Pienza vacation rentals

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Top-rated vacation rentals in Pienza

Guests agree: these vacation rentals are highly rated for location, cleanliness, and more.

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Guest favorite

Cottage in Geggiano

4.99 out of 5 average rating, 108 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 31 – Apr 7

G$132,867 GYD 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 11 – 18

G$33,209 GYD 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.

Jan 18 – 25

G$22,918 GYD per night

Guest favorite

Home in San Quirico D'orcia

4.99 out of 5 average rating, 178 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.

Apr 9 – 16

G$62,655 GYD per night

Guest favorite

Apartment in Montepulciano

4.99 out of 5 average rating, 219 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.

Jan 10 – 17

G$18,402 GYD 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 8 – 15

G$45,971 GYD 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 25 – Apr 1

G$34,593 GYD per night

Guest favorite

Home in Castelnuovo dell'Abate

4.91 out of 5 average rating, 237 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.

Nov 17 – 24

G$33,980 GYD per night

Guest favorite

Apartment in Ville di Corsano

4.97 out of 5 average rating, 201 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...).

Mar 14 – 21

G$27,395 GYD 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 15 – 22

G$66,642 GYD per night

Guest favorite

Apartment in Monticchiello

4.99 out of 5 average rating, 298 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 ...

Jan 31 – Feb 7

G$52,215 GYD per night

Guest favorite

Farm stay in Pari

4.98 out of 5 average rating, 225 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 15 – 22

G$20,597 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

Farm stay in Greve in Chianti

4.99 out of 5 average rating, 310 reviews

Typical Tuscan country house

Nov 30 – Dec 7

G$33,104 GYD per night

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

Oct 16 – 23

G$27,171 GYD per night

Guest favorite

Condo in Asciano

4.95 out of 5 average rating, 240 reviews

Yellow Romantic apartment in the Sienese crete

Sep 29 – Oct 6

G$16,997 GYD per night

Guest favorite

Apartment in San Gusmé

4.99 out of 5 average rating, 278 reviews

Beautiful medieval village!!!

Dec 1 – 8

G$23,008 GYD per night

Guest favorite

Apartment in Montepulciano

4.97 out of 5 average rating, 271 reviews

Caratello - Smart studio Apartment in old town

Jul 21 – 28

G$21,004 GYD per night

Guest favorite

Farm stay in Castiglione d'Orcia

4.89 out of 5 average rating, 202 reviews

agriturismo il Poduccio studio

Jul 28 – Aug 4

G$23,707 GYD per night

Guest favorite

Home in Montepulciano

4.91 out of 5 average rating, 117 reviews

Montepulciano

Oct 31 – Nov 7

G$17,301 GYD per night

Guest favorite

Farm stay in Ruscello

4.99 out of 5 average rating, 320 reviews

Agriturismo Fattoria La Parita

Oct 13 – 20

G$32,849 GYD per night

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Other great vacation rentals in Pienza

Guest favorite

Apartment in Pienza

5.0 out of 5 average rating, 22 reviews

“Nel Blu” - Stunning views & Private Concierge

Oct 28 – Nov 4

G$45,272 GYD per night

Guest favorite

Villa in Pienza

4.91 out of 5 average rating, 74 reviews

Amazing view of Val d'Orcia Pienza

Jan 4 – 11

G$34,373 GYD per night

Guest favorite

Apartment in Montepulciano

5.0 out of 5 average rating, 25 reviews

Lo Storico Montepulciano, Cozy apartment in Center

Dec 28 – Jan 4

G$24,757 GYD 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 25 – Nov 1

G$31,617 GYD per night

Guest favorite

Guesthouse in Montefollonico

4.95 out of 5 average rating, 64 reviews

Casale Santa Barbara - Exclusive Apartment

Dec 8 – 15

G$43,289 GYD per night

Guest favorite

Apartment in Montepulciano

5.0 out of 5 average rating, 13 reviews

Tuscany on the terrace, Montepulciano Centro

Jan 10 – 17

G$18,514 GYD per night

Guest favorite

Apartment in Pienza

4.97 out of 5 average rating, 39 reviews

Apartment Centro Storico Pienza

Sep 10 – 17

G$24,744 GYD per night

Guest favorite

Apartment in Montepulciano

4.96 out of 5 average rating, 47 reviews

The Tramonti di Eramo , downtown Montepulciano.

Nov 11 – 18

G$26,171 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$10,424 GYD 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

Apartments

Houses

Hotels

Popular amenities for Pienza vacation rentals

Stay near Pienza's top sights

Other great vacation rentals in Pienza

Farm stay in Greve in Chianti

Apartment in Montepulciano

Condo in Asciano

Apartment in San Gusmé

Apartment in Montepulciano

Farm stay in Castiglione d'Orcia

Home in Montepulciano

Farm stay in Ruscello

Other great vacation rentals in Pienza

Apartment in Pienza

Villa in Pienza

Apartment in Montepulciano

Apartment in San Quirico d'Orcia

Guesthouse in Montefollonico

Apartment in Montepulciano

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