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Search results; Over 1,000 homes in Montespertoli

Superhost
Cottage in Montespertoli
Chianti Barn with Pool and Vineyard View
2 bedrooms, 3 beds, 1 private bathroom
7–12 Oct, Individual host
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4.79 out of 5 average rating, 288 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
Home in Montespertoli
Casa Greta - Flo Apartments
Business host
9–14 Sept
Superhost
Villa in Montespertoli
Tuscan barn with private pool VacaVilla Excl.
Business host
23–28 Sept
New place to stay
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 Noce
Villa in Tuscany with a private panoramic swimming pool
Business host
11–16 Nov
5.0 out of 5 average rating, 35 reviews
Apartment in Montespertoli
Malvasia - Tuscany between art, wine and landscape
Individual host
16–21 Sept
Top guest favourite
Villa in Poppiano
Chianti VILLA for 21 ppl/Air-Co/Sw-pool/Chef/Wi-Fi
Business host
20–25 Sept
4.94 out of 5 average rating, 33 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
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
Superhost
Home in Montelupo Fiorentino
Aureva Tuscany, modern villa with private pool
Business host
19–24 Sept
5.0 out of 5 average rating, 3 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
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
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
Flat in Montespertoli
GinCat Chianti House - 3 Bedrooms, Terraces & BBQ
Individual host
9–14 Sept
5.0 out of 5 average rating, 4 reviews
Superhost
Rooms in Montespertoli
i Casciani - Depéndance
Business host
15–20 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