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Pienza vacation rentals
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Best Vacation rentals and Airbnb offers in Pienza

Browse Vacation Rentals in the Historic District of Pienza

From vibrant downtown areas to historic streets, these Pienza vacation rentals put you close to everything worth seeing.

At The Arch - In The Heart Of The Val D'orcia - Pienza
10 108 reviews

At The Arch - In The Heart Of The Val D'orcia

apartment, Pienza
This Pienza apartment boasts an exceptional central location, steps from Piazza Pio II, Palazzo Borgia, and the Diocesan Museum, offering easy access to all amenities.
The two-bedroom, one-bathroom rental sleeps three guests and includes a fully equipped kitchen with a refrigerator, freezer, and dishwasher, air conditioning, a garden, and parking.
Nel Cuore Di Pienza, A Soli 50 Metri Dal Duomo! - Pienza
10 47 reviews

Nel Cuore Di Pienza, A Soli 50 Metri Dal Duomo!

apartment, Pienza
This Pienza apartment rental boasts a prime location in the historic center, just 164 feet from the Duomo and Palazzo Piccolomini, offering easy access to Pienza's main street, Corso Il Rossellino, and the Casello viewpoints.
The one-bedroom, one-bathroom unit sleeps three, features a fully equipped kitchen with fridge, freezer, and dishwasher, and provides complimentary internet access.
La Casa Di Agnese Accogliente Appartamento - Pienza
10 5 reviews

La Casa Di Agnese Accogliente Appartamento

apartment, Pienza
This apartment is located a short distance from Pienza's historic center, providing convenient access to its Renaissance architecture.
This two-bedroom rental accommodates up to three guests and features a fully equipped kitchen, a private garden, and heating for year-round comfort.
Samsara Apartment - Pienza
10 10 reviews

Samsara Apartment

apartment, Pienza
Samsara Apartment in Pienza, Italy offers a family-friendly rental conveniently located near the thermal baths of Bagno Vignoni and Montepulciano Terme (both approximately 6 miles away), with Mount Amiata about 17 miles distant.
This 700-square-foot (approximately 65-square-meter) apartment features two bedrooms, one bathroom, and sleeps eight, boasting a fully equipped kitchen with a dishwasher and microwave, air conditioning, and free Wi-Fi.

Best Pienza vacation rentals with air conditioning

Villa Tiberini Wine Relais - Pienza
9.7 23 reviews

Villa Tiberini Wine Relais

farm, Torrita di Siena
Villa Tiberini Wine Relais, located in Osteria Delle Noci, is 28 miles from Piazza Grande and offers city views.
This farm stay provides self-catering accommodations with a kitchen, refrigerator, dishwasher, free Wi-Fi, private parking, an outdoor swimming pool, a children's playground, and barbecue facilities, with select units featuring terraces or balconies and mountain or lake vistas.
Appartamento Con Vista - Montepulciano - Pienza
9.2 44 reviews

Appartamento Con Vista - Montepulciano

apartment, Montepulciano
This Montepulciano apartment rental is conveniently located near Montepulciano Terme, approximately 3.7 miles away, offering easy access to other thermal baths such as Bagno Vignoni and Bagni San Filippo.
The 540-square-foot (50-square-meter) unit features one bedroom, one bathroom, and can comfortably accommodate three guests; amenities include a fully equipped kitchen, air conditioning, free Wi-Fi, private parking, and a balcony with stunning Tuscan countryside views.
Agriturismo Il Macchione - Pienza
9.3 535 reviews

Agriturismo Il Macchione

house, Pienza
This 18th-century farmhouse is located in the Val d'Orcia Natural Park, just 0.9 miles outside of Pienza, a charming medieval town. This property boasts excellent user, location, and cleanliness ratings.
The farmhouse offers spacious apartments with a rustic style, featuring wood-beamed ceilings and antique furniture. Guests can enjoy a swimming pool with a hydromassage area, a fitness center, a tennis court, a garden, and a barbecue area.
70 M² Apartment ∙ 2 Bedrooms ∙ 4 Guests - Pienza
No reviews

70 M² Apartment ∙ 2 Bedrooms ∙ 4 Guests

apartment, Trequanda
This apartment is centrally located in Petroio, a historic village known as the "terracotta capital," offering panoramic views of the Val d'Orcia countryside and convenient proximity to the main square, just 150 feet away.
This 750-square-foot dwelling accommodates up to 4 guests with 2 bedrooms and 1 bathroom, featuring air conditioning, Wi-Fi, a fully equipped kitchen, and allowing one small pet, with nearby access to Pienza, Montepulciano, and Montalcino.

Frequently Asked Questions about vacation rentals in Pienza

  • What are some interesting places to visit in or near Pienza?

    Pienza is a beautiful town, and you shouldn't miss the Duomo, a stunning cathedral with a Renaissance-era facade. The town is also known for its historic center, which is a UNESCO World Heritage Site. If you want to explore nearby, the Val d'Orcia region is a short drive away and offers rolling hills, vineyards, and charming villages like Montepulciano and Montalcino.
  • What are the best Airbnb and vacation rentals in Pienza?

    Agriturismo Il Macchione, Residenza D'epoca La Rosa and La Casa Nel Borgo are the most popular Airbnb and vacation rentals in Pienza among travelers.

  • Which walking or cycling routes are the best in Pienza?

    The best walking route is the 'Sentiero del Vino' - it's a 6-mile loop that takes you through vineyards and olive groves, with stunning views of the Val d'Orcia. For cycling, try the 'Strada del Vino Nobile di Montepulciano', a 30-mile route that passes through vineyards and charming towns.
  • What are the most popular Airbnbs in Pienza?

    Among the Airbnbs in Pienza, The Cedar House, La Dimora Di Pienza Family 2 Rooms and Panoramic Apaertment Val D'orcia are the most popular ones.

  • What sports or outdoor activites can visitors enjoy in and around Pienza?

    Pienza is a great place for hiking, biking, and horseback riding. You can also go wine tasting in the vineyards, or take a cooking class and learn how to make local dishes. In the summer, there are many festivals and events, including the Palio di Siena, a horse race held in nearby Siena.
  • What are the best vacation rentals with a pool in Pienza?

    Agriturismo Il Macchione, Poggio Ai Gelsi and Agriturismo La Collina are the best vacation rentals with a pool in Pienza.

  • What other towns or cities can be easily accessed from Pienza?

    Siena, with its famous Piazza del Campo, is about a 40-minute drive from Pienza. Florence, the capital of Tuscany, is about a 1.5-hour drive. You can also easily reach the charming towns of Montepulciano and Montalcino, both known for their wines.
  • What are the best rentals for families and kids in Pienza?

    The best rentals for families and kids in Pienza are Agriturismo Il Macchione, Residenza D'epoca La Rosa and La Casa Nel Borgo.

  • What amenities are commonly available in vacation rentals in Pienza?

    Most vacation rentals in Pienza have kitchens, bathrooms, and bedrooms. Many also have Wi-Fi, air conditioning, and laundry facilities. Some even have private pools or gardens.
  • What are the best rentals or Airbnbs with a jacuzzi in Pienza?

    The best vacation rentals or Airbnb with a jacuzzi in Pienza are Agriturismo Il Macchione, Residenza D'epoca La Rosa and Poggio Ai Gelsi.

  • What time of year is best to rent a vacation rental Pienza?

    Spring and fall are the best times to visit Pienza, as the weather is mild and the crowds are smaller. Summer can be very hot, and winter can be cold and rainy.
  • What are the local dishes in Pienza region?

    Pienza is famous for its pecorino cheese, a sheep's milk cheese that is produced in the region. Other local dishes include ribollita, a Tuscan bread soup, and pici, a thick pasta that is often served with a simple tomato sauce.

Popular destinations

Top Vacation Rentals with Balconies in Pienza

Start your morning right with a vacation rental in Pienza featuring a private balcony and stunning views.

Terre Di Nano - Pienza
10 19 reviews

Terre Di Nano

farm, Pienza
Terre di Nano farm, in Tuscany's Val d'Orcia, offers stunning views of Montepulciano, Pienza, and Monticchiello, with Monticchiello di Pienza a 10-minute drive away (approximately 6 miles).
This one-bedroom, one-bathroom apartment rental boasts a kitchen, fireplace, and access to a pool, plus on-site olive oil and Chianti Terre di Nano wine tasting and estate tours.
Silver Dream House - Pienza
9.2 75 reviews

Silver Dream House

apartment, San Quirico d'Orcia
Silver Dream House is a 2-bedroom apartment in San Quirico d'Orcia, located 3 miles from Bagno Vignoni and 28 miles from Piazza del Campo.
This 840 sq ft rental accommodates up to 7 guests and features air conditioning, WiFi, a fully equipped kitchen with a dishwasher, and a terrace, with parking available.
90 M² House ∙ 3 Bedrooms ∙ 6 Guests - Pienza
No reviews

90 M² House ∙ 3 Bedrooms ∙ 6 Guests

house, Torrita di Siena
This restored 17th-century stone house, Casa Mulinello, is located in Torrita di Siena, offering panoramic views of the Montepulciano valley, San Biagio Temple, Monte Amiata, and Val d'Orcia hills, and is situated 0.8 miles from Montefollonico and 4.3 miles from Montepulciano. This pet-friendly, family-friendly villa spans 970 square feet, accommodates up to six guests in three bedrooms and two bathrooms, and features a kitchen with a fridge and dishwasher, a terrace, a garden, and parking, with internet access provided.
Poggio Paradiso Resort & Spa - Pienza
9.4 157 reviews

Poggio Paradiso Resort & Spa

resort, Torrita di Siena
Poggio Paradiso Resort & Spa is a family-friendly resort located in the countryside of Torrita di Siena, Tuscany. The resort has received very good ratings from users and is known for its beautiful location, comfortable accommodations, and excellent amenities.
The resort offers a variety of amenities and activities, including a swimming pool, Jacuzzi, sauna, spa, restaurant, bar, and room service. Guests can also enjoy the resort's beautiful gardens and terrace. The resort is also pet-friendly and offers free parking.

Discover Family-Friendly Vacation Rentals in Pienza

The right family vacation rental in Pienza makes all the difference, keeping you close to top city attractions.

Palazzo Massaini - Cavarciano - Pienza
9.2 1009 reviews

Palazzo Massaini - Cavarciano

farm, Pienza
Palazzo Massaini - Cavarciano is a farm stay located in the Tuscan countryside, just 3.1 miles from Pienza and a short drive from the San Biagio Church and Chianciano Terme. This farm stay has received excellent ratings for its location, cleanliness, and overall user experience.
The farm features spacious rooms and apartments with private bathrooms and kitchenettes. Guests can enjoy a sweet Italian breakfast daily, access to a swimming pool at a nearby property, and free on-site parking. The farm also produces its own wheat, olives, and wine, offering a taste of authentic Tuscan life.
La Colonna Di Montisi - Pienza
9.3 3 reviews

La Colonna Di Montisi

apartment, Montalcino
This spacious 940 square foot apartment in Montisi, a district of Montalcino, offers a family-friendly retreat 29 miles from Siena's Piazza del Campo and 14 miles from the thermal baths of Bagno Vignoni, with convenient on-site private parking and complimentary WiFi.
This air-conditioned unit features a fully equipped kitchen with a dishwasher and oven, accommodating up to 13 guests with a private entrance and close proximity to Montepulciano Terme (15 miles) and Bagni San Filippo (24 miles).
La Violetta Di San Quirico, Centro Storico. - Pienza
9.8 133 reviews

La Violetta Di San Quirico, Centro Storico.

apartment, San Quirico d'Orcia
This San Quirico d'Orcia apartment boasts breathtaking 360-degree views of the Val d'Orcia, overlooking rolling hills, vineyards, and olive groves, and is situated atop a building requiring stair climbing.
The recently renovated one-bedroom, one-bathroom unit sleeps two, features a fully equipped kitchen (fridge, freezer, microwave, dishwasher), and offers complimentary Wi-Fi and parking; guests can enjoy local insider tips from the hosts to enhance their Tuscan experience.
Cozy Home In San Quirico D'orcia - Pienza
9.1 9 reviews

Cozy Home In San Quirico D'orcia

apartment, San Quirico d'Orcia
This Tuscan vacation rental is situated near San Quirico d'Orcia, a short walk from the Renaissance garden at the Church of Santa Maria Assunta.
The one-bedroom, two-bathroom house sleeps four, features a fully equipped kitchen with a refrigerator and dishwasher, offers free parking and Wi-Fi, and includes linens and towels; pets are welcome.

Best Pienza vacation rentals with parking

Charming Tuscan Home · Montepulciano & Val D'orcia - Pienza
10 3 reviews

Charming Tuscan Home · Montepulciano & Val D'orcia

apartment, Torrita di Siena
Apartment 'Villa Tiberini 2' With Garden View, Shared Pool And Wi-fi - Pienza
No reviews

Apartment 'Villa Tiberini 2' With Garden View, Shared Pool And Wi-fi

apartment, Torrita di Siena
Agriturismo Marinello - Pienza
9.4 608 reviews

Agriturismo Marinello

farm, Pienza
La Casa Nel Borgo - Pienza
9.8 966 reviews

La Casa Nel Borgo

house, Pienza

Best 5-Star Vacation Rentals in Pienza

Discover ultimate relaxation in a luxury Pienza vacation rental, where comfort meets a central, prime location.

Agriturismo I Capraccioni Monticchiello - Pienza - Pienza
9.3 184 reviews

Agriturismo I Capraccioni Monticchiello - Pienza

gîte, Pienza

Find the Best Dog-Friendly Vacation Rentals in Pienza

Experience a pet-friendly stay in Pienza with vacation rentals located steps away from city dog parks and walking trails.

Villa Tre Civette: A Characteristic And Welcoming Apartment That Is Part Of An Ancient Country House Located In The Heart Of The Val D'orcia, With Free Wi-fi. - Pienza
No reviews

Villa Tre Civette: A Characteristic And Welcoming Apartment That Is Part Of An Ancient Country House Located In The Heart Of The Val D'orcia, With Free Wi-fi.

apartment, Pienza
Slow Living In A Tuscan Village - Pienza
9.1 7 reviews

Slow Living In A Tuscan Village

apartment, Torrita di Siena
195 M² Apartment ∙ 3 Bedrooms ∙ 8 Guests - Pienza
10 8 reviews

195 M² Apartment ∙ 3 Bedrooms ∙ 8 Guests

apartment, Pienza
Quercia Apartment - Cignella Resort Tuscany - Pienza
No reviews

Quercia Apartment - Cignella Resort Tuscany

apartment, Trequanda

Search Vacation Rentals with Swimming Pool in Pienza

Choose a Pienza rental with a pool for a refreshing swim right in the heart of the city.

Abbadia Sicille Relais - Pienza
9.1 1830 reviews

Abbadia Sicille Relais

resort, Trequanda
Palazzo Massaini - Le Scuderie - Pienza
9.3 346 reviews

Palazzo Massaini - Le Scuderie

farm, Pienza
115 M² Farmhouse ∙ 3 Bedrooms ∙ 6 Guests - Pienza
9.7 49 reviews

115 M² Farmhouse ∙ 3 Bedrooms ∙ 6 Guests

farm, Pienza
Elegant And Spacious Two-storey Villa Of 156 M2 Consisting Of A Large Living Room, Kitchen Complete With Dishwasher, Microwave Oven, Electric Oven, Coffee Machine, Kettle, Fridge And Freezer, Internal And External Dining Area, A Master Double Bedroom Wit - Pienza
No reviews

Elegant And Spacious Two-storey Villa Of 156 M2 Consisting Of A Large Living Room, Kitchen Complete With Dishwasher, Microwave Oven, Electric Oven, Coffee Machine, Kettle, Fridge And Freezer, Internal And External Dining Area, A Master Double Bedroom Wit

house, Trequanda

Top-Rated Vacation Rentals with a Hot Tub in Pienza

Unwind in style with a Pienza vacation rental featuring a hot tub, ideal for relaxing after a day in the city.

Podere Bagnolo 8, Emma Villas - Pienza
No reviews

Podere Bagnolo 8, Emma Villas

house, Pienza
Casa Valerie - Pienza
9.5 2 reviews

Casa Valerie

house, Trequanda
157 M² Villa ∙ 4 Bedrooms ∙ 8 Guests - Pienza
No reviews

157 M² Villa ∙ 4 Bedrooms ∙ 8 Guests

house, Pienza
La Casetta Degli Innamorati - Pienza
8.8 12 reviews

La Casetta Degli Innamorati

house, Torrita di Siena
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