Villa Rosa

Tuscany , Italy

In this section...

  • 8
  • 4
  • 4
  • Historic 19th century building
  • Extensive private grounds
  • 16-metre swimming pool
  • Tower lounge with beautiful views
  • Castiglioncello beach 52km/1hr drive.

2024 Holidays... 2023 Prices

Our 2024 holidays are now priced online and with our early bird promise, you can enjoy December 2022 prices when you book by 31 December 2023. View Price Freeze Terms & Conditions here.

Nestled into 5000m2 of private, landscaped grounds, lovely Villa Rosa is the perfect base for some gregarious, Italian-style family fun, with a generous sprinkling of Tuscan culture on the side for those who wish. The original building dates back to the 1800s, and occupies an enviable sweet spot between medieval San Gimignano and the beaches of the Etruscan coast. In reality there’s no requirement to stray that far however, for Villa Rosa offers all the space and comfort you need to spread out and enjoy the pure pleasure of holiday time with friends and family. The 16-metre pool provides a glorious focal point on long summer days, with built-in hydro-massage jets to soothe knotted shoulders and restore travel-weary limbs. There’s masses of play space for those with energy to burn, a gazebo for shade-lovers plus an outdoor kitchen area to make catering a very relaxed affair even when you’ve brought a crowd.

Inside, the villa manages to feel both homely and grand, with statement lighting hanging from double-height ceilings and underfloor heating providing a cosy welcome for an early or late season stay. Each of the four bedrooms has its own bathroom, including one on the ground floor making life easier for elderly legs, with inside and outside dining areas so you can take your pick depending on the day. Our favourite spot however is the little lounge ‘nest’ built into the central roof tower, where you can sit with your pre-dinner drink and enjoy 360-degree views across the cypress trees and rolling hills of a classic Tuscan landscape.

Good to know... All stays at Villa Rosa include a wine tasting in a traditional cellar and complimentary light taster meal with wine, platter of cold cuts, cheeses and other typical Tuscan produce.

Explore our pre-bookable experiences in Tuscany



  • 4 bedroom villa (sleeps 2-8)

Ground Floor

  • Kitchen with utility area; includes hob, oven, fridge-freezer, dishwasher, washing machine
  • Sitting/dining room with doors onto covered dining terrace
  • Sitting room with fireplace
  • Double/twin bedroom with doors to garden and en-suite shower room and WC
  • Shower room and WC

First floor

  • 2 x double/twin bedrooms with TV, en-suite shower room and WC
  • Double bedroom with TV, en-suite shower room and WC
  • All bedrooms on first floor have Juliette balconies and wood burners

Second floor

  • Steep spiral staircase leads to tower viewpoint


  • Simpson Travel telephone representative
  • Complimentary WiFi
  • Air-conditioning
  • Under floor heating available on request (€250 per week, payable locally)
  • TV/DVD
  • Washing machine and tumble dryer
  • Iron, ironing board, hairdryer
  • Simpson Travel pool towels
  • Beautiful fenced gardens
  • Loggia with outdoor dining area
  • Barbecue
  • Gazebo with seating area
  • Table tennis
  • Boules court
  • Cot and highchair
  • Children's play area with swing
  • Private fully-fenced gated swimming pool 16m x 8m (depth to 1.50m) with hydro-massage jets
  • Small children's pool (depth 0.4m)
  • Additional mid-week cleaning service available on request at €20/hr (payable locally)
  • Mid-week linen change available on request at €15 per person (payable locally)
  • All stays include a wine tasting in a traditional cellar and complimentary light taster meal with wine, platter of cold cuts, cheeses and other typical Tuscan produce
  • Daily bread, focaccia, croissant, pizza delivery service available on request at 9am daily, except Sunday (payable locally)
  • Private chef available on request (payable locally)
  • Pets are welcome and are charged at £50 per pet, per week
  • 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 email checking. We aim to offer an uninterrupted service but sometimes due to factors beyond our control reliability can be affected.

Access times

  • Check in time – 4pm
  • Check out time – 10am


  • Montelopio (shop) 5min walk
  • Peccioli (shops/restaurants) 15min drive
  • Volterra 30min drive
  • San Gimignano 40min drive
  • Castiglioncello beach 1hr drive.
  • Pisa airport 50min drive
  • Florence 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.


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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