Pienza holiday rentalscozycozy

Holiday Rentals in Pienza

114 available vacation rental offers

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114 Holiday rentals and Airbnb in Pienza

Santa Margherita - Pienza
9.5 14 reviews
Pienza
2 2
84 â‚¬/nighttotal: 504 â‚¬ (6 )

Santa Margherita

house - Castiglione d'Orcia
Santa Margherita is a country house situated in Castiglione d'Orcia, 8.2 km from Bagno Vignoni and 30.6 km from Mount Amiata, offering a peaceful retreat amidst the Tuscan countryside. The property has received excellent ratings for cleanliness, location, and overall experience.
The house provides comfortable accommodation for up to four guests, spanning 90 square metres with two bedrooms and a fully equipped kitchen. Enjoy the private pool, outdoor fireplace, and garden, or explore the region with the convenience of packed lunches and bike rentals.
La Casa Di Memmo - Pienza
Pienza
3 2
275 â‚¬/nightfor 1 night

La Casa Di Memmo

apartment - Trequanda
This 70m² flat is centrally located in Petroio, a historic village near the main square, offering panoramic views of the Val d'Orcia countryside and close proximity to the Terracotta Museum.
This pet-friendly apartment sleeps four guests across two bedrooms and one bathroom, featuring air conditioning, Wi-Fi, and a fully equipped kitchen with a fridge, freezer, microwave, and dishwasher, with parking available and easy access to Pienza, Montepulciano, and Montalcino within 20 kilometers.
La Cocca Luxury Villa In Monticchiello, Your Heaven In Tuscany - Pienza
9.8 78 reviews
Pienza
2 2
158 â‚¬/nighttotal: 632 â‚¬ (4 )

La Cocca Luxury Villa In Monticchiello, Your Heaven In Tuscany

house - Pienza
La CoCCa Luxury Villa is situated in Monticchiello, a charming village in the Tuscan countryside, just a short drive from the historic towns of Montepulciano Terme and Bagno Vignoni. The villa has consistently received excellent ratings for its location, cleanliness, and overall user experience.
This two-bedroom villa comfortably accommodates up to four guests and offers a fully equipped kitchen, air conditioning, and a private garden. Guests can enjoy the peaceful surroundings, explore the nearby towns and countryside by bicycle, and relax in the villa's spa.
Apartment Azzurro- Cignella Resort Tuscany - Pienza
Pienza
4 2
241 â‚¬/nightfor 1 night

Apartment Azzurro- Cignella Resort Tuscany

chalet - Trequanda
Apartment Azzurro, a chalet in Trequanda, is located in Osteria Delle Noci, 46.66 kilometres from Piazza Grande and 17.70 kilometres from Montepulciano Terme, with Perugia San Francesco d'Assisi Airport 80.47 kilometres away.
This 118 square metre holiday home sleeps up to 7 guests in 2 bedrooms and 2 bathrooms, featuring air conditioning, a fully equipped kitchen, free WiFi, a private entrance, a terrace, garden, outdoor swimming pool, and parking, with proximity to Tuscan towns such as Montepulciano Terme and Bagno Vignoni.
Casina Belvedere - Pienza
9.3 10 reviews
Pienza
2 1
154 â‚¬/nighttotal: 308 â‚¬ (2 )

Casina Belvedere

apartment - San Quirico d'Orcia
Casina Belvedere, situated in San Quirico d’Orcia, is a short 5.3km drive from Bagno Vignoni and offers easy access to other Tuscan towns like Montepulciano Terme (24km).
This 68 square metre apartment features one bedroom, two bathrooms, and sleeps seven, boasting a fully equipped kitchen, private balcony, free Wi-Fi, and on-site parking.
Casa Beccofino - Pienza
8.7 210 reviews
Pienza
2 1
140 â‚¬/nightfor 1 night

Casa Beccofino

apartment - Pienza
Casa Beccofino, a one-bedroom apartment in Pienza, enjoys an excellent location, a short drive (approx. 16km) from Montepulciano Terme and Bagno Vignoni, and within a reasonable distance of Bagni San Filippo (26km) and Mount Amiata (45km).
This self-catering flat sleeps three, features a terrace, air conditioning, free on-site parking, a fridge and microwave, and is rated very good for cleanliness and location.
Chalet Cigno - Apartment In Tuscany - Pienza
Pienza
2 2
172 â‚¬/nightfor 1 night

Chalet Cigno - Apartment In Tuscany

chalet - Trequanda
Chalet Cigno is located in Osteria Delle Noci, Trequanda, offering easy access to Montepulciano Terme (17.7 kilometres) and Bagno Vignoni (24.1 kilometres).
This 70 square metre chalet accommodates up to five guests, featuring two bedrooms, one bathroom, air conditioning, a kitchenette, a swimming pool, and a private balcony with garden views, with complimentary WiFi and parking available.
Pienza Skyline Incredible View - Pienza
9.9 31 reviews
Pienza
2 2
153 â‚¬/nighttotal: 459 â‚¬ (3 )

Pienza Skyline Incredible View

apartment - Pienza
This Pienza apartment, perfect for families, is situated in [insert precise district/area of Pienza, and distance to a specific landmark e.g., "the historic Piazza Pio II, less than 1km away"], offering easy access to the town's attractions.
Sleeping up to four guests, this two-bedroom, one-bathroom flat features a well-equipped kitchen (fridge, freezer, dishwasher), parking, and internet access; further details regarding the property's size and specific layout are unavailable.
Casa Meloni 1 - Pienza
10 1 review
Pienza
2 1
140 â‚¬/nighttotal: 560 â‚¬ (4 )

Casa Meloni 1

apartment - Castiglione d'Orcia
Casa Meloni 1, an apartment in Castiglione d'Orcia, is located near Mount Amiata (32 km), Parco dei Mulini (5.9 km), and Bagni San Filippo (17.7 km).
This 55 square metre flat sleeps up to three guests, offering one bedroom, one bathroom, a fully equipped kitchen, air conditioning, and a spacious terrace, with complimentary WiFi and parking provided.
Dolce Pienza  Modern Home In The Historic Center - Pienza
9.9 28 reviews
Pienza
2 1
155 â‚¬/nighttotal: 1085 â‚¬ (7 )

Dolce Pienza Modern Home In The Historic Center

apartment - Pienza
This Pienza apartment, situated in the historic centre, offers easy walking access to Piazza Pio II and the Duomo.
Sleeping up to five guests, the self-catering flat features a master bedroom, a fully equipped kitchen with fridge and freezer, air conditioning, and parking; a bathroom with bathtub and bidet completes this one-bedroom property.
Locanda Di Montisi Contrada Room Among The Hills Of Montalcino - Pienza
Pienza
2 1
112 â‚¬/nightfor 1 night

Locanda Di Montisi Contrada Room Among The Hills Of Montalcino

apartment - Montalcino
This one-bedroom flat is located in the medieval village of Montisi, within the Crete Senesi region, offering a convenient base for exploring notable Tuscan towns such as Siena (approximately 50 kilometers away), Pienza (approximately 30 kilometers away), Montalcino (approximately 20 kilometers away), and Montepulciano (approximately 35 kilometers away).
This property accommodates two guests and features a traditional Tuscan style with exposed beams and terracotta floors, providing air conditioning, Wi-Fi, a TV, and self check-in, with nearby opportunities for spa visits, food and wine tours, and cycling.
Panoramic Apaertment Val D'orcia - Pienza
9.7 172 reviews
Pienza
2 2
114 â‚¬/nighttotal: 456 â‚¬ (4 )

Panoramic Apaertment Val D'orcia

apartment - Pienza
This B&B is located in the historic centre of Pienza, just a 10-minute drive from the thermal baths of Bagno Vignoni and the picturesque town of Montepulciano.
The studio apartment features a fresco depicting a temple and architectural motifs, a private bathroom, and secure motorcycle parking.

Best family friendly Pienza holiday rentals

Among the 114 accommodations in Pienza, here are the 4 best family friendly rentals

Nonna Mari - Pienza
9.0 34 reviews
Pienza
2 3
620 â‚¬/nightfor 1 night

Nonna Mari

apartment - Montepulciano
This apartment is situated in a peaceful location, just 5.5 kilometres from Montepulciano Terme and within easy reach of other thermal baths such as Bagno Vignoni (21 kilometres) and Bagni San Filippo (27 kilometres). It consistently receives excellent ratings for its location, cleanliness, and overall experience.
The apartment has three bedrooms and two bathrooms, offering ample space for six guests across 80 square metres. Enjoy modern amenities such as a flat-screen TV and free Wi-Fi, and take advantage of its proximity to the picturesque village of Pienza (16 kilometres) and the historic city of Siena (48 kilometres).
90 M² Apartment ∙ 2 Bedrooms ∙ 7 Guests - Pienza
Pienza
2 2
225 â‚¬/nighttotal: 1350 â‚¬ (6 )

90 M² Apartment ∙ 2 Bedrooms ∙ 7 Guests

apartment - San Quirico d'Orcia
This apartment is located in the Val d'Orcia, 4 kilometres from Pienza and 8 kilometres from Bagno Vignoni, offering panoramic views of the Tuscan countryside.
This family-friendly property spans 90 square metres, featuring two bedrooms, two bathrooms, and sofa beds to accommodate up to 7 guests, with amenities including air conditioning, Wi-Fi, a kitchen with a fridge, and access to shared facilities like a swimming pool and an on-site restaurant.
Larocchettina - Pienza
9.4 73 reviews
Pienza
2 1
118 â‚¬/nighttotal: 236 â‚¬ (2 )

Larocchettina

apartment - Castiglione d'Orcia
Larocchettina is a self-catering apartment situated in the peaceful Tuscan village of Rocca D'Orcia, just a short drive from the thermal springs of Bagno Vignoni and the medieval town of Pienza. The property has consistently received excellent ratings for location, cleanliness, and overall experience.
The apartment is a beautifully restored stone tower, offering a unique and memorable stay. Guests can enjoy a comfortable seating area, a private bathroom, and a fully equipped kitchenette, allowing them to prepare their own meals. The property also features a terrace, garden, and free Wi-Fi.
90 M² Apartment ∙ 2 Bedrooms ∙ 5 Guests - Pienza
Pienza
4 2
948 â‚¬/nightfor 1 night

90 M² Apartment ∙ 2 Bedrooms ∙ 5 Guests

apartment - Torrita di Siena
This Tiberini Estate apartment in Torrita di Siena offers an immersive Tuscan countryside experience, located within easy reach of the Valdichiana and Val d'Orcia wine regions.
This 90 square metre flat accommodates up to six guests across three bedrooms and two bathrooms, featuring a kitchen with a fridge, freezer, and dishwasher, alongside access to shared amenities including a swimming pool, garden, playground, ping pong table, and communal kitchen.

Best Pienza holiday rentals with parking

Casa Della Fonte - Pienza
9.0 331 reviews
Pienza
2 2
108 â‚¬/nighttotal: 432 â‚¬ (4 )

Casa Della Fonte

apartment - San Quirico d'Orcia
Casa della Fonte is a self-catering apartment located in San Quirico d'Orcia, a short distance from the picturesque village centre and close to Mount Amiata and Fontebranda. The apartment has received excellent ratings for location, cleanliness, and overall user satisfaction.
The apartment offers a private entrance and a peaceful garden where you can relax after exploring the region. It is fully equipped with modern amenities, including air conditioning, a flat-screen TV, and free Wi-Fi, as well as a kitchen with a fridge, freezer, microwave, and oven. Guests can also enjoy fresh pastries for breakfast and take advantage of the nearby cycling opportunities.
La Terrazza Sulla Val D'orcia - Pienza
9.8 82 reviews
Pienza
2 2
117 â‚¬/nighttotal: 3276 â‚¬ (28 )

La Terrazza Sulla Val D'orcia

apartment - Castiglione d'Orcia
"La Terrazza sulla Val d'Orcia" is located in Castiglione d'Orcia, a charming village in the heart of Tuscany, just 40 kilometres from Pienza, 26 kilometres from Montepulciano and Montalcino, and 5 kilometres from the Bagno Vignoni Spa centre. The property has received excellent ratings for its location, cleanliness, and overall user experience.
This two-bedroom apartment offers 75 square metres of space, comfortably accommodating up to four guests. The apartment features a fully equipped kitchen, a terrace with stunning views of the Val d'Orcia, a garden, parking, and free Wi-Fi, making it the perfect base for exploring the region.
Giotto-terrace Apartment With Views Of Val D'orcia - Pienza
9.9 15 reviews
Pienza
2 1
147 â‚¬/nighttotal: 588 â‚¬ (4 )

Giotto-terrace Apartment With Views Of Val D'orcia

apartment - Pienza
This two-room flat is located in Monticchiello, a UNESCO World Heritage village, offering unparalleled panoramic views of the Val d'Orcia and is mere metres from its historic centre, with Pienza and Montepulciano both a 15-kilometre drive away.
This property, ideal for two guests, features a kitchen with a fridge and freezer, a garden, and serves as an excellent base for exploring the Val d'Orcia, including proximity to the Eroica cycling route.
Chalet Cigno - Apartment In Tuscany - Pienza
Pienza
2 2
186 â‚¬/nightfor 1 night

Chalet Cigno - Apartment In Tuscany

chalet - Trequanda
Chalet Cigno, a detached holiday home in Trequanda, offers convenient access to shopping at Valdichiana Outlet Village and Piazza Italia, and is within easy reach of the Historic Centre of Pienza and Val di Chiana, all within a 15 kilometre radius.
This 70 square metre, two-bedroom cottage accommodates up to three guests, featuring a fully equipped kitchen, air conditioning, Wi-Fi, private garden, and access to resort common areas including a swimming pool, with underfloor heating ensuring comfort throughout the year.

Frequently asked questions about holiday rentals in Pienza

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

    Pienza is a beautiful town with plenty to see. You should definitely visit the Duomo, a stunning example of Renaissance architecture, and the Palazzo Piccolomini, a magnificent palace with a beautiful courtyard. For a stunning view of the Val d'Orcia, head to the Fortezza, a medieval fortress on a hill overlooking the town. If you want to explore the surrounding area, you can visit the nearby towns of Montepulciano, Montalcino, and San Quirico d'Orcia, all of which are within a 30-minute drive.
  • What are the best Airbnb and holiday rentals in Pienza?

    Agriturismo Il Macchione, Residenza D'epoca La Rosa and La Casa Nel Borgo are among the best Airbnb and holiday rentals in Pienza.

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

    For walking, you can take a stroll around the historic centre, visiting the main sights. There's also a lovely walk along the Via Cassia, an ancient Roman road that runs through the Val d'Orcia. For cycling, the Val d'Orcia is a great place to explore, with rolling hills and stunning views. You can follow the Via Cassia or head out to the nearby town of Montepulciano for a longer ride.
  • 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 outdoor activities. You can go hiking in the surrounding hills, go for a swim in the nearby Lake Trasimeno, or play tennis at the local tennis club. There are also several horse riding schools in the area, so you can enjoy a horseback riding tour of the Val d'Orcia.
  • What are the best holiday rentals with a pool in Pienza?

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

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

    Pienza is well-connected to other towns and cities in Tuscany. You can easily reach Siena, Florence, and Rome by car or train. If you're looking for a day trip, you can visit the nearby towns of Montepulciano, Montalcino, and San Quirico d'Orcia.
  • 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?

    Vacation rentals in Pienza typically come with a range of amenities. Most rentals have a kitchen, a bathroom, and a living area. Many also have a private garden or terrace, and some even have a swimming pool. You can find rentals that are perfect for families, couples, or groups of friends.
  • 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?

    The best time to visit Pienza is during the spring or autumn, when the weather is mild and the crowds are smaller. The summer months can be very hot and crowded, but if you don't mind the heat, you can enjoy the many outdoor activities that Pienza has to offer.

Popular destinations

Best Pienza holiday rentals with a balcony

30 M² Apartment ∙ 1 Bedroom ∙ 2 Guests - Pienza
Pienza
2 1
153 â‚¬/nighttotal: 4284 â‚¬ (28 )

30 M² Apartment ∙ 1 Bedroom ∙ 2 Guests

apartment - Castiglione d'Orcia
La Casina, a pet-friendly apartment in Castiglione d'Orcia, Tuscany, offers easy access to the town's amenities and attractions.
This 30 square metre self-catering flat features one bedroom, one bathroom, sleeps two, and includes a private terrace, shared pool, garden, parking and high-speed Wi-Fi.
Villa Basilico - Cignella Resort Chalet In Tuscany - Pienza
Pienza
2 2
237 â‚¬/nighttotal: 474 â‚¬ (2 )

Villa Basilico - Cignella Resort Chalet In Tuscany

chalet - Trequanda
This chalet in Trequanda is located near cultural sites such as the Artemisia Gallery and Palazzo Borgia, and historical landmarks including Chiesa di San Francesco and Palazzo Piccolomini, offering a gateway to the region's heritage.
This 93 square meter property accommodates up to four guests across two bedrooms and two bathrooms, featuring a well-equipped kitchen, air conditioning, Wi-Fi, a swimming pool, and a terrace, with parking available.
Wine Loft - Pienza
9.4 6 reviews
Pienza
2 2
745 â‚¬/nighttotal: 1490 â‚¬ (2 )

Wine Loft

apartment - San Quirico d'Orcia
Wine Loft, a recently renovated apartment near Bagno Vignoni, is conveniently located approximately 37 kilometres from Monte Amiata and 48 kilometres from Piazza del Campo in Siena.
This 72-square-metre self-catering flat boasts two bedrooms, two bathrooms, a terrace, garden, parking, and can comfortably accommodate six guests, offering free Wi-Fi and a dishwasher.
Tenuta Santo Pietro - Pienza
9.3 816 reviews
Pienza
2 1
383 â‚¬/nightfor 1 night

Tenuta Santo Pietro

farm - Pienza
Tenuta Santo Pietro is a working farm located just three miles from the historic town of Pienza, nestled in the Tuscan countryside. The farm enjoys excellent ratings for its location, cleanliness, and overall experience.
The farmhouse dates back to the 13th century and has been beautifully restored, featuring terracotta floors and exposed wooden beams. Guests can enjoy a swimming pool, a restaurant serving traditional Tuscan cuisine, and a range of activities including wine and olive oil tastings, as well as exploring the peaceful gardens.

Best pet friendly Pienza holiday rentals

Among the 114 accommodations in Pienza, here are the 4 best pet friendly rentals

Masseria Del Bosco Poderuccio - Pienza
8.0 74 reviews
Pienza
2 1
134 â‚¬/nightfor 1 night

Masseria Del Bosco Poderuccio

farm - Chianciano Terme
Masseria del Bosco Poderuccio, a self-catering property in Chianciano Terme, is conveniently located near Montepulciano Terme (14km), Bagno Vignoni (21km), and Bagni San Filippo (21km), offering easy access to renowned thermal baths.
This one-bedroom cottage boasts 16 square metres of space, a private garden, swimming pool, free Wi-Fi, and parking, perfect for a couple seeking a relaxing Tuscan getaway with stunning mountain views.
Lignanello Country House - Pienza
9.4 35 reviews
Pienza
2 3
192 â‚¬/nighttotal: 1344 â‚¬ (7 )

Lignanello Country House

apartment - Pienza
Lignanello Country House is situated in the countryside near Pienza, just 14 kilometres from Montepulciano Terme and 16 kilometres from Bagno Vignoni, offering a peaceful retreat away from the town. The property has consistently received excellent ratings for its location, cleanliness, and overall guest experience.
This spacious three-bedroom apartment, spanning 120 square metres, comfortably accommodates up to six guests. Enjoy a fully equipped kitchen, a terrace with mountain views, a garden, a children's playground, and free parking and Wi-Fi.
'Acacia' Room With Mountain View, Shared Pool, And Wi-fi - Pienza
Pienza
2 1
134 â‚¬/nightfor 1 night

'Acacia' Room With Mountain View, Shared Pool, And Wi-fi

apartment - Chianciano Terme
Room Acacia, a farm stay in Chianciano Terme, offers a peaceful retreat approximately 20km from Sarteano, providing easy access to the thermal baths of Piscine Termali Theia and Terme di Chianciano, and within driving distance of Pienza.
This pet-friendly rural retreat boasts a 16 square metre room, a shared garden with a pool, and amenities including a shared kitchen area with a fridge and kettle, sleeping up to two guests.
Frattina1860
Romantic Apartment
Free Parking - Pienza
9.8 25 reviews
Pienza
2 1
96 â‚¬/nighttotal: 192 â‚¬ (2 )

Frattina1860 Romantic Apartment Free Parking

apartment - Montalcino
This self-catering apartment is situated in the Crete Senesi, 12km from Pienza, 30 minutes’ drive from Montalcino and Montepulciano, offering easy access to the A1 motorway (20 minutes from the exit).
The one-bedroom, one-bathroom flat sleeps two guests and includes a fully equipped kitchen (microwave, coffee machine, kettle), air conditioning, parking, internet access, complimentary breakfast, and welcome bathroom amenities.
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