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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
Large space between ancient and modern in the center of Montepulciano
Be enveloped by the feeling of intimacy and warmth of this large space where the various areas are divided by original solutions. The original features, such as the exposed beams, are associated with fresh and 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 15 – 22
$116 per night
4.98 out of 5 average rating, 257 reviews
Guest favorite
Cottage in Geggiano
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.
Feb 27 – Mar 6
$441 per night
4.99 out of 5 average rating, 102 reviews
Guest favorite
Apartment in Montepulciano
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.
Dec 21 – 28
$142 per night
4.97 out of 5 average rating, 326 reviews

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
Home in Montepulciano
Residence In Search of Author
Aug 3 – 10
$287 per night
4.98 out of 5 average rating, 291 reviews
Superhost
Apartment in Pienza
"Il Casello" - Holidays in Tuscany
Sep 29 – Oct 6
$88 per night
4.8 out of 5 average rating, 201 reviews
Guest favorite
Home in Scrofiano
Jenny's Barn
Oct 10 – 17
$123 per night
4.96 out of 5 average rating, 113 reviews
Guest favorite
Farm stay in Ruscello
Agriturismo Fattoria La Parita
Jan 12 – 19
$130 per night
4.99 out of 5 average rating, 316 reviews
Guest favorite
Apartment in Montepulciano
Stuart Black Tea Amazing View & Super Central
Nov 12 – 19
$130 per night
4.96 out of 5 average rating, 131 reviews
Guest favorite
Apartment in Montepulciano
Casa Ricci Apartment in 1300's palace
Jul 11 – 18
$124 per night
4.96 out of 5 average rating, 204 reviews
Superhost
Farm stay in Montepulciano
La Manonera Cottage for 2 people
Oct 29 – Nov 5
$72 per night
4.79 out of 5 average rating, 215 reviews
Guest favorite
Farm stay in Castiglione d'Orcia
Agriturismo IL PODERUCCIO STUDIO
Sep 25 – Oct 2
$94 per night
4.89 out of 5 average rating, 201 reviews
Guest favorite
Apartment in Pienza
“Nel Blu” - Stunning views & Private Concierge
Nov 6 – 13
$176 per night
5.0 out of 5 average rating, 21 reviews
Superhost
Apartment in Pienza
Val d 'Orcia apartment "L' Ovile"
Jan 14 – 21
$82 per night
4.9 out of 5 average rating, 99 reviews
Guest favorite
Condo in Pienza
Mascagni Farmhouse in Val d 'Orcia Pienza
Sep 5 – 12
$190 per night
5.0 out of 5 average rating, 50 reviews
Guest favorite
Cottage in Osteria delle Noci
Your Tuscan oak tree house, enchanting Val d'Orcia
Jan 24 – 31
$186 per night
5.0 out of 5 average rating, 56 reviews

Other great vacation rentals in Pienza

Guest favorite
Home in Pienza
Pienza Centro, Residence De charme Baylón,
Jan 3 – 10
$137 per night
5.0 out of 5 average rating, 11 reviews
Guest favorite
Apartment in San Quirico d'Orcia
Antica Loggia - Apartment with view
Nov 23 – 30
$135 per night
5.0 out of 5 average rating, 41 reviews
Guest favorite
Cottage in Pienza
Cottage San Lorenzo
Apr 18 – 25
$327 per night
4.95 out of 5 average rating, 20 reviews
Guest favorite
Apartment in Montalcino
Castel Brunello
Oct 18 – 25
$620 per night
4.99 out of 5 average rating, 80 reviews
Guest favorite
Farm stay in Montalcino
Agriturismo MONSOLE - Sleep in a dream ...
Aug 9 – 16
$407 per night
4.97 out of 5 average rating, 30 reviews
Guest favorite
Apartment in Pienza
Via del Bacio Uno (literally Kiss Street One)
Nov 4 – 11
$71 per night
4.95 out of 5 average rating, 61 reviews
Guest favorite
Apartment in Pienza
La Casetta di Monticchiello with panoramic views
Aug 31 – Sep 7
$79 per night
4.9 out of 5 average rating, 42 reviews
Guest favorite
Villa in Montepulciano
Amazing Tuscany Villa, FREE parking
Jan 2 – 9
$319 per night
4.98 out of 5 average rating, 93 reviews
Guest favorite
Villa in Monticchiello
The Cardinal's Garden.
Feb 8 – 15
$696 per night
4.95 out of 5 average rating, 42 reviews
Guest favorite
Tiny home in Pienza
Agriturismo Selvoli - La Scuola
Oct 31 – Nov 7
$90 per night
5.0 out of 5 average rating, 5 reviews
Guest favorite
Villa in Montepulciano
Wine Experience Villa in Montepulciano
Feb 19 – 26
$555 per night
4.96 out of 5 average rating, 72 reviews
Guest favorite
Apartment in Pienza
Apartment alla Arco
Apr 30 – May 7
$143 per night
5.0 out of 5 average rating, 19 reviews

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

$50 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