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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
1–6 Sept, Individual host
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4.93 out of 5 average rating, 283 reviews
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Top guest favourite
Barn in Montespertoli
Tuscan Farmhouse – Private Pool & Chianti Views
Business host
19–24 Oct
5.0 out of 5 average rating, 53 reviews
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Top guest favourite
Home in Montespertoli
Villa Tirinzano for 14 guests with private pool
Individual host
3–10 Apr
4.93 out of 5 average rating, 42 reviews
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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
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Superhost
Villa in Montespertoli
Tuscan barn with private pool VacaVilla Excl.
Business host
23–28 Sept
New place to stay
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Top guest favourite
Villa in Noce
Historic villa with private pool in Tuscany
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
5–10 Sept
5.0 out of 5 average rating, 10 reviews
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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
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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, 140 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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Apartment in Montespertoli
Malvasia - Tuscany between art, wine and landscape
Individual host
16–21 Sept
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Superhost
Home in Montespertoli
Casa Greta - Flo Apartments
Business host
2–7 Sept
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Top guest favourite
Holiday home in San Casciano In Val di Pesa
Mucciana 3
Individual host
4–9 Sept
5.0 out of 5 average rating, 11 reviews
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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, 10 reviews
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Villa in Poggibonsi
New for 2026 - Casa nel Chianti - relaxation & design
Individual host
15–20 Sept
New place to stay
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Guest favourite
Home in Castelfiorentino
Casa Farsetti
Individual host
25–30 Sept
5.0 out of 5 average rating, 6 reviews
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Superhost
Rooms in Montespertoli
i Casciani - Depéndance
Business host
9–14 Oct
5.0 out of 5 average rating, 3 reviews
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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, 86 reviews
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Flat in Montespertoli
GinCat Chianti House - 3 Bedrooms, Terraces & BBQ
Individual host
2–7 Sept
5.0 out of 5 average rating, 4 reviews