The 10 best holiday rentals in Castiglion Fiorentino, Italy | Booking.com
Skip to main content

Holiday Rentals in Castiglion Fiorentino

Find the holiday rentals that appeal to you the most

Holiday Rentals for every style

Find the right holiday rental for you in Castiglion Fiorentino

The best holiday rentals in Castiglion Fiorentino

Check out our pick of great holiday rentals in Castiglion Fiorentino

Most booked holiday rentals in Castiglion Fiorentino and surroundings in the past month

See all

These holiday rentals in Castiglion Fiorentino and nearby have options with free cancellation

  • Scored out of 10, guest rating 8.6
    Fabulous - What previous guests thought, 7 reviews

    Housed in a historic building, Camera e Appartamento Toscana - B&B Palazzo Robicci offers accommodation with a garden and free WiFi in Castiglion Fiorentino, 20 km from Piazza Grande.

    From US$133.53 per night
  • Casa Traquandi

    Castiglion Fiorentino
    Free cancellation options available
    Scored out of 10, guest rating 8.3
    Very good - What previous guests thought, 17 reviews

    Set in Castiglion Fiorentino, 20 km from Piazza Grande and 44 km from Terme di Montepulciano, Casa Traquandi offers air-conditioned accommodation with a balcony and free WiFi.

    From US$136.81 per night
  • Scored out of 10, guest rating 8.0
    Very good - What previous guests thought, 1 review

    Set in Castiglion Fiorentino, within 46 km of Magione Motorspeedway, Borgo Dolci Colline Resort Cipresso is an accommodation offering quiet street views.

    From US$181.10 per night
  • Casa di Mezzacosta

    Castiglion Fiorentino
    Free cancellation options available
    Scored out of 10, guest rating 8.9
    Fabulous - What previous guests thought, 85 reviews

    Offering garden views, Casa di Mezzacosta is an accommodation located in Castiglion Fiorentino, 24 km from Piazza Grande and 47 km from Terme di Montepulciano.

    From US$69.11 per night
  • La Cantina Relais - Fattoria Il Cipresso

    Arezzo
    Free cancellation options available
    Scored out of 10, guest rating 9.6
    Exceptional - What previous guests thought, 952 reviews

    Featuring a wide garden with swimming pool, La Cantina Relais offers rooms with Wi-Fi in Rigutino. This country house produces organic products including Vin Santo wine, olive oil, honey and jams.

  • Margherita Holiday Home

    Cortona
    Free cancellation options available
    Scored out of 10, guest rating 9.5
    Exceptional - What previous guests thought, 56 reviews

    Boasting pool with a view and views of pool, Margherita Holiday Home is a farm stay set in a historic building in Cortona, 28 km from Piazza Grande.

    From US$182.96 per night
  • Cortona Shabby Chic House

    Cortona
    Free cancellation options available
    Scored out of 10, guest rating 9.6
    Exceptional - What previous guests thought, 63 reviews

    Set within the Cortona Old Town district in Cortona, Cortona Shabby Chic House has air conditioning, a balcony, and inner courtyard views.

    From US$158.13 per night
  • SIGNORELLI HOUSE

    Cortona
    Free cancellation options available
    Scored out of 10, guest rating 10.0
    Exceptional - What previous guests thought, 9 reviews

    Offering city views, SIGNORELLI HOUSE is an accommodation located in Cortona, 37 km from Terme di Montepulciano and 48 km from Perugia Train Station.

    From US$878.51 per night

Highly rated holiday rentals in Castiglion Fiorentino and nearby

  • Scored out of 10, guest rating 8.2
    Very good - What previous guests thought, 10 reviews

    Boasting a seasonal outdoor swimming pool and views of mountain, Giglio Dorato is an apartment set in a historic building in Castiglion Fiorentino, 18 km from Piazza Grande.

    From US$451.72 per night
  • Scored out of 10, guest rating 8.4
    Very good - What previous guests thought, 28 reviews

    Set just 24 km from Piazza Grande, La Maestà Tuscan Sun provides accommodation in Castiglion Fiorentino with access to a rooftop pool, a garden, as well as luggage storage space.

    From US$223.84 per night
  • Appartamento Grey

    Arezzo
    8.0+ review score
    Scored out of 10, guest rating 9.6
    Exceptional - What previous guests thought, 158 reviews

    Appartamento Grey is located in Arezzo and has a private pool and inner courtyard views. There is a private entrance at the apartment for the convenience of those who stay.

    From US$105.42 per night
  • Leopoldina L'Orto

    Arezzo
    8.0+ review score
    Scored out of 10, guest rating 9.1
    Superb - What previous guests thought, 121 reviews

    Offering a garden and garden view, Leopoldina L'Orto is situated in Arezzo, 14 km from Piazza Grande and 43 km from Terme di Montepulciano.

    From US$58.57 per night
  • Agrisalotto

    Cortona
    8.0+ review score
    Scored out of 10, guest rating 9.4
    Superb - What previous guests thought, 142 reviews

    Boasting an infinity pool and views of pool, Agrisalotto is a farm stay set in a historic building in Cortona, 30 km from Piazza Grande.

    From US$128.85 per night
  • Noi Due a Cortona

    Cortona
    8.0+ review score
    Scored out of 10, guest rating 9.5
    Exceptional - What previous guests thought, 63 reviews

    Set in Cortona, 30 km from Piazza Grande and 37 km from Terme di Montepulciano, Noi Due a Cortona offers air conditioning.

    From US$128.85 per night
  • Casa Teatro

    Cortona
    8.0+ review score
    Scored out of 10, guest rating 8.8
    Fabulous - What previous guests thought, 26 reviews

    Set in Cortona, 37 km from Terme di Montepulciano and 48 km from Perugia Train Station, Casa Teatro offers air conditioning.

    From US$148.82 per night
  • Casa Ambra

    Cortona
    8.0+ review score
    Scored out of 10, guest rating 8.8
    Fabulous - What previous guests thought, 57 reviews

    Located in Cortona, 30 km from Piazza Grande, Casa Ambra has free bikes, private parking and rooms with free WiFi access.

    From US$140.56 per night

Enjoy breakfast in Castiglion Fiorentino and nearby

  • Dolce Maria

    Cortona
    Breakfast options
    Scored out of 10, guest rating 9.2
    Superb - What previous guests thought, 417 reviews

    Just 100 metres from Piazza della Repubblica, the Dolce Maria is located in the mediaeval hill town of Cortona.

    From US$134.71 per night
  • B&B San Francesco

    Cortona
    Breakfast options
    Scored out of 10, guest rating 8.4
    Very good - What previous guests thought, 425 reviews

    Located in Cortona, 31 km from Piazza Grande and 37 km from Terme di Montepulciano, B&B San Francesco provides accommodation with free WiFi in a historic building.

    From US$121.82 per night
  • Scored out of 10, guest rating 9.3
    Superb - What previous guests thought, 3 reviews

    Located within 30 km of Piazza Grande and 37 km of Terme di Montepulciano in Cortona, Sotto il Sole di Cortona features accommodation with seating area. The accommodation features a spa bath.

  • B&B Piccolo Hotel

    Cortona
    Breakfast options
    Scored out of 10, guest rating 8.9
    Fabulous - What previous guests thought, 247 reviews

    Located in Cortona, 30 km from Piazza Grande, B&B Piccolo Hotel features accommodation with spa facilities and wellness packages.

    From US$141.73 per night
  • Casa Dreosti

    Cortona
    Breakfast options
    Scored out of 10, guest rating 9.5
    Exceptional - What previous guests thought, 201 reviews

    Set within 32 km of Piazza Grande and 38 km of Terme di Montepulciano, Casa Dreosti offers rooms with air conditioning and a private bathroom in Cortona.

    From US$138.22 per night
  • Locanda Petrella

    Cortona
    Breakfast options
    Scored out of 10, guest rating 9.0
    Superb - What previous guests thought, 391 reviews

    With a quiet location in Cortona's pedestrian area, Locanda Petrella is a 5-minute walk from Cortona Cathedral. It is set on the second floor of a historic building dating back to the 1800s.

    From US$152.28 per night
  • Casa Kita

    Cortona
    Breakfast options
    Scored out of 10, guest rating 8.5
    Very good - What previous guests thought, 224 reviews

    Featuring mountain views, Casa Kita offers accommodation with terrace, around 31 km from Piazza Grande. With lake views, this accommodation provides a patio. The guest house features family rooms.

    From US$111.28 per night
  • Scored out of 10, guest rating 8.2
    Very good - What previous guests thought, 19 reviews

    Situated in Castiglion Fiorentino, 20 km from Piazza Grande and 44 km from Terme di Montepulciano, Casa Letizia features accommodation with free WiFi in a historic building.

    From US$139.39 per night

FAQ about holiday rentals in Castiglion Fiorentino

Holiday rentals that guests love in Castiglion Fiorentino

See all
  • Scored out of 10, guest rating 9.6
    Exceptional - What previous guests thought, 5 reviews
    Perfect location, lovely owners who supplied us with a small gift of their garden products. Very good location, clean and lovely house, air conditioning working perfectly. We wholeheartedly recommend this place to anyone considering a vacation rental in Tuscany.
    Guest review by
    chomik
    Solo traveller
  • Scored out of 10, guest rating 10.0
    Exceptional - What previous guests thought, 4 reviews
    The host Manuela was super nice, easy to communicate with, always helping solve our requests or questions. The villa is amazing, nice pool big house.. just perfect!
    Guest review by
    Petr
    Family with young children
  • Scored out of 10, guest rating 9.9
    Exceptional - What previous guests thought, 15 reviews
    Beautiful house with amazing view. We have been to Tuscany a few times and this was by far the best location we had. The house was fully equipped with everything imaginable. With a fully gated, large garden, it is also a petfriendly location. A 15-20 minute drive to the old village with great restaurants, while the house is quiet, private and surrounded by nature. Leo and Elena were great hosts, and we would be very happy to come again.
    Guest review by
    Silke Pinkhof
    People with friends
  • Scored out of 10, guest rating 8.3
    Very good - What previous guests thought, 3 reviews
    This place felt more personal than a lot of other villa's we have stayed in.
    Guest review by
    Kelly
    Solo traveller
  • Scored out of 10, guest rating 9.8
    Exceptional - What previous guests thought, 5 reviews
    Everything was amazing. The villa, the pool, the property. We enjoyed our stay so much.
    Guest review by
    Mikhail
    Family with young children
  • Scored out of 10, guest rating 9.8
    Exceptional - What previous guests thought, 5 reviews
    Beautiful villa nestled in a gorgeous medieval town.
    Guest review by
    Daniel
    People with friends
  • Scored out of 10, guest rating 9.3
    Superb - What previous guests thought, 37 reviews
    Authentic and romantic palace or villa at the medieval wall in Castiglion Fiorentina. Tosca is a very pleasant and professional host to accommodate an unforgettable stay.
    Guest review by
    Anonymous
    Young couple
  • Scored out of 10, guest rating 10.0
    Exceptional - What previous guests thought, 1 review
    Beautiful villa, very peaceful, very well equipped with everything you need. Only a 20 minute walk to town/station. Panacotta made for us one evening by the host
    Guest review by
    Alison
    Family with young children