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Search results; Over 1,000 homes in Montepulciano

Top guest favourite
Villa in Montepulciano
Wine Experience Villa in Montepulciano
4 bedrooms, 5 beds, 2.5 private bathrooms
15–20 Nov, Business host
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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
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
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
Villa in Pienza
Pennella | Private villa with panoramic pool
Business host
12–19 Sept
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
Flat in Montepulciano
Dimora Nobile
Individual host
8–13 Sept
New place to stay
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
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 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
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
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
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
Top guest favourite
Flat in Montepulciano
Dimora dell'Erbe - Rooftop Apartment
Business host
7–12 Nov
5.0 out of 5 average rating, 120 reviews
Top guest favourite
Villa in Sinalunga
The twigs
Individual host
26–31 Oct
5.0 out of 5 average rating, 97 reviews