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Siena villas
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113 Villa rentals in Siena

Best Holiday Houses with Swimming Pool in Siena

Having a pool at your vacation home in Siena lets you enjoy a proper swim in the city without any extra planning.

Agriturismo Il Poggiarello - Siena
9.0 308 reviews
Siena
08/28 – 08/31
$183/nighttotal: $549 (3 )

Agriturismo Il Poggiarello

1 2
farm , Siena
Agriturismo Il Poggiarello is a Tuscan farmhouse located near San Rocco a Pilli, a short drive from Siena and the Abbey of St Galgano. The farm has excellent ratings for cleanliness, location, and overall experience.
The farmhouse offers a peaceful escape in the Tuscan countryside. Guests can enjoy the outdoor pool, comfortable sun loungers, and a garden. The property also provides modern amenities like free Wi-Fi, parking, and well-equipped kitchens in the apartments.
54 M² House ∙ 2 Bedrooms ∙ 4 Guests - Siena
Siena
09/07 – 09/08
$336/nightfor 1 night

54 M² House ∙ 2 Bedrooms ∙ 4 Guests

2 2
house , Castellina in Chianti
This Tuscan villa rental is located in an ancient village in the Sienese hills, situated between Castellina in Chianti and San Gimignano.
This 580 square feet apartment accommodates up to 6 guests with 2 bedrooms and a sofa bed, featuring a kitchen, fireplace, garden with gazebo, shared pool with a children's pool, tennis court, and parking.
Villa Capannina With Private Pool, Wi-fi And Air Conditioning - Siena
Siena
09/07 – 09/08
$1629/nightfor 1 night

Villa Capannina With Private Pool, Wi-fi And Air Conditioning

4 2
house , Siena
Villa Capannina, a renovated former stable, is situated in Vico d’Arbia, approximately 6 miles south of Siena's city center, offering a peaceful retreat with olive tree views and convenient access to landmarks like Porta Camollia and San Spirito. This family-friendly villa accommodates up to 8 guests in 4 bedrooms and 3 bathrooms, featuring air conditioning in bedrooms, a fully equipped kitchen with a fridge, microwave, and dishwasher, an outdoor pool open from May to October, and a garden, making it ideal for exploring Florence and the Tuscan coast or cycling in the surrounding countryside.
Casa Regina - Siena
8.3 15 reviews
Siena
06/26 – 06/27
$240/nightfor 1 night

Casa Regina

3 2
house , Siena
Casa Regina, located in Val di Pugna, is a 3.1-mile drive from Siena's Piazza del Campo and 27 miles from Piazza Matteotti in Tuscany.
This 1,290-square-foot house features three bedrooms, two bathrooms, and accommodates up to 17 guests, offering a private pool, terrace, garden, free Wi-Fi, and free parking, along with a fully equipped kitchen including a dishwasher and microwave.

Best family friendly Siena villas and beach houses

Among the 113 accommodations in Siena, here are the 4 best family friendly villas and beach houses

Scorpione - Siena
9.2 32 reviews
Siena
09/07 – 09/14
$194/nighttotal: $1358 (7 )

Scorpione

3 2
house , Gaiole in Chianti
Bacco is a vacation rental located in Gaiole in Chianti, just 16 miles from Piazza del Campo in Siena and the town center of Gaiole. The house has received very good ratings for location, cleanliness, and overall user experience.
The rental offers a private entrance and outdoor seating for enjoying the peaceful surroundings. Guests can take advantage of amenities like a fully equipped kitchen, air conditioning, free Wi-Fi, and parking, as well as a swimming pool, Jacuzzi, and a garden.
Agriturismo San Sano - Siena
9.4 2651 reviews
Siena
08/28 – 08/31
$190/nighttotal: $570 (3 )

Agriturismo San Sano

1 2
farm , Gaiole in Chianti
Agriturismo San Sano is a 3-star hotel surrounded by vineyards and olive groves in the heart of the Chianti region. It is within a 6-mile radius of major tourist attractions and landmarks in Gaiole in Chianti. The hotel has excellent user ratings and offers a private pool, fireplace, spacious 3-bedroom villa with a patio and free WiFi, a fully equipped kitchen, garden, barbecue grills, and more.
The hotel is located in a unique situation in the heart of the Chianti region, surrounded by vineyards and olive groves. It is within a 6-mile radius of major tourist attractions and landmarks in Gaiole in Chianti, all within a 6-mile radius. The hotel has a private pool and fireplace for relaxation and comfort. It also has a spacious 3-bedroom villa with a patio and free WiFi, a fully equipped kitchen with refrigerator and oven, garden and barbecue grills for outdoor enjoyment, and more.
Double Room "Maggiorana" - Siena
9.8 133 reviews
Siena
10/18 – 10/30
$119/nighttotal: $1428 (12 )

Double Room "Maggiorana"

1 2
gîte , Siena
This charming cottage is located just outside of Siena, within a 3km radius of attractions like Terra di Seta and Casalvento's Wines, offering a peaceful retreat while still being close to the city's buzz. This rental boasts excellent ratings for location, cleanliness, and overall experience.
The cottage features a bedroom and bathroom, a fully equipped kitchen, and a terrace with access to the garden and pool. Enjoy the tranquility of the Tuscan countryside, relax in the Jacuzzi, or take a dip in the seasonal pool.
Borgo A Monti Di Sotto - Siena
9.6 162 reviews
Siena
08/13 – 08/16
$432/nighttotal: $1296 (3 )

Borgo A Monti Di Sotto

2 3
house , Gaiole in Chianti
This family-friendly house is located in Monti di Sotto, a district just 11 miles from Siena's Piazza del Campo, a historic square renowned for its beauty and bustling atmosphere.
The house features a private garden, a swimming pool, and a fully equipped kitchen, perfect for enjoying a relaxing vacation in the Tuscan countryside.

Frequently Asked Questions about villa rentals in Siena

  • What are the must-see attractions in Sienne?

    You absolutely have to see the Piazza del Campo, the main square in Siena, which is a UNESCO World Heritage Site. The Siena Cathedral, also known as the Duomo, is another must-see. It's a stunning example of Romanesque and Gothic architecture. And don't forget to visit the Palazzo Pubblico, which houses the city's historical archives and art collections.
  • What are the best villa rentals in Siena?

    Among the villa rentals in Siena, Wine Resort Dievole, Casa Di Campagna In Toscana and Ripostena are the most popular ones.

  • What indoor activities for families are available in Sienne on rainy days?

    If the weather isn't cooperating, head to the Museo dell'Opera del Duomo, which houses a collection of sculptures and paintings from the Siena Cathedral. The Museo di Palazzo Chigi Saracini is also a great option, showcasing a collection of art and furniture from the 14th to 19th centuries. And for a fun and interactive experience, check out the Santa Maria della Scala, a former hospital that now houses a museum and a multimedia exhibit.
  • What are the best villa rentals with a pool in Siena?

    Wine Resort Dievole, Casa Di Campagna In Toscana and Ripostena are the best villa rentals with a pool in Siena.

  • What are the best activities in Sienne?

    Siena is a city you can explore on foot. Take a stroll through the historic center and admire the medieval architecture. You can also visit the various museums, including the Museo dell'Opera del Duomo and the Pinacoteca Nazionale. And of course, no trip to Siena is complete without attending the Palio, the famous horse race that takes place twice a year in the Piazza del Campo.
  • What are the best villa rentals with a jacuzzi in Siena?

    The best villa rentals with a jacuzzi in Siena are Casa Di Campagna In Toscana, Pieve Marsina & Borgo Argenina and Antica Fonte Residenza Di Siena.

  • What are the advantages of renting a house or a villa in Sienne

    Renting a villa in Siena gives you the freedom to cook your own meals and enjoy a more relaxed pace of life. You'll also have more space and privacy than you would in a hotel. Plus, many villas come with amenities like a private pool and garden, which can be a real treat, especially in the summer.
  • What are the best villa rentals for families and kids in Siena?

    The best villa rentals for families and kids in Siena are Wine Resort Dievole, Casa Di Campagna In Toscana and Ripostena.

  • What exclusive experiences are available when visiting Sienne?

    For a truly unique experience, consider taking a cooking class at a local farm or attending a private wine tasting at a historic winery. You can also arrange a private tour of the Duomo with a local guide or a guided walk through the city's hidden alleyways and secret gardens.
  • What are the best pet friendly villa rentals in Siena?

    The best pet friendly villa rentals in Siena are Wine Resort Dievole, Casa Di Campagna In Toscana and Ripostena.

  • Which part of Sienne would be ideal for a villa rental?

    The hills surrounding Siena, especially the areas of Monteriggioni and San Gimignano, are popular for villa rentals. These areas offer stunning views of the Tuscan countryside and are close enough to Siena to easily visit the city center. If you prefer to be closer to the city, the area of Fontebranda is a good option. It's a quiet residential neighborhood with easy access to the Piazza del Campo.
  • What are the best villa rentals with parking in Siena?

    Wine Resort Dievole, Casa Di Campagna In Toscana and Ripostena are the best villa rentals with parking in Siena.

Destinations nearby

Best Siena houses with parking

Rocca Di Castagnoli - Siena
8.6 405 reviews
Siena
06/30 – 07/03
$1101/nighttotal: $3303 (3 )

Rocca Di Castagnoli

6 12
farm , Gaiole in Chianti
Rocca di Castagnoli, a farm stay in the Chianti Classico region, is located 3.1 miles from the town of Gaiole in Chianti, offering easy access to local amenities.
This Tuscan countryside retreat provides guest rooms and apartments, featuring a swimming pool, fitness center, on-site restaurant serving Chianti Classico wine, and free Wi-Fi, plus parking.
Holiday Home L'oliviera By Interhome - Siena
8.5 2 reviews
Siena
10/16 – 10/21
$147/nighttotal: $735 (5 )

Holiday Home L'oliviera By Interhome

2 2
house , Siena
Holiday Home L'Oliviera, located in Certano, offers a peaceful escape 5.6 miles from Siena's Piazza del Campo and within a 3-7 mile radius of other major attractions like the National Picture Gallery and Palazzo Chigi-Saracini.
This 650-square-foot (approximately 60-square-meter) Siena rental boasts two bedrooms, one bathroom, and accommodates up to seven guests, featuring a fully equipped kitchen, free Wi-Fi, private parking, and a terrace or balcony.
Villa Delizia - Arceno Rentals Club - Siena
9.8 8 reviews
Siena
08/13 – 08/16
$259/nighttotal: $777 (3 )

Villa Delizia - Arceno Rentals Club

2 3
house , Castelnuovo Berardenga
Villa Delizia is a house located in San Gusmè, 14 miles from Piazza del Campo and 25 miles from Piazza Matteotti, offering a tranquil setting in the Chianti region.
This air-conditioned villa spans 1290 square feet, features 2 bedrooms, 2 bathrooms, and accommodates up to 6 guests with amenities including a full kitchen, private balcony, barbecue, and garden, plus shuttle service and bicycle rentals for exploring the area.
Rietine24 - Siena
9.7 165 reviews
Siena
06/20 – 06/23
$166/nighttotal: $498 (3 )

Rietine24

1 2
farm , Gaiole in Chianti
Rietine24 is a farm stay located in the heart of the Chianti region, just 17 miles from Siena and 19 miles from Gaiole in Chianti. The farm stay offers stunning views of the rolling hills and vineyards, and is just a short drive from popular tourist attractions.
Rietine24 has excellent user and location ratings. The farm stay offers air-conditioned rooms with patios or balconies, as well as a shared lounge and seating areas. Guests can enjoy a refreshing swim in the seasonal outdoor pool, relax in the garden, or gather around the outdoor fireplace. The farm stay also offers bike rentals, and an airport shuttle service.

Best Siena houses with a garden

Exclusive Villa Mami - Siena
10 1 review
Siena
08/06 – 08/08
$3310/nighttotal: $6620 (2 )

Exclusive Villa Mami

6 8
house , Siena
Exclusive Villa Mami, a six-bedroom, six-bathroom estate in Siena, Italy, is located approximately 4.7 miles from Piazza del Campo and 3.4 miles from the National Museum of Etruscan Archaeology.
This 3230-square-foot villa boasts a private infinity pool, a garden, free Wi-Fi, free parking, and can comfortably accommodate up to 24 guests, offering a fully equipped kitchen and convenient access to airport shuttle services.
50 M² Farmhouse ∙ 1 Bedroom ∙ 4 Guests - Siena
10 1 review
Siena
08/28 – 08/31
$192/nighttotal: $576 (3 )

50 M² Farmhouse ∙ 1 Bedroom ∙ 4 Guests

1 2
farm , Siena
Farm listing for 4 guests with an excellent rating of 100% based on 1 reviews. You will be located in Siena.
Services and facilities include a kitchen, a barbecue and a swimming pool.
Podere La Strega - Siena
9.2 556 reviews
Siena
10/16 – 10/21
$375/nighttotal: $1875 (5 )

Podere La Strega

1 2
house , Siena
Podere La Strega, a restored 18th-century farmhouse, is situated 2.5 miles from Siena, Italy, a 5-minute drive from Siena Train Station, offering easy access to San Gimignano (a 50-minute drive).
This Siena vacation rental boasts a swimming pool, terrace, and garden, plus amenities including Wi-Fi, air conditioning, and on-site parking, and it accommodates families and pets.
Villa L’avvenire – Villa Lusso Con Piscina A Siena - Siena
Siena
07/24 – 07/25
$3302/nightfor 1 night

Villa L’avvenire – Villa Lusso Con Piscina A Siena

1 6
house , Siena
This 19th-century historic villa, offering exclusive use and Tuscan privacy, is located just minutes from Siena's center, providing a secluded Tuscan experience within easy reach of the city and surrounding countryside. This estate accommodates up to 16 guests with 8 bedrooms and 1 bathroom, featuring a seasonal swimming pool, a garden, air conditioning, internet, a full kitchen, and private parking, with optional concierge services available.
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