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Our Top Selection of Villas in Tuscany for Groups: The Ultimate Guide to Your Dream Vacation

Jesse Andrews by Jesse Andrews
January 8, 2026
in Italy Destinations
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Imagine waking up to the golden hues of the Tuscan sunrise, sipping a cappuccino on your private terrace, and immersing yourself in the timeless beauty of Italy’s most iconic regions.  Renting a private villa in Tuscany can be a wonderful way to enjoy this incredible region in central Italy.  However, when renting a private villa in Tuscany, particularly for larger families and groups there are many factors to keep in mind and one of the most important things to consider is LOCATION & Tuscany is a HUGE region, much larger than it may seem on Google maps and the north of Tuscany is much more industrial and flat in many places than say Chianti or the Orcia Valley, which may come as a surprise to many people.

To be honest, Tuscany is simply not all that pretty in certain sections.  It is in fact, very industrial and home to many of Italy’s major factories and production plants.  Over the years, we have learned that sometimes a picture tells a thousand lies and we have been on the receiving end of phone calls where many clientss who did not rely on our expertise and knowledge, ended up being forced to stay in locations that were less than desirable. 

This is why, particularly when there are multiple participants involved, knowing the particulars of the locations of each property, the specific amenities, owners and activities available from each property has become ever-more important to us, because let’s face it, renting a villa for a group can not only be a more economical option, it can also be more intimate and create bonding experiences both for the group members, but also with the communities where these properties are located, because being in a central location for a week, will allow for more community interaction while grocery shopping, visiting the local coffee shops, wineries and producers in the area.  Having a home away from home for a week, forces you to slow down more than a one or two night stay at a hotel where breakfast times are usually between 7 and 10 and the cleaning staff is knocking on your door or maybe banging in the room next door to make room for other guests arriving.  While hotels can feel hectic, renting a private villa in Tuscany, can allow you to enjoy a true holiday in Italy.

Below, we have compiled a list of our top villas in Tuscany for groups of friends and families we believe are ideal, the reasons we have cited below. 

 

 Villa La Campagna – Val D’Orcia

Villa La Campagna is a peaceful retreat surrounded by lush gardens and vineyards, offering a quintessential Tuscan experience for up to 12 guests. This villa features elegantly furnished rooms, a cozy living area, and a private pool. Whether you’re hiking nearby trails or exploring picturesque villages, you’ll love the serenity and charm of this countryside escape.

 

Villa Antico Pozzo – Val D’Orcia

Villa Antico Pozzo, nestled in the stunning Val D’Orcia, offers an unforgettable Tuscan retreat. Accommodating up to 14 guests, this villa features seven double bedrooms, each with a private bathroom. Ideal for families, some rooms can be interconnected to suit various needs. Surrounded by gardens filled with lavender, roses, and rosemary, the villa boasts a picturesque swimming pool and panoramic views of the historic towns of Pienza, Montalcino, and Montepulciano. Its prime location within walking distance of Montichiello provides easy access to local shops and restaurants. Experience the charm and luxury of this beautifully restored family-owned villa.

 

 

 Villa Bellissimo Palazzo – Livorno

Step into a world of grandeur and elegance at Villa Bellissimo Palazzo. This magnificent villa, accommodating up to 20 guests, is a masterpiece of luxury and comfort. With its opulent interiors, spacious rooms, and a lavish garden featuring a sparkling private pool, every moment here feels like a scene from a movie. Located in the heart of Tuscany, this villa offers breathtaking views and is perfect for hosting grand family reunions or a getaway with a large group of friends.

 

 Villa La Casa Dell’Alba – Grosseto

Experience the enchanting blend of old-world charm and contemporary comforts at Villa La Casa Dell’Alba. This villa, accommodating up to 14 guests, is a haven of peace and beauty. With cozy interiors, a picturesque garden, and a private pool, it’s the perfect retreat for families and friends. Located near vineyards and olive groves, this villa invites you to indulge in wine tasting and savor the essence of Tuscany.

 

 Villa Serenissima – Grosseto

Luxury and serenity define Villa Serenissima, a splendid villa that can host up to 18 guests. Known for its elegant decor and vast outdoor spaces, this villa offers a sublime Tuscan experience. Relax by the large swimming pool, stroll through the landscaped gardens, or enjoy the panoramic views from the terraces. Its strategic location allows easy access to historic towns and the enchanting countryside.

 

 Villa Palazzetto Albertini Solare – Chianti

Villa Palazzetto Albertini Solare is a gem of Tuscan architecture, blending traditional aesthetics with modern amenities. Hosting up to 12 guests, this villa features spacious bedrooms, a well-equipped kitchen, and inviting living areas. The outdoor space, with its private pool and terrace, is perfect for relaxing and dining under the Tuscan sky. Centrally located, it’s an ideal base for exploring Tuscany’s cultural and historical treasures.

 

Villa Cedro d’Oro – Chianti

Villa Cedro d’Oro is a luxurious 15th-century estate located in the heart of Tuscany, between Florence and Siena. It features 13 elegantly decorated bedrooms, accommodating up to 26 guests, with an additional dependence for six more. The villa offers modern amenities, including air conditioning, satellite TV, a pool, jacuzzi, sauna, gym, and a private tennis court. Guests can enjoy lush gardens, al fresco dining, and various activities such as wine cellar tours, hot-air balloon excursions, cooking lessons, and horseback riding.

 

Villa Amore – Lucca

Nestled between Montecatini and Lucca, Villa Amore is a secluded haven just outside Capannori, offering up to 30 guests a serene escape surrounded by lush gardens, vineyards, and olive groves. Despite its proximity to town, it maintains a peaceful atmosphere. Ideal for groups, this villa features unique amenities like an independent Yoga Studio and a large kitchen perfect for cooking experiences or banquets. Villa Amore’s 15 luxurious bedrooms, with options for twin, queen, or king beds, blend historic charm with modern comfort.

 

Tuscany is a land of unparalleled beauty and charm, offering a variety of exquisite villas that cater to families and friends seeking an extraordinary vacation. Whether you’re drawn to the grandeur of Villa Bellissimo Palazzo, the rustic elegance of Bella Villa di Campagna, or the intimate charm of Villa Gioia Eterna, these villas provide the perfect backdrop for creating lifelong memories. Dive into the heart of Tuscany, and let its magic captivate you.

 

Write today to: team@italyvacationspecialists.com

 

 

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