Casa Papa

Tuscany, Italy

  • 2-4
  • 2
  • 2
  • Charming hillside villa
  • Classic Tuscan views
  • Outdoor kitchen with barbecue and pizza oven
  • 2min drive to Castelfiorentino

Enjoying a charming spot in the hills close to Castelfiorentino, Casa Papa exudes relaxed Tuscan living and enjoys a lovely flow between its homely interiors and the well-kept gardens which are such a feature of the property. The comfortable open-plan living area on the upper level leads directly onto a covered veranda complete with outdoor kitchen, barbecue and pizza oven; a blissfully private spot to enjoy a leisurely lunch or dinner. There are further options for alfresco lounging and dining in the gardens, on the upper terrace and down by the inviting pool below, both designed to make the most of the enchanting views across this iconic landscape. Two bedrooms and a bathroom on the lower level complete the picture of this appealingly simple Italian home; perfectly suited to families or two couples travelling together.

Casa Papa is wonderfully placed for exploring the region’s world-famous highlights, including the medieval walled town of San Gimignano, a 30-minute drive from the property. Florence and Siena can be accessed by road or rail, with a direct train service available just 5-minutes’ drive from the property, and Pisa is also easily reached in under an hour. Closer to home, pretty Castelfiorentino is home to a small selection of bars and restaurants and everything needed for day to day living. In the fourth week of May, it plays host to the annual In/Canti & Banchi Festival, when the streets bustle with performers’ exhibitions and antique markets; well-worth a visit if you are lucky enough to be resident at this time.



  • 2-bedroom villa (sleeps 2-4)

Upper floor

  • Living/dining/kitchen area with oven, hob, microwave, fridge-freezer, dishwasher
  • Shower room with WC

Lower floor

  • Double bedroom
  • Twin bedroom (can be converted into a double on request)
  • Shower room with WC


  • Complimentary WiFi
  • Air-conditioning throughout
  • Iron, ironing board, hairdryer
  • Simpson Travel pool towels
  • Barbecue and pizza oven
  • Outside shaded dining and seating area with kitchen work surface and sink
  • Washing machine outside (under covered area)
  • Private swimming pool 9m x 4m (depth 1.25m throughout), accessed via steps, pre-fabricated and partially sunk into the ground
  • Electric gates and steep concrete driveway leads up to villa
  • Our Covid-19 pledge means your holiday is fully protected. However, there may be special conditions surrounding flexible booking at this property. For further details, please visit: /covid-pledge-flexible-booking.


  • All properties with WiFi are able to support basic functionality such as web browsing and checking emails. We aim to offer an uninterrupted service but sometimes, due to factors beyond our control, reliability can be affected.


  • Castelfiorentino 15min walk, no pavement or lighting
  • Nearest restaurant 3min drive
  • Train station (trains to Florence and Siena) 5min drive
  • San Gimignano 30min drive
  • Siena 55min drive
  • Pisa airport 55min drive
  • Florence 1hr drive
  • Castiglioncello (beach) 1hr 30min drive


This property is priced on an accommodation-only basis. To view details of recommended flights please click here.

Car hire

We are happy to arrange your car hire in Italy; please click here to view options and prices. All hire cars booked with us include: 

  • Fully inclusive insurance, with zero excess*
  • Free additional driver

When you book your car with us, we'll also make sure the paperwork is done in advance, leaving you free to simply check and sign for the vehicle when you arrive. For further information regarding travel arrangements click here.

* For this particular destination, the undercarriage is not included in the cover.

We thoroughly enjoyed our time at Casa Papa. Thank you to Pino and his family for welcoming us into their beautiful home. The villa is ideally located for easy day trips to Siena, Florence (via train in Castelforentino 5 mins away), San Gimignano and Certaldo Alto. Many thanks to Amanda from Simpson travel and the Papa family for a brilliant first trip to Tuscany, the villa and pool were brilliant, and the villa was in a great location... We will be back!
Lucy Wood, September 2022

I will definitely visit Casa Papa again. The villa and views were absolutely amazing. The host made us very welcome and the Simpson representative was always available for help and advice during the holiday. Thank you Simpson Travel for making this holiday a very enjoyable experience.
Teresa Crowther, September 2022

We had the most amazing holiday at Casa Papa….. Pino the owner and his wife greated us when we arrived with a great welcome pack of food and drinks and an extremely friendly, warm welcome. The villa was fantastic, full of Italian charm with the most stunning views. The beds where comfy, we have everything we needed to cool with and the outside spaces where great in the evening or for breakfast. Pino came and cleaned the pool every morning and even left us fresh eggs and figs, all home grown in the gardens at the villa. The location was great for trips to Florence and Siena either by train or car. Amanda the rep for Simpson Travel was exceptional and a real credit to Simpson Travel. She helped us on a Sunday find a doctor for our daughter who came down with tonsillitis and was extremely helpful with local information and places to go and see. We would like to say a massive thank you to Pino, his family and Amanda for making our first villa holiday an amazing one….. no more hotels for us!
Mark Crumplin, August 2022

Casa Papa is a beautiful villa, in a stunning location. We received a wonderful welcome from the Papa family when we arrived which made us feel at home immediately! The villa is very well situated to visit some of the lovely Tuscan towns. We particularly liked Certaldo Alto which is 15 minute drive away, and St. Gimignano which was a little further. Amanda was very helpful indeed when we needed recommendations on where to eat or other information. We will definitely be back.
Karen Rowland, June 2022

We had a wonderful stay at Casa Papa - the villa exceeded expectations. It was spacious, well-equipped and the outdoor space and views were incredible. The hosts were so welcoming and left a lovely welcome hamper. Our Simpson Travel concierge was helpful and I'd recommend booking with Simpson - thank you!
Helen Bailey, June 2022

Our choice of Italian properties is diverse, ranging from simple charm to genuine luxury and style. Much of our portfolio is privately owned, and price alone is therefore not a universal guide. We contract all our accommodation in person, and each property has its individual appeal.

To help you make the right choice based on your own priorities, we have devised a simple grading guide to be considered in conjunction with each individual property description, awarding up to a maximum of five stars for the below categories.


Property Grading Key:

  • 5/5


  • 4/5

    Very good

  • 3/5


  • Location


    Position, view, serenity, privacy

  • Comfort


    Space, style, overall furnishings

  • Facilities*


    Property enhancements

  • Amenities*


    Proximity to beaches, restaurants and shops

* * For further clarification on Facilities and Amenities, please view the 'Details' tab for each property or speak to one of our experienced sales consultants.

From the moment you arrive in Tuscany, you are invited to share in its grand passions and indulgent pleasures – world-famous wine, mouth-watering food and epic histories. Each of Tuscany’s ten provinces has its own unique personality, but wherever you stay, you’ll find yourself surrounded by a verdant patchwork of olive groves, cypress trees and vineyards. From the birthplace of the Renaissance, Florence, to the narrow streets of hilltop San Gimignano, Tuscany makes for a stunning escape. 

To complete the picture, explore our collection of handpicked villas and charming apartments.

Explore our pre-bookable experiences in Tuscany



Read more on our Tuscany region page

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