Luxury rentals in San Gimignano

Podere Maiano

Make a romantic Tuscan getaway at Villa Di Montesoli. Though the spacious nine-bedroom property offers accommodations in both a main villa and guest house, its interiors feel traditional and intimate, and amenities like a spa area, jetted tub and billiards room are hotel-worthy perks. If you can tear yourself away from the comforts of this renovated farmhouse, the surrounding Val d’Orcia landscape is worth exploring, and the city of Siena is a short drive away. Start your stay by soaking the cares away in the large pool or whirlpool spa, or sweat them out in the sauna. Take a stroll around the grounds, see what’s growing in the kitchen garden, prepare the produce on the outdoor grill and enjoy meals or a glass of wine at the al-fresco dining area. In the evening, challenge friends and family to a game of billiards or ping-pong, or relax with television or Wi-Fi access. The villa’s living spaces combine rustic architecture and formal furnishings. In one living room, stone floors and vaulted brick ceilings showcase a remodeled fireplace, traditional roll-arm sofas, carved-wood chairs and Persian-style rugs; in another, striped sofas are pulled around a large farmhouse-style fireplace. Likewise, the dining room mixes beamed ceilings and tile floors with a crystal chandelier, while red upholstered chairs provide a pop of color. The well-equipped kitchen displays country charm in wood cabinets and a cheery pottery collection. There are eight bedrooms in the main house and one bedroom in the guest house; all nine have en-suite bathrooms and either air conditioning.There are also five bedrooms with queen beds, all of which have ceiling fans. In the guest house, the bedroom has a queen bed and air conditioning. Villa Di Montesoli is about 2 miles outside the town of Buonconvento, where you’ll find restaurants, a grocery store, a church and train station. Play a match at the tennis court, 5 km away, or a round at the Borgo la Bagnaia golf course, 30 km away. Take a day trip to Siena, about 28 km away, or make the longer drive to Florence, about 95 km away. It’s 140 km to Pisa, and Rome is 230 km away. Copyright © Luxury Retreats. All rights reserved. BEDROOM & BATHROOM Main House • Bedroom 1: King size bed, En-suite bathroom with shower and bathtub, Air conditioning • Bedroom 2: King size bed, En-suite bathroom with shower, Air conditioning • Bedroom 3: King size bed, En-suite bathroom with shower and bathtub, Air conditioning, Ceiling fan • Bedroom 4: Queen size bed, En-suite bathroom, Air conditioning, Ceiling fan • Bedroom 5: Queen size bed, En-suite bathroom, Air conditioning, Ceiling fan • Bedroom 6: Queen size bed, En-suite bathroom, Air conditioning • Bedroom 7: Queen size bed, En-suite bathroom, Air conditioning, Ceiling fan • Bedroom 8: Queen size bed, En-suite bathroom, Air conditioning, Ceiling fan Guest House • Bedroom 9: Queen size bed, En-suite bathroom, Air conditioning FEATURES & AMENITIES • Alarm system • Jetted tub • Bocce Court • Vegetable garden • More under “What this place offers” below SERVICES INCLUDED • Gardener • Linen change on Saturdays • Bath linen change on Wednesday & Saturday  • Products from the Organic Vegetable garden and hen eggs from the henhouse. • More under “What this place offers” below SERVICES AT EXTRA COST • Activities and excursions • Catering service • Cooking class • Wine tasting • Villa heating • Baby equipment • Event fee • Mandatory departure cleaning fee • Mandatory per day utility fee • Additional housekeeping • More under “What this place offers” below

Villa Montemaggio

The Tuscan sun soaks into the stone walls of this 17th-century farmhouse—and into the grapes clustered in the organic vineyards in the surrounding Chianti countryside. The Roman road from Siena to Florence once traced these hills; today, they’re home to the 70-hectare Montemaggio estate, which produces organic wine and olive oil. Siena is 40 minutes away by modern road; Florence, 1 hour. Smell the flowers in the gardens, pick fresh mulberries and figs to snack on, and see if you and the kids can find the playhouse hidden away on the estate’s grounds. There’s a private gym for workouts, a swimming pool for refreshment, and a rooftop terrace just made for the evening’s first bottle of local wine. While the villa still has some of its 17th-century farmhouse charm—spot beamed ceilings, doorways framed in elaborate molding, and a wide hearth on the living room fireplace—it’s been fully renovated. A pair of plump sofas invites you to stay a while in the living room, and there are plenty of chairs around the dining table that takes center stage in the fully equipped kitchen. Learn more about the Montemaggio estate by booking a cooking class, featuring fresh produce from the gardens, or a wine tour. Be sure to ask about the festivals in nearby villages, which range from celebrations of wine to a fete dedicated to bruschetta. Beyond Tuscany’s medieval towns and fortresses, the cities of Siena and Florence are close enough for a day trip. Copyright © Luxury Retreats. All rights reserved. BEDROOM & BATHROOM • Bedroom 1 - Primary: King size bed, Ensuite bathroom with stand-alone rain shower & bathtub, Dual vanity, Bidet, Television, Desk • Bedroom 2: King size bed, Ensuite bathroom with stand-alone rain shower, Television • Bedroom 3: Queen size bed, Ensuite bathroom with stand-alone rain shower, Bidet, Television, Desk FEATURES & AMENITIES • More under “What this place offers” below Extra Cost (advance notice may be required): • Activities and excursions • More under “Add-on services” below

Villa Chianti Fornace

Experience the epitome of Tuscan luxury at Villa Chianti Fornace — a meticulously restored historic villa nestled between Florence and Siena. This exquisite retreat features expansive gardens, a private spa, and a panoramic pool with sweeping views of rolling vineyards. Whether you're planning a romantic escape or a family holiday, immerse yourself in the authentic charm and serene beauty of the Chianti countryside at this unparalleled haven.

Villa Finesterra

Preserving the historical character of the structure through an innovative approach: the design of Villa Volterra has been curated with the intention of creating the right balance between rustic and modern, tradition and design. The beating heart of the property is the living area, which is adorned by a panoramic glass wall with a spectacular view of the swimming pool that creates a seamless bridge to the garden.

Villa Sarah Tenuta Melograni

Villa Sarah enjoys spectacular views of the famous towers of San Gimignano. A large garden surrounds the entire structure and also the four-sided infinity pool with spa whirlpool, made with valuable stone of Cardoso, renowned local stone. Next to the swimming pool is a big dependance with large panoramic terrace, equipped outdoor kitchen, bbq, bar area, relaxation area and a large table to enjoy outdoor dining.

Villa Vianci RBO, your home away in Tuscany

Imagine relaxing in the heart of the Tuscan countryside, staying in a charming villa where history meets comfort. Ideal for families and groups, you'll love the bright, airy rooms and the villa's convenient location close to top sights. Enjoy the delicious local food and create memories to last a lifetime at this delightful getaway.

Mugnello Radicondoli

Villa Mugnello in Radicondoli Siena is the ideal place to enjoy your stay in the most authentic and uncontaminated Tuscany. Large families or groups of friends can spend relaxing holidays in Mugnello to experience moments of authentic joy, well-being and beauty.

Barone Achille -La Dimora degli Affreschi Florence

Dimora degli Affreschi… An entire Florentine palazzo transformed Barone Achille New LISTING Our Florence palazzo restoration has finally reached fruition near the banks of the Arno in the thriving district of Santa Croce

Villa Marcellina

Part of the Ville La Marcellina estate (20-acres estate), this villa is an expansive property with all modern amenities making it perfect for big group holidays.