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Search results; Over 1,000 homes in Montecastelli Pisano

Top guest favourite
Villa in Montecastelli Pisano
Exclusive villa with pool jacuzzi wifi and green
2 bedrooms, 3 beds, 2 shared bathrooms
20–27 Mar, Business host
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4.96 out of 5 average rating, 53 reviews
Top guest favourite
Home in Greve in Chianti
Relaxation and charm in the Chianti hills
Individual host
10–15 Sept
4.99 out of 5 average rating, 114 reviews
Guest favourite
Villa in Montecastelli Pisano
Holiday Home in Montecastelli with River Views
Business host
19–24 Sept
4.84 out of 5 average rating, 38 reviews
Top guest favourite
Home in Montegufoni
Villa of the Hydrangeas
Individual host
15–20 Oct
4.98 out of 5 average rating, 46 reviews
Top guest favourite
Home in Morrona
Villino Isotta (exclusive private villa)
Individual host
15–20 Oct
4.99 out of 5 average rating, 69 reviews
Villa in Castelfiorentino
[Florence 45min] 4-bedroom panoramic villa with swimming pool
Individual host
20–25 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
Villa in Poggibonsi
New for 2026 - Casa nel Chianti - relaxation & design
Individual host
15–20 Sept
New place to stay
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
Top guest favourite
Farm stay in Lastra a Signa
Farmhouse in Tuscany hills
Business host
18–23 Oct
4.97 out of 5 average rating, 118 reviews
Top guest favourite
Townhouse in Colle di Val d'Elsa
Il Cristallo – Dream Getaway in Tuscany
Business host
9–14 Sept
5.0 out of 5 average rating, 10 reviews
Guest favourite
Home in Bagno A Ripoli
Historic Stone Villa | Pool | 15min Florence
Individual host
1–6 Oct
5.0 out of 5 average rating, 11 reviews
Guest favourite
Home in Poggibonsi
Le Casacce Farmhouse
Individual host
11–16 Oct
5.0 out of 5 average rating, 5 reviews
Top guest favourite
Villa in Peccioli
Luxury Villa "Le Rondini" – Peccioli
Individual host
8–13 Oct
5.0 out of 5 average rating, 17 reviews
Top guest favourite
Villa in Linari
Entire villa with private pool, stunning view!
Individual host
18–23 Sept
4.98 out of 5 average rating, 60 reviews
Top guest favourite
Villa in Radda in Chianti
Villa with pool in Chianti - Castellare Petroso
Business host
3–8 Oct
5.0 out of 5 average rating, 33 reviews
Guest favourite
Villa in Montecastelli Pisano
Cozy 2-Bedroom Apartment
Business host
31 Oct – 5 Nov
4.95 out of 5 average rating, 21 reviews
Top guest favourite
Villa in San Miniato
Lorianaintuscany YellowHouse
Individual host
22–28 Sept
5.0 out of 5 average rating, 12 reviews
Top guest favourite
Home in Galenda
Casa Pernice · Chianti villa with private pool
Business host
7–12 Oct
5.0 out of 5 average rating, 15 reviews