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Holiday rentals in Pienza

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Pienza

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

Guest favourite

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.

4–11 Nov

€ 626 per night
Guest favourite

Flat 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.

26 Mar – 2 Apr

€ 153 per night
Guest favourite

Farm stay in Seggiano

4.98 out of 5 average rating, 189 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.

8–15 Jan

€ 103 per night

Popular amenities for Pienza holiday 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 holiday rentals in Pienza

Guest favourite

Flat in Montepulciano

4.98 out of 5 average rating, 258 reviews

Large space between ancient and modern in the center of Montepulciano

27 Oct – 3 Nov

€ 127 per night
Guest favourite

Flat in Pienza

5.0 out of 5 average rating, 21 reviews

“Nel Blu” - Stunning views & Private Concierge

12–19 Nov

€ 185 per night
Guest favourite

Apartment in Pienza

5.0 out of 5 average rating, 50 reviews

Mascagni Farmhouse in Val d 'Orcia Pienza

18–25 Oct

€ 199 per night
Guest favourite

Apartment in Montepulciano

5.0 out of 5 average rating, 14 reviews

Dimora Valinda, Montepulciano Piazza Grande +A/C

8–15 Feb

€ 74 per night
Superhost

Flat in Pienza

4.9 out of 5 average rating, 99 reviews

Val d 'Orcia apartment "L' Ovile"

21–28 Feb

€ 88 per night
Guest favourite

Cottage in Osteria delle Noci

5.0 out of 5 average rating, 57 reviews

Your Tuscan oak tree house, enchanting Val d'Orcia

11–18 Mar

€ 196 per night
Guest favourite

Villa in Pienza

4.91 out of 5 average rating, 74 reviews

Amazing view of Val d'Orcia Pienza

20–27 Nov

€ 162 per night
Guest favourite

Flat in San Quirico d'Orcia

5.0 out of 5 average rating, 41 reviews

Antica Loggia - Apartment with view

3–10 Nov

€ 142 per night
Guest favourite

Villa in Pienza

4.98 out of 5 average rating, 56 reviews

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

16–23 Nov

€ 176 per night
Guest favourite

Guest house in Montefollonico

4.95 out of 5 average rating, 61 reviews

Casale Santa Barbara - Exclusive Apartment

11–18 Jul

€ 194 per night
Guest favourite

Flat in Montepulciano

5.0 out of 5 average rating, 18 reviews

Lo Storico Montepulciano, Cozy apartment in Center

17–24 Jan

€ 80 per night
Guest favourite

Flat in Pienza

4.95 out of 5 average rating, 61 reviews

Via del Bacio Uno (literally Kiss Street One)

12–19 Dec

€ 81 per night

Quick stats about holiday 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

€ 46 before taxes and fees

Destinations to explore

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