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Top guest favourite
Home in Marina
Beachfront Tuscany
3 bedrooms, 5 beds, 3 private bathrooms
16–21 Oct
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5.0 out of 5 average rating, 48 reviews
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Top guest favourite
Villa in Peccioli
Luxury Villa "Le Rondini" – Peccioli
2 bedrooms, 3 beds, 4 bathrooms
8–13 Oct
5.0 out of 5 average rating, 18 reviews
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Top guest favourite
Villa in Cortona
Stunning Tuscan Villa & Panoramic Infinity Pool
5 bedrooms, 8 beds, 4 bathrooms
6–11 Oct
5.0 out of 5 average rating, 96 reviews
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Top guest favourite
Flat in San Gimignano
Luxury Residence in the Heart of San Gimignano
3 bedrooms, 3 king beds, 2 bathrooms
28 Oct – 2 Nov
5.0 out of 5 average rating, 6 reviews
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Top guest favourite
Home in Castiglion Fiorentino
Villa with Private Pool in the Tuscan Countryside
3 bedrooms, 4 beds, 2 bathrooms
13–18 Oct
5.0 out of 5 average rating, 23 reviews
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Featured hotel
Hotel in Florence
B&B HOTEL Firenze City Center, Triple Room
1 bedroom, 1 bathroom
30 Oct – 4 Nov
New place to stay
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Top guest favourite
Home in Galenda
Casa Pernice · Chianti villa with private pool
3 bedrooms, 4 beds, 3 bathrooms
7–12 Oct
5.0 out of 5 average rating, 15 reviews
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Superhost
Home in Greve in Chianti
Villa with a swimming pool in the heart of Chianti | Florence
3 bedrooms, 3 double beds, 3 bathrooms
10–15 Oct
5.0 out of 5 average rating, 4 reviews
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Top guest favourite
Home in Barberino Tavarnelle
Peaceful and Relaxing Tuscan Retreat with Views
1 bedroom, 2 beds, 1 bathroom
20–25 Nov
5.0 out of 5 average rating, 90 reviews
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Villa in Poggibonsi
New for 2026 - Casa nel Chianti - relaxation & design
3 bedrooms, 3 beds, 3 bathrooms
7–12 Oct
5.0 out of 5 average rating, 4 reviews
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Home in Colle di Val d'Elsa
Casa Emilio
2 bedrooms, 2 beds, 1 bathroom
1–6 Oct
5.0 out of 5 average rating, 4 reviews
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Home in Greti
Casa Citille - by Happy Rentals
3 bedrooms, 4 beds, 2 bathrooms
7–12 Oct
5.0 out of 5 average rating, 5 reviews
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Top guest favourite
Villa in Cavo
"Semaforo di Monte Grosso" (Monte Grosso Semaphore) / Monte Grosso, Elba
6 bedrooms, 7 beds, 4.5 bathrooms
8–15 May
5.0 out of 5 average rating, 15 reviews
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Top guest favourite
Villa in Magione
Villa Trasimena Luxury Estate -Trasimeno Lake
5 bedrooms, 5 queen beds, 6 bathrooms
10–15 Oct
5.0 out of 5 average rating, 15 reviews
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Guest favourite
Flat in Siena
La Papessa: next piazza del Campo, wi fi, ac, view
2 bedrooms, 3 beds, 2 bathrooms
1–6 Oct
5.0 out of 5 average rating, 5 reviews
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Top guest favourite
Villa in Panicale
Escape to Umbria, Villa Maria
8 bedrooms, 10 beds, 8 bathrooms
26–31 Oct
5.0 out of 5 average rating, 6 reviews
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Superhost
Holiday home in Buti
Rivolta Home – Oasi con Vista e Piscina
1 bedroom, 2 beds, 1 bathroom
14–19 Oct
5.0 out of 5 average rating, 4 reviews
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Top guest favourite
Flat in San Gimignano
Private Courtyard | 3BR/3BA | Garage
3 bedrooms, 3 king beds, 3 bathrooms
18–23 Oct
5.0 out of 5 average rating, 15 reviews
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Luxe
Holiday home in Passignano sul Trasimeno
Private Winery Apartment
2 bedrooms, 2 king beds, 2 bathrooms
2–7 Oct
5.0 out of 5 average rating, 6 reviews