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408 Holiday homes in Siena Province

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Filters applied: City breaks (408)

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408 Results  |  
24 Photos

Guest house | 7 Bedrooms | sleeps 14

Short stays welcome

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from £606 /night

£4240 - £6106 / week

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Key info:

  • Beach / lakeside relaxation
  • Nearest beach 100 km
  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Air conditioning
  • May take pets – please enquire
  • Private garden
Villa in the historical and cultural heart of Tuscany near the centre of Montepulciano, with restaurant, market and cafe/bar, all at our door step. We offer Internet connection, buffet breakfast, dinner in private terrace, wine tour, Jacuzzi and a wanderfull gaden. Ardene provides its guests with a high standard of accommodation. The private swimmingpool is wonderful!  …see more

24 Photos

Villa | 6 Bedrooms | sleeps 12

Excellent 5/5 

3 Nights min stay

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from £219 /night

£1527 - £2968 / week

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Key info:

  • Nearest beach 120 km
  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • No pets allowed
  • Private garden
The place is peaceful, outside in the garden; you have the possibility to relax under the trees or to eat under the stars. Beautiful structure for a relaxing holiday in the tuscany area . ask for availability we have several solution for you. also self catering apartments with breakfast service.  …see more

20 Photos

Apartment | 1 Bedroom | sleeps 4

1 night min stay

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from £111 /night

£772 - £1010 / week

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Key info:

  • Nearest beach 84 km
  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • Air conditioning
  • Pets welcome
  • Private garden
Self catering holiday apartments in heart of Tuscany; excellent for families and couples seeking relaxation. Just few minutes to Siena, San Gimignano and Florence. Pool and fresco dining area. In our restaurant is possible to take: Breakfast Dinner Wine tasting  …see more

Featured properties

20 Photos

Apartment | 1 Bedroom | sleeps 2

1 night min stay

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from £85 /night

£594 - £832 / week

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Key info:

  • Nearest beach 84 km
  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • Air conditioning
  • Pets welcome
  • Private garden
Self catering holiday apartments in heart of Tuscany; excellent for families and couples seeking relaxation. Just few minutes to Siena, San Gimignano and Florence. Pool and fresco dining area. In our restaurant is possible to take: Breakfast Dinner Wine tasting  …see more

19 Photos

Apartment | 1 Bedroom | sleeps 4

1 night min stay

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from £128 /night

£891 - £1188 / week

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Key info:

  • Nearest beach 84 km
  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • Air conditioning
  • Pets welcome
  • Private garden
Self catering holiday suite apartment in heart of Tuscany; excellent for families and couples seeking relaxation. Just few minutes from Siena, San Gimignano and Florence. Fantastic view from terrace. Shared pool  …see more

20 Photos

Apartment | 3 Bedrooms | sleeps 8

1 night min stay

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from £117 /night

£815 - £1900 / week

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Key info:

  • Nearest beach 84 km
  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • Air conditioning
  • Pets welcome
  • Private garden
Self catering holiday apartments in heart of Tuscany; excellent for families and couples seeking relaxation. Just few minutes to Siena, San Gimignano and Florence. Pool and fresco dining area. In our restaurant is possible to enjoy: Breakfast Dinner Wine tasting  …see more

24 Photos

Farmhouse | 4 Bedrooms | sleeps 8

1 night min stay

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from £64 /night

£448 - £2201 / week

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Key info:

  • Nearest beach 80 km
  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Pets welcome
  • Private garden
Quiet and cosy farm house, with view on the ancient city of Siena and on the Tuscan countryside. At only 3 Km from Siena, and at the very centre of Tuscany, La Prodaia is the ideal place for visiting the town of the "Palio" and the many other Tuscan attractions. Enjoy our private garden and swimming pool with amazing view!  …see more

15 Photos

Apartment | 1 Bedroom | sleeps 5

Very Good 4/5 

3 Nights min stay

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from £38 /night

£265 - £371 / week

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Key info:

  • Suitable for children of all ages
  • Car advised
  • No pets allowed
Fully equipped self catering apartment, ideally located for exploring the spectacular castles, cities and villages of the beautiful wine making region of Tuscany and beyond. Perfect for families, lovers of good food and wine, short breaks and long stays.  …see more

22 Photos

Apartment | 3 Bedrooms | sleeps 6

Excellent 5/5 

2 Nights min stay

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from £105 /night

£730 - £1018 / week

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Key info:

  • Nearest beach 70 km
  • Suitable for children of all ages
  • Car advised
  • May take pets – please enquire
  • 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

22 Photos

Apartment | 3 Bedrooms | sleeps 6

7 Nights min stay

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from £61 /night

£424 - £933 / week

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Key info:

  • Nearest beach 70 km
  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • May take pets – please enquire
  • Private garden
ARCOBALENO 110 m2 - 6 Guest . coveredy by free Wi-Fi Charmed Villa located 1km far from Radda in Chianti, Siena-Tuscany, in the heart of the Chianti Classico- with private garden, indipendent entrance, tv/sat, free WI-FI nternet connection and swimmingpool.  …see more

24 Photos

House | 2 Bedrooms | sleeps 4

1 night min stay

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from £103 /night

£716 - £960 / week

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Key info:

  • Nearest beach 90 km
  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • No pets allowed
  • Private garden
Appartamento Il Riccio A is a romantic and welcoming two-story apartment surrounded by vineyards and olive groves. It sleeps four people. From Appartamento Il Riccio A you will enjoy an enchanting view of the Tuscan countryside and of the towers of San Gimignano  …see more

20 Photos

Villa | 3 Bedrooms | sleeps 8

Very Good 4.5/5 

Short stays welcome

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from £79 /night

£548 - £1248 / week

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Key info:

  • Nearest beach 107 km
  • Swimming pool
  • Suitable 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 villa located within walking distance of the village of Gaiole in Chianti, near Siena, Tuscany  …see more

23 Photos

Apartment | 2 Bedrooms | sleeps 6

1 night min stay

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from £95 /night

£664 - £936 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Pets welcome
  • Private garden
Casa Genziana A is a characteristic and welcoming one-story apartment that is part of an ancient country house built on a hillside, surrounded by meadows and woods. It sleeps six people. From Casa Genziana A you will enjoy a view of the Tuscan countryside  …see more

24 Photos

Apartment | 2 Bedrooms | sleeps 4

1 night min stay

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from £149 /night

£1040 - £1136 / week

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Key info:

  • Nearest beach 100 km
  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • No pets allowed
  • Private garden
Villa Leopoldo A is an enthralling 110–square–meter (about 1,184 square feet) apartment which sleeps four people. It features a wide private terrace with a view to a valley and shared swimming pool and garden  …see more

16 Photos

Apartment | 1 Bedroom | sleeps 2

1 night min stay

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from £61 /night

£424 - £720 / week

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Key info:

  • Suitable for children of all ages
  • Car advised
  • No pets allowed
Appartamento Orietta is a romantic and welcoming apartment located in the medieval center of Siena. It sleeps two people. It is appoximately 30 square meters (320 square feet). It features winter heating  …see more

24 Photos

House | 2 Bedrooms | sleeps 5

1 night min stay

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from £78 /night

£544 - £768 / week

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Key info:

  • Nearest beach 120 km
  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • May take pets – please enquire
  • Private garden
Casa Genziana B is a charming one-story apartment that is part of a villa on a luscious property dappled with potted flowers. It sleeps five people. From Casa Genziana B you will enjoy a view of the Tuscan countryside  …see more

20 Photos

House | 3 Bedrooms | sleeps 6

1 night min stay

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from £98 /night

£685 - £992 / week

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Key info:

  • Nearest beach 120 km
  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • Pets welcome
  • Private garden
Casa Monia A is a bright and elegant apartment with the strong charachter which derives from it actually being a restored old mill. It sleeps six people. From Casa Monia A you will enjoy a thrilling view of the Tuscan hills and of the vineyards  …see more

20 Photos

Apartment | 3 Bedrooms | sleeps 11

Excellent 5/5 

1 night min stay

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from £149 /night

£1040 - £1120 / week

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Key info:

  • Nearest beach 80 km
  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • No pets allowed
A short distance away we meet: 7 km Siena, San Gimignano 50 km, Pienza 60 km, 10 km the Crete Senesi, heritage sites recognized by UNESCO. Also nearby we Murlo 5 km village of Etruscan origin, Monteriggioni and 15 km the famous medieval castle by Dante (Inf. XXXI, 41), For these locations we can arrange guided tours, wine tasting. For total relaxation are present in the immed  …see more

7 Photos

Apartment | 1 Bedroom | sleeps 3

Short stays welcome

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from £85 /night

£593 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car not necessary
  • Pets welcome
Is really a caratteristic apartment in pure Tuskany stile.  …see more

24 Photos

Farmhouse | 5 Bedrooms | sleeps 10

Short stays welcome

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from £302 /night

£2112 / week

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Key info:

  • Nearest beach 80 km
  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Pets welcome
  • Private garden
Podernovo is farmhouse, of the 19th century, surrounded by greenery with a breath-taking swimming pool. 5 Bedrooms, 5 Bathrooms, Panoramic Private Pool, Car Parking, Outdoor Facilities. Halfway between Rome and Florence. 5 km from the well-known SPA resort Fonteverde Come to relax and find out how to get lost in nature and rediscover yourself.  …see more

21 Photos

Villa | 15 Bedrooms | sleeps 37

3 Nights min stay

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from £1372 /night

£9600 - £11200 / week

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Key info:

  • Nearest beach 45 km
  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Air conditioning
  • May take pets – please enquire
  • Private garden
Luxury Villa seventeenth century, Private Chapel , private pool 10x20, sauna,Kitchen pool area Ideal location for weddings and parties Luxury villa, Ideal location for weddings and parties  …see more

12 Photos

Apartment | 2 Bedrooms | sleeps 5

Short stays welcome

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from £93 /night

£650 - £1540 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Air conditioning
  • Pets welcome
  • Private garden
Pleasant and cosy annex that has been recently renovated. In a dominant and quiet position (500m a.s.l.) amidst vineyards and olive tree groves. The annex is part of a small farm with its own wine and olive oil production in the heart of the Chianti Classico.  …see more

20 Photos

Barn | 2 Bedrooms | sleeps 6

Short stays welcome

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from £123 /night

£857 - £1512 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • May take pets – please enquire
  • Private garden
2 Double beds, 1 Double sofa, 2 Bedrooms, 2 Bathroom, 1 Living room, 1 Kitchen (110 sqm)  …see more

18 Photos

Apartment | 3 Bedrooms | sleeps 6

7 Nights min stay

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from £92 /night

£639 - £840 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Pets welcome
Ttypical apartments in an old, characteristic agricultural hamlet, whose origins date back to a large farm in the 17th century.  …see more

19 Photos

House | 1 Bedroom | sleeps 4

Short stays welcome

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from £43 /night

£297 - £424 / week

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Key info:

  • Nearest beach 110 km
  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Pets welcome
  • Private garden
The apartment is situated in a residence which rapresent the perfect tuscan style. Centuries ago it was a convent, then it was inhabitated by farmers. It's the perfect place where you can spend your holidays in tranquility and relax, inside the typical Tuscan country.  …see more

20 Photos

Apartment | 3 Bedrooms | sleeps 5

7 Nights min stay

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from £218 /night

£1520 - £1840 / week

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Key info:

  • Swimming pool
  • Not suitable for children
  • Car advised
  • May take pets – please enquire
  • Private garden
Apartment in a naturally cool stone villa with large pool & gardens in San Gimignano area  …see more

16 Photos

Castle | 2 Bedrooms | sleeps 4

1 night min stay

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from £29 /night

£202 - £1367 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • No pets allowed
  • Private garden
Relais chianti, luxury apartment chianti, hamlet chianti, medieval village, infinity swimming pool ,outdoor dining area , barbecue grill.  …see more

24 Photos

Villa | 9 Bedrooms | sleeps 20

Excellent 5/5 

1 night min stay

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from £303 /night

£2120 - £3308 / week

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Key info:

  • Nearest beach 90 km
  • Swimming pool
  • Suitable 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

23 Photos

Villa | 6 Bedrooms | sleeps 11

Excellent 5/5 

1 night min stay

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from £237 /night

£1654 - £3477 / week

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Key info:

  • Nearest beach 60 km
  • Swimming pool
  • Suitable 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 willing to pay an exta  …see more

20 Photos

Villa | 3 Bedrooms | sleeps 6

Excellent 5/5 

7 Nights min stay

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from £218 /night

£1520 - £1840 / week

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Key info:

  • Swimming pool
  • Not suitable for children
  • Car advised
  • May take pets – please enquire
  • Private garden
Naturally cool stone villa for 11 persons with large private pool & gardens in San Gimignano area  …see more

10 Photos

Apartment | 2 Bedrooms | sleeps 5

Excellent 5/5 

2 Nights min stay

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from £61 /night

£424 / week

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Key info:

  • Suitable for children of all ages
  • Car not necessary
  • Pets welcome
Appartamento con bellissima vista sui cedri secolari di Certano e la campagna circostante. L'abitazione è in stile rustico toscano ingentilito da qualche tocco elegante. Dalle finestre vista stupenda sulla campagna toscana, sul giardino pensile della villa padronale.  …see more

14 Photos

Apartment | 1 Bedroom | sleeps 3

3 Nights min stay

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from £54 /night

£374 - £467 / week

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Key info:

  • Nearest beach 70 km
  • Swimming pool
  • Suitable for over 5s only
  • Car essential
  • No pets allowed
  • Private garden
We are in the heart of Tuscany. Our accommodation is an oasis of relaxation in the spectacular landscapes of the Tuscan hills. My wife and I have restored this accommodation to offer to our guest the most nice and comfortable holiday.  …see more

10 Photos

Apartment | 2 Bedrooms | sleeps 4

2 Nights min stay

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from £43 /night

£297 - £314 / week

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Key info:

  • Suitable for children of all ages
  • Car advised
  • Pets welcome
Grazioso appartamento nel cuore del centro storico di Chianciano Terme; ideale per chi vuole bagnarsi nelle acque termali della cittadina toscana o per chi vuole gustare il tramonto in Val d'Orcia o in Val di Chiana di fronte ad un calice di vino rosso.  …see more

18 Photos

House | 2 Bedrooms | sleeps 5

2 Nights min stay

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from £43 /night

£296 / week

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Key info:

  • Nearest beach 50 km
  • Suitable for children of all ages
  • No pets allowed
  • Private garden
Bellissimo appartamento situato nelle colline di San Gimignano, adatto per chi desidera tranquillità immersi tra i paesaggi inconfondibili di questa terra ricca di storia cultutale ed enogastronomica. Parcheggio privato , 5 posti letto.  …see more

19 Photos

Apartment | 2 Bedrooms | sleeps 4

Excellent 5/5 

1 night min stay

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from £67 /night

£467 / week

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Key info:

  • Suitable for children of all ages
  • Car essential
  • May take pets – please enquire
  • Private garden
Torre Moreschini, Montefollonico, Siena.  …see more

12 Photos

Apartment | 2 Bedrooms | sleeps 4

Excellent 5/5 

2 Nights min stay

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from £49 /night

£340 / week

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Key info:

  • Swimming pool
  • Suitable for over 5s only
  • May take pets – please enquire
  • 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

17 Photos

Villa | 4 Bedrooms | sleeps 8

Very Good 4/5 

Short stays welcome

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from £122 /night

£848 - £1696 / week

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Key info:

  • Swimming pool
  • Suitable for children of all ages
  • Car essential
  • May take pets – please enquire
  • Private garden
Fontecaresino, located in the hills of Chianti, in the heart of Tuscany, with ready access to the culinary, cultural and artistic heritage of this region, is only 4 km from Gaiole in Chianti, 35 km from Siena, and 55 km from Florence. EXCLUSIVE USE of the Swimming Pool! The swimming pool is available from April 1 to October 15, it may varies depending on weather conditions.  …see more

24 Photos

Apartment | 1 Bedroom | sleeps 5

2 Nights min stay

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from £30 /night

£204 - £323 / week

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Key info:

  • Suitable for children of all ages
  • May take pets – please enquire
Apartment in Tuscany countryside Appartamento nella campagna toscana. Between Siena and Florence. A metà strada tra Siena e Firenze  …see more

12 Photos

Apartment | 1 Bedroom | sleeps 4

3 Nights min stay

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from £48 /night

£331 - £484 / week

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Key info:

  • Nearest beach 60 km
  • Swimming pool
  • Suitable for children of all ages
  • Car advised
  • Pets welcome
farm house inTuscany Italy, between Sienna Florence swimming pool facing San Gimignano, horseback riding, for families, food and wine tasting in the very nearby, bikes, relax, free wi-fi, Easy to reach 3 kinds of apartments available, tables in the garden  …see more

20 Photos

House | 3 Bedrooms | sleeps 5

Excellent 5/5 

2 Nights min stay

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from £67 /night

£467 - £509 / week

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Key info:

  • Suitable for children of all ages
  • Car advised
  • May take pets – please enquire
Casa 5 posti letto a Montepulciano, ottima posizione panoramica sulla campagna. Circondata da uliveti. Vicinissima al Centro Storico di Montepulciano raggiungibile a piedi a circa 1 chilometro. Posto auto riservato. Caminetto, lavatrice, ampie terrazze. Riscaldamento. Montepulciano è punto di partenza per visitare tante città d'arte: Pienza,Siena,Perugia, Arezzo,Firenze ecc.  …see more

17 Photos

Farmhouse | 4 Bedrooms | sleeps 8

2 Nights min stay

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from £146 /night

£1018 - £1357 / week

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Key info:

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

14 Photos

Apartment | 2 Bedrooms | sleeps 5

Excellent 5/5 

2 Nights min stay

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from £73 /night

£509 - £806 / week

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Key info:

  • Suitable for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
Residenza storica del XIV secolo, sita nel centro storico di Montefollonico. Bellissima veranda con vista sulla Valdichiana. Vicina a Pienza, Montepulciano, Monticchiello, Bagno Vignoni, Valdorcia. Ottima posizione per tour gastronomico e passeggiate a piedi. Presenti tutti i servizi primari: ufficio turistico, 4 ristoranti, farmacia, banca, market  …see more

24 Photos

Log cabin | 2 Bedrooms | sleeps 6

2 Nights min stay

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from £49 /night

£340 - £450 / week

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Key info:

  • Suitable for children of all ages
  • Car advised
  • May take pets – please enquire
  • Private garden
Casa Merope è una capanna totalmente ristrutturata, immersa nel verde delle campagne Toscane, tra vigneti ed oliveti, a due passi dalla bellissima San Gimignano, conosciuta anche come "la città delle torri".  …see more

16 Photos

Apartment | 1 Bedroom | sleeps 4

1 night min stay

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from £43 /night

£297 / week

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Key info:

  • Suitable for children of all ages
  • Pets welcome
Questa graziosa mansarda in stile rustico toscano offre al turista un ambiente comodo ed elegante in un piacevole contesto storico a due passi da Siena.  …see more

22 Photos

Apartment | 1 Bedroom | sleeps 2

Excellent 5/5 

3 Nights min stay

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from £40 /night

£280 - £408 / week

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Key info:

  • Suitable for children of all ages
  • Car essential
  • No pets allowed
  • Private garden
In campagna per relax e tranquillità, ma a 10 minuti da Siena. Al centro della Toscana, per le migliori escursioni. Proprietario in zona e disponibile per aiuto e informazioni, è felice di accogliere gli ospiti con un assaggio dell'olio di oliva biologico che produce.  …see more

19 Photos

Apartment | 2 Bedrooms | sleeps 8

Excellent 5/5 

3 Nights min stay

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from £49 /night

£340 - £1272 / week

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Key info:

  • Suitable for children of all ages
  • Air conditioning
  • May take pets – please enquire
  • Private garden
Agriturismo nel sud della Toscana , a Montepulciano , tra la Val d'Orcia e la Valdichiana , a conduzione familiare , di piccole dimensioni ,vicino al centro storico, con vista panoramica , coltivazioni biologiche di uva , olivi , alberi da frutta IL Sorbo è assolutamente indipendente e gode di una splendida vista sulla tipica campagna toscana  …see more

13 Photos

House | 3 Bedrooms | sleeps 5

7 Nights min stay

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from £77 /night

£535 - £721 / week

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Key info:

  • Swimming pool
  • Suitable for over 5s only
  • May take pets – please enquire
maison toscane, appartement, piscine, chianti, gaiole in chianti, Sienne, visites de producters de vin, dégustations de vin, outlet shopping, siteseeing, marcher Distances airport 60km gare 16km emplettes 10 km hopital 16 km  …see more

7 Photos

Apartment | 2 Bedrooms | sleeps 3

3 Nights min stay

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from £56 /night

£391 - £543 / week

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Key info:

  • Suitable for children of all ages
  • May take pets – please enquire
.Il Poderaccio è anche una Fattoria con tanti animali cavalli, una mucca, un asinello e animali da cortile che i bambini possono imparare a conoscere, inoltre, i cani e i gatti che vi abitano.  …see more

9 Photos

Apartment | 2 Bedrooms | sleeps 6

Very Good 4/5 

2 Nights min stay

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from £49 /night

£340 - £382 / week

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Key info:

  • Suitable for over 5s only
  • Pets welcome
  • Private garden
Appartamento immerso nelle colline di San Gimignano  …see more

12 Photos

Townhouse | 2 Bedrooms | sleeps 5

Excellent 5/5 

1 night min stay

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from £37 /night

£255 - £382 / week

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Key info:

  • Suitable for children of all ages
  • Air conditioning
  • No pets allowed
appartamento, Siena, relax, famiglia, vacanze, terme, holiday  …see more