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

Castelfiorentino Holiday Rentals

  • 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
25 Sept - 27 Sept
In two months
6 Nov - 8 Nov
In three months
4 Dec - 6 Dec
In four months
1 Jan - 3 Jan

Our top choices for Castelfiorentino holiday rentals

View from room

1. B&B Palazzo Tortoli

B&B Palazzo Tortoli
San Gimignano City Centre
9.2 out of 10, Wonderful, (64 reviews)
"In the center of town overlooking a plaza (other rooms overlook the valley). Multiple museums, and dining and shopping options within very easy walking distance. The town and surroundings are beautiful."
United States
Harold
The price is S$208
includes taxes & fees
29 Sept - 30 Sept
B&B Palazzo Tortoli
Property entrance

2. Villa il Fedino

Villa il Fedino
San Casciano in Val di Pesa
9.6 out of 10, Exceptional, (104 reviews)
"This is an excellent property. Very historic, rustic and with great views across the Tuscan landscapes. Lorenzo and his mother were super duper hosts who took great care of us. The property dates back to 1380 and the rooms are decorated with choicest artifacts that adds greatly to the experience. The location is fantastic too with the local market and restaurants in easy walking reach. The breakfast service is fabulous with many choices and Lorenzo himself is great chef as well! Highly recommend...
United States
Nilesh
The price is S$345
includes taxes & fees
6 Oct - 7 Oct
Villa il Fedino
Balcony

3. Palazzo al Torrione 2

Palazzo al Torrione 2
San Gimignano City Centre
9.2 out of 10, Wonderful, (113 reviews)
"They were very helpful to me when I arrived. I difficulty accessing there messages to me. They put me at ease"
United States
Angela
The price is S$192
includes taxes & fees
13 Oct - 14 Oct
Palazzo al Torrione 2
View from room

4. Chianti Village Morrocco

Chianti Village Morrocco
3.0 star property
Tavarnelle Val di Pesa
8.6 out of 10, Excellent, (117 reviews)
"Front desk was very helpful and very comfortable room. "
United States
Chris
The price is S$115
includes taxes & fees
9 Oct - 10 Oct
Chianti Village Morrocco
Terrace/patio

5. Camping Boschetto Di Piemma

Camping Boschetto Di Piemma
3.0 star property
San Gimignano
8.8 out of 10, Excellent, (89 reviews)
"Great experience, close to a beautiful city and castle on a hill. "
New Zealand
Anonymous traveller
The price is S$71
includes taxes & fees
22 Sept - 23 Sept
Camping Boschetto Di Piemma
Terrace/patio

6. Palazzo Pacini

Palazzo Pacini
Colle di Val d'Elsa
9.8 out of 10, Exceptional, (100 reviews)
"We love this beautiful exquisitely appointed hotel in a town with unexpected treasures and great food "
United Kingdom
John
The price is S$218
includes taxes & fees
1 Oct - 2 Oct
Palazzo Pacini
Exterior

7. DomuS Miniato

DomuS Miniato
San Miniato
10.0 out of 10, Exceptional, (2 reviews)
"Super clean, felt brand new with a beaaautiful view on the terrace! Quite a few stairs (heavy luggage :D) but definitely worth it! Sadly we only stayed two nights"
United Kingdom
Celesta
The price is S$137
includes taxes & fees
5 Oct - 6 Oct
DomuS Miniato
Restaurant

8. Relais Villa Olmo

Relais Villa Olmo
Impruneta
9.4 out of 10, Exceptional, (264 reviews)
"Delightful location, comfortable bed, excellent food."
Canada
Rupert
The price is S$263
includes taxes & fees
5 Oct - 6 Oct
Relais Villa Olmo
Rooftop pool

9. Fattoria il Milione Agriturismo

Fattoria il Milione Agriturismo
4.0 star property
Florence
8.4 out of 10, Very good, (261 reviews)
"Great location easy access to Firenze"
Canada
Donnie
The price is S$156
includes taxes & fees
27 Sept - 28 Sept
Fattoria il Milione Agriturismo
Exterior

10. Antico Borgo il Cardino

Antico Borgo il Cardino
San Gimignano
9.4 out of 10, Exceptional, (85 reviews)
"It was perfect for my one night stop before moving on to another location in Toscana."
United States
Craig
The price is S$208
includes taxes & fees
12 Oct - 13 Oct
Antico Borgo il Cardino
Courtyard

11. I Parigi Corbinelli

I Parigi Corbinelli
Florence
9.6 out of 10, Exceptional, (170 reviews)
"Beautiful setting, stunning views, incredible pool and gardens and so easy to jump on the bus into the city."
United Kingdom
Jacqui
The price is S$163
includes taxes & fees
20 Sept - 21 Sept
I Parigi Corbinelli
Property amenity

12. hu Firenze Certosa camping in town

hu Firenze Certosa camping in town
Impruneta
8.4 out of 10, Very good, (101 reviews)
"Lovely location in the hills. Really nice pool and bar."
United Kingdom
Jessica
The price is S$68
includes taxes & fees
12 Oct - 13 Oct
hu Firenze Certosa camping in town
Outdoor dining

13. La Locanda di Pietracupa

La Locanda di Pietracupa
Tavarnelle Val di Pesa
9.6 out of 10, Exceptional, (38 reviews)
"Great place, wonderful restaurant"
Germany
Isabell
The price is S$245
includes taxes & fees
3 Oct - 4 Oct
La Locanda di Pietracupa
Restaurant

14. Marignolle Relais and Charme

Marignolle Relais and Charme
Florence
9.2 out of 10, Wonderful, (92 reviews)
"Good stay"
Canada
David Joseph
The price is S$357
includes taxes & fees
6 Oct - 7 Oct
Marignolle Relais and Charme
Terrace/patio

15. Numa Florence Palazzo San Niccolò

Numa Florence Palazzo San Niccolò
Historic Centre of Florence
9.4 out of 10, Exceptional, (206 reviews)
"Great stay!"
Sweden
Henrik
The price is S$258
includes taxes & fees
13 Sept - 14 Sept
Numa Florence Palazzo San Niccolò
Food court

16. Home in Florence

Home in Florence
Historic Centre of Florence
9.0 out of 10, Wonderful, (77 reviews)
"Wonderful stay again here-our second time. Beautifully clean, perfect location and friendly staff-thankyou for another lovely stay!"
United Kingdom
Victoria
The price is S$177
includes taxes & fees
13 Sept - 14 Sept
Home in Florence
Garden

17. Serristori Palace Residence

Serristori Palace Residence
Historic Centre of Florence
9.6 out of 10, Exceptional, (229 reviews)
"Great location, perfect for 2-3 people. Nice kitchen area, garden sitting area. Recommend!"
United States
Eileen
The price is S$344
includes taxes & fees
13 Sept - 14 Sept
Serristori Palace Residence
Property entrance

18. Residenza D'Epoca Sant Anna

Residenza D'Epoca Sant Anna
Historic Centre of Florence
7.8 out of 10, Good, (288 reviews)
"Lovely and friendly upon arrival, bed was comfortable, black out blinds also made a great night sleep. 15 minute walk into the centre so good location would recommend for a cheap stay!"
United Kingdom
Lily
The price is S$266
includes taxes & fees
13 Sept - 14 Sept
Residenza D'Epoca Sant Anna
Terrace/patio

19. Relais Piazza Signoria

Relais Piazza Signoria
Historic Centre of Florence
9.4 out of 10, Exceptional, (871 reviews)
"great staff. Very accessible and close to very good restaurants and gelaterias."
Canada
Melika
The price is S$354
includes taxes & fees
12 Oct - 13 Oct
Relais Piazza Signoria
Breakfast area

20. Terre di Baccio

Terre di Baccio
Greve in Chianti
9.8 out of 10, Exceptional, (79 reviews)
"The stay was great, and the staff were wonderful. "
United States
SYDNEY
The price is S$428
includes taxes & fees
28 Sept - 29 Sept
Terre di Baccio
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

Hotel Horto Convento

Hotel Horto Convento

8/10 Good
"Staff were very helpful. Property at good location. Very clean and well Maintained"
Anish 4-night trip
Posted 2 hours ago
Hotel Horto Convento

Frequently asked questions

Can I find a holiday rental in Castelfiorentino?

Yes, there are holiday rentals close to the most popular sights in Castelfiorentino, or you can select a more secluded option if you're looking for a relaxing stay. Our travellers say Castelfiorentino has a good selection of restaurants. Make sure you have time to check out the theatres and wineries during your trip.

What are some of the best holiday rentals that Castelfiorentino has to offer?

Villa La Stella - Casa per Ferie: This holiday home rental outside of Castelfiorentino is located near the airport, and has a garden, a library and air conditioning to put you at ease in your new surroundings. This holiday rental also comes with free parking to give you added peace of mind.

How many holiday rentals are there in Castelfiorentino?

Expedia has 12 holiday rentals for your stay in Castelfiorentino.

What can I see and do in Castelfiorentino?

Cultural attractions to visit include Benozzo Gozzoli Museum and Teatro del Popolo. Other places in town to visit include Castle of Oliveto and Castello di Coiano.

What are holiday rentals like in Castelfiorentino?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Castelfiorentino. Holiday rentals feature extras like kitchens and laundry facilities so you'll have a home away from home. If you're concerned about cleanliness, a holiday rental can offer a sense of safety away from shared hotel lifts and busy concierge desks while still allowing you the excitement and enjoyment of travel. You'll also have more space in a holiday rental than in a traditional hotel, which makes a holiday rental a great option for a family trip or a small group gathering.