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Le Cannelle, Castellina Marittima - Pisa and Valdera
Find a place at the table, pour the Chianti and tuck into something delicious because 2021 is the year for celebrating simply being together

Let’s party like it’s 2021

By Sean Caulfield

Covid-19 has scuppered many people’s plans this year, although we continue to welcome many guests to our luxury villas in Tuscany. But we know that lots of you are already making big plans to get together with family and friends next year. So to help you find the perfect villa we’ve picked six of our best properties for large groups, sleeping 12 or more people. They’ve got flexible accommodation, secluded locations and spacious interiors and grounds. And, don’t forget, all our big villas in Tuscany have private pools, too.

Agresto - To Tuscany

The delightful pool area, surrounded by shrubs and trees, is one of the many tranquil spots in the grounds of Villa Agresto

Villa Agresto, near Gaiole in Chianti

Ideally located for exploring the Chianti region, Villa Agresto is a six-bedroom property hidden away in the Siena hills. It offers sweeping views of the vineyards and forest below and plenty of tranquil spots – including a delightful pool area – from which to admire them. Inside, the décor blends traditional features with a contemporary colour palette. The kitchen and its mod cons, as well as large indoor and outdoor dining areas, make this a good choice for groups who like to host large, convivial meals. Sleeps 12, from *£4,778.

Palazzone - To Tuscany

Palazzone has two stylish lounges, so there is plenty of space for everyone to relax

Palazzone, near Torrita di Siena

Palazzone, an imposing stone villa surrounded by lush lawn, is an elegant retreat for friends or family. Six bedrooms offer flexible accommodation – two of them housed in a separate, cottage for extra privacy. There are two lounges in the main house – including one with a striking glass-covered atrium – so everyone can find a peaceful spot. The outdoor lounge or the Jacuzzi by the pool are ideal for gazing towards Montepulciano and the mountains. Plus, historic Montefollonico and Siena are a short trip away. Sleeps 12, from *£5,096.

Borgo San Polino, Gaiole in Chianti - Siena and Chianti

The chic country retreat of Borgo San Polino is pure Tuscan with designer elegance.

Borgo San Polino, Gaiole in Chianti

Nestled in the heart of the Chianti region – which, for some, is the only place to stay in Tuscany – Borgo San Polino offers a tranquil setting, surrounded by manicured olive groves, vineyards and wild oak woodland. And yet, the popular day trip spots of Siena, San Gimignano and Florence are just a short distance away. The property itself, spread over three grouped cottages, lends itself perfectly to an extended family getaway, with both large, elegant communal areas for coming together – including an incredibly positioned swimming pool – and cosy nooks for enjoying some well-deserved ‘me’ time. Sleeps 18-22, from £10,290.

La Lepraia, Castellina Marittima - Pisa and Valdera

Panoramic vistas, wide open space and idyllic comfort are waiting for you at Le Cannelle.

Le Cannelle, Castellina Marittima

New to the To Tuscany portfolio for 2021, Le Cannelle is an incredibly special and unique find when it comes to Tuscany rental properties. Not only is this villa a short distance from the coast so you can enjoy warm sandy beaches at your leisure but it is also perfectly located for exploring Tuscany’s Archipelago and Bolgheri’s five-star vineyards. That’s if you can tear yourself away. Reached by a winding private road, flanked by centuries old oak forest, the property comprises of three cottages, each with their own private entrance, kitchen and living areas, and each the perfect balance of traditional splendour and modern amenities. Sleeps 24, from £6,370.


Villa il Santo, Barberino Val d'Elsa

Step out onto the pool terrace and take up your first class seat in front of Il Santo’s awe-inspiring views

Villa il Santo, Barberina Val d’Elsa

This exquisite property is a perfect marriage of traditional and contemporary styles – where an historic tower and barn have been sensitively united by a modern glass structure. Villa il Santo, luxuriating in its surroundings on top of a Chianti hill, is a study in stripped-back style and serenity. The spacious yet comfortable interiors are enhanced by the light from huge arched windows, while outside the fragrant gardens also seem endless… until you stumble across the studio cottage and the swimming pool with adjoining hot-tub. Sleeps 16, from *£9,310.


Villa Querciola’s pool, complete with bridge and suspended terrace, is pretty spectacular

Villa Querciola, near Volterra

True to traditional Tuscan style, but with modern splashes of colour, Villa Querciola is a comfortable and stylish eight-bedroom villa. On one side, the outdoor lounge overlooks the historic town of Volterra and the rest of the 360-degree views offer a sweeping panorama of hills and valleys – best viewed from the Jacuzzi on the veranda. The dining room with large table and the lounge with billiards table are perfect spaces for the whole group to come together. But the standout asset must be the pool with its unique bridge and suspended veranda. Sleeps 16, from *£4,645.

*All prices quoted are for seven nights in 2021.

To Tuscany has a range of fantastic villas across the region.



Over 20 years ago, I moved to Tuscany with my Italian wife and founded To Tuscany as a villa rental company. Our first rentals were in a country residence in Chianti and we offered guests a tailored vacation using our local knowledge and personal service. Today, you can experience the same at over 600 superb villas.

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