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Pienza vacation rentals

Book unique vacation rentals, houses, and more on Airbnb

Top-rated vacation rentals in Pienza

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

Guest favorite

Apartment in Montepulciano

4.98 out of 5 average rating, 258 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.

Oct 27 – Nov 3

G$28,680 GYD per night
Guest favorite

Cottage in Geggiano

4.99 out of 5 average rating, 103 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 8 – 15

G$105,054 GYD per night
Guest favorite

Apartment in Montepulciano

4.97 out of 5 average rating, 326 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.

Mar 26 – Apr 2

G$34,084 GYD per night

Popular amenities for Pienza vacation rentals

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

Apartment in Pienza

4.87 out of 5 average rating, 186 reviews

Renaissance Apartment

Oct 29 – Nov 5

G$39,027 GYD per night
Guest favorite

Apartment in Montepulciano

5.0 out of 5 average rating, 126 reviews

The source

Mar 6 – 13

G$24,715 GYD per night
Guest favorite

Home in Montepulciano

4.98 out of 5 average rating, 291 reviews

Residence In Search of Author

Aug 11 – 18

G$68,511 GYD per night
Guest favorite

Farm stay in Ruscello

4.99 out of 5 average rating, 316 reviews

Agriturismo Fattoria La Parita

Feb 18 – 25

G$30,787 GYD per night
Guest favorite

Apartment in Montepulciano

4.99 out of 5 average rating, 214 reviews

Montepulciano Downtown Storico

Dec 24 – 31

G$18,696 GYD per night
Guest favorite

Home in Panzano In Chianti

4.98 out of 5 average rating, 351 reviews

Old farmhouse near Panzano Castle Abbacìo

Feb 12 – 19

G$23,235 GYD per night
Guest favorite

Apartment in Pienza

5.0 out of 5 average rating, 21 reviews

“Nel Blu” - Stunning views & Private Concierge

Nov 12 – 19

G$41,783 GYD per night
Guest favorite

Condo in Pienza

5.0 out of 5 average rating, 50 reviews

Mascagni Farmhouse in Val d 'Orcia Pienza

Oct 18 – 25

G$45,053 GYD per night
Guest favorite

Condo in Montepulciano

5.0 out of 5 average rating, 14 reviews

Dimora Valinda, Montepulciano Piazza Grande +A/C

Feb 8 – 15

G$15,505 GYD per night
Superhost

Apartment in Pienza

4.9 out of 5 average rating, 99 reviews

Val d 'Orcia apartment "L' Ovile"

Feb 21 – 28

G$19,459 GYD per night
Guest favorite

Villa in Pienza

4.91 out of 5 average rating, 74 reviews

Amazing view of Val d'Orcia Pienza

Nov 20 – 27

G$34,922 GYD per night
Guest favorite

Apartment in San Quirico d'Orcia

5.0 out of 5 average rating, 41 reviews

Antica Loggia - Apartment with view

Nov 3 – 10

G$32,122 GYD per night

Other great vacation rentals in Pienza

Guest favorite

Apartment in Pienza

4.95 out of 5 average rating, 61 reviews

Via del Bacio Uno (literally Kiss Street One)

Dec 12 – 19

G$16,990 GYD per night
Guest favorite

Cottage in Pienza

4.95 out of 5 average rating, 20 reviews

Cottage San Lorenzo

Apr 21 – 28

G$77,889 GYD per night
Guest favorite

Apartment in Pienza

4.9 out of 5 average rating, 42 reviews

La Casetta di Monticchiello with panoramic views

Sep 4 – 11

G$18,692 GYD per night
Guest favorite

Condo in Montefollonico

4.9 out of 5 average rating, 29 reviews

Il Chicchino,Swimmingpool,Tennis,Wi-Fi, Park

Dec 7 – 14

G$23,559 GYD per night
Guest favorite

Apartment in Montalcino

4.99 out of 5 average rating, 80 reviews

Castel Brunello

Oct 18 – 25

G$147,468 GYD per night
Guest favorite

Apartment in Laviano

4.96 out of 5 average rating, 97 reviews

Farmhouse with swimming pool with wonderful view

Oct 11 – 18

G$26,009 GYD per night
Guest favorite

Home in Città della Pieve

5.0 out of 5 average rating, 26 reviews

La Terrazza di Vittoria

Jul 28 – Aug 4

G$27,036 GYD per night
Guest favorite

Villa in Monticchiello

4.95 out of 5 average rating, 42 reviews

Villa with garden. Il Giardino del Cardinale.

Nov 18 – 25

G$153,029 GYD per night
Guest favorite

Farm stay in Montalcino

4.97 out of 5 average rating, 30 reviews

Agriturismo MONSOLE - Sleep in a dream ...

Oct 26 – Nov 2

G$56,931 GYD per night
Guest favorite

Home in Monticchiello

5.0 out of 5 average rating, 14 reviews

Cute dream home

Jan 23 – 30

G$28,459 GYD per night
Guest favorite

Villa in Montepulciano

4.98 out of 5 average rating, 92 reviews

Amazing Tuscany Villa, FREE parking

Dec 30 – Jan 6

G$93,221 GYD per night
Guest favorite

Apartment in Pienza

5.0 out of 5 average rating, 20 reviews

Apartment alla Arco

Aug 12 – 19

G$32,986 GYD per night

Quick stats about vacation rentals in Pienza

Total rentals

70 properties

Rentals with dedicated workspaces

30 properties have a dedicated workspace

Pet-friendly rentals

30 properties allow pets

Family-friendly rentals

30 properties are a good fit for families

Total number of reviews

2.7K reviews

Nightly prices starting at

G$10,472 GYD before taxes and fees

Frequently Asked Questions

  • 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 $80 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.

Destinations to explore

  1. Airbnb
  2. Italy
  3. Tuscany
  4. Province of Siena
  5. Pienza