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Search results; Over 1,000 homes in Montepulciano

Superhost
Villa in Montepulciano
Noble villa on a winemaker’s estate
8 bedrooms, 10 beds, 6.5 shared baths
Aug 30 – Sep 4
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4.83 out of 5 average rating, 87 reviews
Top guest favorite
Loft in Montepulciano
Fireplace and valley views in Montepulciano
5.0 out of 5 average rating, 508 reviews, 2 beds, 1 bath
Aug 14 – 19
Top guest favorite
Apartment in Montepulciano
17th-century Tuscan style near a vineyard
5.0 out of 5 average rating, 212 reviews, 1 bedroom, 3 beds, 2 baths
Oct 30 – Nov 4
Top guest favorite
Condo in Montepulciano
Hilltop terrace with Val d’Orcia views
5.0 out of 5 average rating, 128 reviews, 1 bedroom, 1 bed, 1 bath
Nov 3 – 8
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
Villa in Chianciano Terme
Hot tub with a view in Tuscany
4.97 out of 5 average rating, 127 reviews, 2 bedrooms, 4 beds, 2 baths
Aug 13 – 18
Top guest favorite
Condo in San Quirico d'Orcia
Panoramic views in Val d’Orcia’s heart
4.99 out of 5 average rating, 98 reviews, 2 bedrooms, 2 beds, 1 bath
Sep 1 – 6
Top guest favorite
Villa in Montepulciano
Vineyard villa with pool and hot tub
4.97 out of 5 average rating, 123 reviews, 4 bedrooms, 5 beds, 2.5 baths
Nov 15 – 20
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
Condo in Asciano
Hilltop garden in the Crete Senesi
4.98 out of 5 average rating, 320 reviews, 2 bedrooms, 4 beds, 1 bath
Oct 26 – 31
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
Apartment in Montepulciano
Frescoed ceilings with panoramic valley views
4.93 out of 5 average rating, 153 reviews, 2 bedrooms, 5 beds, 1 bath
Oct 4 – 9
Top guest favorite
Farm stay in San Quirico d'Orcia
Vineyards and Val d’Orcia views from balconies
4.98 out of 5 average rating, 115 reviews, 5 bedrooms, 5 beds, 5.5 baths
Aug 30 – Sep 4
Top guest favorite
Apartment in Montepulciano
Panoramic hill views and designer furniture
4.97 out of 5 average rating, 322 reviews, 2 bedrooms, 3 beds, 2 baths
Nov 15 – 20
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
Top guest favorite
Apartment in Montepulciano
Exposed beams and a private courtyard
4.91 out of 5 average rating, 77 reviews, 2 bedrooms, 2 beds, 1 bath
Aug 13 – 18
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
Top-floor views beyond the city walls
4.99 out of 5 average rating, 301 reviews, 1 bedroom, 2 beds, 1 bath
Nov 8 – 13
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