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Search results; Over 1,000 homes

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Top guest favourite
Flat in San Gimignano
Luxury Residence in the Heart of San Gimignano
Individual host
28 Oct – 2 Nov
5.0 out of 5 average rating, 7 reviews
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Top guest favourite
Home in Barberino Tavarnelle
Peaceful and Relaxing Tuscan Retreat with Views
Individual host
20–25 Nov
5.0 out of 5 average rating, 90 reviews
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Top guest favourite
Home in Camaiore
Your Tuscan Hideaway Awaits You
Individual host
1–6 Oct
5.0 out of 5 average rating, 8 reviews
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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
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Top guest favourite
Home in Castiglion Fiorentino
Villa with Private Pool in the Tuscan Countryside
Individual host
13–18 Oct
5.0 out of 5 average rating, 23 reviews
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Top guest favourite
Villa in Panicale
Escape to Umbria, Villa Maria
Business host
26–31 Oct
5.0 out of 5 average rating, 6 reviews
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Home in Greti
Casa Citille - by Happy Rentals
Business host
7–12 Oct
5.0 out of 5 average rating, 5 reviews
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Top guest favourite
Home in Galenda
Casa Pernice · Chianti villa with private pool
Business host
7–12 Oct
5.0 out of 5 average rating, 15 reviews
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Home in Pergine Valdarno
Casa Vecchia | Private Pool & Garden
Business host
3–8 Oct
5.0 out of 5 average rating, 4 reviews
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Top guest favourite
Apartment in Volterra
Marta's Domus
Individual host
3–8 Oct
5.0 out of 5 average rating, 29 reviews
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Guest favourite
Home in Montefollonico
Charming Tuscan Home · Montepulciano & Val d'Orcia
Individual host
13–18 Oct
5.0 out of 5 average rating, 5 reviews
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Top guest favourite
Flat in San Gimignano
Private Courtyard | 3BR/3BA | Garage
Individual host
18–23 Oct
5.0 out of 5 average rating, 15 reviews
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Villa in Poggibonsi
New for 2026 - Casa nel Chianti - relaxation & design
Individual host
7–12 Oct
5.0 out of 5 average rating, 4 reviews
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Top guest favourite
Villa in Peccioli
Luxury Villa "Le Rondini" – Peccioli
Individual host
8–13 Oct
5.0 out of 5 average rating, 18 reviews
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Superhost
Home in Greve in Chianti
Villa with swimming pool in the heart of Chianti | Florence
Individual host
10–15 Oct
5.0 out of 5 average rating, 4 reviews
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Guest favourite
Flat in Marina di Castagneto Carducci
Seafront Apartment
Individual host
13–18 Oct
5.0 out of 5 average rating, 12 reviews
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Home in Dovadola
Torre di Vedetta medieval rustic farmhouse with 10 beds
Individual host
1–6 Oct
5.0 out of 5 average rating, 3 reviews
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Tower in San Donato
Luxury apartment in an 11th-century tower
Business host
20–25 Nov