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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
19–24 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
21–26 Nov
5.0 out of 5 average rating, 54 reviews
Guest favourite
Villa in Montespertoli
Villa Moneta, a Slice of Tuscan Paradise
Individual host
8–13 Sept
5.0 out of 5 average rating, 12 reviews
Guest favourite
Flat in Montespertoli
La Casa di Madina – Flo Apartments
Business host
26 Sept – 1 Oct
5.0 out of 5 average rating, 10 reviews
Superhost
Villa in Montespertoli
Tuscan barn with private pool VacaVilla Excl.
Business host
23–28 Sept
New place to stay
Apartment in Montespertoli
Malvasia - Tuscany between art, wine and landscape
Individual host
16–21 Sept
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
9–14 Sept
Guest favourite
Room in Montespertoli
Agriturismo Manetti with pool, Family room
Business host
20–25 Sept
5.0 out of 5 average rating, 8 reviews
Top guest favourite
Home in Barberino Tavarnelle
Peaceful Tuscan Home with Breathtaking Views
Individual host
3–8 Nov
5.0 out of 5 average rating, 87 reviews
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
Superhost
Rooms in Montespertoli
i Casciani - Depéndance
Business host
15–20 Oct
5.0 out of 5 average rating, 3 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
Flat in Montespertoli
GinCat Chianti House - 3 Bedrooms, Terraces & BBQ
Individual host
9–14 Sept
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Holiday home in San Casciano In Val di Pesa
Mucciana 3
Individual host
11–16 Sept
5.0 out of 5 average rating, 12 reviews
Guest favourite
Villa in San Casciano In Val di Pesa
Archipettoli - Exclusive villa 360 view AC WIFI
Individual host
19–26 Sept
5.0 out of 5 average rating, 11 reviews
Villa in Poggibonsi
New for 2026 - Casa nel Chianti - relaxation & design
Individual host
15–20 Sept
New place to stay
Guest favourite
Home in Poggibonsi
Le Casacce Farmhouse
Individual host
11–16 Oct
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Home in Impruneta
Casale Carla
Individual host
8–13 Jan
5.0 out of 5 average rating, 34 reviews