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Search results; Over 1,000 homes in Pienza

Top guest favorite
Apartment in Pienza
Terrace views over Pienza and Val d’Orcia
4 bedrooms, 5 beds, 3 private baths
Nov 16 – 21
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4.89 out of 5 average rating, 267 reviews
Top guest favorite
Condo in Pienza
A 1500s barn on an organic farm
5.0 out of 5 average rating, 158 reviews, 2 bedrooms, 2 beds, 2 baths
Oct 30 – Nov 4
Top guest favorite
Villa in Pienza
17th-century farmhouse amid olive groves
4.99 out of 5 average rating, 110 reviews, 2 bedrooms, 3 beds, 1 bath
Nov 11 – 16
Top guest favorite
Apartment in Pienza
Historic 1400s building near the Duomo
4.98 out of 5 average rating, 46 reviews, 3 bedrooms, 4 beds, 2 baths
Aug 22 – 27
Guest favorite
Home in Pienza
Free parking near Pienza’s historic center
5.0 out of 5 average rating, 6 reviews, 3 bedrooms, 1 bed, 3 baths
Sep 17 – 22
Top guest favorite
Apartment in Castiglioncello del Trinoro
360-degree Val d’Orcia views, 14th-century palazzo
5.0 out of 5 average rating, 363 reviews, 1 bedroom, 1 bed, 1.5 baths
Aug 19 – 24
Top guest favorite
Home in Castiglion Fiorentino
500-year-old home on 33 private acres
5.0 out of 5 average rating, 53 reviews, 3 bedrooms, 3 beds, 3 baths
Oct 26 – 31
Top guest favorite
Farm stay in Monticchiello
Val d’Orcia views and a travertine pool
4.99 out of 5 average rating, 67 reviews, 4 bedrooms, 4 beds, 4 baths
Oct 30 – Nov 4
Top guest favorite
Home in Montalcino
Renovated farmhouse with a panoramic garden
5.0 out of 5 average rating, 11 reviews, 4 bedrooms, 5 beds, 5 baths
Aug 13 – 18
Top guest favorite
Apartment in Monticchiello
Countryside views and cypress-lined Val d’Orcia hills
4.97 out of 5 average rating, 186 reviews, 3 bedrooms, 4 beds, 2 baths
Nov 17 – 22
Top guest favorite
Guesthouse in Macciano
Tuscan views, pool, and pizza oven
4.97 out of 5 average rating, 238 reviews, 1 bedroom, 2 beds, 1 bath
Oct 30 – Nov 4
Top guest favorite
Apartment in Monticchiello
Medieval building from 1200 in Monticchiello
5.0 out of 5 average rating, 102 reviews, 1 bedroom, 1 bed, 1 bath
Aug 23 – 28
Top guest favorite
Farm stay in Pienza
Medieval castle with exposed beams and pool
4.97 out of 5 average rating, 181 reviews, 1 bedroom, 1 bed, 1 bath
Mar 25 – 30
Guest favorite
Apartment in Montepulciano
Elegant Tuscan home in the historic center
4.96 out of 5 average rating, 67 reviews, 2 bedrooms, 3 beds, 1.5 baths
Sep 26 – Oct 1
Top guest favorite
Vacation home in Siena
18th-century duplex with countryside views
5.0 out of 5 average rating, 12 reviews, 3 bedrooms, 4 beds, 2 baths
Aug 24 – 29
Top guest favorite
Apartment in Montepulciano
Wine-inspired Tuscan villa with gardens
4.89 out of 5 average rating, 28 reviews, 2 bedrooms, 2 beds, 1 bath
Oct 12 – 17
Top guest favorite
Condo in Montepulciano
Terrace with rooftop views near Piazza Grande
4.92 out of 5 average rating, 184 reviews, 1 bedroom, 2 beds, 1 bath
Oct 29 – Nov 3
Top guest favorite
Apartment in Quercegrossa
Renovated farmhouse on a Chianti winery
4.97 out of 5 average rating, 77 reviews, 3 bedrooms, 3 beds, 2.5 baths
Oct 29 – Nov 3
Home in Castiglione d'Orcia
Panoramic valley views from a restored home
New place to stay, 1 bedroom, 1 bed, 1 bath
Aug 27 – Sep 1