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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.

Casa Vacanze Oliviera Pienza - Pienza
9.6 22 reviews

Casa Vacanze Oliviera Pienza

apartment, Pienza
This apartment is located near Pienza, about 9.3 miles from Bagno Vignoni, 10 miles from Montepulciano Terme, and 16 miles from Bagni San Filippo, offering easy access to thermal baths and scenic landscapes while maintaining a peaceful setting. Guests have consistently rated the apartment as very good for cleanliness and location, making it a comfortable and convenient choice for travelers.
The one-bedroom apartment has a floor area of 380 square feet and includes a fully equipped kitchenette, free Wi-Fi, and amenities like towels and bed linen, along with parking and the option to bring pets. Enjoy the opportunity to prepare your own meals, explore the nearby hiking trails, and stay connected during your stay.
La Terrazza Di Maria - Pienza
9.4 15 reviews

La Terrazza Di Maria

apartment, Pienza
La Terrazza di Maria is a spacious 1140 sq ft apartment located in Pienza, offering proximity to Bagno Vignoni (9.2 miles), Montepulciano Terme (10 miles), and Bagni San Filippo (17 miles), with Mount Amiata 29 miles distant. This air-conditioned rental accommodates up to 7 guests with 2 bedrooms and 2 bathrooms, featuring a full kitchen with a dishwasher and fridge, complimentary WiFi, a private terrace with garden views, and an outdoor dining area.
Agriturismo Podere San Gregorio - Pienza
9.2 219 reviews

Agriturismo Podere San Gregorio

farm, Pienza
Agriturismo Podere San Gregorio is a charming farmhouse located just outside Pienza, a short walk from the town center and a short drive from Montepulciano and Siena. This property consistently receives excellent ratings for its location, cleanliness, and overall experience.
This farmhouse features one bedroom with wood-beamed ceilings and terracotta floors. Guests can enjoy a peaceful garden with BBQ facilities, a complimentary breakfast basket, free Wi-Fi, and free parking.
Casa Beccofino - Pienza
8.5 213 reviews

Casa Beccofino

apartment, Pienza
Casa Beccofino in Pienza offers a one-bedroom apartment conveniently located near Montepulciano Terme (16 km), Bagno Vignoni (15 km), and Bagni San Filippo (26 km), providing easy access to Tuscan thermal spas and attractions.
This rental sleeps three, features a terrace, air conditioning, free parking, a kitchen with a refrigerator and microwave, and a flat-screen TV.

Best Pienza vacation rentals with air conditioning

Locanda Di Montisi San Martino Room Among Montalcino Hills - Pienza
No reviews

Locanda Di Montisi San Martino Room Among Montalcino Hills

apartment, Montalcino
This apartment is located in the medieval village of Montisi, Crete Senesi region, approximately 12 miles from Montalcino and a short drive to Siena, Pienza, and Montepulciano.
This one-bedroom, one-bathroom unit accommodates two guests and offers air conditioning, Wi-Fi, a workspace, and is pet-friendly, serving as an ideal base for exploring local thermal baths, wine routes, and cycling trails.
Comodo Appartamento Centrale Dimora Delle Mura - Pienza
9.9 122 reviews

Comodo Appartamento Centrale Dimora Delle Mura

apartment, San Quirico d'Orcia
This San Quirico d'Orcia apartment is uniquely located on a street bordering the historic town walls, offering immediate access to San Quirico's main attractions.
The two-bedroom, one-bathroom rental sleeps four guests and features a fully equipped kitchen with modern appliances, including a dishwasher, plus a private garden and parking.
Villa Meravigliosa - Six Bedroom Villa, Sleeps 12 - Pienza
No reviews

Villa Meravigliosa - Six Bedroom Villa, Sleeps 12

house, Pienza
This 19th-century Tuscan farmhouse, located in Pienza, offers spectacular views of the Val d'Orcia's rolling hills, with the Historic Centre of Pienza and Garden of Daniel Spoerri less than 1 mile away.
This 3,770 square foot villa accommodates up to 12 guests with 6 bedrooms and 6 bathrooms, featuring a 4 x 18 meter swimming pool, air conditioning, internet, and parking.
Frattina1860 - Pienza
9.2 13 reviews

Frattina1860

apartment, Montalcino
This Montalcino rental apartment, Frattina1860, is located in Montisi, 13 miles from Bagno Vignoni and 16 miles from Montepulciano Terme, with Siena's Piazza del Campo, Piazza Grande, National Picture Gallery, and San Cristoforo Church all within a 28-30 mile radius.
This 390 square foot condo accommodates two guests and offers a fully equipped kitchen with an oven and microwave, free Wi-Fi, air conditioning, a garden with an outdoor dining area, complimentary private parking, and an Italian breakfast.

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.

Agriturismo Capannacce - Pienza
9.8 161 reviews

Agriturismo Capannacce

apartment, Castiglione d'Orcia
This apartment is located in Bagno Vignoni, a charming village in Tuscany, just a short drive from Castiglione d'Orcia and 44 kilometers from Mount Amiata. This property has received excellent ratings for its location, cleanliness, and overall experience.
The apartment offers a comfortable and relaxing space with one bathroom and features a kitchen equipped with a fridge and microwave. Enjoy the outdoor amenities like the garden, terrace, and BBQ facilities, perfect for enjoying the Tuscan sunshine.
Villa Falco-cignella Resort Apartments In Tuscany - Pienza
No reviews

Villa Falco-cignella Resort Apartments In Tuscany

house, Trequanda
This villa is located in the Cignella Resort area of Trequanda, offering panoramic Tuscan countryside views and close proximity to landmarks such as the Church of San Francesco and Palazzo Piccolomini.
This 1530 square feet villa accommodates up to 4 guests with 2 bedrooms and 2 bathrooms, featuring a fully equipped open-space living area, complimentary Wi-Fi, free private parking, and exclusive access to resort common areas including a swimming pool and gardens.
Lovely Apartment In Villa For 6 People With A/c, Wifi, Tv And Veranda, Close To Montepulciano - Pienza
No reviews

Lovely Apartment In Villa For 6 People With A/c, Wifi, Tv And Veranda, Close To Montepulciano

apartment, Pienza
This holiday home in Monticchiello, within the Orcia Valley, is located 5.6 miles from Montepulciano and near Pienza landmarks like Chiesa di San Francesco and Palazzo Piccolomini.
This spacious 4310 sq ft residence accommodates up to 6 guests in 3 bedrooms and 3 bathrooms, featuring air conditioning, WiFi, a shared garden with barbecue, and private parking for two cars.
Noi2vacanze Fortino D'amore - Pienza
9.3 44 reviews

Noi2vacanze Fortino D'amore

house, Radicofani
Noi2Vacanze FORTINO D'AMORE, located in Contignano near Radicofani, Italy, offers easy access to Bagni San Filippo (8.9 miles) and Mount Amiata (19 miles), perfect for exploring Tuscany's natural beauty.
This 650-square-foot (approximately 60 square meters) one-bedroom rental, sleeping up to three guests, features two bathrooms, a fully equipped kitchen with a dishwasher, air conditioning, Wi-Fi, and a terrace—ideal for a relaxing Tuscan getaway.

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.

15 Min Da Montepulciano - Villa Chiara - Pienza
8.5 39 reviews

15 Min Da Montepulciano - Villa Chiara

apartment, Torrita di Siena
This three-bedroom, two-bathroom apartment rental in Montefollonico, a short drive from Montepulciano and other Tuscan towns, offers stunning mountain views and easy access to local attractions.
The 1390-square-foot residence features a garden, terrace, parking, and amenities such as a fully equipped kitchen, Wi-Fi, and can comfortably accommodate up to 11 guests.
Foresteria Del Teatro Povero - Pienza
9.2 36 reviews

Foresteria Del Teatro Povero

apartment, Pienza
Foresteria del Teatro Povero is located in Monticchiello, a charming village just 6.5 miles from Montepulciano Terme and 8.2 miles from Bagno Vignoni, offering a peaceful escape from the tourist crowds. The apartment boasts excellent ratings for user experience, location, and cleanliness.
This 2-bedroom, 1-bathroom apartment spans 680 square feet and accommodates up to 3 guests. Enjoy amenities like a fully equipped kitchen, a cozy fireplace, and free Wi-Fi, along with on-site dining, bike rentals, and a tour desk for exploring the Tuscan countryside.
Samsara Apartment Elegant Apartment In The Historical Center. - Pienza
10 2 reviews

Samsara Apartment Elegant Apartment In The Historical Center.

apartment, Pienza
This Pienza apartment is located a short distance from Artemisia Gallery and Palazzo Borgia, with Enoteca Di Ghino and Triacca Winery offering local experiences nearby.
This 700 square foot unit offers 2 bedrooms, 1 bathroom, and sleeps up to 5 guests, featuring a minimalist design, aromatherapy diffusers, a library, and family amenities including a crib and high chair, with air conditioning and parking available.
Palazzo Massaini - Le Scuderie - Pienza
9.4 319 reviews

Palazzo Massaini - Le Scuderie

farm, Pienza
Palazzo Massaini - Le Scuderie, a Pienza farmhouse stay, is conveniently located 8.1 miles from Montepulciano Terme and 11 miles from Bagno Vignoni, offering easy access to major Tuscan towns.
This one-bedroom, one-bathroom rural retreat sleeps two guests and boasts an infinity pool, on-site yoga classes, bicycle rentals, a private terrace, and a complimentary continental breakfast featuring local specialties.

Best Pienza vacation rentals with parking

Chez Anna - Pienza
8.7 9 reviews

Chez Anna

apartment, San Quirico d'Orcia
Agriturismo Bombina - Pienza
9.4 139 reviews

Agriturismo Bombina

farm, Montalcino
Stunning Apartment In Monticchiello With Wifi - Pienza
9.0 8 reviews

Stunning Apartment In Monticchiello With Wifi

apartment, Pienza
Casa Oliveto - Pienza
10 8 reviews

Casa Oliveto

house, Trequanda

Best 5-Star Vacation Rentals in Pienza

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

La Tresa Country Living - Pienza
9.5 22 reviews

La Tresa Country Living

farm, Montepulciano

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.

156 M² Villa ∙ 3 Bedrooms ∙ 6 Guests - Pienza
No reviews

156 M² Villa ∙ 3 Bedrooms ∙ 6 Guests

house, Trequanda
Pienza Romantica Valdorcia La Torre Di S.guglielmo - Pienza
9.7 107 reviews

Pienza Romantica Valdorcia La Torre Di S.guglielmo

gîte, Pienza
Locanda Di Montisi Torre Room Among The Montalcino Hills - Pienza
No reviews

Locanda Di Montisi Torre Room Among The Montalcino Hills

apartment, Montalcino
Suite Gioconda A Pienza - Pienza
9.5 26 reviews

Suite Gioconda A Pienza

house, Pienza

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.

Farmhouse With Pool, Views - Pienza
9.4 512 reviews

Farmhouse With Pool, Views

house, Castiglione d'Orcia
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.indoor And Outdoor Dining Area, A Master Double Bedroom With Pr - 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.indoor And Outdoor Dining Area, A Master Double Bedroom With Pr

house, Trequanda
Casa Dracena Q: A Welcoming Cottage Situated In The Heart Of The Tuscan Countryside, With Free Wi-fi. - Pienza
No reviews

Casa Dracena Q: A Welcoming Cottage Situated In The Heart Of The Tuscan Countryside, With Free Wi-fi.

apartment, Trequanda
Villa Salvia- Cignella Resort Tuscany - Pienza
No reviews

Villa Salvia- Cignella Resort Tuscany

apartment, Torrita di Siena

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.

Beautiful Private Villa For 10 People With Hot Tub, A/c, Wifi, Tv And Patio - Pienza
No reviews

Beautiful Private Villa For 10 People With Hot Tub, A/c, Wifi, Tv And Patio

house, Montepulciano
Montepulciano Central Villa  Sauna & Jacuzzi - Pienza
9.7 152 reviews

Montepulciano Central Villa Sauna & Jacuzzi

house, Montepulciano
Villa Montepulciano Vineyard - Pienza
9.3 3 reviews

Villa Montepulciano Vineyard

house, Montepulciano
Villa In Totona With 6 Bedrooms Sleeps 12 - Pienza
No reviews

Villa In Totona With 6 Bedrooms Sleeps 12

house, Montepulciano
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