Castelfiorentino
A vacation rental in Castelfiorentino within the Chianti tourist area in Tuscany is a great choice if you are planning to spend a holiday togeteher with family or friends in Italy. Browsing holiday rentals near Castelfiorentino with guest reviews is a good way to start planning your trip. Unlike a typical hotel stay, or a common holiday rental, our vacation rentals in Castelfiorentino are carefully selected to offer the best experience with all the comforts you expect for your stay. Also consider other vacation rentals nearby Castelfiorentino as villas with pool in Castelfiorentino, last minute rentals near Castelfiorentino, apartments in Castelfiorentino and luxury villas for rent in Castelfiorentino. If you don’t find the right solution here we suggest you to expand your search to see our villas in Tuscany or all our holiday rentals in Italy.
Peace of Mind, Even in Unexpected Situations
Discover our cancellation cost coverResults 1 - 15 of 49
- 17
- 9
- 6
- 300 m2
- Charming Tuscan country property
- Common area with also sauna and gym
- Perfect for organising events
from 547 $per night
Someone else is currently looking at this property!
- 4
- 2
- 1
- 50 m2
- Beautiful detached house in Chianti
- Large terrace with swimming pool
- Basic services within walking distance
from 107 $per night
- 5
- 19
- 7
- 5
- Complex of 5 apartments with swimming pool
- View of the Tuscan hills
- Large park
from 97 $per night
- 12
- 6
- 7
- 250 m2
- Large villa in the Tuscan countryside
- 6 bedrooms, each with private bathroom
- Electric charging station
from 1135 $per night
- 5
- 30
- 15
- 15
- Beautiful property in the Tuscan countryside
- Padel court and five-a-side football pitch
- Private lake with picnic area
from 221 $per night
- 7
- 46
- 16
- 12
- Enchanting property with panoramic views
- Children's Separate swimming pool and play area
- Tennis court available
from 126 $per night
La Valle 1
6
2
2
80 m2
from181 $
per night
per night
La Valle 2
8
3
2
90 m2
from202 $
per night
per night
La Valle 3
8
3
2
120 m2
from202 $
per night
per night
La Valle 4
6
2
2
70 m2
from155 $
per night
per night
La Valle 5
4
1
1
45 m2
from126 $
per night
per night
La Valle 6
8
3
2
80 m2
from184 $
per night
per night
La Valle 7
6
2
1
70 m2
from155 $
per night
per night
- 6
- 3
- 2
- 240 m2
- Detached villa in the countryside
- Hilly and panoramic position
- Close to San Gimignano and the Via Francigena
from 278 $per night
- 12
- 6
- 6
- 350 m2
- Luxury villa in Tuscany with heatable pool
- Panoramic views of San Gimignano
- Indoor spa with jacuzzi, sauna e steam room
from 2026 $per night
- 3
- 10
- 3
- 3
- Historic building in a small medieval village
- Free access to the tower with panoramic view
- Basic services within walking distance
from 64 $per night
Certaldo 1
3
1
1
50 m2
from64 $
per night
per night
Certaldo 2
3
1
1
41 m2
from64 $
per night
per night
Certaldo 3
4
1
1
54 m2
from69 $
per night
per night
- 8
- 4
- 3
- 230 m2
- Historical villa of the Buonaparte family
- Hilly and panoramic position
- Large park with olive grove
from 614 $per night
- 6
- 3
- 3
- 200 m2
- Large villa with luxury furnishings
- Enchanting view of the Tuscan countryside
- 3 bedrooms, each with private bathroom
from 285 $per night
- 5
- 28
- 13
- 10
- Beautiful property in the Tuscan countryside
- Swimming pool with panoramic view over the hills
- Riding stables just 2 km away
from 127 $per night
Casa Rossa 3
4
1
1
47 m2
from127 $
per night
per night
Casa Rossa 4
6
3
3
95 m2
from169 $
per night
per night
Casa Rossa 5
6
3
2
95 m2
from169 $
per night
per night
Casa Rossa 6
6
3
2
95 m2
from169 $
per night
per night
Casa Rossa 7
6
3
2
95 m2
from169 $
per night
per night
- 3
- 12
- 5
- 6
- Beautiful apartments in a medieval village
- Basic services within walking distance
- Magnificent panoramic view
from 227 $per night
La Terrazza
4
2
2
100 m2
from238 $
per night
per night
La Pergola
4
1
1
70 m2
from227 $
per night
per night
La Loggia
4
2
3
90 m2
from238 $
per night
per night
- 4
- 2
- 1
- 65 m2
- Pretty house with private pool
- Completely surrounded by greenery
- 6 km from the medieval village of Certaldo
from 139 $per night
- 39
- 159
- 68
- 56
- Original 12th Century Castle in the Tuscan countryside
- Frescos and decorations of 18th century
- Suitable to host events
from 93 $per night
Tettoia
4
2
2
85 m2
from134 $
per night
per night
Torre
2
1
1
75 m2
from110 $
per night
per night
Montegufoni 10
2
1
1
45 m2
from93 $
per night
per night
Montegufoni 11
3
1
1
45 m2
from99 $
per night
per night
Montegufoni 13
4
1
1
75 m2
from99 $
per night
per night
Acciaioli 14
6
3
3
113 m2
from180 $
per night
per night
Montegufoni 17
4
1
1
55 m2
from105 $
per night
per night
Montegufoni 18
5
2
1
80 m2
from105 $
per night
per night
Acciaioli 1Bis
6
3
3
120 m2
from180 $
per night
per night
Montegufoni 22
2
1
1
32 m2
from99 $
per night
per night
Montegufoni 23
6
3
1
120 m2
from140 $
per night
per night
Montegufoni 27
5
2
1
100 m2
from122 $
per night
per night
Montegufoni 28
3
1
1
70 m2
from99 $
per night
per night
Montegufoni 29
3
2
1
65 m2
from110 $
per night
per night
Montegufoni 3
5
2
1
75 m2
from99 $
per night
per night
Montegufoni 30
4
2
2
80 m2
from128 $
per night
per night
Acciaioli 3
2
1
2
90 m2
from105 $
per night
per night
Tiglio
5
2
2
90 m2
from140 $
per night
per night
Acciaioli 4
5
2
2
70 m2
from140 $
per night
per night
Torre 2
2
1
1
35 m2
from105 $
per night
per night
Villa Acciaioli
8
4
3
180 m2
from199 $
per night
per night
Bellavista
2
1
1
50 m2
from99 $
per night
per night
Archi
4
1
1
45 m2
from205 $
per night
per night
Camino
2
1
1
25 m2
from99 $
per night
per night
Forno
4
2
1
65 m2
from105 $
per night
per night
Giardino
4
1
1
75 m2
from140 $
per night
per night
Guardiano
3
1
1
70 m2
from99 $
per night
per night
Segretario
5
2
1
100 m2
from151 $
per night
per night
Tramonto
4
2
2
80 m2
from140 $
per night
per night
Fattoressa
4
1
1
70 m2
from105 $
per night
per night
Montegufoni 19B
5
3
2
80 m2
from146 $
per night
per night
Cappella
3
1
1
45 m2
from93 $
per night
per night
Bastione
2
1
1
65 m2
from117 $
per night
per night
Galleria
9
4
3
310 m2
from333 $
per night
per night
La Grotta
5
2
2
100 m2
from169 $
per night
per night
Cardinale
6
3
2
110 m2
from151 $
per night
per night
Teatro
3
1
1
90 m2
from122 $
per night
per night
Montegufoni 7
4
1
1
60 m2
from140 $
per night
per night
Cupola
4
2
1
75 m2
from128 $
per night
per night
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Guido Posarelli
Founder of Posarelli Villas, hand-picking all the vacation rentals in Italy we offer on our website.
Why Book With Us Founder of Posarelli Villas, hand-picking all the vacation rentals in Italy we offer on our website.
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