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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 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.

Villa Eterna, Tuscan Haven in the Heart of Chianti

VILLA ETERNA - RADDA IN CHIANTI Only a five-minute walk from Radda in Chianti, the villa is set just outside the charming village. Surrounded by rolling vineyards, and postcard-perfect valleys, the villa offers spectacular views across the Florentine hills. Guests can walk to Radda for shops, restaurants, wine bars, and essential services, while the central Chianti location makes day trips to Florence, Siena, San Gimignano, Volterra, Montalcino, and other Tuscan highlights wonderfully easy.

Isola Serena - New Private Luxury Villa in Chianti

Located in Castellina in Chianti in Tuscany, Italy, Isola Serena is a beautiful private luxury villa on 4 acres of land with the most breathtaking views in the Tuscan countryside. Covered in vineyards, olive groves, and captivating forestry, the villa finished restoration in 2014 and expanded in 2023 to include 2 additional guesthouses. The property now has a total of 10 bedrooms all with ensuite bathrooms and can sleep up to 23 people, making this one of the biggest villas in Chianti.

La Tuscia - Tenuta di Toscana, Boutique Villa

Casa La Tuscia is a beautifully restored 1700s farmhouse blending original “Pietra” and “Travi” with modern, luxurious interiors. This exclusive-use Luxe Villa is ideal for families, couples, friends, or small business groups. Set in the Tuscan countryside, it’s surrounded by its own vineyards and orchards. Guests enjoy an elegant experience with a serene spa, panoramic heated pool, jacuzzi in the olive grove, daily housekeeping, and high-speed Wi-Fi throughout the estate.

Villa Mandorla by My Villa Collection

Villa Mandorla, a beautifully restored estate dating back to around 1000 AD, offers a luxurious countryside escape in the heart of Tuscany. This historical property features a central farmhouse and two converted barns, with a total of 7 bedrooms and 7 bathrooms. The villa combines the charm of the past with modern comforts, making it an ideal retreat for families or groups. The expansive grounds include lush gardens and multiple outdoor lounges and dining areas.

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.

600-Year Chianti Farmhouse | Pool | By Cuvée

A 600-year-old Chianti Classico estate restored by Cuvée. Six ensuite suites, an infinity pool cascading into the vineyards, wood-burning fireplaces, a centuries-old pizza oven, an organic kitchen garden, and a private helicopter pad. One hour from Florence, a short walk from the Vertine castle village.

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.

Tenuta Ceccatelli

Set among vineyards and olive groves in the hills of Chianti Classico, Tenuta Ceccatelli is a restored 17th-century estate designed for exclusive use.

Il Casolese di Vignamaggio

Villa con 9 camere da letto con bagno privato e piscina. Perfetta per le famiglie e i gruppi di amici che vogliono passare del tempo insieme

Le Pratola

Note: The property has gates and security cameras. All security cameras are external.