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Vacation rentals in Pienza

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Top-rated vacation rentals in Pienza

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

Guest favourite
Apartment in Pienza
“Nel Blu” - Stunning views & Private Concierge
Located in the heart of Pienza, “Nel Blu” is a little treasure hidden within the historic buildings of the town, overlooking the breathtaking landscapes of the Val d’Orcia. The newly refurbished top-floor apartment provides the ideal combination of luminosity, coziness, and a modern yet romantic design, creating the ideal space for couples looking to “live like a local”. Additionally, we offer a private concierge service, in order for you to discover authentic Tuscany and its hidden treasures!
Nov. 6 – 13
$272 CAD per night
5.0 out of 5 average rating, 21 reviews
Guest favourite
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. 26 – Mar. 5
$695 CAD per night
4.99 out of 5 average rating, 102 reviews
Guest favourite
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
$222 CAD 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 favourite
Cottage in Pienza
Cottage San Lorenzo
May 18 – 25
$519 CAD per night
4.95 out of 5 average rating, 20 reviews
Guest favourite
Condo in Pienza
Mascagni Farmhouse in Val d 'Orcia Pienza
Dec. 4 – 11
$284 CAD per night
5.0 out of 5 average rating, 50 reviews
Guest favourite
Villa in Pienza
Amazing view of Val d'Orcia Pienza
Aug. 27 – Sep. 3
$238 CAD per night
4.91 out of 5 average rating, 74 reviews
Guest favourite
Guesthouse in Montefollonico
Casale Santa Barbara - Exclusive Apartment
Nov. 2 – 9
$286 CAD per night
4.95 out of 5 average rating, 60 reviews
Guest favourite
Farm stay in Montalcino
Agriturismo Monolle - sleep in a dream ...
Aug. 9 – 16
$551 CAD per night
4.97 out of 5 average rating, 30 reviews
Guest favourite
Apartment in Montalcino
Castel Brunello
Oct. 18 – 25
$959 CAD per night
4.99 out of 5 average rating, 80 reviews
Guest favourite
Villa in Pienza
Unplug at a 17th-Century Farmhouse Enveloped by Olive Groves
Nov. 24 – Dec. 1
$259 CAD per night
4.98 out of 5 average rating, 55 reviews
Guest favourite
Home in Pienza
Pienza Centro, Residence De charme Baylón,
Jan. 3 – 10
$223 CAD per night
5.0 out of 5 average rating, 11 reviews
Superhost
Apartment in Pienza
Val d 'Orcia apartment "L' Ovile"
Feb. 20 – 27
$129 CAD per night
4.9 out of 5 average rating, 99 reviews
Guest favourite
Condo in Montepulciano
Dimora Valinda, Montepulciano Piazza Grande +A/C
Jan. 10 – 17
$99 CAD per night
5.0 out of 5 average rating, 12 reviews
Guest favourite
Farm stay in Montepulciano
Large Villa 3bdr in Pienza | Orio
Sep. 6 – 13
$1,077 CAD per night
4.96 out of 5 average rating, 71 reviews
Guest favourite
Apartment in San Quirico d'Orcia
Antica Loggia - Apartment with view
Nov. 23 – 30
$209 CAD per night
5.0 out of 5 average rating, 41 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

$68 CAD before taxes and fees

Destinations to explore

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