Pienza vacation rentals

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Top-rated vacation rentals in Pienza

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Guest favorite

Farm stay in Ruscello

4.99 out of 5 average rating, 323 reviews

Agriturismo Fattoria La Parita

Provençal-style apartment nestled between the vineyard and olive trees. You will enjoy the tranquility of the countryside 10 km from the city and 4 from the highway. The singing of the acorn and cuckoo will be the soundtrack to the living room while the roe deer burn among the olive trees. It includes a basic Italian breakfast (coffee, tea, milk, cookies, etc.) that you can prepare on your own, if you want to try one of the famous breakfasts prepared and served by Sandra, the cost is €10 per person (6€ 5 to 15 years)

Jan 13 – 20

G$30,509 GYD per night

Guest favorite

Cottage in Geggiano

4.99 out of 5 average rating, 109 reviews

Villa di Geggiano - Guesthouse

The 18th century Villa di Geggiano, surrounded by vineyards and lovingly cared gardens, is located in the Chianti area near Siena, one of the most beautiful regions of Italy which will provide an idilic and enchanting backdrop to your vacation. Our guesthouse is located in one of the garden pavilions of the villa. PLEASE NOTE THAT BEING IN THE COUNTRYSIDE WITH FEW PUBLIC TRANSPORTATION OTHER THAN TAXI THE BEST WAY TO ENJOY YOUR STAY AND TO VISIT THE BEAUTIFUL SURROUNDINGS IS TO HAVE A CAR.

Jan 11 – 18

G$104,106 GYD per night

Guest favorite

Apartment in Montepulciano

4.97 out of 5 average rating, 332 reviews

A view from the top

A View From the Top is an apartment in the most peaceful part of Montepulciano. The house with Ac is 250 metres from the piazza and the main street, and has 2 double rooms, 2 bathrooms with shower and a large kitchen-living room with a small terrace overlooking the hills From summer 2024 our wine tasting will be available in the new garden and we have a young private chef for cooking class at home ,not in the weekend. Guests will park close the apartment,in the street 50 mt away.

Jan 19 – 26

G$33,435 GYD per night

Guest favorite

Farm stay in Seggiano

4.98 out of 5 average rating, 194 reviews

Terra Delle Sidhe, Seggiano, Tuscany

Terra delle Sidhe is a small organic farm located in southern Tuscany overlooking a beautiful valley located on the slopes of Monte Amiata, between the medieval towns of Castel del Piano and Seggiano. A 250 year old chestnut dryer stone house in use till 30 years ago, the holiday cottage we offer is surrounded by an organic chestnut forest and olive trees that are hundreds of years old. This charming cozy house it has now been lovingly renovated with taste and simplicity.

Oct 13 – 20

G$23,074 GYD per night

Guest favorite

Home in San Quirico D'orcia

4.99 out of 5 average rating, 179 reviews

Alma Vignoni - Vignoni Val d 'Orcia - Bagno Vignoni

Alma Vignoni is an elegant and exclusive holiday house in Vignoni Alto that recalls Tuscan style and is enriched by unusual and personal details. The house consists of an open-space with fireplace in the center. On the one hand the room with stunning views over the surrounding hills (Pienza, Monticchiello and Montepulciano) on the other the kitchen area. Two cozy rooms overlook the ancient Via Francigena and the Orcia river valley. The bathroom has a large shower.

Aug 22 – 29

G$63,083 GYD per night

Guest favorite

Loft in Montepulciano

5.0 out of 5 average rating, 388 reviews

La Piazzetta - Cozy open space in the historic center of Montepulciano

Pour a glass of wine and sit next to the fireplace of this open space with a warm Tuscan atmosphere: wooden beams, terracotta flooring, stone walls. Then go out and take in the magnificent view of the Valdichiana. Pour yourself a glass of wine and sit next to the fireplace of this open space with a warm Tuscan atmosphere: wooden beams, terracotta floors, stone walls. Enjoy yourself and relax! Then go out and admire the magnificent view of the Valdichiana.

Nov 10 – 17

G$46,285 GYD per night

Guest favorite

Apartment in Monticchiello

4.98 out of 5 average rating, 121 reviews

Casa Bonari - a paradise for the eyes

Casa Bonari is an independent apartment on one level within a villa at the foot of Monticchiello. It consists of 3 bedrooms, 2 bathrooms, equipped kitchen and living room. The rooms are bright and furnished in Tuscan style, with renovated old family furniture combined with contemporary elements. The kitchen is fully equipped and the apartment is surrounded on each side by a large garden, so that all rooms boast a beautiful view of the countryside.

Jan 29 – Feb 5

G$34,829 GYD per night

Guest favorite

Home in Castelnuovo dell'Abate

4.91 out of 5 average rating, 242 reviews

La Casetta di Brunello,very panoramic with terrace

STIAMO LAVORANDO PER VOI! ... WE ARE WORKING FOR YOU! The house is completely renovated and furnished in 2018 with classic-Tuscan style furniture. The colors are warm and enveloping to better rest during your holiday of peace and relaxation. In addition to the two double bedrooms, you have a kitchen with an equipped kitchenette, fridge, induction cooker and a furnished terrace with a beautiful view of the surrounding countryside.

Apr 27 – May 4

G$31,776 GYD per night

Guest favorite

Apartment in Ville di Corsano

4.97 out of 5 average rating, 202 reviews

"Red Rose" apartment with a view of Siena.

Caggiolo is a completely renovated farm consisting of several apartments, with a panoramic view of Siena. Located in the Villas di Corsano, just 14 km from the city. Ideal place to spend days in total relaxation and enjoy the wonders that this area offers (Chianti, Val d 'Orcia, Crete Senesi...).

Dec 19 – 26

G$31,135 GYD per night

Guest favorite

Home in Monticchiello

4.97 out of 5 average rating, 135 reviews

"La Lambarda" tower Suite

In Val d'Orcia there is a small medieval village called Monticchiello, surrounded by walls and protected by four towers; one of these is the "La Lambarda", which stands at the highest point of the country and enjoys a panoramic view across the valley.

Jul 12 – 19

G$67,097 GYD per night

Guest favorite

Apartment in Monticchiello

4.99 out of 5 average rating, 299 reviews

Romantic Tower's dating 1200

The residence "Il Torrino" is a panoramic apartment obtained from the restauration of an ancient tower belonging to the boundaries of the medieval suburb Monticchiello. The apartment has an incredible view on the Val d'Orcia. You can't imagine ...

Mar 13 – 20

G$52,571 GYD per night

Guest favorite

Farm stay in Pari

4.98 out of 5 average rating, 227 reviews

TUSCANY farm house SWIMMING POOL

Our little farm is a beautiful location for a relaxing vacation with a private swimming pool. We are close to the naturally occurring hot springs of Petriolo and 30 km. far from Siena. We are only two km. from Pari, an ancient medieval village.

Apr 25 – May 2

G$20,737 GYD per night

Vacation rentals for every style

Get the amount of space that is right for you

Popular amenities for Pienza vacation rentals

Gym

BBQ grill

Laptop-friendly workspace

Wifi

Air conditioning

Stay near Pienza's top sights

Pienza Cathedral3 locals recommend

Corsignano3 locals recommend

Piazza Pio II4 locals recommend

Trattoria La Buca delle Fate8 locals recommend

Sette Di Vino7 locals recommend

Trattoria da Fiorella4 locals recommend

Other great vacation rentals in Pienza

Guest favorite

Condo in Asciano

4.97 out of 5 average rating, 175 reviews

Celeste - The Color of the Summer Sky in Tuscany

Mar 17 – 24

G$25,263 GYD per night

Guest favorite

Apartment in Montepulciano

4.99 out of 5 average rating, 220 reviews

Montepulciano Downtown Storico

Feb 22 – Mar 1

G$18,527 GYD per night

Guest favorite

Apartment in Montepulciano

4.98 out of 5 average rating, 269 reviews

Large space between ancient and modern in the center of Montepulciano

Sep 25 – Oct 2

G$27,356 GYD per night

Guest favorite

Apartment in San Gusmé

4.99 out of 5 average rating, 280 reviews

Beautiful medieval village!!!

Jan 30 – Feb 6

G$24,447 GYD per night

Guest favorite

Farm stay in Greve in Chianti

4.99 out of 5 average rating, 311 reviews

Typical Tuscan country house

Nov 30 – Dec 7

G$34,062 GYD per night

Guest favorite

Farm stay in Castiglione d'Orcia

4.89 out of 5 average rating, 202 reviews

agriturismo il Poduccio studio

Sep 10 – 17

G$22,995 GYD per night

Guest favorite

Apartment in Pienza

4.88 out of 5 average rating, 193 reviews

Renaissance Apartment

Nov 23 – 30

G$36,761 GYD per night

Guest favorite

Apartment in Bagnoregio

4.98 out of 5 average rating, 356 reviews

L'Incanto di Civita (La Terrazza)

Nov 24 – Dec 1

G$39,226 GYD per night

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Other great vacation rentals in Pienza

Guest favorite

Apartment in Pienza

4.98 out of 5 average rating, 40 reviews

Apartment Centro Storico Pienza

Dec 10 – 17

G$24,356 GYD per night

Guest favorite

Villa in Pienza

4.98 out of 5 average rating, 57 reviews

Unplug at a 17th-Century Farmhouse Enveloped by Olive Groves

Dec 12 – 19

G$39,483 GYD per night

Guest favorite

Cottage in Osteria delle Noci

5.0 out of 5 average rating, 63 reviews

Your Tuscan oak tree house, enchanting Val d'Orcia

Feb 24 – Mar 3

G$43,841 GYD per night

Guest favorite

Home in Pienza

5.0 out of 5 average rating, 18 reviews

Pienza Centro, Residence De charme Baylón,

Feb 23 – Mar 2

G$31,332 GYD per night

Guest favorite

Condo in Montepulciano

5.0 out of 5 average rating, 26 reviews

Dimora Valinda, Montepulciano Piazza Grande +A/C

Dec 11 – 18

G$23,210 GYD per night

Guest favorite

Apartment in Montepulciano

5.0 out of 5 average rating, 15 reviews

Tuscany on the terrace, Montepulciano Centro

Jan 14 – 21

G$18,641 GYD per night

Guest favorite

Home in Montefollonico

4.93 out of 5 average rating, 15 reviews

Frignano Farm

Aug 1 – 8

G$25,288 GYD per night

Guest favorite

Guesthouse in Montefollonico

4.95 out of 5 average rating, 64 reviews

Casale Santa Barbara - Exclusive Apartment

Nov 8 – 15

G$43,585 GYD per night

Show all

Quick stats about vacation rentals in Pienza

Total rentals
80 properties
Rentals with dedicated workspaces
30 properties have a dedicated workspace
Pet-friendly rentals
40 properties allow pets
Family-friendly rentals
30 properties are a good fit for families
Total number of reviews
2.6K reviews
Nightly prices starting at
G$10,441 GYD before taxes and fees

Frequently Asked Questions

Are there vacation rentals with a dedicated workspace in Pienza?
Yes! Work meets play with ease at over 30 vacation rentals in Pienza featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there pet-friendly vacation rentals in Pienza?
Four-legged friends are welcome in Pienza. Choose from more than 40 vacation rentals for guests traveling with pets.
How much does it cost to stay in bed and breakfast rentals in Pienza?
Experience the best of Pienza with our bed and breakfast rentals, starting at about $70 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Are there family-friendly apartment rentals in Pienza?
Pienza has more than 10 family-friendly apartment rentals. Amenities on the property may include high chairs, travel cribs, or strollers.
What are the most popular amenities for Apartment Rentals in Pienza?
Enhance your stay in our Apartment Rentals with the most popular amenities: over 10 homes with air conditioning, over 30 homes with wifi, and more. Indulge in the ultimate retreat, tailored to your preferences.
Do apartment rentals in Pienza have air conditioning?
Absolutely! We offer over 10 apartment rentals with air conditioning in Pienza. Enjoy a tailored experience with all the comforts you desire.

Pienza vacation rentals

Top-rated vacation rentals in Pienza

Vacation rentals for every style

Apartments

Houses

Hotels

Popular amenities for Pienza vacation rentals

Stay near Pienza's top sights

Other great vacation rentals in Pienza

Condo in Asciano

Apartment in Montepulciano

Apartment in Montepulciano

Apartment in San Gusmé

Farm stay in Greve in Chianti

Farm stay in Castiglione d'Orcia

Apartment in Pienza

Apartment in Bagnoregio

Other great vacation rentals in Pienza

Apartment in Pienza

Villa in Pienza

Cottage in Osteria delle Noci

Home in Pienza

Condo in Montepulciano

Apartment in Montepulciano

Home in Montefollonico

Guesthouse in Montefollonico

Quick stats about vacation rentals in Pienza

Total rentals

Rentals with dedicated workspaces

Pet-friendly rentals

Family-friendly rentals

Total number of reviews

Nightly prices starting at

Frequently Asked Questions

Are there vacation rentals with a dedicated workspace in Pienza?

Are there pet-friendly vacation rentals in Pienza?

How much does it cost to stay in bed and breakfast rentals in Pienza?

Are there family-friendly apartment rentals in Pienza?

What are the most popular amenities for Apartment Rentals in Pienza?

Do apartment rentals in Pienza have air conditioning?

Destinations to explore