Luxury rentals in San Gimignano

Find and book unique accommodations on Airbnb

Top-rated luxury vacation rentals in San Gimignano

Guests agree: these stays are highly rated for location, cleanliness, and more.

0 of 0 items showing

1 of 3 pages

Luxe

Villa in Palaia

5 out of 5 average rating, 4 reviews

Valle

Once a farmhouse and hayloft, the recently restored villa Valle is now a luxurious country retreat. With seven bedrooms divided between the main house and guest cottage and expansive yet private outdoor spaces, the property gives guests plenty of room to relax. But it’s also in the heart of Tuscany, close enough to the cities of Pisa, Florence, Siena and Lucca for day trips. Restored in 2007, the villa is now air-conditioned and has a Wi-Fi connection and gated access. The enclosed garden has a broad lawn and bocce court, and the main house and guest cottage are connected by a terrace with a pool, barbecue and outdoor dining area. Adults can while away the afternoon over a book in the sun room, and kids can entertain themselves in the billiards room. The interiors of Valle are warm and comfortable, drawing country charm from restored rustic fireplaces and beamed ceilings in the living spaces. With warm yellow walls, damask drapes and traditional-style furnishings, the living room is cozy and welcoming. A formal dining room is decorated in rich, earthy Tuscan reds and golds that glow under a chandelier and sconces. The sunny, modern eat-in kitchen has stainless steel appliances and a breakfast bar. There are five bedrooms in the villa’s main house and two bedrooms in the guest cottage. In the main house, you’ll find three bedrooms with king beds, one bedroom with a double bed and one bedroom with a queen bed. Each of the five bedrooms has an en-suite bathroom and air conditioning. In the guest house, there’s one bedroom with a double bed and one bedroom with a single bed; both are air-conditioned and have bathroom access. During your stay, take the time to stroll the estate on which the villa is located, or walk to the local church, 15 minutes away. By car, it’s only 5 minutes to downtown, which offers a grocery store, restaurant and seasonal truffle sales and tastings. A tennis court and clinic are 10 minutes away, and a hospital and train station are 36 km away. Enjoy a leisurely afternoon at the golf course, 45 km away, or the beach, 48 km away. When it’s time to leave, it’s a 35 km drive to the airport. Copyright © Luxury Retreats. All rights reserved. BEDROOM & BATHROOM Main Villa • Bedroom 1: King size bed, En-suite bathroom with tub and shower, Air conditioning, Television • Bedroom 2: King size bed, En-suite bathroom with tub and shower, Air conditioning, Television • Bedroom 3: Double bed, En-suite bathroom with tub and shower, Air conditioning, Television • Bedroom 4: 2 Twin beds, En-suite bathroom with tub, Air conditioning, Television • Bedroom 5: King size bed, En-suite bathroom with tub and shower, Air conditioning, Television Guesthouse • Bedroom 6: Double bed, Bathroom with shower, Air conditioning • Bedroom 7: Single bed, Bathroom with shower, Air conditioning FEATURES & AMENITIES • Billiard table • More under “What this place offers” below SERVICES INCLUDED • Linen change - weekly • Pool maintenance - Daily • Garden maintenance • More under “What this place offers” below SERVICES AT EXTRA COST • Activities and excursions • Heating consumption • Pool heating (advance notice required) • Excessive phone charges • Additional housekeeping • More under “What this place offers” below ADDITIONAL INFORMATION Villa Saletta estate, once owned by the Riccardi family (bankers to the Medici), covers approximately 1,760 acres. In total, there are more than 20 old farmhouses on the estate, mostly dating back to the 1800s. Each one has its own story to tell, being unique and individual in size and location. Three of these farmhouses have been restored so far. Every restored villa has its own private grounds with electric gates, outdoor swimming pool, barbecue and comfortable shaded seating areas. Please note estate roads are not suitable for vehicles with poor ground clearance.

Luxe

Villa in Buonconvento

5 out of 5 average rating, 6 reviews

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

Luxe

Villa in Radda in Chianti

5 out of 5 average rating, 4 reviews

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

Luxe

Villa in Gaiole

5 out of 5 average rating, 6 reviews

Villa Rietine

Villa Rietine embodies Tuscan serenity amid a lush landscape of olive, oak, and vineyards. With wide views of the Chianti hills around Lecchi and Gaiole, the lower and upper terraces welcome sunny pool plunges and meals in the aromatic breeze. Modern interiors emphasize rustic origins, with an eat-in kitchen, fireplaces in the salon and dining room, and arched doors to the veranda. Radda and Siena are an easy drive away. Copyright © Luxury Retreats. All rights reserved. BEDROOM & BATHROOM • Bedroom 1: Double size bed, Ensuite bathroom with stand-alone shower • Bedroom 2: Double size bed, Ensuite bathroom with stand-alone shower • Bedroom 3: Double size bed, Ensuite bathroom with stand-alone shower & bathtub • Bedroom 4: 2 Twin size bed (can be converted to a double bed), Ensuite bathroom with stand-alone shower FEATURES & AMENITIES • More under “What this place offers” below Extra cost (advance notice may be required): • Activities and excursions • Heating consumption • Tourist tax : 1,50 Euro per person, per night for the first 7 nights • More under “Add-on services” below

Luxe

Villa in Volterra

5 out of 5 average rating, 7 reviews

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.

Luxe

Villa in Tavarnelle Val di Pesa

4.85 out of 5 average rating, 13 reviews

Villa Chianti Fornace

Villa Chianti Fornace is a centuries-old Luxury Villa located between Florence and Siena. A stay in this Villa is your chance to live out your own “Under the Tuscan Sun” movie experience. Airy and spacious, the Villa offers a Hollywood-worthy retreat in the Tuscan countryside. Located 5 minutes away from the village of Tavarnelle V.P, the Villa is the perfect getaway for those who are looking for pure relaxation

Luxe

Villa in San Gimignano

5 out of 5 average rating, 3 reviews

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.

Luxe

Villa in Poggibonsi

4.33 out of 5 average rating, 6 reviews

Villa Vianci

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.