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Search results; Over 1,000 homes in Montespertoli
Over 1,000 homes in Montespertoli
Top guest favourite
Guest favourite
Cottage in Montespertoli
Lovely countryhouse on Chiant hills
2 bedrooms
,
·
3 beds
,
·
2 private bathrooms
2–7 Sept
2–7 Sept
,
·
Individual host
£1,029
total
Show price breakdown
£1,029 total
,
·
4.93 out of 5 average rating, 283 reviews
4.93 (283)
Top guest favourite
Guest favourite
Barn in Montespertoli
Tuscan Farmhouse – Private Pool & Chianti Views
Business host
Business host
29 Nov – 4 Dec
29 Nov – 4 Dec
£821
£740
total
Show price breakdown
Free cancellation
5.0 out of 5 average rating, 53 reviews
5.0 (53)
Guest favourite
Guest favourite
Villa in Montespertoli
Villa Moneta, a Slice of Tuscan Paradise
Individual host
Individual host
7–12 Sept
7–12 Sept
£6,571
£5,582
total
Show price breakdown
5.0 out of 5 average rating, 12 reviews
5.0 (12)
Top guest favourite
Guest favourite
Holiday home in Montespertoli
Rondini Blu Vacation Home - Uva Apartment
Business host
Business host
25–30 Oct
25–30 Oct
£567
£500
total
Show price breakdown
Extended stay discount
Free cancellation
4.97 out of 5 average rating, 29 reviews
4.97 (29)
Superhost
Superhost
Villa in Montespertoli
Tuscan barn with private pool VacaVilla Excl.
Business host
Business host
23–28 Sept
23–28 Sept
£2,183
total
Show price breakdown
£2,183 total
New place to stay
New
Guest favourite
Guest favourite
Flat in Montespertoli
La Casa di Madina – Flo Apartments
Business host
Business host
5–10 Sept
5–10 Sept
£1,020
£941
total
Show price breakdown
5.0 out of 5 average rating, 10 reviews
5.0 (10)
Top guest favourite
Guest favourite
Villa in Noce
Villa in Tuscany with a private panoramic swimming pool
Business host
Business host
11–16 Nov
11–16 Nov
£1,811
£1,292
total
Show price breakdown
Free cancellation
5.0 out of 5 average rating, 35 reviews
5.0 (35)
Superhost
Superhost
Home in Montespertoli
Casa Greta - Flo Apartments
Business host
Business host
3–8 Sept
3–8 Sept
£921
£786
total
Show price breakdown
Top guest favourite
Guest favourite
Villa in Barberino Tavarnelle
Luxury Villa in Chianti • Private Natural Pool
Individual host
Individual host
2–7 Oct
2–7 Oct
£3,703
total
Show price breakdown
£3,703 total
5.0 out of 5 average rating, 30 reviews
5.0 (30)
Guest favourite
Guest favourite
Villa in Il Pino
Exclusive villa private pool florentine farmland
Business host
Business host
3–8 Oct
3–8 Oct
£4,056
£3,064
total
Show price breakdown
5.0 out of 5 average rating, 6 reviews
5.0 (6)
Top guest favourite
Guest favourite
Home in San Filippo a Ponzano
Infinity pool in Chianti 1
Business host
Business host
20–25 Oct
20–25 Oct
£2,095
£1,823
total
Show price breakdown
Free cancellation
5.0 out of 5 average rating, 141 reviews
5.0 (141)
Top guest favourite
Guest favourite
Home in Barberino Tavarnelle
Relaxing Tuscan Country Home with Beautiful Views
Individual host
Individual host
3–8 Nov
3–8 Nov
£714
total
Show price breakdown
£714 total
Free cancellation
5.0 out of 5 average rating, 87 reviews
5.0 (87)
Top guest favourite
Guest favourite
Holiday home in San Casciano In Val di Pesa
Mucciana 3
Individual host
Individual host
5–10 Sept
5–10 Sept
£1,932
£1,738
total
Show price breakdown
5.0 out of 5 average rating, 11 reviews
5.0 (11)
Superhost
Superhost
Rooms in Montespertoli
i Casciani - Depéndance
Business host
Business host
9–14 Oct
9–14 Oct
£1,309
total
Show price breakdown
£1,309 total
5.0 out of 5 average rating, 3 reviews
5.0 (3)
Villa in Poggibonsi
New for 2026 - Casa nel Chianti - relaxation & design
Individual host
Individual host
15–20 Sept
15–20 Sept
£2,997
total
Show price breakdown
£2,997 total
New place to stay
New
Home in Poggibonsi
Le Casacce Farmhouse
Individual host
Individual host
30 Sept – 5 Oct
30 Sept – 5 Oct
£1,123
£901
total
Show price breakdown
Free cancellation
5.0 out of 5 average rating, 5 reviews
5.0 (5)
Villa in Castelfiorentino
[Florence 45min] 4-bedroom panoramic villa with swimming pool
Individual host
Individual host
6–11 Sept
6–11 Sept
£1,750
£1,495
total
Show price breakdown
New place to stay
New
Flat in Montespertoli
GinCat Chianti House - 3 Bedrooms, Terraces & BBQ
Individual host
Individual host
3–8 Sept
3–8 Sept
£613
£566
total
Show price breakdown
5.0 out of 5 average rating, 4 reviews
5.0 (4)
Apartment in Montespertoli
Malvasia - Tuscany between art, wine and landscape
Individual host
Individual host
16–21 Sept
16–21 Sept
£386
total
Show price breakdown
£386 total
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