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Search results; Over 1,000 homes in Montepulciano

Top guest favourite
Apartment in Montepulciano
Residence In cerca d'Autore
2 bedrooms, 2 beds, 2 bathrooms
24–29 Oct, Individual host
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4.97 out of 5 average rating, 344 reviews
Top guest favourite
Villa in Montepulciano
Wine Experience Villa in Montepulciano
Business host
15–20 Nov
4.97 out of 5 average rating, 125 reviews
Top guest favourite
Home in Lucignano
Belvedere Antico [Tuscan pool and garden]
Individual host
15–20 Sept
4.98 out of 5 average rating, 48 reviews
Top guest favourite
Home in Castiglion Fiorentino
Hidden gem in Tuscany
3 bedrooms, 3 beds, 3 bathrooms
26–31 Oct
5.0 out of 5 average rating, 54 reviews
Top guest favourite
Flat in Montepulciano
A view from the gate, Montepulciano.
Individual host
15–20 Nov
4.97 out of 5 average rating, 326 reviews
Top guest favourite
Flat in Monticchiello
Casa Bonari - a paradise for the eyes
Individual host
17–22 Nov
4.97 out of 5 average rating, 187 reviews
Top guest favourite
Villa in Cortona
Stunning Tuscan Villa & Panoramic Infinity Pool
Individual host
6–11 Oct
5.0 out of 5 average rating, 96 reviews
Villa in Pienza
Pennella | Private villa with panoramic pool
Business host
12–19 Sept
Flat in Montepulciano
Dimora Nobile
Individual host
8–13 Sept
New place to stay
Home in Cortona
Relais Tosca Slow and Rural Life
Individual host
26 Sept – 1 Oct
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Farm stay in Monte San Savino
LUXURY VILLA SALTWATER POOL 35 min FROM CORTONA
Business host
30 Oct – 4 Nov
4.99 out of 5 average rating, 113 reviews
Top guest favourite
Holiday home in Monticchiello
Elegant farmhouse overlooking Pienza
Individual host
29 Oct – 3 Nov
5.0 out of 5 average rating, 36 reviews
Top guest favourite
Villa in Chianciano Terme
Charming TuscanVilla with View for Family&Friends
Business host
27 Sept – 2 Oct
4.97 out of 5 average rating, 128 reviews
Top guest favourite
Villa in Pienza
Unplug at a 17th-Century Farmhouse Enveloped by Olive Groves
Business host
11–16 Nov
4.99 out of 5 average rating, 112 reviews
Top guest favourite
Flat in Montepulciano
The source
Individual host
30 Oct – 4 Nov
5.0 out of 5 average rating, 214 reviews
Top guest favourite
Farm stay in Pienza
Selvoli Farmhouse - La Chiocciola
Business host
11–16 Oct
4.97 out of 5 average rating, 37 reviews
Top guest favourite
Home in Monticchiello
"La Lambarda" tower Suite
Business host
1–6 Nov
4.98 out of 5 average rating, 221 reviews
Top guest favourite
Villa in Pienza
Villa I Cipressini Tuscany Private luxury pool spa
Business host
26 Sept – 1 Oct
4.93 out of 5 average rating, 44 reviews
Top guest favourite
Cottage in Osteria delle Noci
Your Tuscan oak tree house, enchanting Val d'Orcia
Individual host
4–9 Oct
5.0 out of 5 average rating, 115 reviews