Last Updated on August 22, 2024
If there was a model Tuscan town that would make for an ideal guidebook cover, it would have to be the medieval town of San Gimignano. I recall the first time my family visited and we were so impressed by this charming village. Though it was only a day trip, we promised ourselves we would return for a longer stay.
This small town in the heart of Tuscany, Italy, is known for its well-preserved towers and rich history. Located about halfway between Florence and Siena, San Gimignano is often called the “Town of Fine Towers” due to the 15 medieval structures that dominate the skyline here. These are remnants of the 72 towers that once existed here.
The town’s center is a UNESCO World Heritage Site, reflecting its historical and architectural significance. The narrow, winding streets and stone buildings transport visitors back to the Middle Ages. Aside from the charming piazzas (main squares), impressive Romanesque church, art and culture, San Gimignano is also known for its Vernaccia di San Gimignano wine, one of Italy’s finest whites.
The local cuisine is rooted in traditional Tuscan flavors with an emphasis on fresh, local ingredients, which it has been for years before farm to table was a trend.
With its combination of history, architecture and culture, San Gimignano makes for a popular destination and ideal location for travelers exploring the Tuscany region.
These charming vacation rental villas from romantic one-bedrooms to six-bedroom structures will set the stage for an unforgettable Tuscan experience, no matter what your needs.
Villas in the Countryside
Brunello Stone House
Located in a peaceful and panoramic position on the verdant rolling hills just outside of the town of San Gimignano, this cozy cottage has been completely renovated, transforming a former barn into a rustic style home with modern amenities, all while maintaining its history.
The two-bedroom, two-bath cottage can accommodate four guests and also features a private pool, fireplace and furnished terrace with magnificent views. It’s a magical trip back in time and guests can enjoy a stop off at the Tenuto Torciano Winery, only a two-minute drive from the property.
Views of the San Gimignano Towers
You will love this four-bedroom, 4.5-bath villa with panoramic views of the town and rolling hill countryside of the Chianti region.
The historic seven-room stone house pays homage to its Tuscan heritage in so many ways and guests will enjoy their own private pool, stunning views of San Gimignano towers, wood-burning fireplace, Tuscan décor and yet be within walking distance from the town.
La Villa in the Tuscan Countryside
Framed by the vineyards of Vernaccia, Chianti and olive groves, this lovely villa offers privacy while being only 4 kilometers from the historic center of San Gimignano.
The beautiful architectural structure with large white oak beams and Tuscan style piatra coating offers two balconies with wrought iron railings along with four bedrooms, four baths, a fireplace, a hot tub, and outdoor pool. This property is well-appointed, well-equipped and so iconically Tuscan.
Villa Iris Luxury
If you’re traveling with a large group, you’ll be thrilled to share the cost of this magnificent luxury villa with six bedrooms and 7.5 baths perched on a hill and created from a meticulous restoration of an ancient brick kiln dating back to 1737.
The villa that sleeps 12 promises guests all the comforts needed for an enchanting vacation that include a Finnish sauna, chromotherapy, sensory shower and gym, stunning infinity pool and spa with a whirlpool and picturesque gardens. Yet, you’ll love the San Gimignano tower views and vineyard vistas in the distance.
Vacation Rentals in the Heart of San Gimignano
Renovated, Romantic Apartment in the Heart of Town
If you’re looking for a smaller vacation villa that’s right in the heart of the historic district, this one will fit the bill.
The one-bed, one-bath romantic apartment is just a few steps to the Duomo and famous Pizza della Cisterna. The furniture is shabby-chic which lovingly blends with the original-beamed ceilings and original rock walls of the property.
Tusci Loft San Gimignano
Here’s another option in-town for a couple or small family. The one-bedroom, one-bath beautifully-appointed loft with kitchen can sleep up to four guests and offers stunning views out of its windows of the cobblestone streets and historic structures of San Gimingano.
Guests are only a two-minute walk to Piazza Duomo, Piazza della Cisterna, the San Gimignano Communal Palace and the delightful Italian eateries and boutiques.
La Rocca Romantica
This delightful two-person renovated and refurbished apartment is located close to all the city’s attractions, bars, restaurants, shops, museums and churches.
The one-bedroom, one-bath property is equipped with all the comforts you’ll need and the windows of the apartment overlook the Rocca park, a quiet and peaceful place only 80 meters away from Piazza del Duomo. You will sleep peacefully and wake up to the singing of the birds.
Casa San Gimi
If you’re needing a bit more space, Casa San Gimi, located within the medieval walls of the historic center is ideal. Not only are you in a great location but this stylish two-bedroom, one bath can sleep three.
Views from the kitchen window of the countryside are spectacular and yet, you’re just a short stroll to the Piazza, restaurants, boutique shops and historic landmarks of this historic city.
Whether you plan a longer stay in San Gimignano or just a stop-over on your Tuscany adventure, don’t miss staying at one of these incredible properties reflective of the history, culture and warmth of the area.
