List your home
Apply filters
£ to

Holiday homes 39

Reset search

Show results on map

Also consider

Coastal Cottages
222 properties
Sardinia
478 properties
Tuscany
3,181 properties
Lake Garda Area
103 properties
Lake Como Area
494 properties
Sicily
634 properties

Filters applied: Walking holidays (39)

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
39 Results   |  

Excellent 5/5 

17 Photos

Province of Siena / Monteriggioni

Villa / 2 Bedrooms / sleeps 6

Excellent 5/5 

Short stays welcome

Add to shortlist

from £137 / night

£956 - £1250 / week

View

Key info:

  • Nearest beach 80 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Pets welcome
  • Private garden
Wonderful Villa with private pool overlooking the castle of Monteriggioni  …see more

Excellent 5/5 

22 Photos

Province of Siena / Monteriggioni

Apartment / 2 Bedrooms / sleeps 4

Excellent 5/5 

1 night min stay

Add to shortlist

from £43 / night

£295 - £442 / week

View

Key info:

  • Nearest beach 100 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Pets welcome
  • Private garden
Outside of the Magione Agriturismo, a large, fenced garden will allow children to play in complete safety, while also offering the opportunity to dine outside enjoying the barbecues for guests.  …see more

Very Good 4/5 

18 Photos

Province of Siena / Monteriggioni

Farmhouse / 2 Bedrooms / sleeps 6

Very Good 4/5 

3 Nights min stay

Add to shortlist

from £24 / night

£162 - £541 / week

View

Key info:

  • Nearest beach 75 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Pets welcome
  • Private garden
Our farm is the only one with a horse on the property, offers a beautiful view, surrounded by green gardens, with a wood-burning oven in the central courtyard and have WI-FI internet access. We offer many services and activities of a different kind, for everyone.  …see more

Featured properties

Excellent 5/5 

25 Photos

Province of Siena / Monteriggioni

Apartment / 2 Bedrooms / sleeps 6

Excellent 5/5 

3 Nights min stay

Add to shortlist

from £61 / night

£427 - £537 / week

View

Key info:

  • Nearest beach 100 km
  • Great for children of all ages
  • Car advised
  • Some pets are welcome - please contact the owner
Un giro nei dintorni a soli 8 km da Monteriggioni e punto strategico per raggiungere in breve tempo città ricche di arte e bellezza: Siena(4 km) Firenze, San Gimignano, Volterra, Castellina in Chianti, Monteriggioni , Montalcino, Pienza ecc  …see more

Very Good 4.5/5 

23 Photos

Province of Siena / Monteriggioni

Apartment / 1 Bedroom / sleeps 3

Very Good 4.5/5 

3 Nights min stay

Add to shortlist

from £34 / night

£236 - £353 / week

View

Key info:

  • Great for children of all ages
  • Car essential
  • No pets allowed
  • Private garden
It's a must for countryside, peace and relaxation, trekking, biking trail. The nearest shops: restaurants, pharmacy, bar, bakery, are located 2 Km.  …see more

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

£221 - £295 / 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

8 Photos

Province of Siena / Monteriggioni

House / 4 Bedrooms / sleeps 8

3 Nights min stay

Add to shortlist

from £263 / night

£1839 - £2427 / week

View

Key info:

  • Nearest beach 100 km
  • Swimming pool
  • Suitable for children over 5
  • Car advised
  • Some pets are welcome - please contact the owner
If you are searching for something very special, with charm, history and love for details- thats the place to be. It it the perfect hub to discover the jewels of tuscany (if you want to stay in lovely apartments with your friends) or to celebrate a ferry tale wedding-  …see more

20 Photos

Province of Siena / Monteriggioni

Apartment / 3 Bedrooms / sleeps 8

1 night min stay

Add to shortlist

from £89 / night

£618 - £1648 / week

View

Key info:

  • Nearest beach 84 km
  • Swimming pool
  • Great 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

14 Photos

Province of Siena / Monteriggioni

Apartment / 1 Bedroom / sleeps 4

7 Nights min stay

Add to shortlist

from £71 / night

£495 - £880 / week

View

Key info:

  • Swimming pool
  • Suitable for children over 5
  • Car advised
  • Pets welcome
  • Private garden
Il Poderino is an old country farmhouse, situated on a hill overlooking a beautiful landscape of vineyards and olive groves in the heart of Chianti. Pool and views to die for. Siena only 8km!  …see more

23 Photos

Province of Siena / Monteriggioni

Villa / 3 Bedrooms / sleeps 5

7 Nights min stay

Add to shortlist

from £103 / night

£721 - £927 / week

View

Key info:

  • Great for children of all ages
  • Pets welcome
Podere Staggia is a splendid farm house (18 th century) located on the top of a hill. The apartment of this farmhouse offers you the unique and rare possibility to enjoy an old, large (170 m2) and luminous house in the Siena area with a 360° open view. Ideal place for a family or a group of friends to enjoy quiet and restful holidays.  …see more

8 Photos

from £316 / night

£2206 - £3383 / week

View

View

Holiday farmhouse rental

Province of Siena / Monteriggioni

Farmhouse / 6 Bedrooms / sleeps 12

3 Nights min stay

Add to shortlist

from £316 / night

£2206 - £3383 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Some pets are welcome - please contact the owner
The Farm house Tinaione is an ideal locations for a riunion of big family or for a group holiday as it has all the comfort in the rustic simple tuscan way for 12 persons, the appartament is very charmy and the owner knows exately how to look after you. The infinity pool with the stunning views of the tuscan landscape is the perfect setting holiday!  …see more

20 Photos

Province of Siena / Monteriggioni

Apartment / 3 Bedrooms / sleeps 7

3 Nights min stay

Add to shortlist

from £105 / night

£735 - £817 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • No pets allowed
  • Private garden
Large, comfortably equipped and well furnished apartment, all the furniture is from the 19th century and has been recently restored, "La Fattoria" is situated at the centre of the ancient village and has got a private, fenced garden.  …see more

4 Photos

Province of Siena / Monteriggioni

Farmhouse / 1 Bedroom / sleeps 2

30 Nights min stay

Add to shortlist

from £79 / night

£552 / week

View

Key info:

  • Nearest beach 60 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Some pets are welcome - please contact the owner
  • Private garden
ideal place for ritired couples long staying preferred  …see more

19 Photos

from £32 / night

£221 - £368 / week

View

View

Holiday home rental

Province of Siena / Monteriggioni

House / 1 Bedroom / sleeps 4

Short stays welcome

Add to shortlist

from £32 / night

£221 - £368 / week

View

Key info:

  • Nearest beach 110 km
  • Swimming pool
  • Great 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

24 Photos

Province of Siena / Monteriggioni

Farmhouse / 2 Bedrooms / sleeps 8

2 Nights min stay

Add to shortlist

from £43 / night

£295 - £398 / week

View

Key info:

  • Nearest beach 80 km
  • Great for children of all ages
  • Car essential
  • Pets welcome
  • Private garden
The apartment is an excellent starting point for excursions on foot or mountain bike in the via Francigena or Montagnola senese.Siena is about 13 km, Monteriggioni approx. 8 km. you can do excursions also to s. Gimignano, Colle di Val D'elsa, Casole, s. Galgano  …see more

13 Photos

Province of Siena / Monteriggioni

Villa / 3 Bedrooms / sleeps 6

3 Nights min stay

Add to shortlist

from £673 / night

£4706 / week

View

Key info:

  • Nearest beach 100 km
  • Swimming pool
  • Not suitable for children
  • No pets allowed
  • Private garden
Is the perfect mix of luxury and rustic Italian, with a relaxed feel perfect for a holiday with friends and family or for a special celebration! Stomennano's got so much character and charm and you'll be amazed by the beauty of the Villa and the gardens.  …see more

19 Photos

Province of Siena / Monteriggioni

Apartment / 1 Bedroom / sleeps 4

1 night min stay

Add to shortlist

from £57 / night

£398 - £1030 / week

View

Key info:

  • Nearest beach 84 km
  • Swimming pool
  • Great 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

Province of Siena / Monteriggioni

Apartment / 1 Bedroom / sleeps 4

1 night min stay

Add to shortlist

from £48 / night

£331 - £875 / week

View

Key info:

  • Nearest beach 84 km
  • Swimming pool
  • Great 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

21 Photos

Province of Siena / Monteriggioni

Apartment / 2 Bedrooms / sleeps 6

1 night min stay

Add to shortlist

from £64 / night

£442 - £1030 / week

View

Key info:

  • Nearest beach 84 km
  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Air conditioning
  • Pets welcome
  • Private garden
Charming holiday apartment 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.  …see more

21 Photos

Province of Siena / Monteriggioni

Apartment / 2 Bedrooms / sleeps 4

2 Nights min stay

Add to shortlist

from £60 / night

£420 - £662 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Pets welcome
  • Private garden
Apartment in a detached building consisting of two double bedrooms, bathroom, kitchen with fridge, microwave,stove, living room with sofa bed for two additional seats, furnished outdoor living room. By adding two more people to contact for price. The price is per apartment for 4 people. For more persons the extra bed costs €105 per person per week  …see more

20 Photos

Province of Siena / Monteriggioni

Apartment / 1 Bedroom / sleeps 2

1 night min stay

Add to shortlist

from £38 / night

£265 - £721 / week

View

Key info:

  • Nearest beach 84 km
  • Swimming pool
  • Great 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

6 Photos

Province of Siena / Monteriggioni

Apartment / 2 Bedrooms / sleeps 4

7 Nights min stay

Add to shortlist

from £80 / night

£560 - £1140 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
Il Poderino is an old country farmhouse, situated on a hill overlooking a beautiful landscape of vineyards and olive groves in the heart of Chianti. Pool and views to die for. Siena only 8km!  …see more

17 Photos

Province of Siena / Monteriggioni

Apartment / 1 Bedroom / sleeps 2

2 Nights min stay

Add to shortlist

from £43 / night

£295 - £478 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Pets welcome
  • Private garden
Separate entrance with outdoor lounge furnished and shaded, one double bedroom, bathroom with shower, large living room with sofa bed for two additional seats, a kitchen with a refrigerator. By adding two more people to contact for price. The price is per apartment for 2 people. For more persons the extra bed costs €105 per person per week  …see more

4 Photos

Province of Siena / Monteriggioni

Townhouse / 2 Bedrooms / sleeps 4

2 Nights min stay

Add to shortlist

from £69 / night

£477 - £1027 / week

View

Key info:

  • Swimming pool
  • Not suitable for children
  • Pets welcome

"Capanna di Sopra", 3-room semi-detached house 90 m2 on 2 levels, on the ground floor, renovated, nice and tasteful furnishings: living/dining room with open fireplace, dining table and satellite-TV. Exit to the garden, to the terrace. 1 double bedroom. Exit to the terrace.  …see more

18 Photos

Province of Siena / Monteriggioni

Apartment / 3 Bedrooms / sleeps 4

Short stays welcome

Add to shortlist

from £119 / night

£831 - £1655 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car not necessary
  • Air conditioning
  • Pets welcome
The Villa is situated in a splendid 18th century mansion, with typical Sienese architecture. The property position is ideal because one reaches the Chianti region in a few minutes or can enjoy the culture and convenience of the city of Siena (6 km away).  …see more

19 Photos

Province of Siena / Monteriggioni

Apartment / 2 Bedrooms / sleeps 3

2 Nights min stay

Add to shortlist

from £49 / night

£339 - £552 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Pets welcome
Entrance with furnished outdoor living room, double bedroom, one single bedroom pitch, bathroom with bath, large living room with fireplace, sofa-bed, fully equipped kitchen with refrigerator. By adding two more people to contact for price. Max person are 3+2 The price is per apartment for 3 people. For more persons the extra bed costs €105 per person per week  …see more

10 Photos

Province of Siena / Monteriggioni

House / 2 Bedrooms / sleeps 4

3 Nights min stay

Add to shortlist

from £127 / night

£883 - £1177 / week

View

Key info:

  • Nearest beach 100 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Some pets are welcome - please contact the owner
Make Stomemmano the destination, not just the base for your Tuscan holiday!  …see more

4 Photos

Province of Siena / Monteriggioni

Townhouse / 2 Bedrooms / sleeps 4

2 Nights min stay

Add to shortlist

from £69 / night

£477 - £1027 / week

View

Key info:

  • Swimming pool
  • Not suitable for children
  • Pets welcome

"Capanna di Sotto", 3-room semi-detached house 90 m2 on 2 levels, on the ground floor, renovated, tasteful and cosy furnishings: living/dining room with open fireplace, dining table and satellite-TV. Exit to the garden, to the terrace. 1 double bedroom. Exit to the terrace.  …see more

4 Photos

Province of Siena / Monteriggioni

Apartment / 2 Bedrooms / sleeps 4

2 Nights min stay

Add to shortlist

from £69 / night

£477 - £1027 / week

View

Key info:

  • Swimming pool
  • Not suitable for children
  • Pets welcome

"La Tinaia", 3-room apartment 85 m2, on the ground floor, nice and tasteful furnishings: living/dining room with open fireplace and satellite-TV. Exit to the garden, to the terrace. 1 double bedroom. 1 double bedroom. Exit to the garden. Kitchenette (4 hotplates, mini-oven,  …see more

19 Photos

Province of Siena / Monteriggioni

House / 15 Bedrooms / sleeps 30

Min stay varies

Add to shortlist

Pricing unknown

View

Key info:

  • Nearest beach 84 km
  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Air conditioning
  • Some pets are welcome - please contact the owner
Poggiarello is a special place to spend a charming holiday in close contact with nature, where is possible to reach in few minutes Siena, San Gimignano, Firenze, Pisa, Lucca, Monteriggioni,Montalcino.  …see more

12 Photos

Province of Siena / Monteriggioni

Hotel apartment / 10 Bedrooms / sleeps 20

Short stays welcome

Add to shortlist

from £105 / night

£735 - £1025 / week

View

Key info:

  • Nearest beach 70 km
  • Swimming pool
  • Not suitable for children
  • Air conditioning
  • No pets allowed
  • Private garden
Dimora Storica di lusso con migliori viste della Toscana. Vicino a Chianti, Monteriggioni, Siena, San Gimignano, Volterra, Firenze, Pienza e Montepulciano. Sperimentate la magia di un luogo senza tempo dove la storia incontra la natura e la tranquillità avvolge l'anima Appartamenti di Lusso, Spa,Piscina, Sauna, Bagno turco, ristorante, vista su Siena,relax, Tuscan Experience.  …see more

12 Photos

Province of Siena / Monteriggioni

Apartment / 1 Bedroom / sleeps 4

2 Nights min stay

Add to shortlist

from £58 / night

£405 - £449 / week

View

Key info:

  • Great for children of all ages
  • Car not necessary
  • No pets allowed
  • Private garden
Appartamento di 70mq immerso nelle splendide colline del Chianti. La proprietà, con pavimenti in cotto e soffitti a travi, è parte di una casa colonica situata all'interno di un piccolo borgo, Ideale per una vacanza di completo relax o per visitare Siena e dintorni. Principali località turistiche nelle vicinanze: Siena (10 km), Monteriggioni (16 km), San Gimignano (30 km)  …see more

7 Photos

Province of Siena / Monteriggioni

Barn / 1 Bedroom / sleeps 2

Min stay varies

Add to shortlist

from £85 / night

£589 - £920 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Pets welcome
  • Private garden
Monteriggioni, Siena, fienile, casale, campagna, piscina, giardino, barbecue, caminetto, villetta, Firenze,  …see more

17 Photos

Province of Siena / Monteriggioni

Villa / 3 Bedrooms / sleeps 6

7 Nights min stay

Add to shortlist

from £83 / night

£581 - £1420 / week

View

Key info:

  • Nearest beach 75 km
  • Swimming pool
  • Great for children of all ages
  • Car essential
  • No pets allowed
  • Private garden
It is a typical Tuscan retreat immersed in the Chianti of the Siena area, a short distance from the renown town of Monteriggioni, and constituted by a group of “colonica” house which have been restored to high specification but preserving the original and true feeling,  …see more

20 Photos

Province of Siena / Monteriggioni

Apartment / 3 Bedrooms / sleeps 7

5 Nights min stay

Add to shortlist

from £105 / night

£735 - £817 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
Casa Fatina is a gracious apartment of 110 square meters (about 1180 square feet) for seven people, with shared pool and garden. It is part of a farming estate surrounded by vineyards, and is located on a hillside 300 meters (about 980 feet) above sea level  …see more

23 Photos

Province of Siena / Monteriggioni

Villa / 5 Bedrooms / sleeps 10

2 Nights min stay

Add to shortlist

from £1158 / night

£8106 - £10316 / week

View

Key info:

  • Ask owner if suitable for children
  • Car advised
  • Air conditioning
  • Some pets are welcome - please contact the owner
  • Private garden
Born from the careful restoration of an ancient manor, this enchanting property comprises two restored historic farmhouses: the manor's farmhouse and the independent (but equally gorgeous! guest house.  …see more

20 Photos

Province of Siena / Monteriggioni

Apartment / 2 Bedrooms / sleeps 4

4 Nights min stay

Add to shortlist

from £76 / night

£530 - £589 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
Casa Rutilia is a gracious apartment of 80 square meters (about 860 square feet) for four people, with shared pool and garden. It is part of a farming estate surrounded by vineyards, and is located on a hillside 300 meters (about 980 feet) above sea level  …see more

20 Photos

Province of Siena / Monteriggioni

Apartment / 2 Bedrooms / sleeps 6

5 Nights min stay

Add to shortlist

from £94 / night

£656 - £728 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
The house Casa Il Cocchio is a gracious apartment of 100 square meters (about 1076 square feet), for six people, with patio, shared swimming pool and four-hectare (about ten-acre) park  …see more

20 Photos

Province of Siena / Monteriggioni

Villa / 3 Bedrooms / sleeps 6

7 Nights min stay

Add to shortlist

from £153 / night

£1067 - £1875 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
Villa Fragola is a graceful villa surrounded by meadows and by green hills. It sleeps six people. From Villa Fragola you will have a splendid view of the Senesi hills and of the Chiocciola Castle. Villa Fragola is 120 square meters (1290 square feet)  …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