Villas and Vaction Homes in Siena

5983 Villas and Vacation Homes in Siena

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Siena
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Villa In Vagliagli With 40 Bedrooms Sleeps 100 - Siena
Siena
03/06 – 03/09
$44170/nighttotal: $132510 (3 )

Villa In Vagliagli With 40 Bedrooms Sleeps 100

49 3
house, Castelnuovo Berardenga
Villa Nero Scopeti, a historic estate in Castelnuovo Berardenga, offers unparalleled views of Siena, including the Torre del Mangia and Siena Cathedral, and is situated a short distance from the city.
This luxurious villa spans over 58,130 square feet, featuring 49 bedrooms and 49 bathrooms to accommodate up to 100 guests, with amenities such as a private pool, spa, fitness center, and extensive grounds for exclusive events and bespoke experiences.
Holiday Home 'Casale' With Shared Pool, Shared Garden And Wi-fi - Siena
10 2 reviews
Siena
03/07 – 03/08
$805/nightfor 1 night

Holiday Home 'Casale' With Shared Pool, Shared Garden And Wi-fi

2 4
apartment, Castelnuovo Berardenga
Located in Castelnuovo Berardenga, this apartment offers a prime Tuscan experience just a 10-mile drive from the historic city of Siena.
This family-friendly holiday home features 970 square feet of living space with 2 bedrooms and 2 bathrooms, accommodating up to 4 guests, and includes a shared outdoor area with a pool, garden, barbecue, and high-speed Wi-Fi, with options for a whirlpool bathtub and extra activities like truffle hunting.
Villa Capanna: A Window Onto Tuscany - Siena
Siena
04/20 – 04/21
$1973/nightfor 1 night

Villa Capanna: A Window Onto Tuscany

6 4
house, Siena
Experience authentic Tuscan living at this renovated barn, located just 6 miles from Siena's historic center within a Chianti winery estate, offering panoramic views of medieval towers and easy access to attractions like the Chianti Sculpture Park.
This spacious 6-bedroom, 5-bathroom villa comfortably accommodates 10 guests, featuring air conditioning, a private swimming pool open from May to October, a garden with barbecue, fireplace, free Wi-Fi, and private parking, making it an ideal holiday home for exploring the region.
Appartamento Del Campo - Siena
Siena
05/18 – 05/22
$187/nighttotal: $748 (4 )

Appartamento Del Campo

2 2
house, Siena
Appartamento del Campo is located in Siena, just 200 yards from the city center and steps from Piazza del Campo, offering unparalleled proximity to this historic square and walking distance to attractions like the National Museum of Etruscan Archaeology and Palazzo Chigi-Saracini, with Siena Train Station 2.6 miles away.
This 1020 square foot house comfortably accommodates up to 10 guests across its 2 bedrooms and 1 bathroom, and features a fully equipped kitchen with a microwave oven and dishwasher, complimentary Wi-Fi, and city views, making it an ideal holiday home for exploring Siena.
Villa Nannini  Siena - Siena
9.9 66 reviews
Siena
07/10 – 07/14
$1196/nighttotal: $4784 (4 )

Villa Nannini Siena

5 8
house, Siena
Experience Tuscan living in this restored 1800s farmhouse, a luxurious villa located just 15 miles from Siena's historic center, offering easy access to renowned landmarks within a prestigious and tranquil countryside setting.
This expansive holiday home boasts 5,170 square feet, accommodating up to 10 guests across two levels with 5 bedrooms, 3 bathrooms, a well-equipped kitchen, air conditioning in most bedrooms, and an impressive 12m x 6m oval swimming pool set within a fenced garden and olive grove.
Suite La Rosa - Siena
9.3 109 reviews
Siena
05/20 – 05/22
$180/nighttotal: $360 (2 )

Suite La Rosa

1 3
house, Monteroni d'Arbia
Located in Colle Malamerenda, this villa is situated 6.8 miles from Piazza del Campo and 30 miles from Piazza Matteotti, offering proximity to Palazzo Chigi-Saracini and the National Museum of Etruscan Archaeology, both 5 miles away.
This air-conditioned holiday home boasts 840 square feet of living space, accommodating up to 5 guests with 1 bedroom and 1 bathroom, and features a garden with barbecue facilities, a patio with garden views, a living room, an equipped kitchen, a Jacuzzi, and a sun terrace with outdoor dining.
Holiday House In Siena - Siena
10 2 reviews
Siena
02/19 – 07/31
$116/nighttotal: $18792 (162 )

Holiday House In Siena

1 2
apartment, Siena
Just a 7-minute walk from Piazza del Campo and 3 minutes from Piazza San Francesco, this apartment offers exclusive access to expansive private grounds, including a 900 sqm garden and a 30,000 sqm park, providing unparalleled privacy and a tranquil natural setting just outside Siena's historic walls.
This welcoming holiday home features refined Tuscan-style furnishings, a well-equipped kitchen, a dedicated living room with an extensive library focused on Siena, complimentary bicycles, and secure private parking for two cars, ensuring a comfortable and culturally immersive stay.
Chiara Luxury Country Home - Siena
9.8 50 reviews
Siena
03/07 – 03/14
$1074/nighttotal: $7518 (7 )

Chiara Luxury Country Home

6 1
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.
[Duomo 8 Min. Walk]  Luxury Home • Self Check-in - Siena
9.8 319 reviews
Siena
05/01 – 05/03
$423/nighttotal: $846 (2 )

[Duomo 8 Min. Walk] Luxury Home • Self Check-in

3 5
apartment, 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.
Villa Il Principe - Siena
Siena
03/07 – 03/08
$6007/nightfor 1 night

Villa Il Principe

9 4
house, Castellina in Chianti
Located in Castellina in Chianti, this exclusive luxury villa is set amidst world-famous Tuscan hills, surrounded by private vineyards and olive groves, offering a rich historical background with ownership by the same noble family since 1920, and is a short drive from Florence and Siena.
This family-friendly holiday home accommodates up to 16 guests with 9 ensuite bedrooms and 10 bathrooms, featuring air conditioning, a sea water swimming pool, an organic garden, and the option for on-site staff for a blend of private home and luxury boutique hotel experience.
Magione 10 - Siena
9.8 55 reviews
Siena
07/19 – 07/26
$404/nighttotal: $2828 (7 )

Magione 10

2 4
house, Siena
This recently renovated villa, Magione 10, is centrally located in Siena, just a 14-minute walk from the iconic Piazza del Campo and 25 miles from Piazza Matteotti.
Offering 700 square feet of living space, this family-friendly holiday home features 2 bedrooms, a fully equipped kitchen with a fridge and dishwasher, air conditioning, and concierge services, accommodating up to 11 guests with on-site parking and a mini-market for convenience.
Villa "Le Vallecchie" Overlooking Siena And With Private Swimming Pool - Siena
9.5 69 reviews
Siena
07/12 – 07/26
$656/nighttotal: $9184 (14 )

Villa "Le Vallecchie" Overlooking Siena And With Private Swimming Pool

4 7
house, Monteriggioni
Boasting a secluded rural mountain location in Monteriggioni, this independent villa offers easy access to renowned wineries such as Terra di Seta and Lilliano Estate Winery, and is a short drive from local attractions including Terre di Vini and the Chianti Observatory.
Spanning 1940 square feet, this family-friendly holiday home accommodates up to 8 guests across 4 bedrooms and 4 bathrooms, featuring a private outdoor swimming pool, an illuminated garden with an oak grove, a billiards room, and 24/7 emergency assistance.

Villas and Vacation Homes with Pool in Siena

Among the 5983 villas in Siena here are the 8 best villas with pool

Cozy Cottage With Pool 10 Km From Siena, Pets Allowed - Siena
Siena
08/15 – 08/22
$520/nighttotal: $3640 (7 )

Cozy Cottage With Pool 10 Km From Siena, Pets Allowed

2 4
apartment, Siena
This welcoming villa in Siena offers easy access to natural beauty, being a 15-minute walk from Val di Merse and a 12-minute drive to the historic San Leonardo al Lago.
Enjoy a communal pool, garden, deck, and firepit at this family-friendly, pet-friendly apartment, which features 2 bedrooms, 2 bathrooms, air conditioning, and onsite parking for up to 4 guests.
Villa Colombaio - Siena
9.7 13 reviews
Siena
06/26 – 07/02
$964/nighttotal: $5784 (6 )

Villa Colombaio

4 8
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.
Casa Regina - Relax E Arte - Si - Siena
9.9 15 reviews
Siena
08/15 – 08/22
$256/nighttotal: $1792 (7 )

Casa Regina - Relax E Arte - Si

3 4
apartment, 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.
Casa Di Luca Eroica, Pool - Siena
10 1 review
Siena
08/08 – 08/15
$912/nighttotal: $6384 (7 )

Casa Di Luca Eroica, Pool

4 9
house, Castelnuovo Berardenga
Located in the Sienese Chianti region near Castelnuovo Berardenga, this villa is directly on the L'Eroica trail and approximately 30 to 40 minutes by car from Siena, 45 to 55 minutes from San Gimignano, 25 to 35 minutes from Monteriggioni, and 1 hour and 15 minutes from Florence.
This 1720 square foot holiday home accommodates up to 10 guests with 4 bedrooms and 3 bathrooms, featuring a private pool, a 360 m² terrace, a games room with billiards and table tennis, and bicycles available for rent.
La Dimora Di Teresa - Siena
9.5 10 reviews
Siena
07/12 – 07/26
$693/nighttotal: $9702 (14 )

La Dimora Di Teresa

4 7
house, Sovicille
Located in Ancaiano, this villa is 8.9 miles from Piazza del Campo and 7.6 miles from the National Museum of Etruscan Archaeology, offering a secluded retreat.
This spacious 2690 square feet holiday home accommodates up to 14 guests with 4 bedrooms, 4 bathrooms, a private pool, jacuzzi, and expansive garden, perfect for exploring nearby cycling routes.
Casa Regina - Siena
8.5 14 reviews
Siena
05/01 – 05/03
$652/nighttotal: $1304 (2 )

Casa Regina

3 9
house, Siena
Located in Val di Pugna, this welcoming villa is just 3.1 miles from Siena's iconic Piazza del Campo and 48 miles from Florence Airport.
This spacious holiday home offers 1290 square feet of living space with 3 bedrooms and 2 bathrooms, accommodating up to 17 guests with a private pool, garden, and Wi-Fi.
Villa Le Tortore Privata Lusso Piscina Relax Siena - Siena
10 234 reviews
Siena
06/27 – 07/03
$961/nighttotal: $5766 (6 )

Villa Le Tortore Privata Lusso Piscina Relax Siena

1 2
house, Siena
Located in Siena, this luxury villa is a 17-minute walk from Piazza del Campo and close to San Cristoforo Church and Palazzo Chigi-Saracini.
This 1080 sq ft holiday home features 3 bedrooms, 2 bathrooms with hot tubs, a well-equipped kitchen, air conditioning, a swimming pool, Jacuzzi, garden, and tennis court, offering on-site massage services and a free shuttle.
2400 M² Villa ∙ 5 Bedrooms ∙ 10 Guests - Siena
Siena
08/08 – 08/15
$1145/nighttotal: $8015 (7 )

2400 M² Villa ∙ 5 Bedrooms ∙ 10 Guests

5 9
house, Siena
Offering stunning panoramic views of the Siena hills, Val d'Orcia, and Mount Amiata, this villa is located in the Tuscan countryside, just a few miles from the UNESCO World Heritage site of Siena.
This spacious 25,830 sq ft holiday home features 5 bedrooms and 5 bathrooms, accommodating up to 10 guests with air conditioning, Wi-Fi, a fully equipped kitchen, a garden, and a shared swimming pool perfect for enjoying the Italian landscape.

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.

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