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Search results; Over 1,000 homes in Montespertoli

Top guest favourite
Cottage in Montespertoli
Lovely countryhouse on Chiant hills
2 bedrooms, 3 beds, 2 private bathrooms
2–7 Sept, Individual host
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4.93 out of 5 average rating, 283 reviews
Top guest favourite
Barn in Montespertoli
Tuscan Farmhouse – Private Pool & Chianti Views
Business host
29 Nov – 4 Dec
5.0 out of 5 average rating, 53 reviews
Guest favourite
Villa in Montespertoli
Villa Moneta, a Slice of Tuscan Paradise
Individual host
7–12 Sept
5.0 out of 5 average rating, 12 reviews
Top guest favourite
Holiday home in Montespertoli
Rondini Blu Vacation Home - Uva Apartment
Business host
25–30 Oct
4.97 out of 5 average rating, 29 reviews
Superhost
Villa in Montespertoli
Tuscan barn with private pool VacaVilla Excl.
Business host
23–28 Sept
New place to stay
Guest favourite
Flat in Montespertoli
La Casa di Madina – Flo Apartments
Business host
5–10 Sept
5.0 out of 5 average rating, 10 reviews
Top guest favourite
Villa in Noce
Villa in Tuscany with a private panoramic swimming pool
Business host
11–16 Nov
5.0 out of 5 average rating, 35 reviews
Superhost
Home in Montespertoli
Casa Greta - Flo Apartments
Business host
3–8 Sept
Top guest favourite
Villa in Barberino Tavarnelle
Luxury Villa in Chianti • Private Natural Pool
Individual host
2–7 Oct
5.0 out of 5 average rating, 30 reviews
Guest favourite
Villa in Il Pino
Exclusive villa private pool florentine farmland
Business host
3–8 Oct
5.0 out of 5 average rating, 6 reviews
Top guest favourite
Home in San Filippo a Ponzano
Infinity pool in Chianti 1
Business host
20–25 Oct
5.0 out of 5 average rating, 141 reviews
Top guest favourite
Home in Barberino Tavarnelle
Relaxing Tuscan Country Home with Beautiful Views
Individual host
3–8 Nov
5.0 out of 5 average rating, 87 reviews
Top guest favourite
Holiday home in San Casciano In Val di Pesa
Mucciana 3
Individual host
5–10 Sept
5.0 out of 5 average rating, 11 reviews
Superhost
Rooms in Montespertoli
i Casciani - Depéndance
Business host
9–14 Oct
5.0 out of 5 average rating, 3 reviews
Villa in Poggibonsi
New for 2026 - Casa nel Chianti - relaxation & design
Individual host
15–20 Sept
New place to stay
Home in Poggibonsi
Le Casacce Farmhouse
Individual host
30 Sept – 5 Oct
5.0 out of 5 average rating, 5 reviews
Villa in Castelfiorentino
[Florence 45min] 4-bedroom panoramic villa with swimming pool
Individual host
6–11 Sept
New place to stay
Flat in Montespertoli
GinCat Chianti House - 3 Bedrooms, Terraces & BBQ
Individual host
3–8 Sept
5.0 out of 5 average rating, 4 reviews
Apartment in Montespertoli
Malvasia - Tuscany between art, wine and landscape
Individual host
16–21 Sept