Villas and Vaction Homes in Siena

8524 Villas and Vacation Homes in Siena

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Siena
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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.

Chiara Luxury Country Home - Siena
9.8 50 reviews

Chiara Luxury Country Home

house, Monteriggioni
Chiara Luxury Country Home is located in Monteriggioni, a historic walled village, offering convenient access to Siena's Piazza del Campo, just 3.1 miles away, and Piazza Matteotti, 23 miles away.
This spacious 6-bedroom villa features air conditioning, a private swimming pool, jacuzzi, fitness center, and a garden, making it an ideal holiday home for families and groups seeking luxury amenities and ample space.
Luxury Serviced Cottage In A Historical Chianti Borgo - Siena
10 138 reviews

Luxury Serviced Cottage In A Historical Chianti Borgo

house, Castellina in Chianti
Located 10 miles from Piazza del Campo in Castellina in Chianti, this country villa is also 18 miles from Piazza Matteotti and 37 miles from Florence Airport.
This welcoming 2-bedroom holiday home offers a private patio with barbecue, an outdoor bath, a pool with hot tub, and an on-site tennis court, perfect for outdoor adventures and relaxation.
La Capanna Di Elfo Luxury Villa View - Siena
10 128 reviews

La Capanna Di Elfo Luxury Villa View

house, Siena
Located 5.7 miles from Siena's historic center and Piazza del Campo, this welcoming villa offers a tranquil escape with convenient access to Palazzo Chigi-Saracini and the National Museum of Etruscan Archaeology, both 3.8 miles away.
Boasting a generous 1940 square feet of living space, this family-friendly holiday home features 4 bedrooms, a full kitchen with modern appliances, air conditioning, a Jacuzzi, and a beautiful garden, complemented by complimentary Wi-Fi and private parking.
Casa Linda - Siena
10 7 reviews

Casa Linda

house, Siena
Enjoy a peaceful retreat in this tranquil apartment located just 1 mile from Siena's historic center, offering convenient access to its landmarks.
This family-friendly apartment accommodates up to 6 guests with 3 bedrooms and 3 bathrooms, featuring a private garden, shared swimming pool access from June to September, and complimentary parking.

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.

L'arco Tra Le Colline Di Castellina - Siena
No reviews

L'arco Tra Le Colline Di Castellina

house, Castellina in Chianti
L'Arco tra le colline di Castellina is situated in Gropina, offering a countryside escape 8.5 miles from Piazza del Campo and 18 miles from Piazza Matteotti in Castellina in Chianti.
This 580 square foot villa accommodates up to 7 guests with 2 bedrooms and 1 bathroom, featuring a dishwasher, fireplace, year-round outdoor pool, and tennis court, with complimentary WiFi and private parking.
Villa Colombaio, Country-house In Wine Estate 5km From Siena - Siena
10 15 reviews

Villa Colombaio, Country-house In Wine Estate 5km From Siena

house, Siena
Nestled in the Sienese countryside, this welcoming villa is located approximately 3 miles from Siena's historic center, offering easy access to landmarks like San Spirito and Porta Romana within a 20-minute drive.
Spanning 3230 square feet, this family-friendly holiday home accommodates up to 8 guests with 5 bedrooms and 3 bathrooms, featuring a kitchen with a fridge and dishwasher, a swimming pool, jacuzzi, terrace, garden, tennis court, and parking, all on a sprawling 340-acre wine estate with organized activities like wine tastings.
Villa Colombaio - Siena
9.5 15 reviews

Villa Colombaio

house, Siena
Located 5.5 miles from Siena's Piazza del Campo, Villa Colombaio offers a tranquil retreat outside the city center, perfect for exploring the Tuscan countryside.
This spacious 3230 sq ft villa accommodates up to 17 guests across 4 bedrooms and 3 bathrooms, featuring a well-equipped kitchen, two living rooms, a stunning pool with a view, solarium, barbecue, and on-site yoga sessions.
Casagatti Villa Di Lusso - Siena
10 1 review

Casagatti Villa Di Lusso

house, Monteriggioni
Casagatti villa di lusso, a luxurious 4-bedroom villa, is located in Fungaia, 9.3 miles from Piazza del Campo and 28 miles from Piazza Matteotti, with Florence Airport 50 miles away.
This spacious holiday home offers 3230 square feet of living space, accommodating up to 6 guests with a private pool, garden, terrace with mountain views, and complimentary WiFi.

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.

Casa Berto - Siena
9.7 15 reviews

Casa Berto

house, Siena
Casa Berto, a house in Siena, is conveniently located 4.3 miles from the National Museum of Etruscan Archaeology and 5.7 miles from Siena Train Station, with Piazza del Campo just 6.5 miles away.
This welcoming holiday home offers 650 square feet of living space, featuring 2 bedrooms, 1 bathroom, a fully equipped kitchen with a dining area, free WiFi, and private parking, complemented by a tranquil garden with outdoor seating and play equipment.
Charming Villa In The Chianti Vineyards - Siena
9.8 32 reviews

Charming Villa In The Chianti Vineyards

house, Castelnuovo Berardenga
Nestled in the Santa Margherita - La Suvera area of Castelnuovo Berardenga, this exclusive villa offers breathtaking panoramic views amidst the rolling hills and vineyards of Chianti Classico.
This welcoming holiday home accommodates up to 9 guests with 5 bedrooms and 3 bathrooms, featuring a stunning panoramic swimming pool, air conditioning, internet, and exclusive parking for a comfortable stay.
Villa Panoramica Con Piscina Privata, 6km Da Siena - Siena
10 8 reviews

Villa Panoramica Con Piscina Privata, 6km Da Siena

house, Siena
Immersed in the spectacular countryside of Siena, Villa Santa Virginia offers breathtaking views of the Crete Senesi from its prime location on the highest hill of Tenuta Larnianone, just 3.7 miles from Siena's city center.
This exclusive villa accommodates up to 12 guests across seven bedrooms, featuring a private unheated swimming pool open from May 1st to September 30th, a spacious garden, and optional annex for larger groups.
Ocabianca Casa Per Le Vacanze - Siena
9.1 15 reviews

Ocabianca Casa Per Le Vacanze

house, Casole d'Elsa
Located in Casole d'Elsa, Ocabianca casa per le vacanze is situated 13 miles from Piazza del Campo and 29 miles from Piazza Matteotti, offering a tranquil retreat in the Tuscan countryside.
This welcoming 750 square foot villa accommodates up to 7 guests with 2 bedrooms and 2 bathrooms, featuring a well-equipped kitchen, air conditioning, free WiFi, and a garden with patio perfect for outdoor relaxation and cycling enthusiasts.

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.

120 M² Farmhouse ∙ 2 Bedrooms ∙ 5 Guests - Siena
No reviews

120 M² Farmhouse ∙ 2 Bedrooms ∙ 5 Guests

farm, Chiusdino
Farm for 5 people. This accommodation is located in Chiusdino.
Facilities and services include a washing machine, a swimming pool and a restaurant. Take advantage of the terrace in this accommodation in Chiusdino.
Villa Larniano - Siena
9.9 28 reviews

Villa Larniano

house, Siena
Located in Siena, this spacious 5-bedroom villa is just 5.4 miles from Piazza del Campo, offering an exclusive Tuscan experience.
This expansive 5490 sq ft holiday home boasts 3 living rooms, a private garden with a fenced swimming pool, a pool table, barbecue facilities, and indoor and outdoor play areas, with bicycle rentals available for exploring the scenic countryside.
Villa Charming On The Hills | Mixed Of Authentic And Modern Tuscan Style - Siena
No reviews

Villa Charming On The Hills | Mixed Of Authentic And Modern Tuscan Style

house, Siena
Located just a few miles from the historic city of Siena, this villa offers panoramic views of the Tuscan countryside, including Siena hills, Val d'Orcia, and Mount Amiata.
This 25,830 sq ft holiday home accommodates up to 10 guests across 5 bedrooms and 5 bathrooms, featuring a fully equipped kitchen, air conditioning, a garden, and a shared swimming pool.
Terratetto Premium Nel Cuore Di Siena - Via Camollia - Siena
10 2 reviews

Terratetto Premium Nel Cuore Di Siena - Via Camollia

house, Siena
Just a 15-minute walk from Piazza del Campo, this air-conditioned vacation home offers convenient access to Siena's central landmark, with Piazza Matteotti located 25 miles away.
This 1290 sq ft holiday home accommodates up to 7 guests with 2 bedrooms and 3 bathrooms, featuring complimentary WiFi, a fully equipped kitchen, and a flat-screen TV.
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