filters

Search results; Over 1,000 homes

Photo 1 of 29
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
Photo 1 of 29
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
Photo 1 of 29
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
Photo 1 of 29
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, 6 reviews
Photo 1 of 29
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
Photo 1 of 29
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
Photo 1 of 29
Top guest favourite
Apartment in Volterra
Marta's Domus
Individual host
3–8 Oct
5.0 out of 5 average rating, 28 reviews
Photo 1 of 8
Tent in Scansano
One Thousand and One Nights in a Moroccan-style tent
Individual host
12–17 Oct
New place to stay
Photo 1 of 29
Home in Greti
Casa Citille - by Happy Rentals
Business host
7–12 Oct
5.0 out of 5 average rating, 5 reviews
Photo 1 of 29
Apartment in Montevarchi
Loft 57- Between Florence, Siena, Arezzo & Chianti
Individual host
4–9 Oct
5.0 out of 5 average rating, 3 reviews
Photo 1 of 29
Villa in Poggibonsi
New for 2026 - Casa nel Chianti - relaxation & design
Individual host
7–12 Oct
5.0 out of 5 average rating, 3 reviews
Photo 1 of 24
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
Photo 1 of 29
Home in Pergine Valdarno
Casa Vecchia | Private Pool & Garden
Business host
3–8 Oct
5.0 out of 5 average rating, 4 reviews
Photo 1 of 29
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
Photo 1 of 29
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
Photo 1 of 25
Superhost
Apartment in Castiglion Fiorentino
Pendici 15, ivy
Individual host
5–10 Oct
5.0 out of 5 average rating, 3 reviews
Photo 1 of 29
Top guest favourite
Farm stay in Greve in Chianti
Ancient Tuscan farmhouse in the Chianti hills
Business host
23–28 Nov
4.99 out of 5 average rating, 285 reviews
Photo 1 of 25
Top guest favourite
Home in Castiglion Fiorentino
The Refuge of San Filippino
Individual host
14–19 Oct
5.0 out of 5 average rating, 7 reviews