Christmas in Italy is all about warmth, food and big family reunions. If you’re hoping to bring the whole family together this year – from children to grandparents – our collection of fully staffed villas are varied and versatile for multigenerational gatherings.
Spacious living areas mean everyone can gather around the fireplace, while fully equipped kitchens invite long, leisurely meals filled with Tuscan flavours and festive treats. Many of our private villas are set against rolling countryside, where you can enjoy crisp winter walks by day and admire the stars by night.
Some even come with private chefs or local concierges, so you can dive deeper into regional holiday traditions without lifting a finger. It’s a chance to slow down, reconnect and celebrate Christmas the Italian way – with warmth, laughter and plenty of good food shared around the table.
To elevate your stay, you’ll be greeted with a complimentary Christmas treat as part of our exclusive festive offer. Read on to discover our handpicked selection of villas available for Christmas 2025.
Discover more – read our guide to Christmas in Italy
Villa San Martin
Step inside Villa San Martin for a spectacular stay immersed in the countryside, just 20 minutes from Florence’s cosy Christmas markets.
On arrival, the owners put on an incredible display of Christmas decorations, including toy Santa ornaments for the little ones and a huge Christmas tree set up with decorations. Adults are greeted with complimentary prosecco and a festive welcome hamper.
Inside, the villa sleeps up to eight guests in four bedrooms furnished in a traditional, elegant style. Outside, the furnished courtyard is a lovely, scenic spot for family get-togethers. Enjoy a gentle morning swim in the private heated pool before the festivities commence!
Our Local Concierge can help complete your festive celebrations with in-villa chef dinners, heartwarming Italian cooking classes and cosy local experiences with artisans in Florence.
Il Sogno di Leonardo
Spend Christmas in the heart of Tuscany’s ancient landscape. Il Sogno di Leonardo is a fantastic, 16-person villa nestled among the olive groves of Vinci, the birthplace of Leonardo da Vinci.
Downstairs, there’s ample space across the villa for sharing special moments together, including a huge dining area for up to 16 guests. Cosy up in the living room by the roaring fire to unwrap presents and watch the Christmas classics together.
The level of detail and craftsmanship behind the design is reason enough to keep coming back. Staying true to the essence of the region, the villa’s original vaulted ceiling and exposed wooden beams have been restored and kept intact.
Nearby, our Concierge can organise local festive experiences. Just a short journey from Vinci, the hillside village of Petroio hosts a magnificent artistic nativity scene during the Christmas season.
Santa Gelsa
Step inside Santa Gelsa this Christmas for a Tuscan winter holiday. This fully staffed, 18th-century villa rental ticks all the boxes for a big family gathering, Italian style.
For one, it can host up to 24 guests, with extensive lounge and dining areas. Natural light spills through the dining room, with a long dining table and large arched windows. The villa also benefits from a shaded terrace and a spacious professional kitchen. Let your in-villa chefs prepare a sumptuous Italian Christmas feast to remember.
In Tuscany, you can expect tables laden with handmade pasta, roasted meats and festive specialties like crostini di fegatini, hearty ribollita, and sweet panforte from Siena. Local wines flow freely, and no celebration is complete without vin santo and crunchy cantucci to end the meal.
The medieval village of Torrita di Siena is within walking distance, with a charming café bar. The beautiful hilltowns of Montepulciano and Cortona are also within easy reach by car, where you’ll find an array of fine restaurants, pizzerias and wine shops.
The finishing touch? Guests are greeted with a complimentary case of prosecco and welcome hamper on arrival.
I Giullari
Part of a small hamlet where Galileo Galilei once lived, I Giullari benefits from an array of fantastic amenities for hosting a big Christmas family reunion. On arrival, guests are greeted with a case of prosecco and a beautifully decorated Christmas tree.
The villa’s layout can be tailored to suit your group size. Smaller groups may choose the main six-bedroom wing on the first floor, enjoying exclusive use of the pool and gardens. For larger gatherings, the ground floor wing can be opened up, adding two beautifully furnished, light-filled bedrooms and even more space to relax and entertain.
I Giullari is also perfectly positioned for enjoying Florence’s Christmas festivities. Enjoy a short stroll into the city centre to wander through glittering streets lined with fairy lights, browse the wooden stalls of Piazza Santa Croce’s Christmas market, and warm up with mulled wine or roasted chestnuts.
You’ll also find open-air ice rinks, festive concerts and the city’s magnificent Duomo adorned for the season – all just moments from your luxury villa.
Palazzo Nelle
Steeped in historic Tuscan grandeur, Palazzo Nelle is a fully-staffed 13th-century Renaissance villa with a magical atmosphere that comes alive at Christmas. On arrival, guests are greeted with a Christmas basket, two bottles of prosecco and a beautifully decorated Christmas tree.
Its grand halls and vaulted ceilings become the backdrop for cosy conversations in the many communal areas. With staff on hand to prepare traditional festive banquets and ensure every detail is taken care of, guests are encouraged to relax and gather by the fire for mulled wine.
Beyond the villa, the surrounding Chianti countryside offers crisp winter walks. Tour the local shops and eateries of Tavernelle Val di Pesa and San Donato, just 4km away. A short 20-minute drive takes you to Chianti’s well-known towns, including Radda, Panzano, Greve and Castellina.
Palazzo Nelle also comes with complimentary personal concierge, who can help amp up your festive celebrations with unique local festivities.
Santi Terzi
Palatial yet inviting, Santi Terzi is a Renaissance palazzo crowned with its own medieval panoramic tower. History buffs with a love of nature are likely to fall head over heels for this spectacular property.
Once home to Europe’s greatest neoclassical sculptor, Antonio Canova, the villa takes on an extra layer of magic at Christmas – think candlelit halls, twinkling decorations and cosy corners perfect for festive gatherings amidst centuries of history.
At Christmas, Senti Terzi’s lofty ceilings and natural-hued interiors are brought to life with sparkling lights and seasonal décor. With two spacious communal living areas for family gatherings and a cosy library, it’s a wonderfully idyllic setting for celebrating the holidays in style and comfort. A Christmas basket on arrival adds an extra touch of festive cheer.
Santi Terzi is located in San Gemini, a hilltop town that’s delightfully untouched by tourism, home to just over 5,000 inhabitants. At Christmas, its cobbled streets are adorned with twinkling lights and seasonal decorations.
Ca’ Dogaressa
Step inside Ca’ Dogaressa for a traditional Venetian Christmas break. This utterly charming, stone-built villa glows with soft candlelight and seasonal décor. Inside, a beautifully adorned Christmas tree creates a warm, inviting atmosphere on arrival.
Ca’ Dogaressa’s communal living areas are varied and versatile, with an open-plan layout. The outdoor patio also features a relaxed dining space with a traditional wood oven. At Christmas time, these spaces take on an extra layer of warmth.
Winter in Venice is nothing short of magical, with its scenic canals, Christmas lights and marble renaissance palaces best explored without the summer crowds. Try ice skating in Piazza San Polo and sip mulled wine by the Grand Canal.
Fraloga
Escape to the Amalfi Coast this Christmas with a stay at Fraloga, a 12-person luxury villa just a short stroll downhill to Positano’s bars and restaurants.
Fully staffed with flawless housekeeping, Fraloga, with its sweeping terraces and Mediterranean charm, features open-plan living spaces for cosy family reunions. The dining area is a highlight, framed by a wood-burning fireplace and wide-framed windows that let in plenty of natural sunlight.
A beautifully decorated tree and Christmas basket on arrival sets the tone. Fraloga’s panoramic terrace can be decorated with twinkling lights, inviting leisurely limoncellos at sunset. Sit back and enjoy a traditional Christmas Eve dinner prepared by a private chef. Classic recipes feature local festive specialties like fresh seafood, panettone and the region’s famous lemon-infused sweets.
Just a short stroll away in the heart of Positano, bustling Christmas markets offer local sweets, decorations and festive treats. Churches host midnight Mass and nativity concerts.
Vecchia Fattoria
Vecchia Fattoria is a grand Renaissance villa nestled in a peaceful hilltop village near Montepulciano. The restored farmhouse aesthetic feels cosy and relaxed, inviting guests to linger in the beautiful communal spaces. On arrival, guests are greeted with a case of prosecco as a special festive treat on us.
Sleeping up to 11 guests, the villa’s interiors are classy yet understated. At the heart of Vecchia Fattoria is a vast, open-plan living and dining room big enough for the whole family. This is where festive feasts and Christmas games can be enjoyed together around the grand stone fireplace.
The villa’s proximity to Montepulciano means guests can easily explore local Christmas markets and enjoy the town’s magical decorations. Get in touch with our Villa Specialists for personalised recommendations.
Exclusive Christmas Villa Offers in Tuscany
Celebrate the holiday season in a handpicked winter villa in Italy between 20th December – 3rd January and enjoy complimentary gifts on arrival. Our collection of private villas come beautifully decorated for the season, with festive touches that bring warmth and seasonal cheer to your holiday. Select villas will come with a complimentary hamper filled with local treats and/or a case of prosecco, perfect for celebrating the spirit of Tuscany from the moment you arrive. Speak to our Villa Specialists today for more information.