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.

House On Medieval Tannery Near Siena - Siena
No reviews

House On Medieval Tannery Near Siena

house, Chiusdino
Located in Chiusdino, this holiday home offers a historic setting within a medieval tannery, situated 17.7 kilometres from the National Museum of Etruscan Archaeology and 20.9 kilometres from Piazza del Campo.
This spacious villa rental, accommodating up to 15 guests, boasts 200 square meters of floor area, four bedrooms, three bathrooms, a year-round outdoor swimming pool, a terrace with barbecue facilities, and complimentary WiFi.
Beautiful 5 Bedroom Tuscan Villa - Siena
10 4 reviews

Beautiful 5 Bedroom Tuscan Villa

house, Monteroni d'Arbia
South of Siena, this recently restored villa offers a tranquil escape in the rolling hills of Monteroni d'Arbia, a peaceful retreat blending historic charm with modern luxury.
This family-friendly holiday home boasts 5 en-suite bedrooms for 10 guests, featuring a semi-professional kitchen, air conditioning, a swimming pool, garden, fitness centre, and parking, providing an ideal base for exploring the Tuscan countryside.
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.
Luxury Serviced Cottage In A Historical Chianti Borgo - Siena
10 143 reviews

Luxury Serviced Cottage In A Historical Chianti Borgo

house, Castellina in Chianti
Secluded in the renowned Chianti region, this villa is located in Castellina in Chianti, 16 kilometres from Piazza del Campo and 29 kilometres from Piazza Matteotti, with Florence Airport 59 kilometres away.
This holiday home offers a private pool, hot tub, tennis court, and barbecue facilities, alongside a fully equipped kitchen and patio, with cycling and hiking opportunities 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.

800 Sqm, Hot Tub, Pool And Gym, 5 Bedrooms, 1 Family Room, 7 Bathrooms - Siena
9.8 50 reviews

800 Sqm, Hot Tub, Pool And Gym, 5 Bedrooms, 1 Family Room, 7 Bathrooms

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.
Villa Liberty In The Centre - No Ztl - Siena
No reviews

Villa Liberty In The Centre - No Ztl

house, Siena
Directly opposite a public paid parking lot, this elegant Liberty style villa is centrally located in Siena, a brief 5-minute stroll from the historic centre, placing you within easy reach of the Basilica di San Domenico and Fortezza Medicea.
This welcoming holiday home accommodates up to 7 guests across 2 bedrooms and 2 bathrooms, offering a private terrace, air conditioning, a fully equipped kitchen with a fridge, microwave oven, and dishwasher, and is conveniently situated for exploring the Orto Botanico dell'Universita di Siena and Fisiocritici Onlus Academy Natural History Museum.
Casa Dell'alberino - Siena
10 6 reviews

Casa Dell'alberino

house, Siena
This welcoming villa rental in Siena is situated in a quiet, verdant district, offering a convenient 10-minute walk to the historic Piazza del Campo and excellent access to both the Piazzale Rosselli train station and Piazza Gramsci bus station.
Boasting two bedrooms and accommodation for up to six guests, this holiday home features a well-equipped kitchen with a fridge, freezer, microwave, and dishwasher, alongside a garden and parking, with a small balcony providing pleasant outdoor space.
Camera In Centro A Siena - Siena
9.5 30 reviews

Camera In Centro A Siena

house, Siena
Directly opposite Siena's historic city walls, this exceptional villa rental offers unparalleled access to the city centre, with all amenities and the Piazza del Campo just a short walk away.
This welcoming holiday home accommodates two guests across one bedroom and one bathroom, boasting a private garden and parking, making it perfect for exploring Siena's rich history without needing a car.

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.

350 M² Farmhouse ∙ 7 Bedrooms ∙ 17 Guests - Siena
No reviews

350 M² Farmhouse ∙ 7 Bedrooms ∙ 17 Guests

farm, Sovicille
Accommodation for 17 guests. You will stay in Sovicille.
Facilities and services: air conditioning, a washing machine and a swimming pool. The big plus of this accommodation in Sovicille is the jacuzzi!
70 M² Farmhouse ∙ 2 Bedrooms ∙ 4 Guests - Siena
9.5 74 reviews

70 M² Farmhouse ∙ 2 Bedrooms ∙ 4 Guests

farm, Monteriggioni
Farm for up to 4 people with an excellent rating of 95% based on 74 reviews. This accommodation is based in Monteriggioni.
Services and facilities include free parking, a spa and a washing machine. Enjoy a swimming pool in this accommodation in Monteriggioni!
Casa Moderna  Parcheggio Privato  Ztl Free - Siena
9.8 16 reviews

Casa Moderna Parcheggio Privato Ztl Free

house, Siena
This welcoming villa in Siena offers free parking just outside the ZTL, placing you a convenient 15-minute walk from Piazza del Campo and the Duomo.
This pet-friendly holiday accommodation, ideal for families and business travellers, accommodates up to 4 guests and boasts a modern interior with a fridge, freezer, microwave, and dishwasher.
300 M² Villa ∙ 4 Bedrooms ∙ 8 Guests - Siena
No reviews

300 M² Villa ∙ 4 Bedrooms ∙ 8 Guests

house, Siena
Located in Vico d'Arbia, this villa offers stunning panoramic views from its position on a hill, just 10 kilometres from Siena and easily accessible to Florence and the coast.
This exclusive holiday home, a renovated former stable, boasts 300 square metres of living space, accommodating up to 8 guests across 4 bedrooms and 3 bathrooms, and features air conditioning, a fully equipped kitchen, and access to an outdoor swimming pool from May to October.

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.

Casale A Siena Con Piscina E Vista Panoramica - Siena
No reviews

Casale A Siena Con Piscina E Vista Panoramica

house, Castelnuovo Berardenga
Villa Il Colle di Monteaperti, located in Casetta, is situated 12.4 kilometers from Siena's Piazza del Campo and San Cristoforo Church, and 46.7 kilometers from Piazza Matteotti.
This spacious 250 square meter holiday home offers accommodation for up to 11 guests across 5 bedrooms and 3 bathrooms, boasting a private garden, terrace with barbecue facilities, air conditioning (surcharge applies), a hot tub, and spa facilities, with parking and WiFi included.
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.
Relax In The Green, In The Municipality Of Monteriggioni Just 7 Km From Siena - Siena
10 7 reviews

Relax In The Green, In The Municipality Of Monteriggioni Just 7 Km From Siena

house, Monteriggioni
Located in Monteriggioni, this villa is a 17-minute drive from Monteriggioni Castle and a 21-minute drive from Piazza del Campo, offering a tranquil retreat.
Boasting 300 square meters of floor area, this holiday home accommodates up to 6 guests with 4 bedrooms and 4 bathrooms, featuring a private swimming pool, jacuzzi, garden, and free WiFi for a comfortable 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.
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