Villas and Vacation Homes in Siena

8524 Villas and Vacation Homes in Siena

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Siena
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Best villa offers in Siena

Luxury villas in Siena

Restored medieval estates, aristocratic farmhouses, and high-end countryside retreats define Luxury villas in Siena. Perched among rolling Tuscan hills near historic landmarks like the Piazza del Campo and the Duomo, compare premier listings to secure an exclusive Italian sanctuary.

La Grotta Di Montecchino App Susino - Siena
9.2 30 reviews

La Grotta Di Montecchino App Susino

house, Siena
Located in the prime Tuscan countryside, this villa is situated just 3-4 miles from Siena's center and 1-2 miles from the nearest town, offering a peaceful rural experience ideal for exploring architecturally and scenically stunning sites.
This welcoming 650 sq ft holiday home accommodates up to 6 guests, featuring 3 bedrooms, 1 bathroom, a kitchen with a freezer, a shared swimming pool, a garden, and parking, with horseback riding available 1 mile away and tennis just 300 feet away.
Podere Piazza Siena - Siena
9.8 241 reviews

Podere Piazza Siena

house, Siena
Podere Piazza Siena is a peaceful retreat situated 2.7 miles from Piazza del Campo and San Cristoforo Church, offering a serene escape just outside Siena's immediate city center.
This welcoming 1290 square foot holiday home features 3 bedrooms and 2 bathrooms, a well-equipped kitchen with barbecue facilities, complimentary patio, free private parking, free WiFi, a garden, and a children's playground, making it ideal for families and those seeking outdoor activities like cycling.
Casa Torre - Palio Di Siena - Siena
8.7 101 reviews

Casa Torre - Palio Di Siena

house, Siena
Located in Siena's historic center on Via di Salicotto, this apartment is situated within the Torre Contrada, just 250 meters from Piazza del Campo, offering an authentic experience of Siena's Palio traditions with its unique proximity to flag-throwing and drumming practices.
This elegant and comfortable 2-bedroom accommodation, sleeping up to 5 guests, features a split-level layout with a frescoed ceiling in the main room, a mezzanine sleeping area accessed by a spiral staircase, and a secure property with iron grates, making it an ideal holiday home for those seeking a distinctive stay near this iconic villa.
B&b Il Castelletto Siena - Siena
9.2 18 reviews

B&b Il Castelletto Siena

house, Castelnuovo Berardenga
Located in Montaperti, this peaceful retreat is just 8.9 miles from Siena's Piazza del Campo and Piazza Matteotti, offering convenient access to historical sites.
This welcoming 1-bedroom holiday home, spanning 650 square feet and accommodating up to 3 guests, features a full kitchen, a fireplace, and an outdoor seating area, with bicycle rentals available for exploring the Tuscan countryside.

Villas in Siena with pool

A private swimming pool offers a tranquil haven to cool off on your own schedule after a day exploring Chianti vineyards or medieval hill towns. Filter by price, layout, and amenities across top booking platforms to find your ideal poolside retreat surrounded by olive groves and cypress trees.

Ancient Villa - Hills Of Tuscany - Siena
10 16 reviews

Ancient Villa - Hills Of Tuscany

house, Monteroni d'Arbia
Villa Giusterna, an exclusive 18th-century villa, is strategically situated in the Tuscan hills, approximately 6 miles from Monteroni d'Arbia, offering easy access to art cities and scenic Tuscan promenades.
This expansive holiday home accommodates up to 16 guests with 8 bedrooms, each featuring an en-suite bathroom, and boasts exclusive use of a private swimming pool and an 800-square-meter park, complete with a well-equipped kitchen and a grand dining room with a fireplace.
Gli Ulivi Di Siena - Siena
8.0 29 reviews

Gli Ulivi Di Siena

house, Siena
Located in Siena, this welcoming villa offers a tranquil escape just 3.2 miles from Piazza del Campo and the National Picture Gallery Siena, with additional historical sites like the National Museum of Etruscan Archaeology and San Cristoforo Church also conveniently nearby.
This holiday home boasts 700 square feet of living space with 2 bedrooms accommodating up to 5 guests, featuring a fully equipped kitchen, air conditioning, a seasonal outdoor pool, free WiFi, and private parking for a comfortable stay.
Chianti Escape Poolvines Tenuta Bibbiano-i Sodi - Siena
10 3 reviews

Chianti Escape Poolvines Tenuta Bibbiano-i Sodi

house, Castellina in Chianti
Located in Castellina in Chianti, this villa is 16 miles from Piazza del Campo and 18 miles from Piazza Matteotti, offering an authentic Tuscan wine region experience within the Chianti Classico Wine Resort Tenuta di Bibbiano.
This holiday home features 1,500 square feet of living space, air conditioning, a swimming pool, a garden, a sauna, a spa, and accommodates up to 31 guests with 1 bedroom and 6 bathrooms.
Villa Cucule - Siena
9.7 27 reviews

Villa Cucule

house, Siena
Villa Cucule offers a spacious country house escape just 6.2 miles from Siena's Piazza del Campo and 30 miles from Piazza Matteotti, with Florence Airport 52 miles away.
This expansive 3770 sq ft holiday home features 5 bedrooms, 5 bathrooms, a private fenced swimming pool, outdoor barbecue, and bicycle rentals, providing a welcoming base for exploring the Tuscan countryside.

Frequently Asked Questions about Siena

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

    The absolute must-sees in Siena are the Piazza del Campo, the shell-shaped main public space, and the Siena Cathedral (Duomo di Siena) with its stunning black and white striped bell tower. Don't miss climbing the Torre del Mangia for incredible views over the city and the surrounding Tuscan countryside. The Palazzo Pubblico, which houses the city's museum, is also a key historical site on the Piazza del Campo.
  • Which district of Siena is best known for its villas?

    While Siena itself is a compact historic city, the areas just outside the city walls, particularly to the north and west, are where you'll find many of the more prominent villas. These districts offer a blend of proximity to the city and the tranquility of the Tuscan countryside. Specific districts are less defined by villas as a primary characteristic, but the outskirts are where they are most common.
  • What are the advantages of staying in a villa in Siena?

    Staying in a villa near Siena offers a more private and spacious experience compared to a hotel. You often get a kitchen, allowing for self-catering, which can be a cost-saver and a way to enjoy local produce. Many villas come with outdoor spaces like gardens or patios, and some even have private pools, providing a relaxing retreat after exploring the city. It's a great way to experience the Tuscan lifestyle.
  • How much does it cost to rent a villa in Siena on average?

    The cost to rent a villa in Siena can vary significantly based on size, amenities, location, and time of year. Generally, you might expect to pay anywhere from $1,500 to $5,000 per week for a comfortable villa. During peak season, like summer, prices will be at the higher end, while shoulder seasons can offer better value.
  • Are there villas near the city center in Siena?

    Yes, there are some villas located within or very close to Siena's historic center, though they are less common and can be more expensive due to their prime location. Many more villas are situated just a short drive or a pleasant walk from the city walls, offering a good balance of convenience and peaceful surroundings.
  • How far in advance should I book a villa in Siena?

    For the best selection and to secure your preferred villa, it's recommended to book at least 6 to 9 months in advance, especially if you're planning to travel during the popular spring or fall seasons, or for a larger group. For last-minute trips, availability might be limited.
  • Are there wineries or food tours near villas in Siena?

    Absolutely. The countryside surrounding Siena is renowned for its wineries, particularly in the Chianti region. Many villas are located within easy reach of vineyards offering wine tastings and tours. Food tours are also readily available, often focusing on local Tuscan specialties like pici pasta and Pecorino cheese, and can frequently be arranged from your villa.
  • Is a car necessary to stay in a villa in Siena?

    If your villa is located in the heart of Siena's historic center, a car is generally not necessary and can even be a hindrance due to ZTL (limited traffic zones) and parking challenges. However, if your villa is situated in the countryside outside the city walls, a car becomes highly beneficial for exploring the surrounding Tuscan towns, wineries, and enjoying the convenience of independent travel.

Villas in Popular Destinations

Pet-friendly villas in Siena

Enjoy total peace of mind with enclosed gardens, ground-floor layouts, and private outdoor spaces that make traveling with dogs seamless. Search pet-friendly villas in Siena so your whole household can explore winding rural trails and scenic countryside paths together.

Villa Capanna, Private Pool, Breathtaking Views - Siena
9.8 307 reviews

Villa Capanna, Private Pool, Breathtaking Views

house, Siena
Immersed in a historic Chianti wine estate, this restored barn offers breathtaking views of Siena's medieval towers, located just 4 miles from the historic center.
This expansive villa, accommodating up to 10 guests, features 6 air-conditioned bedrooms, 5 bathrooms, a private swimming pool, an expansive garden, and offers exclusive services like private chef and wine tastings for an authentic Tuscan holiday home experience.
Apartment In Piazza Del Campo Area 3 Bedrooms 2 Bathrooms - Siena
No reviews

Apartment In Piazza Del Campo Area 3 Bedrooms 2 Bathrooms

farm, Castelnuovo Berardenga
Centrally located in Castelnuovo Berardenga, this farm is just 100 meters from Piazza del Campo, offering convenient access to cultural sites like the Oratorio di San Bernardino e Museo Diocesano and the Chianti Sculpture Park, with free parking available near the Medicea Fortress.
This welcoming holiday home spans 590 square feet, featuring two bedrooms and two bathrooms to accommodate up to three guests, and includes essential amenities like Wi-Fi and a kitchen with a fridge and microwave.
Casa Regina - Relax E Arte - Si - Siena
9.4 22 reviews

Casa Regina - Relax E Arte - Si

house, Siena
Located just outside Siena, this apartment offers convenient access to the historic city and nearby attractions like Castenuovo and Monteriggioni, making it an ideal holiday home for exploring Tuscany.
This welcoming apartment accommodates up to 9 guests with 3 bedrooms and 2 bathrooms, featuring a shared garden, swimming pool, and kitchen equipped with a fridge, freezer, microwave, and dishwasher, perfect for a comfortable stay.
Finestra Su Siena 16, Emma Villas - Siena
9.0 2 reviews

Finestra Su Siena 16, Emma Villas

house, Siena
This spacious 8-bedroom villa in Siena offers a luxurious retreat, located 8.8 miles from the historic Piazza del Campo and 5.5 miles from the National Museum of Etruscan Archaeology.
Boasting 4840 square feet of living space, this holiday home features a private pool, hot tub, spa, and garden, perfect for relaxation and enjoying the Tuscan surroundings with complimentary Wi-Fi and parking.

Family-friendly vacation homes in Siena

Generous layouts featuring multiple bedrooms, expansive yards, and full kitchens ensure group trips and multi-generational holidays stay comfortable. Whether taking cooking classes, exploring the Val d'Orcia, or taking day trips across Tuscany, compare top vacation homes to book an ideal family base.

Among The Olive Trees 5 Minutes From Siena: House With Garden & Air Conditioning - Siena
No reviews

Among The Olive Trees 5 Minutes From Siena: House With Garden & Air Conditioning

house, Siena
Just 5 minutes from Siena's center, this newly renovated apartment, Lo Scosso, offers a peaceful rural retreat with convenient access to cultural landmarks like Santa Maria della Scala and the Museo dell'Opera del Duomo.
This spacious 1180 sq ft holiday home accommodates up to 6 guests with 3 king bedrooms, features a panoramic terrace overlooking the Tuscan landscape, a private garden, eco-friendly solar panels, and ample private parking for 4 cars, making it an ideal villa for exploring the region.
Country-house In Wine Estate 5km From Siena - Siena
10 26 reviews

Country-house In Wine Estate 5km From Siena

house, Siena
Villa Colombaio, a tranquil escape in the Sienese hills, provides a wonderful base for exploring Tuscan attractions within a 1-2 hour drive.
This welcoming 4-bedroom apartment, accommodating up to 8 guests, features a spacious living room, a vast kitchen opening onto the garden, a covered portico for al fresco dining, and a shared swimming pool located 100 meters away, open from May to September.
70 M² Farmhouse ∙ 2 Bedrooms ∙ 4 Guests - Siena
9.5 74 reviews

70 M² Farmhouse ∙ 2 Bedrooms ∙ 4 Guests

farm, Monteriggioni
Farm for 4 people with an excellent rating of 95% based on 74 reviews. You will be located in Monteriggioni.
Services and facilities: a barbecue, free parking and a washing machine. Take advantage of the Spa in this accommodation!
Casa Duccio Alle Mura Della Città - Siena
9.8 42 reviews

Casa Duccio Alle Mura Della Città

house, Siena
Adjacent to Siena's ancient city walls, this finely renovated house offers tranquil accommodation with privileged access, just a few minutes' walk from the Duomo and Piazza del Campo.
This welcoming villa provides 2 bedrooms accommodating up to 4 guests, featuring modern amenities like air conditioning, high-speed Wi-Fi, a fully equipped kitchen, and convenient parking options, making it an ideal holiday home for exploring Siena.
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