Villas and Holiday homes in Siena

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Siena holiday homes
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113 Villa rentals in Siena

Handpicked Holiday Houses with a Swimming Pool in Siena

Having pool access at your city holiday home makes a proper swim in the heart of Siena a delightful daily highlight.

(Chianti Classico)villa With Private Pool - Siena
9.5 22 reviews
Siena
26/08 – 30/08
£1616/nighttotal: £6464 (4 )

(Chianti Classico)villa With Private Pool

7 10
house , Castelnuovo Berardenga
Villa Il Cerretaccio, a 13th-century watchtower-incorporated villa in the Chianti Classico region, is situated 12 km from Siena and within 15 km of Gaiole, Castellina, and Brolio Castle.
This seven-bedroom, six-bathroom property sleeps fourteen guests and boasts a private swimming pool (open May 1st to October 1st), a 27-hectare estate with olive groves and vineyards, an on-site Tuscan restaurant, and offers yoga and cooking classes.
Villa Montelisi, With The Most Unique View On Siena (6km) - Siena
10 68 reviews
Siena
26/08 – 30/08
£985/nighttotal: £3940 (4 )

Villa Montelisi, With The Most Unique View On Siena (6km)

4 10
house , Siena
This luxurious Tuscan villa, situated 6km from Siena's city centre, offers a secluded yet convenient base for exploring the region, a short drive from supermarkets and within easy reach of San Gimignano, Florence, and Montepulciano.
The 400 square metre property boasts four bedrooms each with en-suite bathrooms, sleeping up to 10 guests, and features a private pool, jacuzzi, tennis court, and on-site wine and olive oil tasting, alongside organised activities such as Palio experiences and truffle hunting.
Villa Siena Bio Agriturismo Private Pool - Siena
9.7 31 reviews
Siena
30/06 – 03/07
£371/nighttotal: £1113 (3 )

Villa Siena Bio Agriturismo Private Pool

1 5
house , Sovicille
Villa Poggio al Sole Bio Agriturismo, a 4-bedroom villa with a private pool, is situated in San Rocco a Pilli, a district in Sovicille, just 2 kilometres from shops and restaurants and a 20-minute drive from Siena.
The 280 square metre villa features a fully equipped kitchen, a fitness centre, a tennis court, a garden and a covered patio with a wood-burning oven, as well as the option of purchasing organic produce directly from the property.
114 M² Farmhouse ∙ 2 Bedrooms ∙ 5 Guests - Siena
Siena
30/06 – 03/07
£307/nighttotal: £921 (3 )

114 M² Farmhouse ∙ 2 Bedrooms ∙ 5 Guests

2 5
farm , Chiusdino
Farm for 5 people. You will be located in Chiusdino.
Services and facilities: a garden, a freeze and a barbecue.

Best family friendly Siena villas and holiday home

Among the 113 accommodations in Siena, here are the 4 best family friendly villas and holiday homes

Casa Vacanze L'oliveta - Siena
9.0 66 reviews
Siena
01/07 – 03/07
£141/nighttotal: £282 (2 )

Casa Vacanze L'oliveta

1 2
house , Siena
Casa Vacanze L'Oliveta is located just outside Siena, a short drive from Piazza del Campo and a 30-minute drive from the city centre. This property has received excellent ratings for cleanliness, location and overall experience.
This one-bedroom house offers a peaceful retreat with a private swimming pool and a garden. Guests can enjoy a range of amenities including a fully equipped kitchen, air conditioning, Wi-Fi and free parking.
50 M² House ∙ 1 Bedroom ∙ 5 Guests - Siena
Siena
27/07 – 28/07
£466/nightfor 1 night

50 M² House ∙ 1 Bedroom ∙ 5 Guests

1 2
house , Monteriggioni
This villa is located in Carpineta, a park setting just 10 kilometres from Siena, a significant Tuscan landmark.
This 50 square metre accommodation offers one bedroom and one bathroom, sleeping up to five guests with a kitchen, air conditioning, Wi-Fi, a swimming pool, terrace, garden, and parking.
Villa Il Castagno Wine & Resort - Siena
9.2 670 reviews
Siena
13/08 – 16/08
£333/nighttotal: £999 (3 )

Villa Il Castagno Wine & Resort

1 2
farm , Siena
Villa il Castagno Wine & Resort is located just outside Siena, a short drive from the city centre and its famous Piazza del Campo. The farm enjoys a tranquil setting in the Tuscan countryside, offering a peaceful escape from the bustling city. The property has excellent ratings for its location, cleanliness, and overall experience.
The farmhouse offers a range of comfortable accommodation options, suitable for couples and small families. Guests can enjoy a range of amenities, including a swimming pool, hot tub, restaurant, and bar, as well as activities like bike rental and hiking trails.
Villa Amedeo - Siena
9.4 151 reviews
Siena
04/07 – 10/07
£270/nighttotal: £1620 (6 )

Villa Amedeo

3 5
house , Sovicille
Villa Amedeo is located in Brenna, a short distance from the River Serse and a 20-minute drive from Siena's centre, offering a peaceful escape into the Tuscan countryside. The property has received very good ratings for its location, user experience and excellent cleanliness.
The villa features exposed wood-beamed ceilings and offers modern amenities such as free Wi-Fi, a satellite TV, a washing machine, a hairdryer, and bathrobes. Guests can enjoy the swimming pool, jacuzzi, terrace, garden, and restaurant on site, as well as explore the surrounding countryside with complimentary bikes.

Frequently asked questions about villa rentals in Siena

  • What are the must-see attractions in Sienne?

    You absolutely must see the Piazza del Campo, the heart of Siena, and the magnificent Duomo with its stunning facade and intricate details. Don't miss the Torre del Mangia for panoramic views of the city.
  • What are the best holiday homes in Siena?

    Among the holiday homes in Siena, Wine Resort Dievole, Casa Di Campagna In Toscana and Ripostena are the most popular ones.

  • What indoor activities for families are available in Sienne on rainy days?

    The Museo Civico, located in the Palazzo Pubblico, is a great option for a rainy day. You can also visit the Museo dell'Opera del Duomo, which houses a collection of art and artefacts related to the Duomo. For a more interactive experience, the Santa Maria della Scala museum offers a glimpse into the city's history.
  • What are the best holiday homes with a pool in Siena?

    Wine Resort Dievole, Casa Di Campagna In Toscana and Ripostena are the best holiday homes with a pool in Siena.

  • What are the best activities in Sienne?

    Besides visiting the Piazza del Campo and the Duomo, you should definitely take a cooking class to learn how to make traditional Sienese dishes like pici pasta and ribollita. You can also enjoy a guided walking tour to discover hidden gems and learn about the city's rich history.
  • What are the best holiday homes with a jacuzzi in Siena?

    The best holiday homes with a jacuzzi in Siena are Casa Di Campagna In Toscana, Pieve Marsina & Borgo Argenina and Antica Fonte Residenza Di Siena.

  • What are the advantages of renting a house or a villa in Sienne

    Renting a villa offers the privacy and space to relax and unwind after a day of exploring the city. You'll also enjoy the convenience of having a fully equipped kitchen, allowing you to prepare meals using fresh local ingredients. Many villas have beautiful gardens or terraces where you can enjoy a meal al fresco.
  • What are the best holiday homes for families and kids in Siena?

    The best holiday homes for families and kids in Siena are Wine Resort Dievole, Casa Di Campagna In Toscana and Ripostena.

  • What exclusive experiences are available when visiting Sienne?

    You can take a private tour of the Duomo's hidden areas, including the Piccolomini Library, with its stunning frescoes by Pinturicchio. If you're interested in the history of the Palio, you can arrange a visit to the Contrada museums, which showcase the history and traditions of each of the 17 contrade (districts) of Siena.
  • What are the best pet friendly holiday homes in Siena?

    The best pet friendly holiday homes in Siena are Wine Resort Dievole, Casa Di Campagna In Toscana and Ripostena.

  • Which part of Sienne would be ideal for a villa rental?

    The hills surrounding Siena, particularly the areas of Castellina in Chianti, Gaiole in Chianti, and Radda in Chianti, are perfect for a villa rental. They offer stunning views of the Tuscan countryside, are close to vineyards and wineries, and offer a peaceful escape from the city.
  • What are the best holiday homes with parking in Siena?

    Wine Resort Dievole, Casa Di Campagna In Toscana and Ripostena are the best holiday homes with parking in Siena.

Destinations nearby

Best Siena villas and holiday homes with parking

Agriturismo Cignanbianco - Siena
9.0 50 reviews
Siena
30/06 – 03/07
£126/nighttotal: £378 (3 )

Agriturismo Cignanbianco

2 5
farm , Castellina in Chianti
Agriturismo Cignanbianco, in Castellina in Chianti, offers self-catering accommodation 24km from Siena's Piazza del Campo and 27km from Piazza Matteotti.
This family-friendly property features a seasonal outdoor pool (May-September), free Wi-Fi, parking, and a barbecue, alongside fully equipped kitchens including dishwashers and stunning garden views.
Exclusive Villa Mami - Siena
10 1 review
Siena
22/10 – 20/11
£1538/nighttotal: £44602 (29 )

Exclusive Villa Mami

6 1
house , Siena
Exclusive Villa Mami, a large house in Siena, is situated 7.6km from Piazza del Campo and 5.5km from the National Museum of Etruscan Archaeology.
This 300 square metre property boasts six bedrooms, six bathrooms, and can accommodate up to 24 guests, offering a private pool, garden, parking, and Wi-Fi; à la carte breakfast and airport shuttle are available.
Farmhouse ∙ 3 Bedrooms ∙ 6 Guests - Siena
Siena
30/06 – 03/07
£238/nighttotal: £714 (3 )

Farmhouse ∙ 3 Bedrooms ∙ 6 Guests

3 5
farm , Monteroni d'Arbia
This Tuscan villa is situated in Ville di Corsano, Siena province, offering convenient access to the region's rolling hills and historic villages, with Siena town being a key nearby attraction.
This family-friendly farmhouse accommodates up to six guests across three bedrooms and three bathrooms, featuring a fully equipped kitchen, private garden with lake views, shared barbecue area, and access to a panoramic swimming pool located 400 meters away.
@151 - Siena
8.8 122 reviews
Siena
15/07 – 17/07
£85/nighttotal: £170 (2 )

@151

1 1
house , Siena
This Siena house rental, located 0.9 km from the National Museum of Etruscan Archaeology and 1.1 km from the San Cristoforo Church, offers easy access to Piazza del Campo and Siena Train Station (5.6 km).
The 50 square metre property comprises one bedroom, one bathroom, and accommodates three guests, featuring a fully equipped kitchen with dishwasher, air conditioning, free Wi-Fi (parking at extra cost), and a private entrance.

Best Siena villas and holiday homes with a garden

Novelleto - Siena
9.2 206 reviews
Siena
15/08 – 18/08
£128/nighttotal: £384 (3 )

Novelleto

1 2
farm , Monteriggioni
Novelleto Farm is situated in the Tuscan countryside, just 3 kilometres from the medieval walled town of Monteriggioni.
This farmhouse offers a choice of rooms and self-catering apartments, featuring an outdoor pool, a garden with barbecue facilities, and a terrace for al fresco dining, all within a peaceful setting.
Capannino - Siena
9.0 10 reviews
Siena
13/08 – 16/08
£150/nighttotal: £450 (3 )

Capannino

1 2
house , Siena
This Siena holiday home in Capannino is located 3.4km from Piazza del Campo, Siena's main square, offering easy access to the historic centre.
The 55 square metre property features one bedroom, one bathroom, sleeps three guests, and includes a fully equipped kitchen, air conditioning, free Wi-Fi, private parking, and a peaceful garden with outdoor seating.
La Casaccia Guelfi - Siena
9.3 52 reviews
Siena
04/07 – 10/07
£190/nighttotal: £1140 (6 )

La Casaccia Guelfi

2 5
farm , Castelnuovo Berardenga
La Casaccia Guelfi farmhouse in Castelnuovo Berardenga offers excellent self-catering accommodation, located 21km from Piazza del Campo in Siena and 43km from Piazza Matteotti.
This family-friendly property features a swimming pool, barbecue facilities, a garden with stunning views, free Wi-Fi, and private parking, perfect for exploring Tuscany's attractions.
Agriturismo Casalino18 - Siena
9.4 439 reviews
Siena
26/08 – 30/08
£562/nighttotal: £2248 (4 )

Agriturismo Casalino18

5 10
farm , Siena
Agriturismo Casalino18, a renovated farmhouse in Tognazza, is situated 10km from Siena's Piazza del Campo and 43km from Piazza Matteotti, offering easy access to Tuscany's attractions.
This family-friendly property provides air-conditioned rooms with private bathrooms, a terrace, free Wi-Fi, parking, and a daily breakfast, plus weekly cleaning services.
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