We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.
We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Holiday Rentals and Homes in Castiglion Fiorentino, Italy

Map
Satellite
Map updates are paused. Zoom in to see updated info.
Reset zoom
Updating Map...
Your filters are still active.
There are no pins in your viewport. Try moving the map or changing your filters.
dd/mm/yyyy dd/mm/yyyy
    There are no pins in your viewport. Try moving the map or changing your filters.
    • {providername} {price}
    {providername} {price}
      {listitems}
    {sold_out_text}
    We can't find prices for this accommodation
    From {rate_price} {rate_periodicity}
    Payment Protection
    Use a credit card to book with our Peace of Mind Protection.Learn more
    Find a rental
    Price per night
    Min
    to
    Max
    Bedrooms
    Any
    Amenities
    Select
    Payment
    Select
    Go to map view
    More filters
    All 127 Rentals in Castiglion Fiorentino
    loading...
    Travellers to Castiglion Fiorentino are booking May dates now. Secure your holiday rental today, and have the perfect trip.
    Sort by
    From
    €68
    / Night
    Payment Protection
    View Details
    1 / 15
    4.5 of 5 stars (15) Very good
    2 Bedrooms / 1 Bathroom / Sleeps 4
    Overview Reviews (15) Make Enquiry
    From
    €60
    / Night
    Payment Protection
    View Details
    1 / 24
    5 of 5 stars (2) Excellent
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    travellers have booked this property
    Overview Reviews (2) Make Enquiry
    From
    €70
    / Night
    Payment Protection
    View Details
    1 / 14
    5 of 5 stars (2) Excellent
    1 Bedroom / 1 Bathroom / Sleeps 2
    traveller have booked this property
    Overview Reviews (2) Make Enquiry
    From
    €190
    / Night
    Payment Protection
    View Details
    1 / 42
    5 of 5 stars (32) Excellent
    3 Bedrooms / 3 Bathrooms / Sleeps 6
    travellers have booked this property
    Overview Reviews (32) Make Enquiry
    Amenities & Details
    • Balcony
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Internet Access
    • Mountain Views
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • ?
    • Wheelchair access
    • Elder access
    • ?
    About this property
    Guest Comment: 'I have never slept so well with the pristine mountain air wafting through the open windows at night. If you want to have a 'non-touristy' true get away this is the house for you' If you are planning a visit to Cortona, Castiglion Fiorentino and beyond, Villa Coppa is really a... View all property information
    Make Enquiry
    5 of 5 stars Reviewed 12 July 2014
    Above the city of Castiglion Fiorentino and 30 minutes from the jewel that is Cortona. Large house, fantastic kitchen with pristine, new appliances. Fantastic dining with a view...
    4 of 5 stars Reviewed 6 September 2013
    All of the previous reviews are correct. The place is situated high on a hill with a view like none other. Inside, the furnishings are very nice. Our only complaints were...
    See all reviews
    From
    €471
    / Night
    Payment Protection
    View Details
    1 / 12
    5 of 5 stars (5) Excellent
    6 Bedrooms / 5 Bathrooms / Sleeps 13
    Overview Reviews (5) Make Enquiry
    Amenities & Details
    • Balcony
    • Dishwasher
    • Fireplace
    • Grill
    • Internet Access
    • Ping Pong Table
    • Private Outdoor...
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • Wheelchair access
    • Elder access
    • x
    About this property
    The beautiful old stone house is quite large, incorporating 4,500 sf (400 sm). It includes a total of six bedrooms and five baths, with a sleeping capacity of 13. The property includes a lovely garden with a small vineyard and numerous olive trees. Il Ceriolo is located just 5km outside the town... View all property information
    Make Enquiry
    5 of 5 stars Reviewed 22 April 2013
    Charming villa, comfortably accommodates 12 adults. Can be divided into 3 separate 2-bedroom apartments, each with its own kitchen/dining/bath and living area, or rented as one...
    5 of 5 stars Reviewed 4 December 2012
    This is a lovely villa located in the Tuscan country side outside Castiglione Fiorentino. The views of Cortona and castle Montechio lit up by the setting sun are marvelous. The...
    See all reviews
    Enquire for rates
    1 / 17
    1 Bedroom / 1 Bathroom / Sleeps 2
    Overview Make Enquiry
    Amenities & Details
    • Dishwasher
    • Washer
    • Wi-Fi
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • Wheelchair access
    • Elder access
    • x
    • x
    About this property
    The house is a typical 'mansarda' wonderfully furnished with original antique pieces that belonged to my grandparents and have been in the family for generations. This little gem is located in the historical center of Castiglion Fiorentino (Arezzo). This charming apartment consists of a big... View all property information
    Make Enquiry
    From
    €126
    / Night
    Payment Protection
    View Details
    1 / 76
    5 of 5 stars (1) Excellent
    2 Bedrooms / 1 Bathroom / Sleeps 3
    Overview Reviews (1) Make Enquiry
    Amenities & Details
    • Balcony
    • Fireplace
    • Grill
    • Internet Access
    • Mountain Views
    • Private Outdoor...
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    'Simple and Lovely' Borgo Tranquilita is a charming peaceful and quiet 'village' of three cottages set amongst some of the most spectacular scenery that makes Tuscany one of the stunning places to visit. It is surrounded by typical Tuscan woodland with some breathtaking views. The cottages are... View all property information
    Make Enquiry
    From
    €135
    / Night
    Payment Protection
    View Details
    1 / 26
    4.5 of 5 stars (4) Very good
    2 Bedrooms / 2 Bathrooms / Sleeps 5
    Overview Reviews (4) Make Enquiry
    Amenities & Details
    • Balcony
    • Dryer
    • Fireplace
    • Grill
    • Internet Access
    • Mountain Views
    • Shared Outdoor Pool...
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    'How lucky the locals are to live in a place as rich in natural beauty as here' Mary-Beth, June 213. Set in one of Tuscany's most pretty valleys you will find this absolutely charming estate and, this lovely cottage with its 'gorgeous pool'. Close to the famous towns of Cortona, Castiglion... View all property information
    Make Enquiry
    5 of 5 stars Reviewed 1 March 2015
    We stayed for a week -- close to the village. Biking to Despar grocery store 5 minutes away. I felt like I guest not a tourist. There are bikes (nothing fancy but usable) for...
    See all reviews
    From
    €2,275
    / Week
    View Details
    1 / 18
    5 Bedrooms / 4 Bathrooms / Sleeps 11
    Overview Make Enquiry
    Amenities & Details
    • Dishwasher
    • Fireplace
    • Grill
    • Private Outdoor...
    • Satellite TV
    • Washer
    • Wi-Fi
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • Wheelchair access
    • Elder access
    • x
    About this property
    The home is carefully decorated in a classic Tuscan style with well maintained outdoor areas. Its large lounge area with wonderful ancient brick arches, the swimming pool bordered by flowers and olive trees, and the elegant Tuscan décor create an enchanting setting for a memorable stay in Tuscany.... View all property information
    Make Enquiry
    From
    €55
    / Night
    Payment Protection
    View Details
    1 / 15
    5 of 5 stars (1) Excellent
    Studio / 1 Bathroom / Sleeps 3
    traveller have booked this property
    Overview Reviews (1) Make Enquiry
    5 of 5 stars Reviewed 15 April 2014
    Owners very welcoming and hospitable. They could not do enough to make sure we were comfortable. They even came out to rescue us on two occasions when we couldn't find our way...
    See all reviews
    List your property for free!
    List your holiday rental where TripAdvisor travellers can find it.
    Add a Listing
    From
    €60
    / Night
    Payment Protection
    View Details
    1 / 9
    5 of 5 stars (4) Excellent
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    travellers have booked this property
    Overview Reviews (4) Make Enquiry
    Amenities & Details
    • Dishwasher
    • Fireplace
    • Internet Access
    • Mountain Views
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • ?
    • ?
    • Wheelchair access
    • Elder access
    • x
    About this property
    L'agriturismo si trova in posizione collinare, immerso nel bosco tra ulivi e querce, a 500 mslm. Il casolare in pietra, ricavato da un'antica cantina ed essiccatoio per uva da vinsanto, è stato appena ristrutturato. L'interno, finemente arredato, è composto da cucina con antico camino, forno... View all property information
    Make Enquiry
    5 of 5 stars Reviewed 25 September 2014
    Having driven up to Castiglion Fiorentino from Rome, it was wonderful to be met in the town by Pamela who led us by car a few minutes up the mountain road to Le Maceie. On...
    5 of 5 stars Reviewed 26 June 2014
    Ein wunderschönes, einsam und idyllisch gelegenes Haus mit allem Komfort, genialer Blick ins Tal. Die Besitzer sind sehr freundlich, hilfsbereit und erfüllen jeden Wunsch. Wir...
    See all reviews
    From
    €295
    / Night
    Payment Protection
    View Details
    1 / 26
    4.5 of 5 stars (3) Very good
    2 Bedrooms / 2 Bathrooms / Sleeps 4
    traveller have booked this property
    Overview Reviews (3) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Internet Access
    • Mountain Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • ?
    • Wheelchair access
    • Elder access
    • ?
    About this property
    Castello Margarita's Garden apartment is the ideal spot for those seeking relaxation and the convenience to explore Tuscany. Ideal for 2- 5 guests, It provides a compelling combination of a great location and charming farmhouse style. The property is offered as either two apartments (one for... View all property information
    Make Enquiry
    5 of 5 stars Reviewed 3 August 2014
    We spent a great week at the garden villa (ie the ground floor villa) in this house. It sits high above the valley with inspiring views. The villa was a great size could easily...
    4 of 5 stars Reviewed 24 May 2013
    We stayed at this villa last Summer. Despite some confusion over our arrival day the owners and family ensured the villa was prepared for us before we settled in. I believe we...
    See all reviews
    From
    €65
    / Night
    Payment Protection
    View Details
    1 / 8
    5 of 5 stars (1) Excellent
    14 Bedrooms / Sleeps 39
    Overview Reviews (1) Make Enquiry
    5 of 5 stars Reviewed 18 September 2014
    This was a perfect 2 week stay for me and 4 of my friends. Very well maintained place, clean apartment, very helpful and responsive staff. It has nice amenities and it is a good...
    See all reviews
    From
    €135
    / Night
    Payment Protection
    View Details
    1 / 15
    5 of 5 stars (1) Excellent
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Reviews (1) Make Enquiry
    Amenities & Details
    • Balcony
    • Dishwasher
    • Fireplace
    • Grill
    • Internet Access
    • Mountain Views
    • Safe
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    Villa Manciano is a very typical old stone Holiday House that was supposed to be also an elementary school about 100 years ago, for the kids of the rural Manciano area. The property is more than 3 acres (12.000 sq. meters) located in the strategical area of the Chiana Valley, in the Cortona area.... View all property information
    Make Enquiry
    5 of 5 stars Reviewed 5 May 2013
    It's already 2 years since our lovely holiday in Tuscany and Villa Manciano, but since we just found Villa Manciano here on tripadvisor we feel that we have to write a few words...
    See all reviews
    From
    €707
    / Week
    View Details
    1 / 28
    2 Bedrooms / 1 Bathroom / Sleeps 4
    Overview Make Enquiry
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    Off the main tourist tracks, situated in the south-eastern part of Tuscany and close to Lake Trasimeno, Polvano was built three hundred years ago and is still owned by the Polvani family, who restored the estate recently. Great care was applied to maintain the estate’s architectural... View all property information
    Make Enquiry
    From
    €257
    / Night
    Payment Protection
    View Details
    1 / 17
    5 of 5 stars (3) Excellent
    5 Bedrooms / 4 Bathrooms / Sleeps 10
    travellers have booked this property
    Overview Reviews (3) Make Enquiry
    Amenities & Details
    • Balcony
    • Dishwasher
    • Fireplace
    • Grill
    • Hot Tub
    • Internet Access
    • Private Outdoor...
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • Wheelchair access
    • Elder access
    About this property
    The ideal destination for combining relax with culture. The unique location of the villa, the accuracy of design and all the comforts inside allow guests to fully enjoy the tuscan countryside by a unique view on it. Furthermore, the villa is situated in a strategic point to reach and visit the main... View all property information
    Make Enquiry
    5 of 5 stars Reviewed 26 July 2014
    We had a wonderful week in the villa in Rigutoni. It is a beautiful setting. Sitting in front of the villa for dinner at night, which we did every night bar one when there was...
    5 of 5 stars Reviewed 8 August 2014
    la villa è stupenda, i posti sono meravigliosi! abbiamo fatto una vacanza indimenticabile da ripetersi assolutamente perché i posti da vedere sono tanti, e poi al Querciolo si sta...
    See all reviews
    From
    €70
    / Night
    Payment Protection
    View Details
    1 / 23
    5 of 5 stars (3) Excellent
    2 Bedrooms / 1 Bathroom / Sleeps 5
    Overview Reviews (3) Make Enquiry
    5 of 5 stars Reviewed 4 September 2014
    I've spent five days at Le Finestre di San Michele with a Group of friends. The apartment is really nice, big, confortable and with a huge view. The owner and her daughter are so...
    5 of 5 stars Reviewed 10 September 2014
    ho soggiornato nell'appartamento "le finestre di San Michele " con 4 amici durante le feste per il patrono. L'appartamento, molto accogliente, spazioso, luminoso è arredato con...
    See all reviews
    From
    €130
    / Night
    Payment Protection
    View Details
    1 / 17
    5 of 5 stars (1) Excellent
    3 Bedrooms / 3 Bathrooms / Sleeps 8
    Overview Reviews (1) Make Enquiry
    5 of 5 stars Reviewed 18 August 2014
    Excellent welcome, beautiful garden with playground and barbecue, owners available. We ave the dog with us and we really enjoyed. Magnificent and peaceful palce..... next year we...
    See all reviews
    From
    €90
    / Night
    Payment Protection
    View Details
    1 / 7
    5 of 5 stars (1) Excellent
    2 Bedrooms / 2 Bathrooms / Sleeps 5
    Overview Reviews (1) Make Enquiry
    5 of 5 stars Reviewed 24 November 2014
    Nous avons séjourné dans cette jolie maison en pierre typiquement Toscane, au charme fou, maison située dans un cadre absolument magnifique, des oliviers à perte de vue, un jolie...
    See all reviews
    From
    €3,684
    / Week
    View Details
    1 / 44
    9 Bedrooms / 12 Bathrooms / Sleeps 18
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Fireplace
    • Internet Access
    • Private Indoor Pool
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • ?
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    In the quiet heartland the Valdichiana, at the top of a hill, stands Villa Mimi. Its high position gives this wonderful holiday home fantastic views across the Italian countryside. This property is an old country villa, carefully restored and now an exclusive private retreat that still enjoys its... View all property information
    Make Enquiry
    Get the List
    From
    €199
    / Night
    Payment Protection
    View Details
    1 / 27
    5 of 5 stars (2) Excellent
    5 Bedrooms / 2 Bathrooms / Sleeps 11
    travellers have booked this property
    Overview Reviews (2) Make Enquiry
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    Just a short distance from the medieval town of Castiglion Fiorentino is 'Casa Usignoli'. This very old manor house dates back to 1759. It has been fully renovated to provide a stylish family home with 5 large bedrooms and two bathrooms. The villa sits in one of the most sought after locations in... View all property information
    Make Enquiry
    From
    €235
    / Night
    Payment Protection
    View Details
    1 / 20
    5 of 5 stars (2) Excellent
    4 Bedrooms / 3 Bathrooms / Sleeps 8
    Overview Reviews (2) Make Enquiry
    Amenities & Details
    • Balcony
    • Dishwasher
    • Fireplace
    • Grill
    • Internet Access
    • Mountain Views
    • Private Outdoor...
    • Safe
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • Wheelchair access
    • Elder access
    • ?
    About this property
    Villa Senaia - Enjoy your stay In stunning Tuscany, along its endless artistic heritage and countryside, where stretches of silvery olive trees stare after vineyards and cypress trees, lies the Villa Senaia. An ancient stone farmhouse, located in a strategic position where it is easy to... View all property information
    Make Enquiry
    5 of 5 stars Reviewed 6 February 2014
    The accomodations were great and Giuseppe was a fabulous host! Sipping coffee in the morning, watching the sunrise slide up over Castiglion Fiorentino and the valey below was...
    5 of 5 stars Reviewed 6 February 2014
    we (a group of 7 adults)have stayed at Villa Senaia twice so far (for 2 weeks at a time) and have planned our 3rd visit for Sept. 2014. There is so many positive about this...
    See all reviews
    From
    €235
    / Night
    Payment Protection
    View Details
    1 / 19
    5 of 5 stars (8) Excellent
    4 Bedrooms / 3 Bathrooms / Sleeps 8
    Overview Reviews (8) Make Enquiry
    Amenities & Details
    • Balcony
    • Dishwasher
    • Fireplace
    • Grill
    • Internet Access
    • Private Outdoor...
    • Safe
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • Wheelchair access
    • Elder access
    • x
    • x
    About this property
    Villa Senaia In stunning Tuscany, along its endless artistic heritage and countryside, where stretches of silvery olive trees stare after vineyards and cypress trees, lies the Villa Senaia. An ancient stone farmhouse, located in a strategic position where it is easy to uncover many of the... View all property information
    Make Enquiry
    5 of 5 stars Reviewed 6 July 2014
    What an incredible place! This villa has absolutely everything you need to make your stay in Tuscany a pleasant one. All rooms are big, clean and with typical furniture and the...
    5 of 5 stars Reviewed 10 May 2014
    Villa Senaia was a truly wonderful experience so much so we return every two years with family & friends. The wonderful panoramic vista from the villa and pool is breath taking as...
    See all reviews
    From
    €60
    / Night
    Payment Protection
    View Details
    1 / 17
    5 of 5 stars (3) Excellent
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    travellers have booked this property
    Overview Reviews (3) Make Enquiry
    Amenities & Details
    • Balcony
    • Dishwasher
    • Internet Access
    • Washer
    • Wi-Fi
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • Wheelchair access
    • Elder access
    • x
    • x
    About this property
    Apartment with 2 bedrooms, 2 bathrooms, living room / kitchen, balcony, private entrance, internet free wi-fi h24. Completely renovated in 2008 respecting the characteristics of the classic Tuscan homes. Partly furnished with antiques expertly blended with modern conveniences. Equipped with TV,... View all property information
    Make Enquiry
    5 of 5 stars Reviewed 24 November 2013
    Abbiamo trascorso un lungo fine settimana a casa di Claudia, è stata un'esperienza fantastica! la casa è bellissima e dotata di tutti i confort, si trova in un vicolo del centro...
    5 of 5 stars Reviewed 20 July 2013
    In pieno centro storico ma con comodo parcheggio gratis per auto nelle immediate vicinanze.La zona del centro in cui è ubicato è molto silenziosa e immersa nella tranqullità più...
    See all reviews
    From
    €75
    / Night
    Payment Protection
    View Details
    1 / 23
    1 Bedroom / 2 Bathrooms / Sleeps 2
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Internet Access
    • Safe
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • x
    • Wheelchair access
    • Elder access
    • x
    About this property
    Set in its spacious garden and surrounded by the countryside, B&B Podere le Spighe (open 2014) is located in Castiglion Fiorentino. It offers an outdoor swimming pool, air-conditioned rooms, and a buffet-style breakfast provided daily. The large rooms have a rustic décor and wooden furnishings.... View all property information
    Make Enquiry
    From
    €265
    / Night
    Payment Protection
    View Details
    1 / 40
    5 of 5 stars (3) Excellent
    5 Bedrooms / 5 Bathrooms / Sleeps 10
    Overview Reviews (3) Make Enquiry
    Amenities & Details
    • Balcony
    • Dishwasher
    • Fireplace
    • Grill
    • Internet Access
    • Mountain Views
    • Private Outdoor...
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • x
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    Set in the grounds of Tenuta San Martino sits this lovely stone villa with private pool, gardens and private access road. The villa enjoys amazing views of the historic Valley of Chio and the medieval town of Castiglion Fiorentino. Nestled amongst ancient olive groves, and surrounded by the... View all property information
    Make Enquiry
    From
    €250
    / Night
    Payment Protection
    View Details
    1 / 24
    5 of 5 stars (2) Excellent
    5 Bedrooms / 5 Bathrooms / Sleeps 10
    Overview Reviews (2) Make Enquiry
    Amenities & Details
    • Dishwasher
    • Grill
    • Ping Pong Table
    • Private Outdoor...
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • Wheelchair access
    • Elder access
    About this property
    San Martino is an ancient farm of 9 ectars located in one of the most beatiful and strategic position of the Valle di Chio and Val di Chiana nearby the HISTORICAL TOWNS of Castiglion Fiorentino ( 10 min. ) and Cortona ( 20 min. ) Florence ( 1 hour ), Siena ( 1 hour ), Perugia ( 1 hour ). The... View all property information
    Make Enquiry
    5 of 5 stars Reviewed 6 June 2013
    Going to Daniele’s villa on the mountain in Castiglion Fiorentino is a great experience, once I experienced it, I fell in love with the place, the atmosphere and the hospitality...
    5 of 5 stars Reviewed 20 May 2013
    We will be returning here for the sixth time this year. Danielle is the perfect host and our return always feels like a 'coming home'. Nothing is too much trouble for him. The...
    See all reviews
    From
    €194
    / Night
    Payment Protection
    View Details
    1 / 26
    5 of 5 stars (19) Excellent
    2 Bedrooms / 1 Bathroom / Sleeps 4
    travellers have booked this property
    Overview Reviews (19) Make Enquiry
    Amenities & Details
    • Balcony
    • Fireplace
    • Grill
    • Internet Access
    • Mountain Views
    • Private Outdoor...
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • Wheelchair access
    • Elder access
    • x
    About this property
    A really charming little cottage/ villa in a very private location with its own private pool. Set along a Tuscan hillside in the middle of olive grove, Casa Serena (Serenity) provides perfect peace and seclusion. From the garden and pool areas, there are spectacular views over the Val di Chio and,... View all property information
    Make Enquiry
    5 of 5 stars Reviewed 30 December 2014
    Casa Serena isn't luxurious, but the location is superb, the pool lovely, and Terry who welcomed us (and runs a B&B in the same valley) was unfailingly helpful. The villa is up...
    3 of 5 stars Reviewed 9 November 2014
    Casa Serena has two bedrooms and sleeps 4 in a double and two single beds. The location is fantastic, being high up in the hills and very secluded and quite. It has great views...
    See all reviews
    From
    €74
    / Night
    Payment Protection
    View Details
    1 / 10
    1 Bedroom / 1 Bathroom / Sleeps 3
    Overview Make Enquiry
    Amenities & Details
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    A large Studio apartment with lots of charm, on the first floor of an historical building from the 16th century located in the historical centre of Castiglion Fiorentino. Just steps away from the town square, Piazza Del Comune, and all things you expect to find in a typical Tuscan medieval town.... View all property information
    Make Enquiry
    From
    €1,350
    / Week
    View Details
    1 / 8
    3 Bedrooms / 3 Bathrooms / Sleeps 6
    Overview Make Enquiry
    Amenities & Details
    • Balcony
    • Dishwasher
    • Fireplace
    • Grill
    • Internet Access
    • Shared Outdoor Pool...
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • ?
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Three Bedroom First Floor Apartment Castiglion Fiorentino Giaggiolo R2 is a spacious apartment on the first of the manor house on a fully restored Tuscan hamlet situated in a gorgeous position on a hilltop. As the house is built of a slope, the apartments entrance is accessed via its' own... View all property information
    Make Enquiry
    From
    €48
    / Night
    Payment Protection
    View Details
    1 / 9
    1 Bedroom / 1 Bathroom / Sleeps 3
    Overview Make Enquiry
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    APARTMENT DESCRIPTION: A few yards from the Town Hall and the Chiesa di Sant'Angelo al Cassero, this elegant, country-style apartment with terracotta floor and exposed wooden beams – is made up of a large living room/dining area with a fireplace, kitchen, a double bedroom with an extra single bed... View all property information
    Make Enquiry
    From
    €120
    / Night
    Payment Protection
    View Details
    1 / 15
    1 Bedroom / 1 Bathroom / Sleeps 4
    Overview Make Enquiry
    Amenities & Details
    • Balcony
    • Dishwasher
    • Fireplace
    • Grill
    • Internet Access
    • Safe
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • ?
    • Wheelchair access
    • Elder access
    About this property
    The Tanganelli family are delighted to welcome you to their tastefully restored 13th century convent Le Santucce. We have lovingly converted this historic building to offer 19 superb rooms/apartments. We offer: - Bedrooms with en-suite bathroom - Single rooms - Double rooms - Triple rooms - 4... View all property information
    Make Enquiry
    From
    €75
    / Night
    Payment Protection
    View Details
    1 / 4
    1 Bedroom / 2 Bathrooms / Sleeps 4
    Overview Make Enquiry
    Amenities & Details
    • Balcony
    • Safe
    • Wi-Fi
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • x
    • Wheelchair access
    • Elder access
    • x
    • x
    About this property
    Spinabbio is an ancient farmhouse rebuilt in its original rustic Tuscan style; at seven hundred meters above sea level among age-old woods of oak and chestnut, it commands a splendid view of the Val di Chiana. Its particular position allows maximal relaxation in contact with the nature, as well as... View all property information
    Make Enquiry
    From
    €63
    / Night
    Payment Protection
    View Details
    1 / 35
    1 Bedroom / 1 Bathroom / Sleeps 4
    Overview Make Enquiry
    Amenities & Details
    • Balcony
    • Grill
    • Internet Access
    • Shared Outdoor Pool...
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • Wheelchair access
    • Elder access
    • x
    • x
    About this property
    2-room semi-detached house 40 m2, on the ground floor, fully renovated, beautiful and tasteful furnishings: living/dining room with 1 double sofabed and satellite TV. 1 double bedroom. Kitchenette (4 hot plates, oven) with dining table. Shower/bidet/WC. Garden, porch. Terrace furniture, barbecue,... View all property information
    Make Enquiry
    From
    €5,841
    / Week
    View Details
    1 / 20
    9 Bedrooms / 9 Bathrooms / Sleeps 18
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Fireplace
    • Grill
    • Hot Tub
    • Internet Access
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    (Minimum of one week rental required) Minimum rental one week rental Saturday to Saturday except for urban apartments. Villa Valdiciana is an old country residence, skillfully restored and transformed into an exclusive private retreat. A 4 acres park, with Italian style garden and olive trees,... View all property information
    Make Enquiry
    From
    €710
    / Week
    Payment Protection
    View Details
    1 / 38
    2 Bedrooms / 2 Bathrooms / Sleeps 4
    Overview Make Enquiry
    Amenities & Details
    • Dishwasher
    • Fireplace
    • Grill
    • Internet Access
    • Private Outdoor...
    • Washer
    • Wi-Fi
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Casa Pantoufle is an old, stone farmhouse surrounded by silver olive trees in a panoramic, hill position at about 800 m above sea level and overlooking the Castle of Montecchio and the whole Valdichiana Valley. The house is reached via a scenic route of which the last 500 m. unpaved, and is only 5... View all property information
    Make Enquiry
    From
    €55
    / Night
    Payment Protection
    View Details
    1 / 11
    2 Bedrooms / 1 Bathroom / Sleeps 4
    Overview Make Enquiry
    Amenities & Details
    • Balcony
    • Internet Access
    • Washer
    • Wi-Fi
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • Wheelchair access
    • Elder access
    • x
    • x
    About this property
    Apartment with 2 bedrooms, 1 bathrooms, living room / kitchen, balcony, private entrance, internet free wi-fi h24. Partly furnished with antiques expertly blended with modern conveniences. Equipped with TV and washing machine. Located in the historic center just a short walk from the famous Cassero... View all property information
    Make Enquiry
    From
    €250
    / Night
    Payment Protection
    View Details
    1 / 50
    6 Bedrooms / 5 Bathrooms / Sleeps 12
    Overview Make Enquiry
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • ?
    • ?
    • Wheelchair access
    • Elder access
    • x
    About this property
    This exceptional, luxurious and impeccable private estate in Castiglion Fiorentino offers seamless indoor-outdoor living in absolute comfort. Extraordinary views of the famed Montechio Castle and, the Etruscan Tuscan hill town of Castiglion Fiorentino can be easily seen from the many terraces... View all property information
    Make Enquiry
    From
    €1,199
    / Week
    Payment Protection
    View Details
    1 / 13
    3 Bedrooms / 3 Bathrooms / Sleeps 6
    Overview Make Enquiry
    Amenities & Details
    • Balcony
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Safe
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • Wheelchair access
    • Elder access
    • x
    About this property
    Villa Sant Antonio is a beautiful holiday property in the heart of Tuscany, in Castiglion Fiorentino, close to Cortona and Arezzo. Great location in the middle of the olive growth, recently restored and beautifully furnished, full of art and antiques, with private swimming pool, makes it a great... View all property information
    Make Enquiry
    From
    €428
    / Week
    View Details
    1 / 35
    1 Bedroom / 1 Bathroom / Sleeps 3
    Overview Make Enquiry
    Amenities & Details
    • Internet Access
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • x
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    Villa Sandia C is a cozy and welcoming apartment. It sleeps three people. From Villa Sandia C you will have a nice view of the garden. Villa Sandia C is 35 square meters (375 square feet). It features a shared swimming pool, a shared garden, a reserved outdoor area, winter heating and WI-FI... View all property information
    Make Enquiry
    From
    €150
    / Night
    Payment Protection
    View Details
    1 / 38
    2 Bedrooms / 2 Bathrooms / Sleeps 4
    Overview Make Enquiry
    Amenities & Details
    • Dishwasher
    • Grill
    • Internet Access
    • Mountain Views
    • Ping Pong Table
    • Private Outdoor...
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • Wheelchair access
    • Elder access
    About this property
    San Martino is an ancient farm ( XIII century ) with three Farm Houses: Villa Bellavista ( 4 sleeps ), unique stone Villa with a relaxing atmosphere, lovingly restored and furnished. The Villa has own Private Pool 12mt x 5mt. The pivacy is guaranted. The property consist of 9 ectares located in... View all property information
    Make Enquiry
    From
    €135
    / Night
    Payment Protection
    View Details
    1 / 14
    2 Bedrooms / 2 Bathrooms / Sleeps 7
    Overview Make Enquiry
    Amenities & Details
    • Balcony
    • Dishwasher
    • Grill
    • Internet Access
    • Safe
    • Satellite TV
    • Shared Outdoor Pool...
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • x
    About this property
    Villa Manciano is a very typical old stone Holiday House that was supposed to be also an elementary school about 100 years ago, for the kids of the rural Manciano area. The property is more than 3 acres (12.000 sq. meters) located in the strategical area of the Chiana Valley, in the Cortona area.... View all property information
    Make Enquiry
    From
    €123
    / Night
    Payment Protection
    View Details
    1 / 20
    4 Bedrooms / 3 Bathrooms / Sleeps 11
    Overview Make Enquiry
    Amenities & Details
    • Balcony
    • Dishwasher
    • Fireplace
    • Grill
    • Private Outdoor...
    • Safe
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • Wheelchair access
    • Elder access
    • x
    • x
    About this property
    Beautiful rural home placed on the silver hills covered with olives groves between Castiglion Fiorentino and Cortona, in a very panoramic position and a stone's throw away from the magnificent medieval castle of Montecchio Vesponi. The villages of Castiglion Fiorentino (4 km far) as well as the... View all property information
    Make Enquiry
    From
    €3,500
    / Week
    Payment Protection
    View Details
    1 / 23
    9 Bedrooms / 10 Bathrooms / Sleeps 18
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Fireplace
    • Grill
    • Hot Tub
    • Internet Access
    • Private Indoor Pool
    • Safe
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • Wheelchair access
    • Elder access
    About this property
    Located half way between Arezzo and Cortona,stands the villa enclosed in its fenced and gated garden. The private swimming pool (12x6m) lies immersed in scented flower-beds and fragrant herbs. A glass veranda frames the elegant manor house and allows to have outdoor meals even when it gets colder.... View all property information
    Make Enquiry
    From
    €2,000
    / Week
    Payment Protection
    View Details
    1 / 16
    4 Bedrooms / 3 Bathrooms / Sleeps 8
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Housekeeping...
    • Internet Access
    • Private Outdoor...
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • Wheelchair access
    • Elder access
    • x
    About this property
    Name: Villa Rossi Accommodation: Ville Location: Castiglion Fiorentino Sleep: 8 Bedrooms: 4 Bathrooms: 3 Description Description The property is located in Poggio Della Coppa near Castiglion Fiorentino at about 650 meters above sea level and is situated on a hillside with amazing views of the... View all property information
    Make Enquiry
    From
    €143
    / Night
    Payment Protection
    View Details
    1 / 22
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Make Enquiry
    Amenities & Details
    • Internet Access
    • Private Outdoor...
    • Safe
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Villa Fiorentina is the ideal place for a relaxing break immersed in nature. The Villa is surrounded by an olive grove of over two acres and enjoys stunning views of the nearby medieval town of Castiglion Fiorentino. It was recently renovated by the owners who have personally followed the work to... View all property information
    Make Enquiry
    From
    €102
    / Night
    Payment Protection
    View Details
    1 / 20
    2 Bedrooms / 2 Bathrooms / Sleeps 4
    Overview Make Enquiry
    Amenities & Details
    • Balcony
    • Dishwasher
    • Fireplace
    • Grill
    • Internet Access
    • Private Outdoor...
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Casa Pantoufle is an old, stone farmhouse surrounded by silver olive trees in a panoramic, hill position at about 800 m above sea level and overlooking the Castle of Montecchio and the whole Valdichiana Valley. The house is reached via a scenic route of which the last 500 m. unpaved, and is only 5... View all property information
    Make Enquiry
    From
    €275
    / Night
    Payment Protection
    View Details
    1 / 22
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Make Enquiry
    Amenities & Details
    • Dishwasher
    • Fireplace
    • Grill
    • Internet Access
    • Shared Outdoor Pool...
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • Wheelchair access
    • Elder access
    • x
    • x
    About this property
    4-room 'Fienile', house, detached, for 6 people, 100 m2 on 2 levels, comfortable and cosy furnishings. Living room with local TV and open fireplace. Smoking not allowed. Internet (Wireless LAN [WLAN]). 1 double sofa bed. Sleeping room with 1 double bed. Sleeping room with 2 single beds.... View all property information
    Make Enquiry
    From
    €290
    / Night
    Payment Protection
    View Details
    1 / 46
    7 Bedrooms / 1 Bathroom / Sleeps 14
    Overview Make Enquiry
    Amenities & Details
    • Dishwasher
    • Fireplace
    • Grill
    • Private Outdoor...
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • Wheelchair access
    • Elder access
    • x
    • x
    About this property
    16-room house for 14 people, 600 m2 on 3 levels, antique and luxurious furnishings. Living/dining room with cable TV, DVD, radio, open fireplace, dining-table and dinette. Smoking allowed. 4 single beds and 5 double beds. Sleeping room with 1 double bed. Sleeping room with 1 double bed. Sleeping... View all property information
    Make Enquiry
    From
    €946
    / Week
    View Details
    1 / 18
    2 Bedrooms / 2 Bathrooms / Sleeps 5
    Overview Make Enquiry
    Amenities & Details
    • Grill
    • Shared Outdoor Pool...
    • Washer
    • Wi-Fi
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • Wheelchair access
    • Elder access
    • x
    • x
    About this property
    Fresh, bright and very well maintained, the villa offers a great holiday home for famiies of all ages. It is located in the lovely Val di Chio a few kilometers from the small town of ancient medieval town of Castiglion Fiorentino - rich in history, in the heart of beautiful Tuscany. The... View all property information
    Make Enquiry