Villas and Vacation Homes in Siena

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Siena

Best villa offers in Siena

Beautiful Villa In The Sienese Hills - Siena
9.9 51 reviews

Beautiful Villa In The Sienese Hills

house, Siena
Offering panoramic views of Siena's iconic Torre del Mangia and Cathedral tower, this enchanting villa is nestled in the Sienese countryside, formerly a refuge for travelers on the Via Francigena.
This family-friendly apartment accommodates up to 8 guests in 4 bedrooms with en-suite bathrooms, featuring a pool table, a grand fireplace, a spacious kitchen, and access to a shared, unheated swimming pool located approximately 0.4 miles away within the estate, with opportunities for wine tastings and cooking lessons on-site.
Terratetto Premium Nel Cuore Di Siena - Via Camollia - Siena
10 2 reviews

Terratetto Premium Nel Cuore Di Siena - Via Camollia

house, Siena
Centrally located on Via Malta in Siena's city center, this terratetto is a 15-minute walk from Piazza del Campo and less than 0.6 miles from San Cristoforo Church.
This spacious 1290 sq ft holiday home offers 2 bedrooms, 3 bathrooms, and can accommodate up to 7 guests with amenities including air conditioning, WiFi, and a kitchenette, making it an ideal villa rental for exploring Siena.
Castelvecchio Number 12 Siena, Long Stay Top Rent. - Siena
9.8 21 reviews

Castelvecchio Number 12 Siena, Long Stay Top Rent.

house, Siena
Located in Siena's exclusive vicolo di Castelvecchio, this historic apartment, reputedly the oldest in the city, offers a unique sense of place within a tranquil setting.
This well-furnished 2-bedroom, 2-bathroom holiday home accommodates up to 4 guests and features a rare private garden terrace, a dedicated library, and significant discounts for longer stays, making it an ideal villa for master's, PhDs, or business travelers.
La Capanna Di Elfo Luxury Villa View - Siena
No reviews

La Capanna Di Elfo Luxury Villa View

house, Siena
House listing. You will be based in Siena.
Facilities and services: a swimming pool, a washing machine and a barbecue.
Casa Brunello 2km From Siena City Center - Siena
9.3 16 reviews

Casa Brunello 2km From Siena City Center

house, Siena
Located just 2 miles from Siena's historic city center, this studio offers a peaceful countryside setting, providing an exclusive base for exploring the region.
This newly renovated barn conversion features a fully equipped kitchen with a fridge, freezer, and microwave, along with internet access and parking, making it an ideal holiday home for two guests seeking comfort and style.
My Exclusive Italy - Villa Hills On The Horizon | Authentic Tuscan Style & Siena - Siena
No reviews

My Exclusive Italy - Villa Hills On The Horizon | Authentic Tuscan Style & Siena

house, Siena
Offering breathtaking panoramic views of the Siena hills, Val d'Orcia, and Mount Amiata, this Tuscan villa is located just a few miles from the historic city of Siena.
This expansive 25,830 sq ft holiday home accommodates up to 8 guests with 4 bedrooms and 4 bathrooms, featuring a fully equipped kitchen, air conditioning, a shared swimming pool, a garden, a tennis court, and parking.
Casa Attilio - Siena
9.9 9 reviews

Casa Attilio

house, Siena
Casa Attilio is a welcoming villa located in Siena, approximately 5.4 miles from Piazza del Campo and 4.1 miles from the National Museum of Etruscan Archaeology.
This holiday home offers 1080 square feet of living space with 2 bedrooms, a fully equipped kitchen, and private parking, accommodating up to 11 guests with complimentary WiFi and outdoor seating.
Villa Le Tortore Privata Lusso Piscina Relax Siena - Siena
No reviews

Villa Le Tortore Privata Lusso Piscina Relax Siena

house, Siena
Vacation house to rent. This accommodation is based in Siena.
Services and facilities: air conditioning, a washing machine and an iron. This house is very convenient for families.

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.

Villa La Strega - Siena
No reviews

Villa La Strega

house, Siena
Accommodation. You will stay in Siena.
Facilities and services: a dish washer, a terrace and a fridge. Enjoy free parking with this accommodation in Siena!
Vignano40 - Siena
9.8 96 reviews

Vignano40

house, Siena
This welcoming villa offers a peaceful retreat just 4.2 miles from Siena's historic Piazza del Campo and 27 miles from Piazza Matteotti.
Enjoy 810 square feet of comfortable living space featuring two bedrooms, a well-equipped kitchen with a dishwasher and microwave, free WiFi, and a private garden with barbecue facilities.
Villa Liberty Townhouse - Siena
No reviews

Villa Liberty Townhouse

house, Siena
This villa in Siena offers convenient access within a paid parking zone, making arrival by car straightforward.
Enjoy essential amenities like a microwave, dishwasher, and air conditioning in this 2-guest capacity house, complete with a terrace/balcony and 1 bathroom, perfect for a comfortable stay.
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 offers convenient access to natural attractions like Parco di Sculture del Chianti and Enoteca Italiana, with sporting venues such as Siena Stadium just a short drive away.
This 1080 sq ft farm accommodates up to 3 guests in 2 bedrooms and 2 bathrooms, featuring a well-equipped kitchen with a refrigerator and microwave, and a private balcony perfect for enjoying the Tuscan surroundings.

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.

Villa Marcolina - Siena
10 3 reviews

Villa Marcolina

house, Castelnuovo Berardenga
Located in Ponte A Bozzone, this villa is conveniently situated 5.6 miles from Siena's Piazza del Campo and 22 miles from Piazza Matteotti.
This welcoming holiday home offers 2690 square feet of living space with 2 bedrooms, 3 bathrooms, and a capacity for 15 guests, featuring a fully equipped kitchen, complimentary WiFi, and a private swimming pool surrounded by a spacious garden.
Tuscany Villa Cardella Siena - Siena
8.9 13 reviews

Tuscany Villa Cardella Siena

house, Siena
Located just 3 miles from Siena's historic center, this villa offers an authentic Tuscan countryside experience amidst 2,000 sqm of olive groves.
This spacious holiday home comfortably accommodates up to 11 guests across two independent apartments, featuring 6 bedrooms, 4 bathrooms, and a private swimming pool with outdoor amenities for ultimate relaxation.
Exclusive Villa Mami - Siena
No reviews

Exclusive Villa Mami

house, Siena
House listing. You will be based in Siena.
Services and facilities include a swimming pool, free parking and a kitchen. This house also has air conditioning!
450 M² Villa ∙ 8 Bedrooms ∙ 16 Guests - Siena
No reviews

450 M² Villa ∙ 8 Bedrooms ∙ 16 Guests

house, Siena
This restored stone farmhouse offers an exclusive villa experience less than 6 miles from Siena's historic Gothic center, providing convenient access to iconic medieval villages like Montalcino and San Gimignano.
Boasting 8 bedrooms and 8 bathrooms across 4 levels with 4,840 square feet of floor area, this spacious holiday home accommodates up to 16 guests and features a private park, swimming pool, and stunning panoramic views of the Tuscan hills.

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.

Living Siena - "Chiantigiana" Apartment - Siena
9.9 21 reviews

Living Siena - "Chiantigiana" Apartment

house, Siena
Located within Siena, this recently renovated apartment offers a welcoming base for exploring the city's historical and cultural sites, with convenient access to attractions.
This house, ideal for up to two guests, features a modern design with a full kitchen, air conditioning, a garden, and parking, making it a perfect holiday home for both short and extended stays.
Living Siena - "La Contrada" Apartment - Siena
10 2 reviews

Living Siena - "La Contrada" Apartment

house, Siena
Newly renovated apartments completed in 2022, Living Siena Apartment is located within Siena, offering convenient access to the city's attractions.
This welcoming accommodation allows up to 2 guests, featuring air conditioning, a garden, and parking, making it an ideal holiday home for exploring Siena.
Gest Short Rent Siena 1 - Siena
9.1 214 reviews

Gest Short Rent Siena 1

house, Siena
Located in Siena's Contrada dell'Onda district, this apartment is just 100 yards from Piazza del Campo and 300 yards from Parking il Campo, offering prime access for exploring the city on foot.
This welcoming apartment accommodates two guests with one bedroom and one bathroom, featuring air conditioning, a kitchenette, and the option to arrange horse riding tours and wine tastings in the Sienese hills, making it an ideal holiday home for an authentic Tuscan experience.
Exclusive Villa Mami - Siena
10 1 review

Exclusive Villa Mami

house, Siena
This exclusive villa in Siena offers a luxurious retreat, located approximately 4.7 miles from Piazza del Campo and 3.4 miles from the National Museum of Etruscan Archaeology.
Boasting 3230 square feet of living space, this accommodation features 6 bedrooms, 6 bathrooms, a private infinity pool, a garden, and air conditioning, with walking and bike tours available for guests.

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.

[Duomo & Piazza Del Campo: 8-min Walk]  Sleeps 8 - Siena
9.7 364 reviews

[Duomo & Piazza Del Campo: 8-min Walk] Sleeps 8

house, Siena
Centrally located in Siena, this newly renovated apartment is an 8-minute walk from the Siena Cathedral and Piazza del Campo, offering prime access to luxury boutiques and amenities.
This 980 sq ft, three-level apartment comfortably accommodates up to 8 guests, featuring a brand-new kitchen, a dedicated Smart Working corner with super-fast WiFi, and luxurious bathrooms with walk-in showers, making it an ideal holiday home for exploring this historic Italian city.
Idyllic Siena Retreat Vineyard View, Private Pool - Siena
9.4 187 reviews

Idyllic Siena Retreat Vineyard View, Private Pool

house, Siena
This exclusive villa offers a secluded Tuscan experience just a 15-minute drive from Siena's historic center, providing peace and quiet while remaining conveniently close to Florence.
Boasting 3,200 square feet of renovated stable space, this family-friendly holiday home accommodates up to 8 guests with 4 air-conditioned bedrooms and 3 bathrooms, featuring a private pool overlooking vineyards and an equipped kitchen.
Beautifully Restored Tuscan Villa, With Private Pool And Breathtaking Views - Siena
10 24 reviews

Beautifully Restored Tuscan Villa, With Private Pool And Breathtaking Views

house, Monteroni d'Arbia
Boasting a unique rural setting amidst rolling hills south of Siena, this villa in Monteroni d'Arbia offers panoramic Tuscan views, with the Torre del Mangia visible from the property's olive groves.
This family-friendly holiday home comfortably accommodates up to 17 guests with 8 en-suite bedrooms, featuring a contemporary semi-professional kitchen, a brand new private swimming pool, an indoor yoga studio, and extensive grounds with woodland, a lavender field, and a pond.
Villa "La Scuola" "The Charming School" - Siena
9.9 95 reviews

Villa "La Scuola" "The Charming School"

house, Siena
Experience a Tuscan farm stay at this 19th-century villa, located on the Montechiaro estate just 7 miles from Siena, offering organic wine and olive oil production.
This family-friendly holiday home features 5 bedrooms, 5 bathrooms, and can accommodate up to 10 guests with two fully equipped kitchens, a private fenced pool, spacious terraces, and a garden with a children's playhouse, all providing stunning panoramic views of the Tuscan countryside.
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