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Search results; Over 1,000 homes in Montespertoli

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Top guest favourite
Home in Montespertoli
Nibbio III - Entire house in the heart of Chianti
2 bedrooms, 4 beds, 1 private bathroom
1–6 Sept
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5.0 out of 5 average rating, 38 reviews
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Top guest favourite
Barn in Montespertoli
Tuscan Farmhouse – Private Pool & Chianti Views
3 bedrooms, 5 beds, 2 bathrooms
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
7 bedrooms, 11 beds, 7 bathrooms
3–10 Apr
4.95 out of 5 average rating, 40 reviews
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Room in Montespertoli
Agriturismo Manetti pool, Family room
3 beds, 1 bathroom
15–20 Sept
5.0 out of 5 average rating, 7 reviews
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Holiday home in Montespertoli
Rondini Blu Vacation Home - Uva Apartment
1 bedroom, 2 beds, 1 bathroom
25–30 Oct
4.97 out of 5 average rating, 29 reviews
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Apartment in Montespertoli
Malvasia - Toscana tra arte, vino e paesaggio
1 bedroom, 2 beds, 1 bathroom
16–21 Sept
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Guest favourite
Flat in Montespertoli
La Casa di Madina – Flo Apartments
3 bedrooms, 3 beds, 2 bathrooms
5–10 Sept
5.0 out of 5 average rating, 9 reviews
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Top guest favourite
Villa in Noce
Historic villa with private pool in Tuscany
2 bedrooms, 4 beds, 2 bathrooms
11–16 Nov
5.0 out of 5 average rating, 35 reviews
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Home in Montespertoli
Casa Greta - Flo Apartments
2 bedrooms, 3 beds, 2 bathrooms
1–6 Sept
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Villa in Montespertoli
Tuscan barn with private pool VacaVilla Excl.
3 bedrooms, 4 beds, 3 bathrooms
23–28 Sept
New place to stay
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Villa in Poggibonsi
New for 2026 - Casa nel Chianti - relaxation & design
3 bedrooms, 3 beds, 3 bathrooms
1–6 Sept
New place to stay
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Guest favourite
Villa in Montespertoli
Villa Moneta, a Slice of Tuscan Paradise
5 bedrooms, 5 queen beds, 5 bathrooms
7–12 Sept
5.0 out of 5 average rating, 12 reviews
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Room in Montespertoli
Agriturismo Manetti, pool, room with two beds.
2 beds, 1 bathroom
21–26 Sept
5.0 out of 5 average rating, 3 reviews
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Home in Barberino Tavarnelle
Charming Country Tuscan House with Fantastic View
1 bedroom, 2 beds, 1 bathroom
3–8 Nov
5.0 out of 5 average rating, 85 reviews
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Top guest favourite
Home in San Filippo a Ponzano
Infinity pool in Chianti 1
3 bedrooms, 4 beds, 2 bathrooms
20–25 Oct
5.0 out of 5 average rating, 140 reviews
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Flat in San Gimignano
Luxury Residence in the Heart of San Gimignano
3 bedrooms, 3 king beds, 2 bathrooms
1–6 Sept
5.0 out of 5 average rating, 4 reviews
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Villa in Castelfiorentino
[Florence 45min] 4-bedroom panoramic villa with pool
4 bedrooms, 6 beds, 4.5 bathrooms
2–7 Sept
New place to stay
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Top guest favourite
Villa in Barberino Tavarnelle
Luxury Villa in Chianti • Private Natural Pool
2 bedrooms, 3 beds, 2 bathrooms
2–7 Oct
5.0 out of 5 average rating, 30 reviews
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Flat in Montespertoli
GinCat Chianti House - 3 Bedrooms, Terraces & BBQ
3 bedrooms, 3 beds, 2 bathrooms
1–6 Sept
5.0 out of 5 average rating, 4 reviews