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.

Staffolino - Siena
9.3 128 reviews
Siena
07/09 – 14/09
£124/nighttotal: £868 (7 )

Staffolino

2 2
farm , Asciano
Staffolino farmhouse, in the Siena countryside, offers self-catering accommodation 15.3 km from Piazza del Campo and Siena train station.
This Asciano property features a private pool, barbecue facilities, free Wi-Fi, and parking, alongside tastefully decorated units with fully equipped kitchens and stunning garden views.
Castel Pietraio Wineresort - Siena
8.5 859 reviews
Siena
14/07 – 15/07
£759/nightfor 1 night

Castel Pietraio Wineresort

4 7
farm , Monteriggioni
Castel Pietraio is a restored medieval castle situated in the Tuscan countryside, just 10km from the walled village of Monteriggioni and less than 30km from Siena. The property has received very good user ratings, with excellent location and cleanliness ratings.
The castle offers a range of modern comforts within its historical setting, including a swimming pool, a jacuzzi, a tennis court, and a restaurant. Guests can enjoy a variety of activities such as horseback riding, walking, and cycling in the surrounding countryside.
L'arco Tra Le Colline Di Castellina - Siena
Siena
28/08 – 31/08
£145/nighttotal: £435 (3 )

L'arco Tra Le Colline Di Castellina

2 2
house , Castellina in Chianti
L'Arco tra le colline di Castellina is a countryside villa located in Gropina, 13.7 kilometres from Piazza del Campo and 29 kilometres from Piazza Matteotti.
This 54 square metre villa accommodates up to 7 guests in 2 bedrooms and features a dishwasher, WiFi, private parking, a garden, a swimming pool, and a tennis court, with cycling opportunities in the Gropina area.
Agriturismo Poggio Bonelli - Siena
8.9 106 reviews
Siena
13/08 – 16/08
£542/nighttotal: £1626 (3 )

Agriturismo Poggio Bonelli

4 3
farm , Castelnuovo Berardenga
Agriturismo Poggio Bonelli is situated in the heart of the Chianti wine region, just 32 kilometres from Siena and 19 kilometres from Gaiole in Chianti.
The self-catering property features a swimming pool, garden, and terrace, offering a peaceful retreat for guests.

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

Borgo Dei Fondi - Siena
9.7 148 reviews
Siena
06/07 – 12/07
£224/nighttotal: £1344 (6 )

Borgo Dei Fondi

1 2
house , Siena
This Siena countryside property, Borgo dei Fondi, is located in Tognazza, a 12km drive from Siena and 10km from the Chianti Classico wine region.
The self-catering villa boasts a private pool, terrace, garden, and parking, plus a fully equipped kitchen, one bathroom, and free Wi-Fi; it's perfect for families and welcomes pets.
Villa Il Castagno Wine & Resort - Siena
9.2 675 reviews
Siena
28/06 – 29/06
£305/nightfor 1 night

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.
Castello Di Bossi - Siena
8.8 1130 reviews
Siena
30/06 – 03/07
£691/nighttotal: £2073 (3 )

Castello Di Bossi

5 12
farm , Castelnuovo Berardenga
Castello di Bossi is a farmhouse situated in Castelnuovo Berardenga, 16 kilometres from Siena's Piazza del Campo and 40 kilometres from the Piazza Matteotti in the town centre.
This family-friendly property offers guests a swimming pool, tennis court, and a restaurant, as well as the opportunity to enjoy scenic views of the surrounding countryside.
Agriturismo Casalino18 - Siena
9.4 439 reviews
Siena
28/08 – 31/08
£115/nighttotal: £345 (3 )

Agriturismo Casalino18

1 2
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.

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

Ca Nova Sud - Siena
10 34 reviews
Siena
13/08 – 16/08
£519/nighttotal: £1557 (3 )

Ca Nova Sud

4 3
farm , Siena
Ca Nova Sud is a farmhouse situated in the countryside near Siena, approximately 7 kilometres from Porta Pispini, one of the city's historic gates, and 10 kilometres from Siena railway station.
This four-bedroom property, spanning 220 square metres, offers a private pool, a shared lounge, and a garden, making it suitable for families or groups of friends looking for a relaxing escape in the Tuscan countryside.
La Casina - Siena
10 20 reviews
Siena
13/08 – 16/08
£91/nighttotal: £273 (3 )

La Casina

1 3
house , Monteriggioni
La Casina, in Acquaviva, offers a convenient base for exploring Tuscany, situated 21km from Siena's Piazza del Campo and 39km from Grosseto's Piazza Matteotti.
This self-catering property boasts a 40 square metre floor area, sleeping up to 5 guests in one bedroom and one bathroom, with a garden, parking, and excellent guest ratings.
La Casaccia Guelfi - Siena
9.3 52 reviews
Siena
06/07 – 12/07
£105/nighttotal: £630 (6 )

La Casaccia Guelfi

1 2
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.
Triangolo - Siena
8.8 5 reviews
Siena
07/09 – 14/09
£90/nighttotal: £630 (7 )

Triangolo

1 2
house , Siena
This semi-detached house in Montecagnano, 12km from Siena and 1.1km from the village centre, offers a peaceful countryside retreat close to the Piazza del Campo and Siena Cathedral.
The 45 square metre property features one bedroom, two bathrooms, sleeps two guests, and includes a private terrace, garden (150m²), shared pool (seasonal), Wi-Fi, and parking; local farm produce is also available nearby.

Best Siena villas and holiday homes with a garden

Villa Il Campo Degli Ulivi -Skyline Siena-terrazza Panoramica - Relax - Parcheggio - 6 Ospiti - Siena
Siena
13/08 – 16/08
£203/nighttotal: £609 (3 )

Villa Il Campo Degli Ulivi -Skyline Siena-terrazza Panoramica - Relax - Parcheggio - 6 Ospiti

3 3
house , Castelnuovo Berardenga
This villa in Ponte a Bozzone, Castelnuovo Berardenga, is located approximately 7.4 kilometres from Piazza del Campo and 41.8 kilometres from Piazza Matteotti, with Florence Airport situated 67.6 kilometres away.
This 120 square metre house offers accommodation for up to 6 guests across 3 bedrooms and 2 bathrooms, featuring a fully equipped kitchen, air conditioning, a garden, and a panoramic terrace, with free private parking and Wi-Fi provided.
Holiday Home Podere San Raffaele - Cinzia By Interhome - Siena
9.8 37 reviews
Siena
20/06 – 23/06
£76/nighttotal: £228 (3 )

Holiday Home Podere San Raffaele - Cinzia By Interhome

1 2
house , Poggibonsi
This holiday home in Poggibonsi is just 26 kilometres from the historic Piazza del Campo in Siena and 31 kilometres from Piazza Matteotti in San Gimignano, making it an ideal base for exploring the Tuscan countryside. The property has excellent user, location and cleanliness ratings.
The house has one bedroom and one bathroom, covering 45 square metres. It offers a private entrance, a garden, free Wi-Fi, a washing machine, a baby cot, and private parking, making it a comfortable and convenient choice for families or couples.
Fattoria Di Cavaglioni - Siena
9.5 2359 reviews
Siena
07/09 – 08/09
£128/nightfor 1 night

Fattoria Di Cavaglioni

2 2
farm , Sovicille
Fattoria Di Cavaglioni, in San Rocco a Pilli, near Sovicille, is a 16th-century farmhouse located approximately 12.6km from Siena's Piazza del Campo, Palazzo Chigi-Saracini, and the National Museum of Etruscan Archaeology.
This self-catering property boasts a swimming pool (open May-September), children's playground, free Wi-Fi, private parking, and offers cycling opportunities in the Tuscan countryside, along with a barbecue and sun terrace.
Chiara Luxury Country Home - Siena
9.8 50 reviews
Siena
23/08 – 28/08
£1190/nighttotal: £5950 (5 )

Chiara Luxury Country Home

6 2
house , Monteriggioni
Chiara Luxury Country Home is situated in Monteriggioni, a short distance from the Palasport Mens Sana and the Basilica di San Domenico, offering a peaceful countryside setting. This property has received excellent user ratings.
This spacious villa has six bedrooms, two living rooms, and seven bathrooms, making it ideal for large groups. The property features a range of amenities, including a swimming pool, jacuzzi, spa, fitness centre, and a garden, ensuring a comfortable and enjoyable stay.
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