Rolling hills, vineyards, and scattered buildings in a hilly landscape.

Holiday Homes in Castelfiorentino

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
13 Nov - 15 Nov
In two months
25 Dec - 27 Dec
In three months
22 Jan - 24 Jan
In four months
19 Feb - 21 Feb

Our top choices for Castelfiorentino holiday homes

A modern kitchen with white cabinets, a microwave, and a dining area with a round table and chairs.

1. New Listing

New Listing
Dogana
The price is NZ$204
includes taxes & fees
2 Nov - 3 Nov
New Listing
A pool area with lounge chairs and umbrellas, surrounded by stone buildings and greenery.

2. Casa Vacanze Le Case

Casa Vacanze Le Case
San Gimignano
9.6 out of 10, Exceptional, (14 reviews)
"The property was perfect and the host was so nice and helpful. We would definitely stay there again."
United States
Andrew
The price is NZ$180
includes taxes & fees
2 Nov - 3 Nov
Casa Vacanze Le Case
A swimming pool with lounge chairs and umbrellas, surrounded by greenery and hills.

3. Villa Il Frantoio with Shared Pool, Private Terrace & Wi-Fi

Villa Il Frantoio with Shared Pool, Private Terrace & Wi-Fi
Montespertoli
The price is NZ$553
includes taxes & fees
2 Nov - 3 Nov
Villa Il Frantoio with Shared Pool, Private Terrace & Wi-Fi
A patio with a table and chairs, an umbrella, and a view of a green fence and plants.

4. Holiday home 'Sandra House Certaldo' with private garden and Wi-Fi

Holiday home 'Sandra House Certaldo' with private garden and Wi-Fi
Certaldo
10.0 out of 10, Exceptional, (1 review)
"Pros: Die familiäre Aufnahme und Unterstützung war sehr angenehm."
Germany
Anonymous traveller
The price is NZ$393
includes taxes & fees
2 Nov - 3 Nov
Holiday home 'Sandra House Certaldo' with private garden and Wi-Fi
An open doorway leading to an outdoor patio with a wooden table and chairs, a stone floor, and a wooden barrel with bottles.

5. Tuscan Farmhouse with Private Pool & Chianti Vineyard Views - 3 Bedr + AC

Tuscan Farmhouse with Private Pool & Chianti Vineyard Views - 3 Bedr + AC
Montespertoli
10.0 out of 10, Exceptional, (1 review)
"We found sanctuary at this lovely farmhouse during the July heat wave--refreshing dip in the pool, relaxing dinner in the courtyard, restful sleep in the air-conditioned home. Got up to watch the sunrise over the vineyards, absolutely stunning scenery, and watched three hot air balloons also taking in the sights. Matteo was very welcoming, and we bridged the language barrier with a little help from Google translate. Wished we could have stayed longer!"
United States
Susan A.
The price is NZ$638
includes taxes & fees
15 Nov - 16 Nov
Tuscan Farmhouse with Private Pool & Chianti Vineyard Views - 3 Bedr + AC
An outdoor patio with a table, chairs, and a view of a landscape.

6. country house with garden ,pool,children's play area ,Tuscany,15 from Florence

country house with garden ,pool,children's play area ,Tuscany,15 from Florence
Toscana
9.8 out of 10, Exceptional, (83 reviews)
"The hostess Sonia was fabulous."
United States
Kim
The price is NZ$287
includes taxes & fees
2 Nov - 3 Nov
country house with garden ,pool,children's play area ,Tuscany,15 from Florence
A garden with a lawn, three white lounge chairs, and a pergola.

7. Apartment House with garden Tuscany Chianti , Florence 15km.

Apartment House with garden Tuscany Chianti , Florence 15km.
Toscana
9.8 out of 10, Exceptional, (75 reviews)
"Great property, well equipped, nice views, well maintained, very friendly and helpful host. We did really enjoy our stay :-)"
Germany
Robert M.
The price is NZ$311
includes taxes & fees
2 Nov - 3 Nov
Apartment House with garden Tuscany Chianti , Florence 15km.
A pool with lounge chairs and umbrellas, surrounded by greenery and buildings.

8. Agriturismo I Borghi – Caffè Apartment with Pool in San Gimignano

Agriturismo I Borghi – Caffè Apartment with Pool in San Gimignano
San Gimignano
Agriturismo I Borghi – Caffè Apartment with Pool in San Gimignano
A large house with a tennis court, surrounded by hills and trees.

9. Holiday Home 'Cottege' with Shared Pool, Private Terrace and Wi-Fi

Holiday Home 'Cottege' with Shared Pool, Private Terrace and Wi-Fi
Palaia
The price is NZ$562
includes taxes & fees
2 Nov - 3 Nov
Holiday Home 'Cottege' with Shared Pool, Private Terrace and Wi-Fi
An outdoor patio with a table, chairs, a grill, and a large umbrella.

10. Vernaccia Country House - Agriturismo Apartment with Pool, Garden & Wi-Fi

Vernaccia Country House - Agriturismo Apartment with Pool, Garden & Wi-Fi
Tavarnelle Val di Pesa
10.0 out of 10, Exceptional, (1 review)
"Das Objekt liegt zwischen Florenz und Siena umgeben von Olivenbäumen. Die Lage ist perfekt für Ausflüge."
Germany
Ramona S.
The price is NZ$556
includes taxes & fees
2 Nov - 3 Nov
Vernaccia Country House - Agriturismo Apartment with Pool, Garden & Wi-Fi
An open wooden door leading to a balcony with a table and chairs, a vase with flowers, and a lush green tree in the background.

11. The Church – San Miniato: Renovated 17th-Century Church in a Renaissance Village

The Church – San Miniato: Renovated 17th-Century Church in a Renaissance Village
Palagio
The price is NZ$1,011
includes taxes & fees
2 Nov - 3 Nov
The Church – San Miniato: Renovated 17th-Century Church in a Renaissance Village
A stone building with a hot tub, surrounded by greenery.

12. Farmhouse "Le Volpaie - Appartamento Maria" with Private Garden, Whirlpool & Wi-Fi

Farmhouse "Le Volpaie - Appartamento Maria" with Private Garden, Whirlpool & Wi-Fi
San Gimignano
10.0 out of 10, Exceptional, (2 reviews)
"It was spacious and clean. Nice kitchen though we did not cook. Coffee maker took some getting used to. Showers on the small side but worked well. Lovely property. Enjoyed our time here. "
United States
Dale M.
The price is NZ$1,069
includes taxes & fees
2 Nov - 3 Nov
Farmhouse "Le Volpaie - Appartamento Maria" with Private Garden, Whirlpool & Wi-Fi
A stone building with a covered outdoor seating area and a brick pathway.

13. Apartment 'La Ripa - Master' with Shared Pool and Wi-Fi

Apartment 'La Ripa - Master' with Shared Pool and Wi-Fi
San Gimignano
10.0 out of 10, Exceptional, (1 review)
"We stayed for a week at La Ripa. It is a very beautiful and quiet place. It is a few minutes from San Gimignano and it is a central place to visit nice villages in Toscany. Rodrigo was there to welcome us and securing for us an optimal stay. He was amicable and available. This is a place we are highly recommending."
Canada
Anne-Marie M.
The price is NZ$964
includes taxes & fees
2 Nov - 3 Nov
Apartment 'La Ripa - Master' with Shared Pool and Wi-Fi
A room with two beds, a window with curtains, a lamp, and a wooden cabinet.

14. Villa 'Villa del Fattore' with Shared Pool, Private Terrace & Wi-Fi

Villa 'Villa del Fattore' with Shared Pool, Private Terrace & Wi-Fi
Montespertoli
8.0 out of 10, Very good, (4 reviews)
"Beautiful stay in a wonderful Italian villa. "
United States
Jessica C.
The price is NZ$1,003
includes taxes & fees
7 Nov - 8 Nov
Villa 'Villa del Fattore' with Shared Pool, Private Terrace & Wi-Fi
A room with a view of a vineyard through an arched window, a bottle of wine, and a plate of fruit.

15. 7 min from Cantina Antinori in Chianti Classico | Pool | Casa Sala & Pepe

7 min from Cantina Antinori in Chianti Classico | Pool | Casa Sala & Pepe
Tavarnelle Val di Pesa
The price is NZ$452
includes taxes & fees
17 Nov - 18 Nov
7 min from Cantina Antinori in Chianti Classico | Pool | Casa Sala & Pepe
A swimming pool with lounge chairs and tables, surrounded by grass and a view of hills.

16. Villa 'La Limonaia' with Shared Pool, Private Terrace & Wi-Fi

Villa 'La Limonaia' with Shared Pool, Private Terrace & Wi-Fi
Montespertoli
6.0 out of 10, (2 reviews)
"Pros: Die Unterkunft ist geräumig und geschmackvoll toskanisch eingerichtet. Die Betten waren bequem, und es war ein Traum morgens ganz alleine im großen Pool seine Bahnen zu ziehen. Der Haustechniker war überaus freundlich und hilfsbereit. Cons: Die Vermieterin war nicht wirklich unfreundlich, aber ruppig und desinteressiert. Bei der Ankunft mussten wir erst einmal jemanden suchen, der uns empfängt. Es gab keine wirkliche Einweisung, wo die Mülltonnen stehen und wo man Wäsche waschen kann. Die...
Germany
Anonymous traveller
The price is NZ$949
includes taxes & fees
2 Nov - 3 Nov
Villa 'La Limonaia' with Shared Pool, Private Terrace & Wi-Fi
A kitchen with a tiled backsplash, a stove, and a refrigerator.

17. Holiday Home 'La Loggia di Giulia' with Private Terrace, Hot Tub and Garden

Holiday Home 'La Loggia di Giulia' with Private Terrace, Hot Tub and Garden
San Gimignano
9.2 out of 10, Wonderful, (13 reviews)
"Great place in the Tuscany area. The views are spectacular, the property is just like the pictures. Would definitely stay here again"
United States
Valerie S.
The price is NZ$1,173
includes taxes & fees
3 Nov - 4 Nov
Holiday Home 'La Loggia di Giulia' with Private Terrace, Hot Tub and Garden
A view through a wooden door of a courtyard with stone walls and potted plants.

18. Chianti Craft House Badia a Passignano

Chianti Craft House Badia a Passignano
Tavarnelle Val di Pesa
10.0 out of 10, Exceptional, (13 reviews)
"Very historic venue, with amazing views"
United States
Oscar O.
The price is NZ$331
includes taxes & fees
2 Nov - 3 Nov
Chianti Craft House Badia a Passignano
A clear blue swimming pool with a view of trees and distant landscape.

19. Tuscan Oasis: Country House with Private Pool, Views, and Private Parking

Tuscan Oasis: Country House with Private Pool, Views, and Private Parking
Capraia e Limite
The price is NZ$753
includes taxes & fees
7 Nov - 8 Nov
Tuscan Oasis: Country House with Private Pool, Views, and Private Parking
A traditional interior with stone arches, a staircase, and a cozy seating area with a table.

20. Agriturismo La Ferrozzola

Agriturismo La Ferrozzola
Castellina in Chianti
9.4 out of 10, Exceptional, (9 reviews)
"Very nice agriturismo. "
United States
Ruth
The price is NZ$255
includes taxes & fees
8 Nov - 9 Nov
Agriturismo La Ferrozzola
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Castelfiorentino Hotel Reviews

Plus Florence - Hostel

Plus Florence - Hostel

10/10 Excellent
"Great value and position , tram straight from airport and a 2 minute walk from tram stop"
Jane 4-night trip
Posted less than an hour ago
Plus Florence - Hostel

Find out more about Castelfiorentino

Castelfiorentino Holiday Homes information

Number of reviews
205
Accommodation
1771 Holiday Homes
Lowest Price
NZ$180
Highest Price
NZ$1,173