Casa Papa

Tuscany , Italy

  • 2-4
  • 2
  • 2
  • Our most popular Tuscan property
  • Charming hillside villa
  • Classic Tuscan views
  • Outdoor kitchen with barbecue and pizza oven
  • 2min drive to Castelfiorentino
  • Convenient nearby rail access to Florence

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.

Local area

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


  • Simpson Travel telephone representative
  • 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


  • 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.


  • Nearest town: Castelfiorentino. Free parking 5min drive, then steps down into town (unlit).
  • 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

For further information regarding travel arrangements click here.

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

Absolutely loved our stay here. We were close to barricading ourselves in on the last day so we didn't have to leave! We'll definitely be back. An absolute gem.

Mr Stuart McMillan , June 2024

Casa Papa is ideally placed for visiting Tuscany, including Florence, Pisa, Livorno, Siena, San Gimignano and beyond. It's easy to walk into nearby Castelfiorentino, where there is also convenient access to the train station. We spent two weeks at Casa Papa venturing out and about, with occasional days at the villa where we could enjoy the sunshine, the pool and the amazing views! Pino and his wife were very gracious hosts and kept the villa and the grounds immaculate during our stay.


The villa is in a perfect location to explore Tuscany. Getting the train to Florence, Pisa etc was very easy. Stunning scenery everywhere you look and definitely worth another visit.

Mrs Ellen Atkinson, May 2024

I would have no hesitation in recommending Casa Papa as a holiday destination. The villa is exceptional and Pino the owner was really kind, caring and very helpful. A peaceful and tranquil location with outstanding quintessentially Tuscan views.

Dr Caroline Gallagher, October 2023

Our holiday with Simpson Travel staying at Casa Papa was wonderful. The villa is situated in the perfect rural location with wonderful views, while having access to the small local town, and easy access via train or car to all of the major cities in Tuscany. The villa itself is charming and has everything you need. The pool & terrace area with stunning views of the countryside were so peaceful, and the covered outdoor area at the back gave us plenty of extra space in the shade. I particularly liked that there are lots of different places to sit and relax & dine, both in the sun and shade. Loads of great places to eat locally, or drive 20 mins into the countryside to find a gem of a restaurant. Our rep was very attentive and informative. Many thanks.

Mr Dominic Beardsworth, September 2023

Thank you very much for your kind hospitality. It really is a beautiful house and we have had a lovely time. We enjoyed a morning trip to Siena, a visit to San Gimignano and an evening in Certaldo – a great place to watch the sunset!

Helen, John, George and Arthur, September 2023

A huge thank you for a wonderful stay. We have had a lovely holiday. A warm and friendly greeting on arrival and Pino and family have been the perfect hosts. The big discovery for us was the use of the train to visit Florence, Siena and Certaldo. It made everything so easy. Super views, fantastic pool and grounds. Many, many thanks.

Chris and Lee, September 2023

Casa Papa is a little gem, very clean and good position for sightseeing the area.

Mrs Atherton, September 2023

We had a lovely week – thank you for your kindness and for all the tips! The villa is well equipped with lots of thoughtful extras. We will miss the view! We enjoyed Certaldo and especially San Gimignano.

Kath, James and Jacob, August 2023

Casa Papa is delightful. Well situated, really clean, and the owners are friendly and helpful. The pool is a consistent depth which my family found reassuring (my daughter could just about stand up at age 8) and Pino cleaned it every morning for us. The views are beautiful and the area feels safe. The local Coop is excellent, which surprised us! If I was the kind of person who went to places a second time, I wouldn't hesitate to go back to Casa Papa. I'll certainly be recommending it to friends.

Michelle Ames, July 2023

Thank you Pino and Salvina – we’ve had a fabulous week. Super pool, views and relaxing time.

Nikki, Marco & Reuben, July 2023

Thank you Casa Papa – you have been a wonderful place to stay. Pitro has been a wonderful host. I would recommend the Taste and Touch Restaurant. The view from the villa is amazing and I think the cosyness is wonderful. I would recommend going to Pisa and seeing the leaning tower. This is a very beautiful place and I am glad that we came here.

Norah (aged 9), July 2023

We had a fabulous stay at Casa Papa. It’s an ideal location for walkers who don’t want to rent a car - easily accessible from Florence airport via tram/train and once in Castelfiorentino there are lots of local walks and towns accessible by bus or train. Pino and his wife were lovely and couldn’t have been more helpful, as was Amanda, our holiday rep. This was our first time booking a villa through a travel company and I’d highly recommend Simpson Travel.

Siobhan Williams, June 2023

We have used Simpson Travel on a number of occasions in different countries, villas and hotels. We would definitely recommend them.

Phillip Hopwood, May 2023

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

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

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

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

Back to top

View holiday Booking Conditions

SearchPopupRoom.mustache file to be converted