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Borgo Gerlino

Stone pathways lead from this lovingly-restored Italian home to a vivid blue swimming pool that overlooks a nearby forest. Inside, rustic brick arches divide spacious rooms featuring finely-crafted furniture and relaxed ambience. At the shaded, viewpoint garden table, guests can plan trips to the medieval village of Rapale, generations-old family trattorias, and Siena’s world-famous piazza. Sunrise at Borgo Gerlino bathes the surrounding woodland, plantations and olive trees in golden light, before spreading across the traditional tiled roof and rich, mottled stone exterior of the home. Guests are served with a delicious breakfast courtesy of the home’s fully equipped kitchen, with a selection of airy alfresco dining spots in the garden. Easily prepare for the day with the home’s 9 ensuite bathrooms, complete with ample space and tiled elegance. As the morning heats up, a comprehensive heating / cooling system ensures the ideal climate is retained. After a full day exploring the locality, relax in the garden with a sunset banquet of local dishes and vibrant wine. The culinary wealth and visual appeal of rural Tuscany is yours to experience from Borgo Gerlino. The hilltop village of Rapale, replete with quiet lanes and fairytale stone towers, is within walking distance. A short drive through lush countryside and olive plantations will bring guests to pleasant roadside restaurants and wineries, where the region’s bounty can be savored. Drink in the frescos and ancient convent at Monte San Savino, or take in the antique splendor of the UNESCO-listed Piazza del Campo in Siena.   Copyright © Luxury Retreats. All rights reserved. BEDROOM & BATHROOM Main House • Bedroom 1: Queen size bed, Ensuite bathroom with stand-alone shower, Television • Bedroom 2: Queen size bed, Ensuite bathroom with stand-alone shower, Television • Bedroom 3: Queen size bed, Ensuite bathroom with stand-alone shower, Television • Bedroom 4: Queen size bed, Twin size bed, Ensuite bathroom with stand-alone rain shower, Television, Desk • Bedroom 5: Queen size bed, Twin size bed, Ensuite bathroom with stand-alone shower, Television, Desk • Bedroom 6: Queen size bed, Ensuite bathroom with stand-alone shower, Television, Desk • Bedroom 7: Queen size bed, Ensuite bathroom with stand-alone rain shower, Television, Desk Annex • Bedroom 8: Queen size bed, Ensuite bathroom with stand-alone shower, Television • Bedroom 9: Queen size bed, Ensuite bathroom with stand-alone shower, Television FEATURES & AMENITIES • Floor cooling system OUTDOOR FEATURES • Swimming pool - heating at extra cost • Security cameras - outward facing STAFF & SERVICES Included: • Gardener/caretaker • Daily breakfast Extra cost (advance notice may be required): • Extra cleaning service • Linen change • House heating system • Lunch and dinner services • Extra virgin oil products

Villa Quercia by Burghesius

Step outside each morning to feel the warm, fresh breeze as you stroll through fruit gardens and forests of oak at this traditional farmhouse estate in the heart of Tuscany. Embark on day trips to nearby villages, vineyards, and the famous Abbey of San Galgano. Return home for an afternoon swim, a delicious alfresco dinner, and a night of incredible Italian wine by the fireplace. Copyright © Luxury Retreats. All rights reserved. BEDROOM & BATHROOM Main House • Bedroom 1 - Primary: King size bed, Ensuite bathroom with shower/bathtub combo, Bidet • Bedroom 2: King size bed, Ensuite bathroom with stand-alone rain shower, Bidet, Balcony • Bedroom 3: 2 Twin size beds (can be converted to a king), Day bed, Ensuite bathroom with stand-alone rain & steam shower, Bidet House 2 • Bedroom 4: King size bed, Ensuite bathroom with shower/bathtub combo, Bidet, Walk-in closet, Sofa, Desk • Bedroom 5: King size bed, Shared access to hallway bathroom, shower/bathtub combo, Dual vanity, Bidet, Desk • Bedroom 6: 2 Twin size beds (can be converted to a king), Ensuite bathroom with stand-alone rain & steam shower, Bidet, Walk-in closet, Desk • Bedroom 7: 2 Twin size beds (can be converted to a king), Ensuite bathroom with stand-alone rain shower, Bidet, Walk-in closet OUTDOOR FEATURES • Outdoor living space STAFF & SERVICES Included: • Linen change - twice per week • Concierge service Extra Cost (advance notice may be required): • Activities and excursions • Additional housekeeping

San Gerolamo

Situated on a hilltop with 360-degree views, San Gerolamo, situated in Crete Senesi, the heart of Tuscany, has been carefully restored and crafted to weave luxury and comfort into a genuine Italian experience. With over 5,500 sq. feet of living space, San Gerolamo has been designed with flexibility in mind to comfortably host groups of up to 10 guests providing ample living spaces, allowing guests opportunities to come together and share, or retreat and relax. Copyright © Luxury Retreats. All rights reserved. BEDROOM & BATHROOM • Bedroom 1 - Primary: King size bed, Ensuite bathroom with stand-alone rain shower & bathtub, Bidet, Dual vanity, Lounge area, Safe • Bedroom 2: King size bed, Ensuite bathroom with stand-alone rain shower & bathtub, Bidet, Dual vanity, Lounge area, Safe • Bedroom 3: 2 Double size beds (can be converted to king), Ensuite bathroom with stand-alone rain shower, Bidet, Dual vanity, Lounge area, Safe • Bedroom 4: King size bed, Ensuite bathroom with stand-alone rain shower & bathtub, Bidet, Dual vanity, Lounge area • Bedroom 5: King size bed, Ensuite bathroom with stand-alone rain shower & bathtub, Bidet, Dual vanity, Lounge area, Safe OUTDOOR FEATURES • Garden • More under “What this place offers” below STAFF & SERVICES Included: • Concierge service Extra Cost (advance notice may be required): • Activities and excursions

Villa Montemaggio

This booking is a chance to stay in a real Tuscan Farmhouse that is situated inside an actual vineyard. Its a private property of the owners of the estate, completely refurbished to give every possible comfort but still live in the middle of nature. The setting is absolutely breathtaking amongst the rolling tuscan hills, far away from the noise of the concrete jungle and busy streets. Here the only noise you will hear is the chirping of the birds or faraway hum of the tractor in the fields.

Restored 16th-Century Estate | Chianti Classico

Cuvée's Tuscan Farmhouse is a 600-year-old estate in the heart of Chianti Classico — restored by Cuvée's design team with six suites, an infinity pool cascading into the vineyards, wood-burning fireplaces, a centuries-old pizza oven on the terrace, organic garden, chicken coop, billiard room, and a private helicopter pad. A short walk to the Vertine castle village. One hour to Florence. Cuvée's Italy team handles vineyard visits, private chef dinners, and every detail.

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 di Tizzano between Chianti and Florence

Surrounded by olive trees and vineyards in the Chianti Classico region, this stunning property is adorned with a tower, a romantic park, and French gardens that enjoy sweeping views of the rolling Italian hillside. When you’re not relaxing by the pool or enjoying alfresco meals on the terrace, venture out on day trips to Florence, Siena, Pisa, and other incredible Tuscan cities. Copyright © Luxury Retreats. All rights reserved.

Villa Castellare de' Sernigi for rent in Tuscany

Villa Castellare de' Sernigi is 500 years old villa, renovated by the owners. The house has 7 ensuite bedrooms, each one with air conditioning,( 1 double, 5 twins/double, 1 single bed) large kitchen, large dining area and 2 living rooms, veranda/porch with view on sunset, extensive lawns, with olive grove, large swimming pool, contemporary art park fully equipped grill and pizza oven

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.

Sole del Chianti

Halfway between Florence and Siena, among the verdant hills and the vineyards of Tuscany, stands the resort “Sole del Chianti”, where the sound of nature prevails along with silence and privacy. Here it’s still possible to experience the country life of times gone by.

Nuova - Villa moderna

Brand new location in the heart of the Tuscan vineyards, offering stunning panoramic views and a truly picturesque, exclusive setting. Fully restored to the highest standard and completed in late 2025. only about 25min south of Florence.

Villa Panzano

In the heart of Chianti Classico, surrounded by its own vineyards and olive groves, lies Villa Panzano, just 3 km from the center of Panzano in Chianti, one of the most charming villages in Tuscany.