List your home
Apply filters
£ to

Holiday homes 2,720

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 (3)
  • Asciano (102)
  • Bagni di San Filippo (2)
  • Bagno Vignoni (6)
  • Buonconvento (33)
  • Campiglia d'Orcia (2)
  • Casciano (1)
  • Casole d'Elsa (142)
  • Castellina In Chianti (120)
  • Castelmuzio (10)
  • Castelnuovo Berardenga (125)
  • Castiglione D'Orcia (24)
  • Cetona (50)
  • Chianciano Terme (29)
  • Chiusdino (15)
  • Chiusi (30)
  • Colle di Val d'Elsa (113)
  • Gaiole in Chianti (148)
  • Gallina (2)
  • La Piazza (1)
  • Le Piazze (8)
  • Lucarelli (3)
  • Montalcino (60)
  • Montepulciano (169)
  • Monteriggioni (61)
  • Monteroni d'Arbia (34)
  • Monticiano (26)
  • Montisi (19)
  • Murlo (16)
  • Orgia (1)
  • Palazzone (15)
  • Piancastagnaio (6)
  • Pienza (85)
  • Pievasciata (4)
  • Pievescola (7)
  • Poggibonsi (122)
  • Radda in Chianti (40)
  • Radicofani (31)
  • Radicondoli (73)
  • Rapolano Terme (54)
  • Rosia (6)
  • San Casciano dei Bagni (34)
  • San Gimignano (337)
  • San Giovanni d'Asso (20)
  • San Lorenzo a Merse (1)
  • San Quirico d'Orcia (14)
  • Sarteano (31)
  • Siena (274)
  • Sinalunga (100)
  • Sovicille (48)
  • Strove (3)
  • Tognazza (1)
  • Torrita di Siena (26)
  • Trequanda (16)
  • Vergelle (1)
  • Ville di Corsano (12)
  • Vivo d'Orcia (1)
  • Volte Basse (1)

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
415 properties
Villas San Gimignano
410 properties
Villas Montepulciano
238 properties
Gaiole in Chianti
178 properties
Villas Casole d'Elsa
171 properties
Villas Castelnuovo Berardenga
169 properties
Villas Castellina In Chianti
155 properties
Villas Poggibonsi
143 properties
Villas Sinalunga
138 properties
Villas Pienza
137 properties
Apartments Colle di Val d'Elsa
128 properties
Villas Montalcino
123 properties
Asciano
122 properties
Villas Monteriggioni
86 properties

Filters applied: Parking (2,720)

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
2,720 Results   |  
20 Photos

Buonconvento / Chiusure

B&B / 6 Bedrooms / sleeps 15

1 night min stay

Add to shortlist

from £43 / night

£295 - £2574 / week

View

Key info:

  • Nearest beach 87 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Pets welcome
A La Ripolina you can find tranquility, a 'family atmosphere and attention to your requests as if you were single. We guarantee huge starry skies, a panorama without horizons, a pool with a very nice view and so many other things you discover coming. Great place for bik  …see more

10 Photos

Province of Siena / Siena

Apartment / 2 Bedrooms / sleeps 4

7 Nights min stay

Add to shortlist

from £106 / night

£736 - £1030 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • Pets welcome
appartamento in campagna a soli 10 minuti da Siena, privacy e tranquillità, servizi essenziali quali market, farmacia, banca ecc.a solo 2 km - Spazioso elegante e con ogni confort - extra i consumi per climatizzatore e riscaldamento - tassa turistica non inclusa nel c  …see more

10 Photos

Province of Siena / Siena

Apartment / 2 Bedrooms / sleeps 4

7 Nights min stay

Add to shortlist

from £94 / night

£657 - £949 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • Some pets are welcome - please contact the owner
casa in campagna piscina Siena Toscana agriturismo  …see more

Featured properties

13 Photos

Gaiole in Chianti / Lecchi

B&B / 1 Bedroom / sleeps 2

1 night min stay

Add to shortlist

from £64 / night

£442 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • No pets allowed
Borgo in genuine Chianti town. Scenery perfect for hiking and biking. Proximity to Siena and Florence alongside other cultural and historical Chianti villages. Excellent local dining and wine tasting. Property provides easy access to spacious terrace and pool area.  …see more

20 Photos

Province of Siena / Gaiole in Chianti

House / 3 Bedrooms / sleeps 5

4 Nights min stay

Add to shortlist

from £76 / night

£526 - £654 / week

View

Key info:

  • Swimming pool
  • Suitable for children over 5
  • Some pets are welcome - please contact the owner
maison toscane, appartement, piscine, chianti, gaiole in chianti, Sienne, visites de producters de vin, dégustations de vin, outlet shopping, siteseeing, marcher, villes d'art, repos, grand panorama, avec restaurant et bar, familiaire,chiens bien venus. Distances airp  …see more

10 Photos

Province of Siena / Trequanda

Farmhouse / 2 Bedrooms / sleeps 3

2 Nights min stay

Add to shortlist

from £61 / night

£424 - £570 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Pets welcome
  • Private garden
The apartment has a separate entrance and overlooks the courtyard of the villa and the hills on the back. It is located on the first floor of the farmhouse and consists of a double bedroom, a single bedroom with a toilet, a bathroom, a living room with kitchenette. Duri  …see more

24 Photos

Siena / Monastero

Farmhouse / 1 Bedroom / sleeps 4

4 Nights min stay

Add to shortlist

from £63 / night

£438 / week

View

Key info:

  • Nearest beach 100 km
  • Great for children of all ages
  • Car advised
  • Some pets are welcome - please contact the owner
Romantic one bedroom apartment in Elegant Liberty country village close to Siena medieval city. Picturesque courtyard and garden for outdoor dining.  …see more

24 Photos

Murlo / Casciano di Murlo

Villa / 4 Bedrooms / sleeps 10

7 Nights min stay

Add to shortlist

from £278 / night

£1942 - £2321 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • Pets welcome
  • Private garden
It's perfect for you if you would like to explore Tuscany's culture and atmosphere. It is surrounded by impressive serene views of woods and vineyards that stretch as far as the eye can see.  …see more

23 Photos

Murlo / Casciano di Murlo

Villa / 5 Bedrooms / sleeps 12

7 Nights min stay

Add to shortlist

from £215 / night

£1504 - £1622 / week

View

Key info:

  • Nearest beach 70 km
  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Air conditioning
  • Pets welcome
  • Private garden
Villa San Donato gives you the unique chance to stay in a residence that was once an ancient church! It is completely refurnished and turned into a beautiful villa, which offers you an unforgettable time in Tuscany.  …see more

14 Photos

Province of Siena / Casole d'Elsa

House / 1 Bedroom / sleeps 2

Short stays welcome

Add to shortlist

from £42 / night

£292 - £657 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • Pets welcome
  • Private garden
Nascosta nel verde delle colline senesi e frutto dell'accurato restauro di un antico borgo situato in una superba posizione panoramica, Ripostena è il rifugio ideale per vacanze rilassanti a contatto con la la nature e punto perfetto per scoprire i tesori della Toscana  …see more

24 Photos

Province of Siena / Chianciano Terme

Villa / 7 Bedrooms / sleeps 18

7 Nights min stay

Add to shortlist

from £245 / night

£1712 - £2482 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • No pets allowed
  • Private garden
Independent Farm house. Childrens play ground with games. Air conditioned with seven bedrooms. Fenced swimming pool. Can sleep up to 18 people if required. Disabled friendly bathroom in one room.  …see more

24 Photos

Province of Siena / Montepulciano

Villa / 7 Bedrooms / sleeps 14

7 Nights min stay

Add to shortlist

from £1479 / night

£10348 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • No pets allowed
  • Private garden
This large farmhouse was famous as far back as the 10th century as a post-house for changing coaches and horses along the Via Francigena and the architecture of the house shows this origin.  …see more

24 Photos

Pienza / Monticchiello

Villa / 6 Bedrooms / sleeps 12

7 Nights min stay

Add to shortlist

from £608 / night

£4252 / week

View

Key info:

  • Swimming pool
  • Ask owner if suitable for children
  • Air conditioning
  • Some pets are welcome - please contact the owner
  • Private garden
This very well furnished farm is situated in one hundred and fifty hectares of farm land producing excellent extra virgin olive oil, the farmhouse is set on a natural terrace overlooking the beautiful valley below.  …see more

17 Photos

Province of Siena / Montalcino

Studio / sleeps 2

2 Nights min stay

Add to shortlist

from £112 / night

£778 / week

View

Key info:

  • Nearest beach 80 km
  • Swimming pool
  • Not suitable for children
  • Car advised
  • Air conditioning
  • No pets allowed
  • Private garden
One large and cosy suite with a high ceiling with the typical wooden beams and wooden floor. There's a fully equipped kitchen, a small sitting area, a double bed with a restored big old Tuscan wardrobe. The private bathroom is with shower in travertine. The suite is equ  …see more

17 Photos

Province of Siena / Trequanda

House / 2 Bedrooms / sleeps 4

2 Nights min stay

Add to shortlist

from £78 / night

£541 - £782 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Air conditioning
  • Pets welcome
  • Private garden
The estate is located on the top of a hill, in the Crete near Pienza, Montepulciano, Cortona, Monte Oliveto Maggiore, Siena. There are four apartments which overlook the garden of the villa or the grove of oaks beside the swimming pool. Homemade breakfast is included.  …see more

Excellent 5/5 

17 Photos

Province of Siena / Siena

House / 2 Bedrooms / sleeps 3

Excellent 5/5 

3 Nights min stay

Add to shortlist

from £63 / night

£438 / week

View

Key info:

  • Nearest beach 95 km
  • Suitable for children over 5
  • Car advised
  • Pets welcome
Renewed house with a character, perfect place for whom is traveling by car, staying with one feet in the countryside and the other in Siena town. Private parking and bus stop for the Siena town center right in front of the villa!  …see more


12 Aug 2015

5/5

"A well appointed villa, convenient location and hospitable owner."

The villa is clean, has one very large bedroom and a smaller bedroom which is still adequate. The kitchen is functional with a small fridge , two ring electric hob, small electric oven and microwave. … More


29 Oct 2014

5/5

"Beautiful Renovated Stable 1 mile from Siena"

On arrival at La Stalla di San Lazzero we were warmly greeted by host Leonardo and his father Carlo. The "stable" has been sensitively renovated to acknowledge its architecture and history while updat… More


31 Jul 2014

5/5

"Wonderful, relaxing holiday"

We recently enjoyed a nine day holiday in la Stalla . This charming apartment is everything the other reviewers have said . It is bright , clean , comfortable and spacious with loads of old world fe… More

See all reviews Continue

Excellent 5/5 

23 Photos

Province of Siena / Pienza

Apartment / 4 Bedrooms / sleeps 8

Excellent 5/5 

4 Nights min stay

Add to shortlist

from £86 / night

£599 - £1103 / week

View

Key info:

  • Great for children of all ages
  • Air conditioning
  • No pets allowed
Terrace - pool - Wine - Brunnello - spa - restaurants - shops - great standard - wine tours - cycling - walking - big jacuzzi on roof terrace - wifi - AC - Sky TV Jacuzzi on the roof terrace with beautiful views over Montalcino - home of the famous Brunello wine. AC/hea  …see more


13 Apr 2015

5/5

"Excellent service and accommodation"

Casa Travertino is a wonderful restoration project. It strikes the perfect balance of having a classic style on the outside, and containing all mod-cons on the inside. The flat has clean lines everywh… More


22 Oct 2013

5/5

"Recommended unreservedly"

Excellent location in delightful hillside village. Comfortable, well-equipped apartment with lovely rooftop terrace - great for drinking prosecco in the afternoon. Brilliant jacuzzi. Ideal for our … More


4 Aug 2013

5/5

"Fantastic place - great selection of restaurants"

Truly a maginificent apartment exceeding our expectations - really nice to cool down in the jacuzzi overlooking Montalcino when the weather was at its hottest ! Also very convenient with regards to… More

Thank you so much for the kind review - we are very happy with the flat and how it turned out after the extensive work we carried out. especially the roof terrace with the new jacuzzi is a big asset :)

See all reviews Continue

Very Good 4/5 

12 Photos

Siena / Cerchiaia

Apartment / 1 Bedroom / sleeps 3

Very Good 4/5 

1 night min stay

Add to shortlist

from £37 / night

£258 / week

View

Key info:

  • Great for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
Siena Città del Palio,tipica capanna toscana ristrutturata in moderno monolocale. Vacanza ideale tra tradizione medioevale e paesaggi suggestivi. Servizi addizionali fornitura biancheria letto e bagno 20,00€ p. p. Pulizie finali:20,00€ lavatrice:20,00€  …see more


7 Sep 2014

5/5

"Tranquillità"

Ho soggiornato in questa piccola e graziosa casetta per circa una settimana, spazio in abbondanza, pulizia e quiete, inoltre proprietario cordiale, attento e molto discreto. a poche decine di metri ci… More


19 Aug 2014

3/5

"Foto ingannevoli, orario di check-in ambiguo"

Abbiamo prenotato con ampio anticipo (un mese e mezzo prima) il monolocale accordandoci per l'arrivo e la consegna delle chiavi alle ore 11:00. Con nostro stupore, 1 ora prima dell' arrivo, mentre er… More

See all reviews Continue

Excellent 5/5 

9 Photos

Sinalunga / Rigomagno

Apartment / 2 Bedrooms / sleeps 4

Excellent 5/5 

1 night min stay

Add to shortlist

from £54 / night

£373 - £730 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Pets welcome
Splendid old farmhouse carefully restored to maintain its original structural features and divided into two apartments.  …see more


29 Jun 2015

5/5

"A quiet retreat in the country."

My husband and I stayed in the lower apartment of this farmhouse for 5 days. It is located about 30 minutes south of Siena. There are many picturesque littlemountaintop towns within a short drive su… More

See all reviews Continue

Very Good 4.5/5 

20 Photos

Province of Siena / Castelnuovo Berardenga

Barn / 2 Bedrooms / sleeps 4

Very Good 4.5/5 

7 Nights min stay

Add to shortlist

from £83 / night

£577 - £1015 / week

View

Key info:

  • Nearest beach 50 km
  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Pets welcome
  • Private garden
This is the most informal apartment of Piaggione of Serravalle, smaller than the other two, for this reason it's undoubtedly the coziest and most intimate. It's located in an independent structure from the main farmhouse, to which it's linked externally to La Loggia.  …see more


18 Aug 2013

5/5

"A Real Gem"

What a find! Genuine Old School Italian Hospitality. Set in Ancient rural area. Gorgeous sunrise/sunsets.Expansive views.Comfortable beds/accomadation. Ample room.Attentive and discreet staff. Everyt… More


8 Jun 2015

4/5

"Excellent setting for a week of R & R in Tuscany"

My husband and I and two adult daughters had a great week at the cottage. The cottage and larger rental house are set amongst a vineyard and olive trees, and the pool area is stunningly beautiful, wi… More

See all reviews Continue

Excellent 5/5 

21 Photos

Province of Siena / Radicondoli

Guest house / 3 Bedrooms / sleeps 5

Excellent 5/5 

4 Nights min stay

Add to shortlist

from £73 / night

£511 - £533 / week

View

Key info:

  • Nearest beach 60 km
  • Suitable for children over 5
  • Car advised
  • Some pets are welcome - please contact the owner
Spacious thirteenth century town house built right on the walls of the historic centre of Radicondoli, perfect for family or couple. Stunning views at all three levels of this historic building.  …see more


21 Aug 2013

5/5

"Paradise in Radicondoli"

We absolutely loved our stay at Casa Sulle Mura. Radicondoli is a beautiful town. We enjoyed the people there and especially enjoyed the evenings when people sit out and enjoy. The house is wonderf… More


3 Oct 2011

5/5

"Fabulous house, fantastic village"

La Casa Sulle Mura is an amazing house in the walls of the town. We stayed as a couple but you could easily sleep 5 people. The house has been renovated to high standard but has kept the traditional… More

Grazie you were nice to spend your time and write a description of your stay. For our work is important and we thank you for write this nice things without we ask you to write, because we do not like to disturb our guest so we are really happy and grateful. Emanuela

See all reviews Continue

Excellent 5/5 

35 Photos

Province of Siena / Radicondoli

Apartment / 2 Bedrooms / sleeps 4

Excellent 5/5 

3 Nights min stay

Add to shortlist

from £76 / night

£526 - £584 / week

View

Key info:

  • Beach / lakeside relaxation
  • Nearest beach 60 km
  • Great for children of all ages
  • Car advised
  • Some pets are welcome - please contact the owner
  • Private garden
Immerse yourself into the authentic Tuscan countryside for a special holiday treat in the middle of olive groves and wineyards with your hosts only too willing to let you taste the produce of such wonders accompanied by their own home cooking.  …see more


29 Apr 2014

5/5

"Very good"

Amazing view around tuscany, nice house, wonderful agriturismo with great products made by the owners. Near to the small town (there is a good pizzeria). It was colder than expected, so we tried to fi… More

See all reviews Continue

Excellent 5/5 

20 Photos

Asciano / Crete Senesi

Farmhouse / 4 Bedrooms / sleeps 8

Excellent 5/5 

3 Nights min stay

Add to shortlist

from £143 / night

£1000 / week

View

Key info:

  • Nearest beach 100 km
  • Great for children of all ages
  • Car advised
  • Some pets are welcome - please contact the owner
Spectacular Views! Well equipped apartment in great location.Great for families. Outside, is a very attractive pergola, with BBQ for drinks and meals, overlooking the beautiful Tuscan hills and valleys. Vouchers for the local spa are provided upon request. Logs for the  …see more


31 Jul 2012

5/5

"A Tuscan dream come true"

What a wonderful experience. The villa itself was beautiful. A classic Tuscan farmhouse. It was centrally located for day trips to several regions. A car is a must. We picked up fresh pasta and wi… More


4 Jun 2012

5/5

"Best kept secret!"

We stayed at farmhouse with our family 6 adults and 2 children ages 2 and 5. The property was fabulous and met the needs of our grandchildren and children. Location is good but a car is needed in or… More

See all reviews Continue

Excellent 5/5 

32 Photos

Province of Siena / Siena

Apartment / 2 Bedrooms / sleeps 5

Excellent 5/5 

3 Nights min stay

Add to shortlist

from £68 / night

£475 - £584 / week

View

Key info:

  • Great for children of all ages
  • Car not necessary
  • No pets allowed
Fully furnished country style apartment 5 minutes away from the historic Medieval city of Siena. Confortable and spacious living-room, private parking, WiF, shops close. 1 hour drive from main Tuscan attractions, Florence, S. Gimignano, Chianti Vineyard, Hill Towns. Si  …see more


27 Jan 2015

5/5

"An Amazing Experience of Confort, Elegance and Tradition"

I spent a week in Maison Costalpino last December when I was travelling around Europe with my husband Peter and my kids Sasha and Gregory. We had been so relaxed in this big apartment in Siena. We fou… More

See all reviews Continue

 

12 Photos

Province of Siena / Radicondoli

Farmhouse / 2 Bedrooms / sleeps 4

 

4 Nights min stay

Add to shortlist

from £52 / night

£361 - £489 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Some pets are welcome - please contact the owner
  • Private garden
Not far from here you can visit San Gimignano that is one of the main villages of the spectacularly beautiful area known as the Valdelsa, arguably the most beautiful part of all Tuscany. Volterra , Monteriggioni, Siena and Florence are not far from here .  …see more


12 Jul 2015

2/5

"Great potential, but certain disappointments"

We stayed at IL TESORO for one week, wanting to be close to other family members who were staying in Radicondoli. The road to the house itself is unpaved, so best to have a jeep or other 4x4 vehicle.… More

See all reviews Continue

17 Photos

Province of Siena / Montepulciano

Farmhouse / 4 Bedrooms / sleeps 8

2 Nights min stay

Add to shortlist

from £148 / night

£1030 - £1177 / week

View

Key info:

  • Great for children of all ages
  • Air conditioning
  • Pets welcome
  • Private garden
Beautiful country house in Tuscany, Siena  …see more

30 Photos

Province of Siena / San Casciano dei Bagni

Villa / 8 Bedrooms / sleeps 16

7 Nights min stay

Add to shortlist

from £292 / night

£2044 - £4088 / week

View

Key info:

  • Nearest beach 0 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Pets welcome
  • Private garden
Villa Le Radici is an ancient residence placed in the south of Tuscany, not far from the village of San Casciano dei Bagni, famous for its thermal waters and spas.  …see more

37 Photos

Province of Siena / Torrita di Siena

Villa / 7 Bedrooms / sleeps 14

Short stays welcome

Add to shortlist

from £187 / night

£1307 - £2519 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Pets welcome
  • Private garden
Beautiful villa situated in an extremely panoramic position surrounded by greenery in the peace and quietness of the Siena countryside.  …see more

11 Photos

Sinalunga / Rigomagno

Farmhouse / 2 Bedrooms / sleeps 4

1 night min stay

Add to shortlist

from £54 / night

£373 - £730 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Pets welcome
Splendid old farmhouse carefully restored to maintain its original structural features and divided into two apartments.  …see more

28 Photos

Province of Siena / Sinalunga

Villa / 3 Bedrooms / sleeps 6

7 Nights min stay

Add to shortlist

from £104 / night

£723 - £1402 / 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
The Agriturismo La Casetta nel Bosco is a beautiful, stone villa divided into two separate units which is part of an agritouristic Farm including olive groves, woods, several crops and a small-scale breeding of horses and ponies.  …see more

32 Photos

Sinalunga / Farnetella

Villa / 4 Bedrooms / sleeps 8

7 Nights min stay

Add to shortlist

from £146 / night

£1022 - £1898 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Some pets are welcome - please contact the owner
  • Private garden
Beautiful and characteristic villa made of stone and bricks and completely restored to be a welcoming holiday home, situated on the green hills of the Siena countryside, 6 km far from the village of Sinalunga endowed with every kind of shops and services.  …see more

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

32 Photos

Province of Siena / Montepulciano

Villa / 5 Bedrooms / sleeps 9

1 night min stay

Add to shortlist

from £110 / night

£767 - £1314 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
it is the ideal place if you are looking to relax, private pool, and beautiful view.  …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

18 Photos

Province of Siena / Poggibonsi

Apartment / 2 Bedrooms / sleeps 6

7 Nights min stay

Add to shortlist

from £125 / night

£869 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • No pets allowed
  • Private garden
Wine testing and oil testing on request, Siena, Chianti, San Gimignano, Expo 2015, pool, tennis Riserva naturale bosco di S Agnese Arriving by car those are the coordinates 43.484388, 11.217959  …see more

34 Photos

from £172 / night

£1198 - £1957 / week

View

Holiday villa in Pienza

Province of Siena / Pienza

Villa / 7 Bedrooms / sleeps 13

7 Nights min stay

Add to shortlist

from £172 / night

£1198 - £1957 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Some pets are welcome - please contact the owner
  • Private garden
it is the ideal place if you are looking to relax, private pool and beautiful view  …see more

31 Photos

Province of Siena / Montepulciano

Villa / 7 Bedrooms / sleeps 14

7 Nights min stay

Add to shortlist

from £138 / night

£964 - £1730 / week

View

Key info:

  • Swimming pool
  • Suitable for children over 5
  • Car advised
  • No pets allowed
  • Private garden
it is the ideal place if you are looking to relax, private pool and beautiful view  …see more

13 Photos

Province of Siena / Torrita di Siena

House / 3 Bedrooms / sleeps 6

7 Nights min stay

Add to shortlist

from £44 / night

£307 - £497 / week

View

Key info:

  • Great for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
it is the ideal place if you are looking to relax  …see more

12 Photos

Province of Siena / Casole d'Elsa

B&B / 1 Bedroom / sleeps 2

1 night min stay

Add to shortlist

from £38 / night

£263 / week

View

Key info:

  • Great for children of all ages
  • Pets welcome
  • Private garden
Il nostro appartamento è un bilocale dove rustico e lusso si mescolano per darvi l'impressione di vivere nella civiltà contadina ma con tutti i conforts di cui si ha bisogno per una vacanza indimenticabile. Posti letto 2 + 1 nel divano Accanto all'appartamento vi è u  …see more

Excellent 5/5 

17 Photos

Province of Siena / Abbadia San Salvatore

Farmhouse / 8 Bedrooms / sleeps 12

Excellent 5/5 

3 Nights min stay

Add to shortlist

from £190 / night

£1324 / week

View

Key info:

  • Suitable for children over 5
  • Car essential
  • Pets welcome
  • Private garden
il casale Roccone è immerso nel verde del monte Amiata, con oltre cento ettari di parco naturale privato all'interno della riserva del Pigelleto. 12 posti letto, possibilità di avere un servizio di cuochi, visite guidate nella miniera, passeggiate nella foresta. Il Ro  …see more


20 Oct 2014

5/5

"Il Roccone fantastico podere in Toscana dove passare un fine settimana con gli amici"

Abbiamo avuto il piacere di conoscere il Podere il Roccone grazie ad una raccomandazione di una amica, siamo rimasti molto contenti sia della località che della struttura. La struttura è circondata … More

See all reviews Continue

Excellent 5/5 

24 Photos

Pienza / Monticchiello

B&B / 4 Bedrooms / sleeps 7

Excellent 5/5 

1 night min stay

Add to shortlist

from £65 / night

£449 - £463 / week

View

Key info:

  • Not suitable for children
  • No pets allowed
B&B di charme dotato di confortevoli camere matrimoniali, tranquillità, relax e benessere per una vacanza indimenticabile. La Val d'Orcia, Monticchiello e l'accoglienza della Casa di Adelina resteranno a lungo nei vostri cuori.  …see more


12 Jan 2015

5/5

"Excellent Accommodation"

This place was wonderful, Francesco couldn't do enough for you. Its located in a gorgeous little town in Val d'Orcia area. There are three restaurants in the town and a magnificent view from the … More


27 Jan 2015

5/5

"“Soggiorno indimenticabile... in un gioiello nella Val d'Orcia”"

Io, mia moglie e la nostra piccola bimba abbiamo avuto il piacere di soggiornare a Maggio 2014 in questa deliziosa struttura, situata nel centro storico di Monticchiello (vicino Pienza e Montepulciano… More

See all reviews Continue

Excellent 5/5 

24 Photos

Montalcino / Val d'Orcia

Villa / 4 Bedrooms / sleeps 9

Excellent 5/5 

1 night min stay

Add to shortlist

from £200 / night

£1398 - £1839 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Some pets are welcome - please contact the owner
  • Private garden
A really charming and full of style apartment in a XVI th century stone villa near Montalcino, Pienza, Siena, Montichiello. An enchanted garden and an amazing swimming pool with view on Montalcino for an unforgettable holiday: good food and wine, art, sport and relax..  …see more


20 Jul 2015

5/5

"Everything we hoped for!!"

We just got back from a week at Simona and Michael's fabulous villa and I'm already planning another trip! The house itself is absolutely beautiful, exactly what you imagine when you think of a Tuscan… More

Thank you for your kind words. It was a real pleasure to meet you all and spend some time together. Special people and special guests! We hope to see you again. All our best. Simona & Michele


5 Jul 2015

5/5

"Amazing villa in a great location for exploring Tuscany"

We spent a lovely week in the ground floor apartment in late June and would definitely recommend this villa to other holidaymakers. The pool and gardens are fantastic. The pool is warm and brillia… More

We are very happy when we see guests happy and appreciating this place we love so much. Thank you for beeing with us with your kindness and enthusiasm.Hope to see you again


15 Jul 2014

5/5

"Fabulous"

Really enjoyed our stay, the hosts Michele and Simona were lovely. We had the whole place to ourselves, so really quiet. Very comfy, cozy done like a family home. All amenities (did not have a micr… More

Thank you and hope to have you again. Simona & Michele

See all reviews Continue

Excellent 5/5 

21 Photos

Montalcino / Val d'Orcia

Apartment / 4 Bedrooms / sleeps 9

Excellent 5/5 

1 night min stay

Add to shortlist

from £190 / night

£1324 - £1508 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Some pets are welcome - please contact the owner
  • Private garden
An amazing holiday in the moast beautiful area of Tuscany, in the natural park of the Val d'Orcia, near Montalcino, Pienza, Siena, Montichiello, Bagno Vignoni. A quiete, relaxing garden with swimming pool, a charming, cosy and comfortable apartment in an ancient villa.  …see more


4 Sep 2013

5/5

"The perfect Tuscan retreat"

We have just returned from a truly memorable stay in Siena. The villa is perfect! Beautifully decorated, light and airy and a huge living space - perfect for families or large groups of friends. … More

Thank you! It was a pleasure to meet you and your family.Perfect guests! Hope to see you again. Simona and Michele


3 Sep 2013

5/5

"Perfect house"

we had a great stay, the house is just beautiful!!!!!! with a lot of atention for details and confort. the garden and pool are just amazing. the owners were very nice and they gave us the best recomme… More


5 Aug 2013

5/5

"Fantastic experience in a gorgeous setting that exceeded all expectations."

My wife and I spent a week here with our three teenage boys and all of us loved the place. The reality of the home is even better than the photos and we hated to leave. Hosts are warm, friendly and gr… More

See all reviews Continue

Excellent 5/5 

12 Photos

Province of Siena / Monteriggioni

Apartment / 2 Bedrooms / sleeps 4

Excellent 5/5 

2 Nights min stay

Add to shortlist

from £32 / night

£219 - £292 / week

View

Key info:

  • Swimming pool
  • Suitable for children over 5
  • Some pets are welcome - please contact the owner
  • Private garden
Appartamento con giardino privato. Piscina condominiale. Ottimo punto di partenza per visitare Siena, San Gimignano, Volterra, Firenze e tutto il Chianti. Noleggio biciclette (10 euro al giorno)  …see more


24 Aug 2014

5/5

"Excellent"

Logement rénovée avec goût. Piscine très spacieuse. Situation idéale au calme mais proche de Sienne et de San Gimignano, et à 50 km de Florence. Hôtes très discrets mais non moins sympathiques… More


9 Jul 2014

5/5

"Magnifique"

Propriété magnifique dans un environnement enchanteur. Accueil chaleureux et logement coquet. Les enfants et les parents ont entre autres beaucoup apprécié la piscine :-)… More


7 Jul 2014

5/5

"Senza parole"

Per il nostro secondo soggiorno nella struttura, ci siamo rivolti ai proprietari di questo appartamento (li avevamo conosciuti l'anno precedente). L'appartamento 14 è bellissimo, ben arredato, fun… More

See all reviews Continue

Very Good 4/5 

21 Photos

Province of Siena / San Gimignano

Townhouse / 2 Bedrooms / sleeps 5

Very Good 4/5 

4 Nights min stay

Add to shortlist

from £77 / night

£533 - £811 / week

View

Key info:

  • Nearest beach 77 km
  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Some pets are welcome - please contact the owner
  • Private garden
It is a typical example of old Tuscan country houses, with floors made with terracotta tiles, and wooden beams on the ceiling, it also has a wide farmyard, still with floor done in terracotta tiles with an enchanting view on the heart of the Tuscan Countryside.  …see more


20 May 2015

4/5

"Great Cottage,lovely patio with wonderful views"

We stayed here for a week in early May with my mother. The owners were waiting with a warm and friendly greeting for us, even though we arrived late due to delays en route. Though they only spoke Ital… More

See all reviews Continue

Very Good 4.5/5 

24 Photos

Siena / Val di Merse

Apartment / 3 Bedrooms / sleeps 7

Very Good 4.5/5 

2 Nights min stay

Add to shortlist

from £115 / night

£803 - £1022 / week

View

Key info:

  • Beach / lakeside relaxation
  • Nearest beach 70 km
  • Great for children of all ages
  • Car advised
  • Some pets are welcome - please contact the owner
Warm and welcoming, ten kilometres away from Siena, this apt is set in an ancient, XVth century villa, recently restored by a sensitive and art historically conscious architect & designer. The very best of the Tuscan tradition can be enjoyed here. Ideal for every confi  …see more


11 Dec 2014

5/5

"Wonderful holiday in Tuscany"

We recently had an extended family holiday in Tuscany. The Villa Amedeo - Leonardo/Tiziano was a wonderful base for us to make our daily trips to Florence, Siena and the wineries within the region. W… More


11 Aug 2013

5/5

"A fantastic Tuscan experience"

My family and I stayed in the Villa Leonardo for 1 week from 27/7/13 in the charming and sleepy village of Brenna which is about 5 miles from Siena. We had travelled from Pisa and Florence (Freinze) … More


15 Jul 2015

4/5

"Lovely country home"

Located in the sleepy village of Brenna, initially the villa was difficult to find. A nice Italian lady was there waiting for us but she spoke little English and eventually another lady came in the mo… More

See all reviews Continue

Excellent 5/5 

22 Photos

Siena / Val di Merse

Apartment / 1 Bedroom / sleeps 2

Excellent 5/5 

2 Nights min stay

Add to shortlist

from £47 / night

£329 - £438 / week

View

Key info:

  • Beach / lakeside relaxation
  • Nearest beach 70 km
  • Great for children of all ages
  • Car advised
  • Some pets are welcome - please contact the owner
Giotto is a warm and welcoming two person apartment, ideal for a romantic stay just 10 kilometres away from Sienna. Set in an ancient, XVth century villa, recently restored by a sensitive and art historically conscious architect and designer.  …see more


28 Feb 2015

5/5

"Really quiet and cool"

This rental is in a really small town called Brenna about 20 minutes south of Siena. The house itself is pretty much at the end of the main road when you drive into the town. The town has one rest… More

Thanks Paul, very nice from you, we try to do our best Agostino

See all reviews Continue

Excellent 5/5 

11 Photos

Province of Siena / Rapolano Terme

Apartment / 2 Bedrooms / sleeps 8

Excellent 5/5 

2 Nights min stay

Add to shortlist

from £94 / night

£657 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Pets welcome
  • Private garden
agriturismo laura  …see more


28 Nov 2014

5/5

"favoloso"

niente da commentare di sfavorevole tutto ok, io e marco ci siamo trovati benissimo per il clima famigliare,la fiducia accordata l'ambiente che noi desideravamo l'abbiamo trovato, nulla di particolare… More

See all reviews Continue

Very Good 4.5/5 

22 Photos

Province of Siena / Ville di Corsano

Apartment / 3 Bedrooms / sleeps 8

Very Good 4.5/5 

5 Nights min stay

Add to shortlist

from £73 / night

£511 - £803 / week

View

Key info:

  • Nearest beach 70 km
  • Great for children of all ages
  • Car advised
  • Some pets are welcome - please contact the owner
  • Private garden
Deep in the heart of the Tuscan hills and just 15 minutes away from Siena, this property offers the ideal place to unwind at any time of year. Agriturismo Andreini has been delightfully renovated into a cosy and attractive holiday getaway.  …see more


8 Apr 2015

5/5

"Perfect vacation in Tuscany"

We had a great time at Agriturismo Andreini. The fireplace, the clean rooms, the view, the price, the food, the service - all perfect. We had a wonderful dinner. Please make sure to be here with a car… More

What a lovely comment and useful comments! It was a great pleasure meeting you and your girlfriend Perfect guests! Maddalena and Monica


10 Oct 2014

5/5

"Freundlich, gutes Essen, nah an Siena"

Wir haben knapp 3 Tage in der Toskana verbracht in diesem wundervollen Agriturismo. Sehr schönes Zimmer, italienisches süßes Frühstück und leckeres, regionales und bodenständiges Abendessen. A… More

Thanks so much for your lovely comment and glad you had a fantastic time with us Sincerely Agriturismo Andreini


8 Aug 2014

5/5

"Assolutamente eccezionale!"

Il posto è incantevole, la camera spaziosa e dal gusto rustico, letto comodissimo, in 2 parole molto accogliente! La struttura è immersa nel verde ed è a gestione familiare, tutti i membri della fa… More

Ringraziamo di cuore per il simpaticissimo commento. Ci fa molto piacere che abbiate gradito la nostra accoglienza e genenuita'. Distinti Saluti Agriturismo Andreini

See all reviews Continue

23 Photos

Montepulciano / Valiano

Villa / 7 Bedrooms / sleeps 23

Min stay varies

Add to shortlist

from £473 / night

£3309 - £5148 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • No pets allowed
  • Private garden
Casale, montepulciano, villa, piscina, vigneti, matrimonio in toscana, matrimonio in Italia, Italy, Tuscany Antico casale, completamente restaurato e suddiviso in 7 accoglienti appartamenti  …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