Villas and Holiday Homes in Siena

8524 Villas and Holiday Homes in Siena

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Siena
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Best villa offers in Siena

Villas and holiday homes with private pool in Siena

Rolling Tuscan hills surround our villas with pool in Siena. Holiday homes with pool are found both in town and scattered across the surrounding countryside.

Exclusive Villa Mami - Siena
10 21 reviews

Exclusive Villa Mami

house, Siena
Offering breathtaking panoramic views of olive groves and Siena's skyline, including the Torre del Mangia, this exclusive villa is located just 3 kilometers from the city centre.
This recently restored holiday home provides luxurious accommodation for up to 11 guests across six en-suite bedrooms, featuring a magnificent 15x4m swimming pool and a fully equipped kitchen for a quintessential Tuscan getaway.
Podere Il Boschetto - Luxury Estate In Siena - Siena
9.9 131 reviews

Podere Il Boschetto - Luxury Estate In Siena

house, Siena
Boasting an excellent user and location rating, this spacious 5-bedroom, 3-bathroom villa offers a luxurious retreat in a rural area of Siena, just a 4-minute drive from Porta Camollia and a 6-minute drive to Piazza del Campo. This expansive holiday home, covering 300 square meters, accommodates up to 10 guests and features a well-equipped kitchen, an outdoor swimming pool, a garden, and a tennis court, with nearby opportunities for cycling and horse riding.
Exclusive Villa Mami - Siena
10 1 review

Exclusive Villa Mami

house, Siena
Exclusive Villa Mami is located in Siena, 7.6 kilometres from the National Museum of Etruscan Archaeology and 7.6 kilometres from Piazza del Campo.
This spacious 6-bedroom villa rental accommodates up to 24 guests and features an infinity pool, a garden, air conditioning, and a fully equipped kitchen, offering an excellent user rating and a memorable stay.
Case Vacanza "La Fornace" - Siena
8.5 38 reviews

Case Vacanza "La Fornace"

house, Castelnuovo Berardenga
Located in Vagliagli, this recently renovated property is 11 kilometres from the renowned Piazza del Campo and 32 kilometres from Piazza Matteotti, offering convenient private parking and access to a fitness room.
This welcoming villa rental boasts a garden with an outdoor fireplace, a fully equipped kitchen, and is family-friendly with amenities like outdoor play equipment and a baby safety gate, with bike rental available nearby.

Luxury villas and holiday homes in Siena

Our platform brings together the finest luxury villas in Siena, from intimate retreats to grand estates. Find your luxury holiday home.

Chiara Luxury Country Home - Siena
9.8 50 reviews

Chiara Luxury Country Home

house, Monteriggioni
Chiara Luxury Country Home is located in Monteriggioni, 5 kilometres from Piazza del Campo and 35 kilometres from Piazza Matteotti.
This spacious 6-bedroom villa offers a private outdoor swimming pool, jacuzzi, spa, fitness centre, and a garden, alongside a fully equipped kitchen and air conditioning, ensuring a luxurious stay for families and groups.
63 M² Farmhouse ∙ 2 Bedrooms ∙ 3 Guests - Siena
9.8 12 reviews

63 M² Farmhouse ∙ 2 Bedrooms ∙ 3 Guests

farm, Monteroni d'Arbia
Farm for up to 3 guests with an excellent rating of 98% based on 12 reviews. Your accommodation will be based in Monteroni d'Arbia.
Services and facilities: a fridge, a barbecue and free parking. This accommodation in Monteroni d'Arbia also has a garden!
Casa Lamartinella, Due Passi Da Piazza Il Campo - Siena
10 1 review

Casa Lamartinella, Due Passi Da Piazza Il Campo

house, Siena
Just steps from Piazza del Campo, this newly renovated house in Siena's historic centre offers modern comfort with elegant details for an authentic Sienese experience.
This 2-bedroom villa rental accommodates 4 guests and features air conditioning, Wi-Fi, and a kitchen with a fridge and dishwasher, perfect for exploring Siena.
Villa Larniano, Panoramic With  Private Pool And Vineyard - Siena
10 65 reviews

Villa Larniano, Panoramic With Private Pool And Vineyard

house, Siena
Offering exclusive access to a 340-acre family-run wine estate, this villa is located within Tenuta Larnianone, just 5 kilometres from Siena's historic city centre and surrounded by vineyards and olive groves.
This spacious 508 m2 villa rental, accommodating up to 11 guests, boasts 5 ensuite air-conditioned bedrooms, a triple living room with fireplace, a games room, and an annexed apartment for additional flexibility, alongside curated activities like wine tastings and truffle hunting.

Frequently Asked Questions about Siena

  • What are the must-see attractions to visit in Siena, Italy?

    When visiting Siena, the Piazza del Campo is a definite highlight. This shell-shaped medieval square is famous for the Palio horse race. The Siena Cathedral, also known as the Duomo di Siena, is another essential stop with its stunning facade and interior. Don't miss climbing the Torre del Mangia for panoramic views of the city and surrounding Tuscan landscape.
  • What are the advantages of staying in a villa in Siena, Italy?

    Staying in a villa in Siena, Italy offers more space and privacy compared to a hotel. It provides a home-like atmosphere with amenities like a full kitchen, living areas, and often private gardens or pools. This setup is particularly beneficial for families or groups, allowing for a more relaxed and self-catered experience while still being close to Siena's attractions.
  • How much does it cost to rent a villa in Siena, Italy on average?

    The average cost to rent a villa in Siena, Italy varies significantly based on size, amenities, location, and the time of year. Prices can range from around 800 euros per week for a smaller property in the off-season to several thousand euros per week for larger, more luxurious villas during peak summer months.
  • Are there villas near the city center in Siena, Italy?

    Yes, there are villas located near the city center of Siena, Italy. These properties often offer a blend of tranquility and convenient access to the historic sights. They might be situated on the outskirts of the immediate centro storico or in quieter residential pockets just a short walk or drive from the main squares and attractions.
  • How far in advance should one book a villa in Siena, Italy?

    It is advisable to book a villa in Siena, Italy at least six months in advance, especially if planning a trip during the popular spring and summer months, or around the time of the Palio horse races in July and August. Booking earlier ensures a wider selection of available properties.
  • Are there wineries or food tours near villas in Siena, Italy?

    Many villas in and around Siena, Italy are situated in the Tuscan countryside, which is renowned for its wineries. It's common for villas to be close to vineyards offering wine tastings, and numerous operators provide guided food and wine tours that explore local specialties and the Chianti region, often including visits to producers.
  • Is a car necessary to stay in a villa in Siena, Italy?

    Whether a car is necessary to stay in a villa in Siena, Italy depends on its location. If the villa is within walking distance of the city center or has good public transport links, a car might not be essential. However, for villas located in more rural areas or for exploring the wider Tuscan countryside, a car offers the most flexibility and convenience.

Villas in Popular Destinations

Villas and family holiday home rentals in Siena

Our listings of holiday homes for families in Siena feature properties with multiple bedrooms and gated pools. Browse our family-friendly villas.

Casa Duprè - Cozy Apartment Near Piazza Del Campo - Siena
9.9 58 reviews

Casa Duprè - Cozy Apartment Near Piazza Del Campo

house, Siena
Primely located in Siena's Onda district, this apartment offers immediate access to the city's historic treasures, situated just 100 meters from the iconic Piazza del Campo and boasting captivating views of the city's lush vegetable garden and historic centre from its bedrooms. This elegant holiday home, a 2-bedroom villa rental on the first floor of a medieval building, accommodates up to 3 guests and features a fully equipped kitchen, spacious living area with smart TV and Wi-Fi, and two bathrooms, including one en-suite.
51 M² Farmhouse ∙ 1 Bedroom ∙ 2 Guests - Siena
9.8 15 reviews

51 M² Farmhouse ∙ 1 Bedroom ∙ 2 Guests

farm, Monteroni d'Arbia
Farm rental for 2 people with an excellent rating of 98% based on 15 reviews. You will stay in Monteroni d'Arbia.
Facilities and services: free parking, a garden and air conditioning. Pets are allowed in this accommodation.
180 M² Farmhouse ∙ 4 Bedrooms ∙ 10 Guests - Siena
No reviews

180 M² Farmhouse ∙ 4 Bedrooms ∙ 10 Guests

farm, Chiusdino
Farm for 10 guests. You will be located in Chiusdino.
Services and facilities include a kitchen, a washing machine and a fridge. This is a family-friendly accommodation!
Virgi House - Siena
10 214 reviews

Virgi House

house, Siena
Just 3 km from Siena's historic centre, this spacious 160 sqm Tuscan countryside villa offers scenic views and two private gardens for relaxation, with parking available on-site.
This family-friendly holiday home boasts three bathrooms, air conditioning, free WiFi, and multiple living areas, comfortably accommodating up to four guests with versatile bedroom configurations.

Rental villas and holiday homes with jacuzzi in Siena

Our villas with hot tub in Siena are the perfect choice for a romantic stay: a private jacuzzi for two in an exceptional setting. Find your holiday home with hot tub.

Elegant Villa Wing Of Castello Di Cacchiano By Vacavilla - Siena
9.4 14 reviews

Elegant Villa Wing Of Castello Di Cacchiano By Vacavilla

house, Gaiole in Chianti
Located in Monti di Sotto, this exclusive villa wing of Castello di Cacchiano is 22 kilometres from Piazza Matteotti and 14 kilometres from Piazza del Campo.
This family-friendly holiday home offers 220 square meters of living space with 4 bedrooms accommodating up to 7 guests, featuring a private swimming pool, hot tub, spa, and an equipped kitchen for a comfortable stay.
La Fonte Di Santa Regina 8, Emma Villas - Siena
9.4 2 reviews

La Fonte Di Santa Regina 8, Emma Villas

house, Siena
Located in Siena, this spacious four-bedroom villa is situated approximately 5 kilometres from Piazza del Campo and Siena Train Station.
This luxurious holiday accommodation boasts a floor area of 340 square meters and features a private infinity swimming pool, jacuzzi, sauna, and a beautiful garden, perfect for a relaxing stay with family and friends.
Villa Rosa: Hot Tube, Garden, 15 Min/siena - Siena
9.6 67 reviews

Villa Rosa: Hot Tube, Garden, 15 Min/siena

house, Sovicille
Nestled in the verdant Val di Merse, this exclusive villa offers a tranquil retreat in Sovicille, boasting an excellent user, location, and cleanliness rating.
This luxurious holiday home features two generous suites, three bathrooms, a fully equipped semi-professional kitchen, air conditioning, a private hot tub, and ample parking, comfortably accommodating up to four guests.
Bell Aria - Siena
9.3 65 reviews

Bell Aria

house, Gaiole in Chianti
Located in Gaiole in Chianti, Bell Aria is a tranquil holiday home offering convenient access to Tuscan landmarks, situated 25.75 kilometres from Piazza Matteotti and 28.97 kilometres from Piazza del Campo, with complimentary on-site parking and free Wi-Fi.
This spacious one-bedroom villa rental boasts a fully equipped kitchen, a dining area, a seating area with a fireplace, and access to an outdoor swimming pool, jacuzzi, fitness centre, and tennis court for an enjoyable stay.
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