlet of about 6 properties. The drive to the property is an experience, some might find it a concern, we loved it, all part of the adventur… More

See all reviews Continue

Excellent 5/5 

25 Photos

Montalcino / Val d'Orcia

Farmhouse / 2 Bedrooms / sleeps 4

Excellent 5/5 

7 Nights min stay

Add to shortlist

from £108 / night

£752 - £1252 / week

View

Key info:

  • Nearest beach 70 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Pets welcome
  • Private garden
Charming farmhouse with garden + pool in a loosely layout hamlet - the castle estate of Vivo d'Orcia. Absolute privacy. Spectacular view over the Orcia valley below. Sleeps 4  …see more


15 Aug 2013

5/5

"Quiet haven with great view"

A beautifull, well tended house in a small hamlet on the grounds of the castle of the count and countess of Vivo d'Orcia. The village of Vivo d'Orcia is a few minutes on foot and has a few nice restau… More

See all reviews Continue

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

£336 - £610 / 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


1 Feb 2014

5/5

"Perfect holiday accommodation"

This accommodation is perfect for a couple but also could accommodate one child. The bedroom and lounge are very well appointed and the scenery breathtaking . The whole apartment is very clean and air… More

See all reviews Continue

Excellent 5/5 

24 Photos

Province of Siena / Gaiole in Chianti

Villa / 5 Bedrooms / sleeps 10

Excellent 5/5 

7 Nights min stay

Add to shortlist

from £177 / night

£1238 - £2741 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
This comfortably furnished country style Tuscan villa sleeps up to ten persons. Set amongst a mature well tended garden with its own private swimming pool. The property is in a great location only five minutes away from Gaiole.  …see more


4 Jun 2012

5/5

"Gorgeous rustic villa in a beautiful area"

Fantastic holiday. Villa was perfect with plenty of social areas. Villa contained everything you could have hoped for, i.e. in the utility room and kitchens. Walking distance to Giaole, a village that… More


4 Nov 2011

5/5

"Perfect peace and relaxation yet close to lovely Gaiole in Chianti"

Sue who owns the property and lives next door was a perfect host and very laid back, just like us, we were there for a 40th Birthday celebration and couldnt have wished for a better place to chill out… More

See all reviews Continue

Excellent 5/5 

24 Photos

Province of Siena / Castellina In Chianti

Villa / 4 Bedrooms / sleeps 8

Excellent 5/5 

7 Nights min stay

Add to shortlist

from £201 / night

£1402 - £2336 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
Villa Casanovina is situated only a few kilometres from the town of Castellina in Chianti. The villa is set in a great location on a hillside overlooking the surrounding Chianti countryside. There are four bedrooms in total - two in the main house and two in the annexe.  …see more


31 Jan 2015

5/5

"Ideal family base for relaxation, exploration, and wine tasting"

We had a lovely week in Casanovina - a really relaxing time enjoying the spectacular views, wine and food! Booking and service prior to going was great, as were our hosts over there, who live in the … More

See all reviews Continue

Excellent 5/5 

22 Photos

Province of Siena / Castellina In Chianti

Villa / 5 Bedrooms / sleeps 9

Excellent 5/5 

7 Nights min stay

Add to shortlist

from £277 / night

£1935 - £3497 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
Casale Cipressi is an exclusive Tuscan country house 2.7km from Castellina in Chianti furnished to a high standard and consists of two floors. Stone built with traditional terracotta tiled floors and chestnut wooden beams gracing the old style ceilings.  …see more


2 Jul 2014

5/5

"Beautiful Tuscan Villa in the heart of Chianti - A winner!"

We booked this villa to accommodate 2 familys - 9 of us in total. We loved our week in Tuscany and it was the perfect base for all that we wanted to see in and around the Chianti region. The views we… More


22 Jan 2012

5/5

"Heaven...this is the place I want to come to to die!!"

We were reallocated to this wonderful place at very short notice by 'To Tuscany' when the place we had booked had a small fire...divine intervention? This was the most magnificent place we have eve… More

See all reviews Continue

Very Good 4/5 

13 Photos

Province of Siena / Montisi

Villa / 5 Bedrooms / sleeps 6

Very Good 4/5 

3 Nights min stay

Add to shortlist

from £73 / night

£508 - £1278 / week

View

Key info:

  • Nearest beach 70 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
  • Private garden
Located on a hill overlooking the Val D'Orcia Tuscany's only Unesco heritage site is truly beautiful. A stay here will relax body and mind. We now offer excellent home cooked food within your house in the traditional tuscan style and cater for large or small groups.  …see more


17 Nov 2012

4/5

"région magnifique idyllique!!"

accueil charmant de paola! maison située ds un hameau entièrement restauré ds une totale harmonie.....très propre, draps et linge de toilette fournis!! confortable (chauffage efficace) décor rus… More

See all reviews Continue

Very Good 4/5 

13 Photos

Monteriggioni / Quercegrossa

House / 2 Bedrooms / sleeps 4

Very Good 4/5 

4 Nights min stay

Add to shortlist

from £74 / night

£514 / week

View

Key info:

  • Ask owner if suitable for children
  • Some pets are welcome - please contact the owner
The big entrance doors of this ex-barn open onto a large living room with a fireplace, sofa and comfortable furniture. Huge glazed panels front the lovely brick pattern barn windows. Metal supports and a metal staircase compliment the ancient brick and stone work. Wide  …see more


18 Nov 2009

5/5

"Blissful Holiday"

I have been holidaying in Tuscany for several years and without doubt the most memorable trip was our visit to Malvasia at Lornano last July. The villa is in an ideal location for exploring all of Tus… More


30 Sep 2011

4/5

"Perfect location with amazing pool"

The house was great, and I would not hesitate to recommend it to anyone. We were able to visit Siena in 10 mins and Florence in 45, or just hang around and play in the wonderful swimming pool. They dr… More


12 Oct 2010

4/5

"Great Place, could use small creature comforts..."

The location is fantastic, pretty much the way you'd imagine it would be in Tuscany...the house is spacious and very clean...the pool is immaculate with sweeping views of the Tuscan hillsides...there … More

See all reviews Continue

Excellent 5/5 

45 Photos

from £945 / night

£6613 - £9722 / week

View

Holiday villa rental

Province of Siena / Brenna

Villa / 7 Bedrooms / sleeps 14

Excellent 5/5 

7 Nights min stay

Add to shortlist

from £945 / night

£6613 - £9722 / week

View

Key info:

  • Ask owner if suitable for children
  • Some pets are welcome - please contact the owner
On a wooded crest of the Montagnola hills outside Siena, this beautifully restored farmhouse gives the immediate impression of protected peace. The surrounding rural landscape is a composite of the ilex oak trees that foster porcini mushrooms, olives groves, whose fruit  …see more


11 Aug 2011

5/5

"Perfect family getawat"

I agree the pictures do not do it justice! We stayed 1 week with extended family, including children between 3 to 12 years, we hardly saw the kids, they were so entertained playing around the property… More


4 Jun 2009

5/5

"Live the dream"

A Truely beautiful house in a stunning setting, the pictures do not do it justice. Silent at night with no light pollution, classic unspoilt tuscan views buy day all finished off elegantly furnished … More

See all reviews Continue

Excellent 5/5 

20 Photos

Province of Siena / Radicondoli

Villa / 4 Bedrooms / sleeps 8

Excellent 5/5 

4 Nights min stay

Add to shortlist

from £136 / night

£952 - £1925 / week

View

Key info:

  • Ask owner if suitable for children
  • Pets welcome
Just outside the village of Radicondoli, facing across rolling, open countryside, stands an attractive old farmhouse, full of charm and character and providing ample accommodation for eight people. The 12 X 6 metre swimming pool, with a lovely surround made from old ter  …see more


27 Sep 2014

5/5

"Great vacation"

Lovely setting at Radicondoli - about 30 minutes drive to Siena, 90 minutes to Firenze and beautiful scenery all around. A lot of space in Ragnana, nice swimming pool and most everything one could ask… More


30 Sep 2013

5/5

"beautifully located, wonderful house for our family holiday"

Ragnana was exactly as expected and described to me by Laura at Invitation to Tuscany. It is a lovely farmhhouse which is large enough for an extended family such as ours, comfortable and welcoming. … More


27 Sep 2013

5/5

"Just brilliant"

Our third stay at this farmhouse,what can I say?, except it was fantastic,lovely house ,patio areas,bbq and pool.Claudio, the owner,arrives every day, very early to sweep and tidy the area around the … More

See all reviews Continue

Excellent 5/5 

23 Photos

Province of Siena / Murlo

Villa / 2 Bedrooms / sleeps 4

Excellent 5/5 

4 Nights min stay

Add to shortlist

from £85 / night

£595 - £655 / week

View

Key info:

  • Ask owner if suitable for children
  • Some pets are welcome - please contact the owner
Like an upturned rounded beehive, the peaceful, historic hamlet of Castello di Murlo is right in the middle of Etruscan territory. Most of the dwellings, including Pozzo, form part of the walls, which enclose two squares, one with an important Etruscan museum in the ex  …see more


21 May 2015

5/5

"Perfect Tuscan Villa"

We stayed at Il Pozzo for the week of May 2-9, 2015 and can highly recommend this villa. We were warmly greeted by Sarah who toured us through the villa, made suggestions on places to visit and then… More


25 Jun 2010

5/5

"A Little Bit of History in a Tuscan Treasure"

What a fabulous place to stay and explore Siena and Southern Tuscany! It was as though we had been transported back in time staying at Castello di Murlo. Our hosts were very helpful and friendly, orga… More

See all reviews Continue

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 / Siena

House / 9 Bedrooms / sleeps 20

7 Nights min stay

Add to shortlist

from £900 / night

£6299 - £8669 / week

View

Key info:

  • Ask owner if suitable for children
  • Air conditioning
  • No pets allowed
(Minimum of one week rental required) Minimum rental one week rental Saturday to Saturday except for urban apartments. Villa "La Contessa" is a must for an unforgettable stay in the heart of Tuscany. Located 35 kms south of Siena in the "Crete", the building dates back  …see more

23 Photos

Montalcino / Val d'Orcia

Cottage / 1 Bedroom / sleeps 2

7 Nights min stay

Add to shortlist

from £76 / night

£526 - £657 / week

View

Key info:

  • Nearest beach 70 km
  • Not suitable for children
  • Car advised
  • Some pets are welcome - please contact the owner
  • Private garden
Situated on the castle estate of Vivo d'Orcia, Casa Gallinaio is a charming restored former chicken coop for 2 with terrace and private garden. View onto the medieval hamlet and the Monte Amiata.  …see more

15 Photos

Province of Siena / Montalcino

Villa / 3 Bedrooms / sleeps 8

3 Nights min stay

Add to shortlist

from £93 / night

£650 - £1457 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • Pets welcome
  • Private garden
Sun baked stone walls, hand made terracotta floors, chestnut beamed ceilings, pergolas twisted with the perfume of jasmine and wisteria, sitting out on your terrace overlooking your swimming pool, Soaking up the radiant glow of the sun setting over the Val d'Orcia Valle  …see more

23 Photos

Montepulciano / Gracciano

Villa / 5 Bedrooms / sleeps 9

7 Nights min stay

Add to shortlist

from £248 / night

£1730 - £3384 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
Maramai, now a charming country house, used to be a small farm with 3 separate buildings. It is named after the Tuscan farmer's family who lived there until the early '70s.  …see more

14 Photos

Province of Siena / Montisi

Villa / 2 Bedrooms / sleeps 4

3 Nights min stay

Add to shortlist

from £63 / night

£438 - £727 / week

View

Key info:

  • Nearest beach 70 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • Pets welcome
  • Private garden
This is a beautiful traditional stone house completely refurbished over two years ago. As a result the fit out is of a very high quality.Located on a hill overlooking a Unesco world heritage site with wonduferfu; views and sunsets to take home.  …see more

43 Photos

Province of Siena / Lucarelli

Villa / 7 Bedrooms / sleeps 14

4 Nights min stay

Add to shortlist

from £695 / night

£4859 - £6363 / week

View

Key info:

  • Not suitable for children
  • Some pets are welcome - please contact the owner
Roseto 14 is a 13th century farmhouse with a small tower and a barn, in the middle of the Chianti Classico area, mid-way between Florence and Siena. On a hill in 15 hectares of its own fenced land, there are beautiful panoramic views of vineyards and olive groves with f  …see more

Excellent 5/5 

20 Photos

Province of Siena / Chianciano Terme

Villa / 4 Bedrooms / sleeps 10

Excellent 5/5 

5 Nights min stay

Add to shortlist

from £146 / night

£1022 - £1935 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • No pets allowed
  • Private garden
Detached villa with private pool in southern Tuscany. 4 bedrooms up to 10 sleeps.  …see more


2 Sep 2013

5/5

"Beautiful Villa in idyllic scenery"

The view from Casal Bancospino is breathtaking; typical Tuscan scenery all around. It feels isolated but you're only a 5 min drive to the supermarket and restaurants. The house itself is attractivel… More


16 Sep 2012

5/5

"EXCELLENT"

We spent a week in perfect settings. The house is spacious, very well furnished and very well located in quiet surroundings. The pool is cleaned every day and has stunning viws on the countryside. T… More


30 Jul 2012

5/5

"Fantastic stay in Tuscany"

We rented this house for one week in July. As the house consists of two apartments (ground floor and first floor), it was perfect for two families. The surroundings were beautiful and the pool area wa… More

See all reviews Continue

Very Good 4/5 

7 Photos

Province of Siena / San Gimignano

House / 1 Bedroom / sleeps 2

Very Good 4/5 

7 Nights min stay

Add to shortlist

from £41 / night

£282 - £325 / week

View

Key info:

  • Not suitable for children
  • Some pets are welcome - please contact the owner
Studio Apartment in Historic Centre of San Gimignano Il Nibbio is a cosy apartment located in the historical town of San Gimignano, on one of the streets leading into the centre, so just a few minutes' walk away from all this gorgeous town has to offer. A highlight of  …see more


17 Jun 2014

4/5

"Il Nibbio was exactly what wanted!"

ll Nibbio was exactly what my wife and I were looking for on our recent six week stay in Italy. We wanted a lovely apartment with a beautiful view to use as a travel base during our four week stay in… More

See all reviews Continue

21 Photos

Province of Siena / Siena

Villa / 9 Bedrooms / sleeps 21

7 Nights min stay

Add to shortlist

from £449 / night

£3139 - £3577 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Some pets are welcome - please contact the owner
  • Private garden
Detached villa with private pool 35 km eastern of Siena. It is an expansive property providing a high standard of accommodation. Tasteful furnished. Hilly and quiet location. The whole property is for private use of the tenant. 9 bedrooms, 17+4 sleeps. Billiard room.  …see more

25 Photos

Province of Siena / Siena

Villa / 5 Bedrooms / sleeps 12

5 Nights min stay

Add to shortlist

from £219 / night

£1533 - £2409 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Air conditioning
  • No pets allowed
  • Private garden
Luxurious detached villa in hilly and quiet location with a beautiful panorama in southern Tuscany. Pool, Jacuzzi (all for private use of the tenant).  …see more

18 Photos

Province of Siena / Radicofani

Villa / 7 Bedrooms / sleeps 14

7 Nights min stay

Add to shortlist

from £150 / night

£1044 - £2336 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • Some pets are welcome - please contact the owner
  • Private garden
Detached 7 bedroom villa with private pool in southern Tuscany near Siena and the Tuscany-Umbria border  …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