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Search results; Over 1,000 homes in Montespertoli

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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, 284 reviews
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Top guest favourite
Barn in Montespertoli
Tuscan Farmhouse – Private Pool & Chianti Views
Business host
21–26 Nov
5.0 out of 5 average rating, 55 reviews
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Top guest favourite
Holiday home in Montespertoli
Rondini Blu Vacation Home - Uva Apartment
Business host
12–17 Oct
4.97 out of 5 average rating, 33 reviews
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Superhost
Villa in Montespertoli
Tuscan barn with private pool VacaVilla Excl.
Business host
23–28 Sept
5.0 out of 5 average rating, 3 reviews
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Guest favourite
Villa in Montespertoli
Villa Moneta, a Slice of Tuscan Paradise
Individual host
20–25 Sept
5.0 out of 5 average rating, 12 reviews
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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
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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
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Guest favourite
Room in Montespertoli
Agriturismo Manetti with pool, Family room
Business host
10–15 Oct
5.0 out of 5 average rating, 8 reviews
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Top guest favourite
Home in Barberino Tavarnelle
Peaceful Tuscan Home with Breathtaking Views
Individual host
20–25 Nov
5.0 out of 5 average rating, 90 reviews
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Superhost
Home in Montespertoli
Casa Greta - Flo Apartments
Business host
17–22 Sept
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Guest favourite
Room in Montespertoli
Agriturismo Manetti with pool, Room with two beds.
Business host
21–26 Sept
5.0 out of 5 average rating, 4 reviews
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Superhost
Rooms in Montespertoli
i Casciani - Depéndance
Business host
15–20 Oct
5.0 out of 5 average rating, 3 reviews
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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
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Top guest favourite
Holiday home in San Casciano In Val di Pesa
Mucciana 3
Individual host
19–24 Sept
5.0 out of 5 average rating, 12 reviews
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Flat in Montespertoli
GinCat Chianti House - 3 Bedrooms, Terraces & BBQ
Individual host
17–22 Sept
5.0 out of 5 average rating, 4 reviews
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Guest favourite
Home in Poggibonsi
Le Casacce Farmhouse
Individual host
11–16 Oct
5.0 out of 5 average rating, 6 reviews
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Flat in Certaldo
La Casa di Mario: Apt near Siena and Florence
Business host
12–17 Oct
5.0 out of 5 average rating, 4 reviews
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Villa in Poggibonsi
New for 2026 - Casa nel Chianti - relaxation & design
Individual host
16–21 Sept
New place to stay
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Top guest favourite
Villa in San Miniato
Lorianaintuscany YellowHouse
Individual host
22–28 Sept
5.0 out of 5 average rating, 13 reviews