Holiday home rentals in San Gimignano

Casa al Gianni - Oak

Hello, we’re Cristina and Carmelo! We look forward to welcoming you to ‘Casa al Gianni’, our farmhouse in the woods of the Montagnola Senese, just 20 minutes from Siena. Here, life slows down: there is only the scent of the earth, the song of the birds, and the companionship of our animals. It is an invitation to rediscover the beauty of the little things, surrounded by the greenery of the most authentic Tuscany. It’s not just a holiday; it’s a return to our roots. This peaceful haven will stay with you forever. We look forward to welcoming you!

San Gimignano, Montegonfoli SIX

Wonderful apartment in the country side of San Gimignano, at about 3Km and 5min from town center by car, far from noise, but close to all you may need. The apartment is suited for 4 people with 2 bedrooms each one with its en-suite bathroom. Bedrooms have an high privacy, splitted by the living room with kitchen, featured by the huge fireplace where our ancient farmer used to sleep over a FIAT 500 seat. First floor, 20 steps, no elevator. Side view on San Gimignano city and towers on the right

Podere La Castellina - No. 1 COTTAGE

Independent stone and brick cottage inside the "Podere la Castellina" (former 13th century convent), in the magnificent natural park of Montagnola Senese. The cottage can comfortably accommodate 5 people and includes: - large living room with TV and fireplace - kitchen with oven - master bedroom - bedroom with three single beds - bathroom with shower Guests have access to a panoramic swimming pool, solarium and terrace with breathtaking views, equipped with a wood-burning oven and barbecue.

Vittoria Chianti Vacations 🍇🍷

Vittoria Chianti Vacations is the ideal solution for those seeking peace and tranquility in the heart of Chianti, close to all comforts. Typical Tuscan farmhouse halfway between Florence and Siena, is located in a strategic position to quickly reach Florence, Siena, San Gimignano, Monteriggioni, Volterra and the Chianti hills. Siena Eye Laser Clinic 2 min. Private parking, two bedrooms, equipped kitchen, private bathroom, Wi-Fi, private garden, barbecue, a wonderful view of the Chianti hills.

Vicolo dell'Inferno* @home in San Miniato old town

Welcome to the historic centre of San Miniato! Our holiday home is located in the charming and quiet Vicolo dell'Inferno, right on the main square. San Miniato was once known as “the city of 20 miles”, located right in the middle between Pisa, Florence, Siena and Lucca. It is ideal for day trips without sacrificing the tranquillity of an authentic medieval village. After a day of good food and visiting cities of art, you can relax on your balcony and enjoy the slow pace of Tuscan life.


Chianti Craft House Badia a Passignano

Ancient house in the historic village of Badia a Passignano, completely and finely restored in 2022. The house is located exactly in the center of the village of Badia a Passignano, overlooking the abbey castle and the Chianti vineyards. The house consists of 2 bedrooms air-conditioned: 1 double bedroom with service bathroom and 1 with 2 single beds and the possibility of a third with sofa chair; a full bathroom with shower, a full kitchen with washing machine and dishwasher, dining area

Barrel Suite Tuscany • Hot Tub • Vineyard View

Wooden barrel suite in Tuscany, nestled in an olive grove in Reggello: breathtaking views over hills and vineyards, total peace. One of the largest barrels in the world (3.5 m x 8 m) with a private bathroom, kitchenette, veranda and small courtyard. All barrels have a hot tub pool for your relaxation. Strategic location: Florence ~40 min, Siena and Arezzo for day trips. Private parking on the property and a welcome Tuscan cold cuts and cheese board. Close to The Mall Luxury Outlet.

Breathe in Tuscany: 180° view of the hills

Please note that the second bedroom is divided from the hallway by a curtain and not by a door. Experience San Gimignano with a splendid view of the Tuscan hills! In the heart of San Gimignano, experience the city with a separate entrance, second floor and breathtaking views of the Tuscan hills. Private parking is available upon request. Entrance, living room, 2 double bedrooms, kitchen and large bathroom. city tax to be added to the price, €2.50 per person per night.

Charming farmhouse with garden, views & pool

Agriturismo Timignano is a beautiful farmhouse surrounded by stunning unspoilt countryside. The stone farmhouse has been restored over the years to create 3 totally separate apartments, each with independent entrance , private terraces and garden space. The farm is surrounded by unspoilt countryside with spectacular views and magnificent sunsets. It is a calm, relaxed place, an idyllic retreat away from the crowds ideal for couples.

In Tuscany Rooms

**Your Dream Retreat in the Heart of Val d'Orcia** Welcome to In Toscana Camere, a charming holiday home located in the historic center of Monticchiello, a Tuscan village full of charm and authenticity. Surrounded by stone walls and enhanced by modern, comfortable interiors, this home offers the perfect balance between tradition and contemporary style. Wake up every morning to a breathtaking view of the stunning Val d'Orcia.

Stunning Tuscan apartment for 2

This apartment - tucked away privately and enjoying a stunning view from its terrace - is part of an 'agriturismo' farm which produces organic Chianti Classico. Spacious and light, it has 1 double bedroom, 1 sitting room, 1 bathroom and a kitchen.

San Gimignano, Tuscany

Set inside the walls of historic San Gimignano, this medieval (but fully refurbished) apartment will stir your senses. San Gimignano is right at your door. Step out into a World Heritage City 45 minutes from Florence, 35 minutes from Siena. Enjoy