Romantic Villa Getaways in Tuscany for Two

For a romantic getaway in Tuscany, choose a private suite or a small villa on an estate: your own front door in the countryside, with restaurants and a spa a short walk away. These are the houses in our collection that suit two.

Our Villas for Two

Casa del Vescovo: a 200 m² two-bedroom suite in the heart of the medieval borgo at Castiglion del Bosco, the Rosewood estate near Montalcino.

Casa Fontaccia: a detached two-bedroom suite in the same borgo, with its own private entrance.

Stefano Ricci La Rocca: the only Stefano Ricci-designed residence available to rent in Tuscany, high in the medieval Rocca at Castelfalfi.

Casa Medici: an address in the historic core of the Castelfalfi borgo, with windows over the Medici Park.

Why an Estate Suits a Couple

You get the privacy of a house and the service of a hotel. On an estate you cook when you want to and book the restaurant when you don't, and the spa, the vineyards and the walks are on the doorstep. A private chef can be arranged for a dinner at home.

Frequently Asked Questions

Where is the most romantic place to stay in Tuscany?

For a couple, a private suite inside a medieval borgo on a resort estate gives you the most: your own front door, with restaurants and a spa a short walk away. Castiglion del Bosco near Montalcino and Castelfalfi between Florence and Pisa both offer this.

When is the most romantic time to visit Tuscany?

Late September and October, for the harvest, golden light and fewer crowds; or May, when the countryside is green and the evenings warm. Our month-by-month guides give the weather for each.

Can we have a private chef for a dinner for two?

Yes. A private chef can be arranged at every villa in our collection, for one dinner or every evening of your stay.

Next Step

Tell us your dates and we'll tell you which of these is free. Or compare the two estates: Castiglion del Bosco and Castelfalfi.