Pienza vacation rentals

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Top-rated vacation rentals in Pienza

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Guest favorite

Apartment in Montepulciano

4.98 out of 5 average rating, 264 reviews

Large space between ancient and modern in the center of Montepulciano

Get surrounded by the feeling of intimacy and warmth of this large space where the various areas are divided by original solutions. Original features, like exposed beams, are associated with fresh, contemporary elements. Bright environment ideal for 2 people but can comfortably accommodate 3 (armchair bed). Kitchen of the house equipped with all services for exclusive use of this room, dining table, TV, wi-fi and private bathroom with shower. Guests have access to the common entrance area of the ManillaHouse and the Esagona room. Lockable safety lock. If necessary, guests can contact me. In any case, the house is well organized and equipped with information sheets to solve small ordinary technical problems. A few steps away are restaurants, bars, shops and various services. In summer, various events are organized such as the International Art Workshop Festival, while in winter the town is embellished with the lights and colors of the Christmas markets. Located in ZTL, the car can be parked in the public car parks P6 P7 P8 , perimeter in the center of the country in the upper part and not far on foot from the accommodation. For further travel there is an urban public transport line called "Pollicino" that connects the historic center to the most recent area of the country. Montepulciano can be reached by car from the A1 Val di Chiana and A1 Chiusi-Chianciano Terme motorway exits (Parking near home n.6-7-8), by train from Chiusi Chianciano Terme station, by bus from Siena, Rome and Florence. It can happen when you stay to hear music from the nearby Music Institute of Montepulciano, violins, pianos, trumpets and bel canto could be the background of your stay but without causing disturbance.

Sep 11 – 18

ﺩ.ﺇ477 per night

Guest favorite

Cottage in Geggiano

4.99 out of 5 average rating, 107 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.

Mar 23 – 30

ﺩ.ﺇ1,816 per night

Guest favorite

Apartment in Montepulciano

4.97 out of 5 average rating, 330 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 2 – 9

ﺩ.ﺇ583 per night

Guest favorite

Farm stay in Seggiano

4.98 out of 5 average rating, 193 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.

Nov 12 – 19

ﺩ.ﺇ402 per night

Guest favorite

Home in San Quirico D'orcia

4.99 out of 5 average rating, 177 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.

Feb 10 – 17

ﺩ.ﺇ1,100 per night

Guest favorite

Apartment in Montepulciano

4.99 out of 5 average rating, 217 reviews

Montepulciano Downtown Storico

Nice 60 sqm apartment located in the main street of the village. It is located on the second and last floor of a historic palace. The entrance is located on the main street of the town while the windows overlook the outside of the walls offering a breathtaking view. Apartment consists of: entrance hall, living room with double sofa bed, bedroom, kitchen, bathroom with roof window. It is equipped with microwave, large oven, dishwasher, washing machine and wi-fi.

Dec 22 – 29

ﺩ.ﺇ323 per night

Guest favorite

Loft in Montepulciano

5.0 out of 5 average rating, 383 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.

Jan 10 – 17

ﺩ.ﺇ807 per night

Guest favorite

Apartment in Monticchiello

4.98 out of 5 average rating, 120 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.

Mar 20 – 27

ﺩ.ﺇ607 per night

Guest favorite

Home in Castelnuovo dell'Abate

4.91 out of 5 average rating, 236 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.

Oct 22 – 29

ﺩ.ﺇ682 per night

Guest favorite

Condo in Asciano

4.96 out of 5 average rating, 169 reviews

Celeste - The Color of the Summer Sky in Tuscany

Apartment consisting of 2 double bedrooms ( one with the possibility of a single bed added on request at €10.00 ) , bathroom, a living room and a fully equipped kitchen for cooking with company. Free parking and wifi Strategic location to get around all of Tuscany and Umbria I look forward to showing you the real Tuscany!

Oct 15 – 22

ﺩ.ﺇ455 per night

Guest favorite

Apartment in Ville di Corsano

4.97 out of 5 average rating, 199 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...).

Jan 4 – 11

ﺩ.ﺇ524 per night

Guest favorite

Home in Monticchiello

4.97 out of 5 average rating, 134 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.

Mar 11 – 18

ﺩ.ﺇ1,170 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

Farm stay in Castiglione d'Orcia

4.89 out of 5 average rating, 202 reviews

agriturismo il Poduccio studio

Oct 6 – 13

ﺩ.ﺇ386 per night

Guest favorite

Apartment in Montepulciano

4.96 out of 5 average rating, 207 reviews

Casa Ricci Apartment in 1300's palace

Jul 26 – Aug 2

ﺩ.ﺇ510 per night

Guest favorite

Home in Montepulciano

4.98 out of 5 average rating, 293 reviews

Residence In Search of Author

Jan 11 – 18

ﺩ.ﺇ1,315 per night

Guest favorite

Apartment in Pienza

4.89 out of 5 average rating, 155 reviews

Back Home - Apartment in Pienza

Jan 20 – 27

ﺩ.ﺇ514 per night

Guest favorite

Condo in Pienza

5.0 out of 5 average rating, 53 reviews

Mascagni Farmhouse in Val d 'Orcia Pienza

Oct 30 – Nov 6

ﺩ.ﺇ779 per night

Guest favorite

Condo in Montepulciano

5.0 out of 5 average rating, 23 reviews

Dimora Valinda, Montepulciano Piazza Grande +A/C

Jan 21 – 28

ﺩ.ﺇ268 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

ﺩ.ﺇ689 per night

Guest favorite

Apartment in Pienza

4.97 out of 5 average rating, 38 reviews

Apartment Centro Storico Pienza

Oct 30 – Nov 6

ﺩ.ﺇ428 per night

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Other great vacation rentals in Pienza

Guest favorite

Villa in Pienza

4.91 out of 5 average rating, 74 reviews

Amazing view of Val d'Orcia Pienza

Feb 15 – 22

ﺩ.ﺇ604 per night

Guest favorite

Apartment in Montepulciano

5.0 out of 5 average rating, 23 reviews

Lo Storico Montepulciano, Cozy apartment in Center

Mar 17 – 24

ﺩ.ﺇ285 per night

Guest favorite

Apartment in Montepulciano

5.0 out of 5 average rating, 13 reviews

Tuscany on the terrace, Montepulciano Centro

Mar 26 – Apr 2

ﺩ.ﺇ325 per night

Guest favorite

Guesthouse in Montefollonico

4.95 out of 5 average rating, 64 reviews

Casale Santa Barbara - Exclusive Apartment

Aug 30 – Sep 6

ﺩ.ﺇ760 per night

Guest favorite

Home in Montefollonico

4.92 out of 5 average rating, 12 reviews

Frignano Farm

Jun 2 – 9

ﺩ.ﺇ464 per night

Guest favorite

Apartment in San Quirico d'Orcia

5.0 out of 5 average rating, 43 reviews

Antica Loggia - Apartment with view

Oct 28 – Nov 4

ﺩ.ﺇ555 per night

Guest favorite

Apartment in Pienza

5.0 out of 5 average rating, 21 reviews

Apartment alla Arco

Jun 11 – 18

ﺩ.ﺇ570 per night

Guest favorite

Apartment in Montepulciano

5.0 out of 5 average rating, 75 reviews

Stuart White Tea Central Panoramic & Garden

Jul 4 – 11

ﺩ.ﺇ469 per night

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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
ﺩ.ﺇ184 before taxes and fees

Frequently Asked Questions

How much does it cost to stay in apartment rentals in Pienza?
Experience the best of Pienza with our apartment 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 apartment rentals with a dedicated workspace in Pienza?
Yes! Work meets play with ease at over 10 apartment rentals in Pienza featuring dedicated workspaces. Stay connected and productive 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.
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.
Are there pet-friendly apartment rentals in Pienza?
Four-legged friends are welcome in Pienza. Choose from more than 10 apartment rentals for guests traveling with pets.
Do bed and breakfast rentals in Pienza have wifi?
Absolutely! We offer over 10 bed and breakfast rentals with wifi 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

Houses

Apartments

Hotels

Popular amenities for Pienza vacation rentals

Stay near Pienza's top sights

Other great vacation rentals in Pienza

Farm stay in Castiglione d'Orcia

Apartment in Montepulciano

Home in Montepulciano

Apartment in Pienza

Condo in Pienza

Condo in Montepulciano

Villa in Pienza

Apartment in Pienza

Other great vacation rentals in Pienza

Villa in Pienza

Apartment in Montepulciano

Apartment in Montepulciano

Guesthouse in Montefollonico

Home in Montefollonico

Apartment in San Quirico d'Orcia

Apartment in Pienza

Apartment in Montepulciano

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

How much does it cost to stay in apartment rentals in Pienza?

Are there apartment rentals with a dedicated workspace in Pienza?

Are there family-friendly apartment rentals in Pienza?

Do apartment rentals in Pienza have air conditioning?

Are there pet-friendly apartment rentals in Pienza?

Do bed and breakfast rentals in Pienza have wifi?

Destinations to explore