Pienza holiday rentals

Holiday Rentals in Pienza

241 available vacation rental offers

2 1
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Best Holiday rentals and Airbnb offers in Pienza

Podere La Miniera - Pienza
8.1Very good 80 reviews
Pienza
2 1
SG$176/nighttotal: SG$1232 (7 )

Podere La Miniera

house - Pienza
Podere la Miniera is a charming holiday home located in Pienza, just a short 10-mile drive from both Bagno Vignoni and Montepulciano Terme, offering easy access to explore the beautiful Tuscan countryside. Guests consistently rate the property highly for its cleanliness, location and overall experience.
This one-bedroom property spans 50 square metres and comfortably accommodates up to five guests. You'll find a fully equipped kitchen, a relaxing fireplace, a private patio for outdoor dining, and a barbecue for enjoying traditional Tuscan meals.
La Dimora Di Pienza - Pienza
9.2Excellent 421 reviews
Pienza
2 1
SG$183/nighttotal: SG$1281 (7 )

La Dimora Di Pienza

apartment - Pienza
La Dimora Di Pienza is situated in the charming town of Pienza, just 9.3 miles from the famous thermal baths of Bagno Vignoni and 28 miles from Mount Amiata, making it an ideal base for exploring the Tuscan countryside. The apartment has consistently received excellent ratings for its location, cleanliness, and overall user experience.
The apartment features a private entrance, a patio with garden views, and a fully equipped kitchen. Guests can enjoy the peaceful surroundings, explore the nearby cycling routes, and take advantage of the convenient location with a coffee shop and mini-market just a short walk away.
Casa Sandro A Podere Pascianella - Pienza
9.0Excellent 7 reviews
Pienza
2 3
SG$325/nighttotal: SG$2275 (7 )

Casa Sandro A Podere Pascianella

house - Trequanda
Casa Sandro a Podere Pascianella is a charming house located in Castelmuzio, a tranquil village just 50 km from Piazza Grande in Arezzo, offering a peaceful escape in the Tuscan countryside. The property enjoys excellent ratings for user experience, location, and cleanliness.
This 3-bedroom, 1-bathroom property spans 250 square metres and comfortably accommodates up to 6 guests. Casa Sandro offers a range of amenities for a relaxing stay, including a private swimming pool, a Jacuzzi, a garden, a spa, parking, and free Wi-Fi.
Villa Poliflora - Pienza
9.9Excellent 245 reviews
Pienza
2 1
SG$118/nighttotal: SG$826 (7 )

Villa Poliflora

apartment - Pienza
Villa PoliFlora is a charming apartment located in the peaceful village of Monticchiello, just a short drive from Pienza and 27 miles from Mount Amiata. It has consistently received excellent ratings for its location, cleanliness, and overall user experience.
This self-catering property features a fully equipped kitchen with a dishwasher and oven, a private terrace, and a garden with barbecue facilities. Guests can enjoy free Wi-Fi, packed lunches, and on-site bicycle and car rental services for exploring the surrounding area.
Agriturismo Santa Maria - Pienza
9.4Excellent 188 reviews
Pienza
2 1
SG$213/nightfor 1 night

Agriturismo Santa Maria

farm - Torrita di Siena
Agriturismo Santa Maria is located just 6.2 miles from Torrita di Siena and 6.8 miles from Montepulciano, in the peaceful Tuscan countryside. This farm stay has received excellent ratings for its location, cleanliness, and overall experience.
The accommodation offers a cosy 20 square metre space with one bedroom, one bathroom, and a capacity for two guests. Enjoy the on-site restaurant serving authentic Tuscan cuisine, relax on the terrace or in the garden, and take advantage of the free Wi-Fi and convenient parking.
Foresteria Del Teatro Povero - Pienza
9.0Excellent 28 reviews
Pienza
2 2
SG$150/nighttotal: SG$1050 (7 )

Foresteria Del Teatro Povero

apartment - Pienza
This charming holiday home, Foresteria del Teatro Povero, is located in the tranquil village of Monticchiello, just a short drive from the popular tourist destination of Pienza, offering easy access to the surrounding Tuscan countryside. The apartment consistently receives excellent reviews for its cleanliness, location, and overall user experience.
The two-bedroom apartment offers 63 square metres of space and comfortably accommodates up to three guests. This family-friendly property includes a fully equipped kitchen, a cosy living room with a fireplace, a restaurant on-site, and a tour desk for exploring the region.
Villa Fonte All'oppio Con Area Piscina Recintata - Pienza
8.9Very good 49 reviews
Pienza
2 1
SG$252/nighttotal: SG$1764 (7 )

Villa Fonte All'oppio Con Area Piscina Recintata

house - Pienza
Villa Fonte all'Oppio is situated in the Tuscan countryside, just a short drive from the charming town of Pienza, a UNESCO World Heritage Site, and a little further from Montepulciano. The property has received very good ratings for cleanliness and user experience, and its location is considered excellent.
The villa offers spacious apartments with fireplaces, equipped kitchens, and private bathrooms. Guests can enjoy a refreshing dip in the private pool, relax in the lush garden, and prepare delicious meals using the provided BBQ facilities.
Independent House In The Historic Center - Pienza
9.6Excellent 27 reviews
Pienza
2 2
SG$301/nightfor 1 night

Independent House In The Historic Center

house - Castiglione d'Orcia
This charming house is located just a short walk from the Fortress of Tentennano, a historic landmark offering stunning views of the Tuscan countryside, and a short drive from Piazza delle Sorgenti, a picturesque square with a fountain and local shops. The property has consistently received excellent ratings for its location, cleanliness, and overall experience.
This two-bedroom house is ideal for families or groups of up to four people, with a spacious 105 square metres of living space. The home offers a fully equipped kitchen, a TV with a DVD player, a washing machine, and internet access, ensuring a comfortable and enjoyable stay.
Agriturismo Zampugna - Pienza
9.4Excellent 437 reviews
Pienza
2 1
SG$432/nightfor 1 night

Agriturismo Zampugna

farm - Trequanda
Agriturismo Zampugna is situated in Montefollonico, a charming village just a short drive from Trequanda and approximately 52 miles from Perugia San Francesco d'Assisi Airport. The farm stay has received excellent ratings for its location, cleanliness and overall user experience.
The property offers a peaceful garden and a private entrance for a relaxing stay. Guests can enjoy a swimming pool with stunning views, a terrace, barbecue facilities, a picnic area, a restaurant and free parking.
Small Lovely Home In Pienza - Pienza
9.3Excellent 23 reviews
Pienza
2 1
SG$186/nighttotal: SG$1302 (7 )

Small Lovely Home In Pienza

house - Pienza
This charming cottage is located in Pienza, just a short drive from the picturesque town of Bagno Vignoni and the renowned Montepulciano Terme, offering a peaceful retreat in the heart of Tuscany. Guests consistently rate the property highly for its cleanliness, location, and overall experience.
The cottage is comfortably sized at 65 square metres, with one bedroom and one bathroom, accommodating up to three guests. Guests can enjoy a fully equipped kitchen, air conditioning, private parking, and free Wi-Fi, ensuring a comfortable and convenient stay.
La Dimora Di Pienza Old Town. Free Wifi. - Pienza
8.9Very good 208 reviews
Pienza
2 1
SG$125/nighttotal: SG$875 (7 )

La Dimora Di Pienza Old Town. Free Wifi.

apartment - Pienza
Vacation rental listing for up to 4 guests with an excellent rating of 89% based on 208 reviews. You will be based in Pienza.
Services and facilities include a kitchen, free parking and a fridge.
Agriturismo Podere San Gregorio - Pienza
9.4Excellent 271 reviews
Pienza
2 1
SG$179/nighttotal: SG$1253 (7 )

Agriturismo Podere San Gregorio

farm - Pienza
Agriturismo Podere San Gregorio is a restored farmhouse located just a short walk from the centre of Pienza, a charming medieval town in the heart of Tuscany. It is also within easy reach of other popular destinations like Montepulciano and Siena. The property has received excellent ratings for its location, cleanliness and overall experience.
The farmhouse offers comfortable accommodation with a private garden and free BBQ facilities. Guests can enjoy a delicious breakfast basket delivered to their room each morning and have the option of purchasing locally produced olive oil and wine.

Other types of accommodation in Pienza

Best Pienza holiday rentals with a pool

Among the 241 accommodations in Pienza, here are the 8 best rentals with a pool

Verdidea - Villa Orcia - Pienza
Pienza
2 8
SG$1942/nighttotal: SG$13594 (7 )

Verdidea - Villa Orcia

house - Pienza
This eight-bedroom villa is located just outside Pienza, within easy reach of the Chapel of our Lady of Vitaleta, Palazzo Chigi, and the Collegiate Church of San Quirico, offering a peaceful escape from the town centre. The surrounding countryside is tranquil and picturesque, perfect for exploring the beauty of Tuscany.
The villa is spacious and comfortable, ideal for families or groups of friends. It comes equipped with a range of modern amenities, including a swimming pool, jacuzzi, tennis court, and a fully equipped kitchen, ensuring a relaxing and enjoyable stay.
Agriturismo Palazzo Conti - B - Pienza
8.6Very good 111 reviews
Pienza
2 1
SG$234/nighttotal: SG$1638 (7 )

Agriturismo Palazzo Conti - B

farm - San Quirico d'Orcia
Agriturismo Palazzo Conti - B is situated in Pienza, a charming town in the Val d'Orcia, just 22 miles from Siena and 29 miles from Arezzo, making it an ideal base for exploring the Tuscan countryside. The property has consistently received excellent ratings for location, cleanliness, and overall experience.
The farm offers comfortable accommodation for up to four guests, with a fully equipped kitchen and a private bathroom. Guests can enjoy a refreshing dip in the seasonal outdoor pool, relax on the terrace or in the garden, and benefit from free Wi-Fi and parking.
Agriturismo La Poderina - Pienza
9.4Excellent 217 reviews
Pienza
2 2
SG$313/nighttotal: SG$2191 (7 )

Agriturismo La Poderina

farm - Castiglione d'Orcia
Agriturismo La Poderina is a farm stay located just 0.6 miles from the spa town of Bagno Vignoni and a 20-minute drive from Montepulciano, set in the peaceful countryside of Castiglione d'Orcia. It has received excellent ratings for location, cleanliness, and user experience. The accommodation offers self-catering apartments with exposed-beam ceilings, creating a warm and inviting atmosphere. Guests can enjoy free Wi-Fi, on-site parking, BBQ facilities, and a swimming pool, as well as a terrace or balcony and a garden.
Agriturismo Bombina - Pienza
9.2Excellent 90 reviews
Pienza
2 2
SG$296/nighttotal: SG$2072 (7 )

Agriturismo Bombina

farm - Montalcino
Agriturismo Bombina is situated in Montisi, a picturesque village near Montalcino, just a short drive from the historic city of Siena and the charming towns of Bagno Vignoni and Montepulciano Terme. This farm stay boasts excellent user, location and cleanliness ratings, ensuring a comfortable and enjoyable experience.
The property offers a range of spacious and well-equipped apartments with modern amenities, including private bathrooms, kitchens and flat-screen TVs. Guests can enjoy a refreshing dip in the private pool, relax on the terrace or in the garden, and make use of the outdoor fireplace and the packed lunches provided for excursions.
Casa Valerie - Pienza
9.1Excellent 18 reviews
Pienza
2 2
SG$407/nighttotal: SG$2849 (7 )

Casa Valerie

house - Trequanda
Casa Valerie is situated in Castelmuzio, a charming village just 14 miles from Bagno Vignoni and 31 miles from Piazza Grande, offering easy access to the region's attractions. The property has received excellent ratings for location, cleanliness, and overall user experience.
This two-bedroom villa, spanning 150 square metres, comfortably accommodates up to four guests. The property features a private pool with mountain views, a spa bath, a fully equipped kitchen, an outdoor fireplace, and a peaceful garden, providing a relaxing and enjoyable stay.
Agriturismo Palazzo Conti A - Pienza
9.0Excellent 125 reviews
Pienza
2 1
SG$208/nighttotal: SG$1456 (7 )

Agriturismo Palazzo Conti A

house - San Quirico d'Orcia
Agriturismo Palazzo Conti A is located just outside Pienza, a short drive from Montalcino, offering stunning views of the Tuscan countryside. The property has received excellent ratings for its location, cleanliness, and overall experience.
The apartments are classically decorated and feature flat-screen TVs, seating areas, and fully equipped kitchenettes. Guests can enjoy a range of amenities including a swimming pool, a natural pool, a garden with BBQ facilities, a spa, a restaurant, a bar, and room service.
Villa Piana - Four Bedroom Villa, Sleeps 9 - Pienza
10Excellent 2 reviews
Pienza
2 4
SG$1253/nighttotal: SG$8771 (7 )

Villa Piana - Four Bedroom Villa, Sleeps 9

house - Pienza
This four-bedroom villa is situated in Pienza, just a short distance from the Art Studio di Adelina Quadri and the beautiful Val di Chiana region, offering a peaceful escape in a picturesque setting. The property has consistently received excellent reviews from previous guests.
The spacious villa, with its 430 square metres of floor area, comfortably accommodates up to nine guests. Enjoy a refreshing dip in the private pool, relax by the fireplace, and make use of the fully equipped kitchen, washing machine, and barbecue grills.
"Casa Sandro" In Podere Pascianella Val D'orcia - With Big Private Garden - Pienza
9.8Excellent 46 reviews
Pienza
2 3
SG$388/nighttotal: SG$2716 (7 )

"Casa Sandro" In Podere Pascianella Val D'orcia - With Big Private Garden

house - Trequanda
This charming house is located in the peaceful Val di Chiana countryside, just a short drive from the Monastery of Sant'Anna in Camprena and other historical sites. It has received excellent user ratings, making it a popular choice for travellers.
The property has three bedrooms and sleeps up to six guests, providing ample space for families or groups of friends. Guests can enjoy a range of amenities, including a swimming pool, jacuzzi, garden, and barbecue facilities, ensuring a relaxing and enjoyable stay.

Best family friendly Pienza holiday rentals

Among the 241 accommodations in Pienza, here are the 8 best family friendly rentals

Le Pietre Antiche - Pienza
9.2Excellent 99 reviews
Pienza
2 3
SG$166/nighttotal: SG$1162 (7 )

Le Pietre Antiche

house - Castiglione d'Orcia
This charming holiday home is located in the heart of Castiglione d'Orcia, a charming medieval town, just 3.1 miles from Bagno Vignoni and 16 miles from Montepulciano. The property has received excellent user ratings for its location, cleanliness, and overall experience.
The home has three bedrooms and can accommodate up to five guests. It features a fully equipped kitchen, a terrace, a garden, and free Wi-Fi, making it perfect for families or groups of friends looking to explore the beauty of Tuscany.
Larocchettina - Pienza
9.4Excellent 59 reviews
Pienza
2 1
SG$155/nighttotal: SG$1085 (7 )

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.
La Mandola - Pienza
9.2Excellent 58 reviews
Pienza
2 2
SG$167/nighttotal: SG$1169 (7 )

La Mandola

apartment - Castiglione d'Orcia
La Mandola is a pet-friendly apartment situated in Rocca d'Orcia, just 3.3 miles from the thermal baths of Bagno Vignoni and within easy reach of Siena and Saturnia. This apartment has received excellent ratings for location, cleanliness, and overall user experience.
The apartment offers two bedrooms and a bathroom, spanning 80 square metres. Guests can enjoy a fully equipped kitchen, a comfortable living space, a flat-screen TV, and private parking.
Le Maribelle - Pienza
8.4Very good 205 reviews
Pienza
2 2
SG$193/nighttotal: SG$1351 (7 )

Le Maribelle

house - Pienza
Le Maribelle is a charming house located in Monticchiello, a picturesque village just a short drive from Pienza and 27 miles from Mount Amiata. Guests have consistently rated the house as very good for cleanliness and location, with excellent overall feedback.
This two-bedroom house features a fully equipped kitchen, a terrace with garden views, and air conditioning. Guests can enjoy the peaceful village atmosphere, explore the surrounding area by bicycle, and make use of the on-site restaurant, mini-market, and ATM.
Residenza D'epoca La Rosa - Pienza
9.2Excellent 1914 reviews
Pienza
2 2
SG$237/nighttotal: SG$1659 (7 )

Residenza D'epoca La Rosa

apartment - Pienza
Residenza d'Epoca La Rosa is situated in the historic centre of Pienza, just 31 miles from Siena and 75 miles from Florence Airport. This apartment has excellent ratings for location, cleanliness, and user experience.
The property is a self-catering apartment with a well-equipped kitchen and comfortable living spaces. Guests can enjoy a range of amenities including a swimming pool, jacuzzi, sauna, and spa, plus a terrace or balcony for relaxing outdoors.
Charming Gateway To Tuscany In San Quirico D'orcia - Pienza
10Excellent 67 reviews
Pienza
2 1
SG$120/nighttotal: SG$840 (7 )

Charming Gateway To Tuscany In San Quirico D'orcia

apartment - San Quirico d'Orcia
This charming apartment is located in the heart of San Quirico d'Orcia, a UNESCO World Heritage Site, just a short walk from the main square and its historic attractions. It has received excellent ratings for location, cleanliness, and overall experience.
The apartment offers one bedroom and one bathroom, with a total floor area of 47 square metres, comfortably accommodating up to four guests. It comes equipped with a fully equipped kitchen, air conditioning, free parking, and fast Wi-Fi for a pleasant and comfortable stay.
Agriturismo Il Macchione - Pienza
9.4Excellent 1207 reviews
Pienza
2 1
SG$621/nightfor 1 night

Agriturismo Il Macchione

house - Pienza
This 18th-century farmhouse is located just 0.9 miles outside of Pienza, overlooking the stunning Val d'Orcia Natural Park, offering a secluded and peaceful retreat. The property has consistently received excellent ratings for location, cleanliness, and overall user experience.
The farmhouse features a spacious terrace with a swimming pool and hydromassage area, perfect for relaxing and enjoying the beautiful surroundings. Guests can also enjoy a range of amenities, including a fitness center, tennis court, and a children's playground, as well as a buffet breakfast and BBQ facilities.
La Miniera - Pienza
9.7Excellent 35 reviews
Pienza
2 1
SG$164/nighttotal: SG$1148 (7 )

La Miniera

apartment - Torrita di Siena
This charming apartment is situated in Montefollonico, a picturesque hilltop village just a short drive from the renowned wine town of Montepulciano. The apartment has received excellent ratings for its location, cleanliness and overall experience, making it an ideal choice for travellers seeking a peaceful retreat in the Tuscan countryside.
The apartment offers 70 square metres of space, comfortably accommodating up to four guests. Guests can enjoy a fully equipped kitchen, a private terrace and garden, a swimming pool, and parking, all while taking in the stunning panoramic views of the surrounding Tuscan landscape.

Frequently asked questions for the vacation rentals in Pienza

Destinations nearby

Best pet friendly Pienza holiday rentals

Among the 241 accommodations in Pienza, here are the 7 best pet friendly rentals

Ermione Seen On The Val D'orcia - Pienza
9.9Excellent 157 reviews
Pienza
2 1
SG$142/nighttotal: SG$994 (7 )

Ermione Seen On The Val D'orcia

house - Castiglione d'Orcia
This charming one-bedroom cottage is situated just half a mile from the historic Fortress of Tentennano in Castiglione d'Orcia, a picturesque town in the heart of Tuscany. It has received excellent ratings for location, cleanliness, and overall user experience.
The cottage comfortably sleeps four guests and features a fully equipped kitchen, a cosy fireplace, and a washing machine. Guests can enjoy the private garden, relax on the sofa bed, and benefit from the convenient parking space.
Residenza Storica Il Pozzo - Pienza
9.1Excellent 82 reviews
Pienza
2 1
SG$118/nighttotal: SG$826 (7 )

Residenza Storica Il Pozzo

apartment - San Quirico d'Orcia
Residenza storica il Pozzo is a charming apartment located in San Quirico d'Orcia, within easy reach of the village centre and just a short drive from the thermal baths of Bagno Vignoni and Bagno San Filippo. This property consistently receives excellent ratings for its location, cleanliness, and overall user experience.
The apartment has one bedroom and one bathroom, providing comfortable accommodation for up to two guests in its 35 square metres of space. Guests can enjoy a fully equipped kitchen, a private garden, and free Wi-Fi, along with a welcome package of treats and the option of parking.
Casa Vacanze "Nonna Vela" - Pienza
9.7Excellent 35 reviews
Pienza
2 1
SG$123/nighttotal: SG$861 (7 )

Casa Vacanze "Nonna Vela"

house - Trequanda
Casa Vacanze "Nonna Vela" is situated in Petroio, a peaceful village just a short drive from Montepulciano Terme and Bagno Vignoni, both renowned for their thermal baths and historical charm. The property consistently receives excellent ratings for its location, cleanliness, and overall guest experience.
This one-bedroom cottage offers 40 square metres of space, comfortably accommodating two guests. The property features a fully equipped kitchen, a terrace for outdoor relaxation, free Wi-Fi, and a flat-screen TV, making it an ideal base for exploring the Tuscan countryside.
Casa Costanza - Pienza
9.3Excellent 31 reviews
Pienza
2 2
SG$142/nighttotal: SG$994 (7 )

Casa Costanza

house - Castiglione d'Orcia
Casa Costanza is located in Castiglione d'Orcia, a short drive from the renowned thermal baths of Bagno Vignoni and the picturesque village of Bagni San Filippo. The property has excellent user, location and cleanliness ratings.
The two-bedroom, two-bathroom property spans 68 square metres. Guests can enjoy stunning views, a shared lounge, an outdoor fireplace, a fully equipped kitchen, a flat-screen TV, complimentary Wi-Fi, bathrobes, towels and bed linen.
Casa Vacanze Oliviera Pienza - Pienza
8.0Very good 5 reviews
Pienza
2 1
SG$197/nighttotal: SG$1379 (7 )

Casa Vacanze Oliviera Pienza

apartment - Pienza
This one-bedroom apartment is conveniently located near Pienza, just a short drive from popular destinations like Bagno Vignoni, Montepulciano Terme, and Bagni San Filippo, allowing you to easily explore the Tuscan countryside. The apartment has received very good ratings for cleanliness, location, and overall experience, ensuring a comfortable and enjoyable stay.
The flat is 35 square metres in size and features a fully equipped kitchenette, free Wi-Fi, and comfortable amenities like towels, bed linen, and a hairdryer. You can enjoy activities like fishing and hiking in the surrounding area, and pets are welcome.
La Cocca Luxury Villa In Monticchiello, Your Heaven In Tuscany - Pienza
10Excellent 36 reviews
Pienza
2 2
SG$219/nighttotal: SG$1533 (7 )

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.
Al Piccolo Ulivo, A Casa Di Mimo&sè - Pienza
9.2Excellent 37 reviews
Pienza
2 2
SG$268/nightfor 1 night

Al Piccolo Ulivo, A Casa Di Mimo&sè

house - Castiglione d'Orcia
Al Piccolo Ulivo is located in Castiglione d'Orcia, just a short drive from the famous thermal baths of Bagno Vignoni and Mount Amiata, offering a peaceful retreat amidst the Tuscan countryside. This property consistently receives excellent ratings for its cleanliness, location, and overall user experience.
The villa provides comfortable accommodation for up to four guests in two bedrooms, spanning 106 square metres. Enjoy a well-equipped kitchen, modern amenities, and a shared lounge, along with a private garden offering stunning views and access to outdoor activities like skiing, cycling, and hiking in the surrounding area.