luxury holidays rental Gaiole in Chianti, Italy

A truly luxury retreat among the world famous Tuscan hills. Villa Caccia Chianti is located only a short drive from Florence and Siena, surrounded by its own private vineyards and olive groves. The estate has a long historical background and it has been owned by the same noble family since 1920. The interior was designed by Princess Ma rianita Ruspoli, a combination of modern elegance and authentic Tuscan style. The villa consists of 9 ensuite bedrooms with private bathrooms fully equipped with BVLGARI bath products. The kitchen has everything one needs to create superb cuisine, using the organic vegetables and fruit from the estate's own garden. There is even a surprise for gelato lovers to have their own home-made ice-cream experience. Go for a walk, sit by the pool with a book or discover the woodland and wildflower meadows near the estate. The perfect place for a group of friends or family to enjoy the wonderful Chianti Region and explore the breathtaking Tuscan hill tops, and close enough to all the major tourist destinations, such as San Gimignano, Cortona and Volterra.

Villa Wisteria is nestled in 50 acres of vineyards and woodlands in Chianti. A former hayloft to a nearby castle, the villa has been totally transformed into a luxurious yet cosy country home. This luxurious country house is situated within the rolling Chianti countryside, famous for its renowned wine. The historic city of Siena is just a short drive from the villa while a sightseeing adventure to Florence is only an hour's drive. For those wishing to repose in the Chianti countryside, a fabulous feature of the villa is the saltwater swimming pool, accompanied by a fragrant landscaped garden that offers the perfect place to relax and cool down on a Tuscan summer's day. The villa has been designed with ample space to provide quiet, memorable moments. It has been decorated with antique and contemporary furniture, old handmade terracotta tiles and beautiful gardens, demonstrating its historic aesthetic with a modern appeal. The large hand-forged windows and doors provide natural light and fresh air to the three-storey villa. There are two large, comfortable indoor living rooms on separate floors as well as a beautiful summer sitting area under a pergola that runs the entire length of the house overlooking the pool. Here, guests can enjoy reposing under the shade while overlooking the pool or enjoying an aperitif al fresco. Leading off the entrance hall on the spacious ground floor is the living room with its large, open fireplace. The adjacent dining room and fully-equiped kitchen open onto the south-facing, wisteria-covered shaded pergola. Villa Wisteria can welcome up to twelve guests. On the first floor are three bedrooms, all with en-suite bathrooms. On the large lower ground level, the sunny living room features a flat screen television and DVD player, great for entertaining children and families. There are also three bedrooms, one with an en-suite bathroom and two with a shared full bathroom, on the ground floor. With breath-taking views of the Chianti countryside and gentle summer breezes, this charming villa, with comfortable and luxurious indoor and outdoor spaces, is the perfect spot for friends and family to gather for a leisurely and luxurious Tuscan retreat.

The residence spans two levels, comfortably accommodating up to 14 guests in its 7 cozy rooms, including 5 doubles and 2 singles, each equipped with its own bathroom facilities. Overall, the villa boasts 5 full bathrooms, featuring either a bathtub or shower, all with double sinks. Additionally, there are 2 shower rooms with sink and toilet, and 2 WC rooms with sink. The ground floor hosts an elegant dining room with a fireplace and a wooden island kitchen, fully equipped with an oven, microwave, stove, dishwasher, 3 refrigerators, blender, electric grill, toaster, and more. From the kitchen, two French doors lead to the terrace/garden, furnished with a long table, chairs, and umbrellas for outdoor dining. Another distinctive cool room with sofas and a library, with access to the external terraces and garden, is also on the ground floor, along with three rooms used for ironing with a bathroom/shower, laundry, and a pantry. A staircase in the courtyard leads to the upper floor, where you'll find a lounge and two twin rooms, each with two bathrooms with a WC and sink, while one of them also has a shower. The varying height of the rooms makes them suitable for younger guests. On the ground floor, the sleeping area consists of 3 spacious double rooms, all with a view of the valley and vineyard, each with a private bathroom (two with a bathtub and double sink, and one with a shower and bathtub). A charming staircase at the main entrance leads to the first floor, where a large and bright living room offers a panoramic view of the surrounding countryside. Furnished with sofas, armchairs, TV, and a gaming table, this space is complemented by a double room with an ensuite bathroom. From the solarium terrace, you can access an independent double room, also with an ensuite bathroom with a shower. INCLUDED SERVICES: Full bed linen Bath towels with change every 4 days Pool towels High chair and crib for children, including linen Final cleaning INCLUDED STAFF: Domestic staff: 10 hours per day in total / excluding Thursday afternoons from 2 PM and the entire Sunday from 9:30 AM Pool maintenance Maintenance of outdoor area setup (furniture, sunbeds, chairs/armchairs), flower garden, lawn watering (nighttime)

In the heart of Chianti Classico, surrounded by vineyards and olive groves one finds Villa Panzano. The villa is in a charming location, an oasis of peace, where you can enjoy a holiday in total relaxation, but also the perfect place to discover Tuscany. Villa Panzano is only 3 km from the center of Panzano in Chianti, one of the most characteristic villages in Tuscany. Villa Panzano offers exclusive hospitality, rooms furnished with tradition and modern elegance, refined, unique materials, the result of a careful and meticulous renovation wanted by the Owner, to transform this place into a real paradise. You can enjoy the view and relax in the beautiful gardens that surround the entire estate, the heated outdoor pool and a sauna built in the old barn. Don't miss the winery tour and the tasting of all the best wines, grappa and extra virgin olive oil. Located in Tuscany, near Panzano in Chianti and in the heart of the Chianti Classico area, Villa Panzano covers an area of 135 hectares, in a suggestive succession of hills and valleys. As for the restoration of the vineyards, also in the reconstruction of the villa the approach was that of a conservative recovery, restoring value to the architectural building aspects dormant over time: the external fixtures and windows have been recovered as well as the internal doors, the load-bearing beams have been replaced and reused for the construction of the oak and chestnut wood flooring in the bedrooms, suites and bathrooms. The avenue of olive trees leading to the entrance, the colorful and fragrant lemon garden and the slopes of shrubs and flowers positioned as if to frame small glimpses of the vineyards and the Tuscan hills create a link between the estate and the surrounding landscape. Villa Panzano has been transformed into a work of art: alive, with different interpretations and, behind it, a glorious story to be told with pride and respect, while keeping an eye towards the future.

From Villa Curiano it is possible to organize beautiful excursions around the towns of the Val d'Orcia, Montalcino 20 Km, Penza 35 Km, Buonconvento 9 Km. There are many excellent restaurants throughout the area. Following the recent renovation, the owners have managed to sensitively maximize the ancient architectural features, ensuring comfort and finishings that are suitable for modern requirements.

This classic Tuscan villa is positioned in a very peaceful area surrounded by cypresses and other centuries-old trees and 70 hectares of ground. Situated in the Tuscan Val d'Arno countryside it is very suitable for those who are looking for total relax and privacy. Villa Martin is elegantly furnished with warm colours and modern comforts and is surrounded by a fenced garden. On the ground floor two French doors open onto the dining room connected with the sitting room and the fully equipped kitchen. The Villa is composed of 5 double bedrooms, each with its own en-suite bathroom: one large double bedroom with walk-in closet and very large bathroom and shower is on the ground floor; 3 large double bedrooms with beautiful bathrooms with walk-in shower are on the first floor and one more double bedroom with amazing view is in the attic. The villa has its own private swimming pool and parking and the entire estate also allows all of its guests access to two tennis courts, mountain bikes, a spa and Cooking classes and Wine tastings. The villa is about 40 minutes from Florence. Other important Tuscan towns and areas such as Arezzo, Cortona, Siena, San Gimignano and the Chianti wine region can all be easily reached from this property. Villa Martin is the perfect place to enjoy the best of Tuscany.

Villa Olivia is a beautiful property immersed in the greenery of the Tuscan countryside, 35 minutes away from Florence. The main building and the independent guesthouse are located on 3,000 square meters of land. The property is the perfect space to get together with friends or family to enjoy the beautiful and natural Tuscan countryside. The property is only a 12-minute drive to the A1 highway leading to Florence and Rome. Its neighbours are the Castle of Sammezzano, the Vallombrosa Abbey, and the surrounding nearby forests. The property is at only 25 kilometers from the city of Florence and only two kilometers to Rignano sull'Arno, where the nearest train station is located. The property is only a 40 minute drive to the enchanting village of Il Borro, where guests can enjoy a world-class restaurant, spa, tennis court, football pitch, horse riding, yoga, golf driving range, artisan workshops, truffle hunting, wine tasting tour and cooking classes. For guests who would prefer to stay within the estate, they can enjoy the gorgeous private swimming pool with a lounge area complete with sunbeds, sun umbrellas and a small gazebo perfect for fun and relaxation during the spring and summer months. Both the villa and guesthouse have a lovely, refined country feel and have been recently renovated. Impeccable taste and care have been placed into finding the perfect furnishings, to create an elegant and timeless beauty while maintaining a welcoming and cozy environment. The main villa features five bedrooms and can sleep up to 10 people while the guesthouse has one bedroom, accommodating two people. Each bedroom is equipped with double beds that can be converted into two single beds, air-conditioning, and private bathrooms. On the first floor of the main villa are a fully-equipped kitchen, a half bathroom, and an open dining room that leads into the two living rooms that offer ample natural light thanks to the large windows and the glass doors. There is also an outdoor loggia in front of the house, perfect for alfresco dining. The guesthouse is on one floor with a living and dining room, a kitchen, and a bedroom with private bathroom. This villa is ideal for families with children, for a group of friends on a holiday, for a getaway, for someone working in Florence or in the Valdarno area that prefers the beauty of the countryside and the convenience of being situated close to Florence.

The Watermill is located in Sambuca Val di Pesa, a small village between Siena and Florence. The property consists of a central building and two barns surrounded by lush and colorful vegetation, filled with fragrances, and sounds that make it a truly unique place to connect with nature. The rustling of leaves blends and the sound of the Pesa River are both soothing and refreshing. On the ground floor of the Villa, a spacious living room leads to a grand dining room with a fireplace and a bread oven followed by a modern kitchen restored and equipped with all the modern conveniences, a bathroom with laundry facilities, and finally the main suite with a large and luxurious private bathroom with travertine shower. On the first floor, a bright living room dominates the scene with its central truss and a fireplace that makes the atmosphere even more special. From here, you have access to two suites, both with private bathrooms and travertine showers. One of these suites features a freestanding bathtub with a panoramic view of the Villa's garden. Another suite, located on the garden floor with direct access to an exclusive patio, has been entirely carved out of the ancient mill's manger used as a horse rest stop and for grain storage, still visible in the suite's private bathroom. What makes this room even more special is its proximity to the mill room where the ancient millstones are still present. Located on the left side of the main building in one of the barns, another suite (the biggest annex) extends over two levels: on the ground floor there is a double bedroom with a bathroom and access to a front patio and a lateral loggia used as a dining area, while on the upper floor, there is a loft with two single beds overlooking the villa's pool. Formerly an ancient sawmill (the small barn annex), is located opposite the main body of the villa and overlooks the park directly through a paved patio. The dependance comprises a living room with a fireplace, a kitchen with a historical marble sink, and a double bedroom with an open shower. The pool is surrounded by lush vegetation, the scent of cypresses, the sound of the river nearby, and the Tuscan hills serve as a background, creating a magical and relaxing atmosphere. The verandas are located on the back part of the villa. These lodges are also accompanied by a round table around an ancient olive tree where a wood-fired oven and a relaxation area are situated. Finally, the riverside beach is a true oasis where you can reconcile with nature and let yourself be lulled by the sound of flowing water and the rustle of leaves that surround it. It can be accessed directly from the villa and features a relaxation area, dining table, and sun loungers.

What started over 500 years ago as a lookout post to defend the valley between Siena and Florence has been restored, with loving passion, into a private escape, idyllically situated amid woodland and vineyard in the heart of Tuscany's famed Chianti Classico region. Villa Fiamma offers every modern amenity discerning travellers require. From air conditioning and in-floor heating to meshed wi-fi and USB ports at bedside, every detail exudes luxurious comfort. A heated infinity pool with expansive pool deck and party pavilion and a full Roman Spa, inspired by the best European Spas, with indoor whirlpool for 10, a steam room, a sensory shower, and a dry sauna, welcome guests to relax and rejuvenate throughout their stay. Numerous Wellness Therapies can also be arranged. In the stone Farmhouse, the Villa’s original residence, a large living area with adjacent bar and expertly stocked cellar provide groups of friends or family an inviting space to gather and recount the day’s adventures in Tuscany. In addition, the cellar is stocked with exceptional vintage and prominent regional wines for purchase. The family kitchen, truly a chef’s dream, is ideal for preparing a breakfast of freshly laid eggs secured from the villa’s hens or meals with ingredients harvested from the villa’s culinary and herb gardens. There are six (6) bedrooms upstairs in the Farmhouse, each with en suite bath; two (2) with private balconies and one (1) with private entry. There is also a studio/office with en-suite on the lower level which can be converted to sleep two (2) additional guests. The Spa Suites, just across the center terrace from the Farmhouse, hosts two (2) spacious bedrooms at ground level, each with large en suite bath and one (1) offering a Manhattan-style kitchenette. The Spa Suites is also home to a separate catering kitchen as well as the Villa’s private spa on the lower level. In all, Villa Fiamma offers eight (8) en suite bedrooms sleeping up to 16 guests plus, a studio/office convertible to a ninth (9th) en suite bedroom sleeping up to two (2) additional guests. There are also two (2) half baths, one (1) in the Farmhouse, the other serving the spa and a separate, handicapped accessible full bath in the Spa Suites. At night, guests will be enveloped by silky soft Yves Delorme cotton sheets and have their choice of pillow types for the most blissful of nights' sleeps. And, French terry robes and slippers as well as sustainable bamboo towels and complimentary bath products make morning rituals another pampered experience. Guests will appreciate the unspoiled warmth and authenticity of Villa Fiamma's rejuvenation. Its meter thick stone walls, barrelled and beamed ceilings and terracotta tile floors were restored but left intact, immediately signifying to guests they have arrived to the real Tuscany. The furnishings, many of which were made by local craftsmen, are not only stylish but exceedingly comfortable, encouraging guests to unwind and feel at home. And, artwork by regional masters adorn nearly every wall and niche to capture guests' imaginations. Nearby Castellina in Chianti, just 12km from Villa Fiamma, offers perhaps the most quintessentially Tuscan walking district of any of the Chiantigiana wine road's storied towns, with its serpentine cobblestoned pathway meandering by art galleries, boutiques, bars and ristorante serving authentic regional fare. Greve, Panzano Gaiole and Radda in Chianti are also a short drive away. Available upon request: Gourmet chef Pizzaiolo (pizza master) Sommelier Butler DJ Personal shopper Nanny

This splendid and charming villa, situated in the heart of a 400-hectare organic farm on the rolling hills between Siena and Montalcino, brings together the charm of the countryside and the comfort of modern luxury for a thoroughly Tuscan experience. The estate is situated within a small, historic hamlet, which dates back approximately 1000 years, on an ancient Roman road between Monteroni D'Arbia and Buonconvento. It is a convenient drive to Buonconvento, a charming medieval town, the towns of Pienza and Siena, both named UNESCO World Heritage Sites, and Montalcino, renowned for its robust sangiovese wine. The villa is also a short distance to some of the best golf courses in the area: Castiglion del Bosco and La Bagnaia Resort. Within the villa, an elevator, air-conditioning in each bedroom, and Wi-Fi provide a superior level of comfort. A pool and gardens surround the principle building, which also includes a wooded area. The woods, which offer fresh air in the summer, are perfect for children where they can find a playhouse and swing-set. The property offers seven classically decorated bedrooms and six bathrooms, with an additional half-bath for guests and a restroom located along the pool; a grand entrance on the ground floor and an entrance on the first floor; and two large living rooms; all of this surrounded by the grand garden and pool. While taking a dip in the pool or enjoying an aperitif al fresco, guests will take in an extraordinary view of the Tuscan hillside that encircles the villa, submerging them in a refuge of blue and green colours.

Beautiful property, ideally located in Province of Siena for family or friends holidays. Villa Cresta can host up to 10 guests, thanks to its 5 bedrooms and 5 bathrooms. Housekeeping included. Our local team and a concierge will be at your disposal to help you organize your tailor made holiday. Please note that a security deposit will be requested for all our rentals. Le Collectionist

Nestled in the heart of the winemaking region of Chianti Classico, this fantastic property is a magnificent 15th Century villa built by the Machiavelli family, bearing the unmistakable touch of the Renaissance master, Michelangelo. Located just 12kms south of Florence, this villa is situated upon 600 acres of flourishing vineyards and olive groves. The private estate produces three award winning wines and a distinctive olive oil which guests can enjoy during their stay. The classic beauty of this villa combined with its history, art, and idyllic countryside setting create the perfect backdrop for an escape to Tuscany. Luxurious facilities complement the private villa, including an outdoor swimming pool, an indoor swimming pool, a spa with a full collection of spa services available, unique sculpture gardens, beautiful grounds to explore, and breathtaking views of the Duomo in Florence. A stay here also allows for easy exploration to Florence, San Gimignano, or the magnificent city of Siena. In the heart of Tuscany, this magnificent villa can host up to 22 guests and offers 10 individually designed bedrooms and suites. In addition, the villa offers ample living and lounge rooms and a beautiful loggia with views of Florence and the surrounding countryside. This world-class, historic villa allows guests to experience the modern-day luxuries seamlessly combined with the splendour of the Renaissance....

Villa I Cedri, only ten minutes from the enchanting city of Florence, is a Renaissance villa originally commissioned in the fifteenth century by the Marquess Niccolò Antinori. Its layout, centred around the paved courtyard, surrounded by formal gardens, and set in a productive agricultural landscape, is the typical design of aristocratic estates from this era. Nestled in the splendour of the Tuscan hills, this estate promises days of indulgence and romance in classical Renaissance style. The property, a dream villa, surrounded by luxury and hospitality, blends beautifully with its natural surroundings. The traditional cypress path leads up the hill to the villa and its spectacular gardens, with the charming pool and the outdoor seating area with a lovely gazebo. The delightfully fragrant roses, olive groves, cypresses, citrus trees, lavender, and a 200-year-old Lebanese cedar comprise this magnificent thirteen-acre traditional Tuscan park within which this phenomenal villa is immersed. While seemingly secluded, the villa is only 10 minutes from the marvellous city of Florence. Over the centuries, the villa has undergone numerous improvements and renovations that have transformed the villa into the extraordinary estate that it is today. The property features an elegant ballroom, a beautiful blue living room, a charming sitting room which faces the garden, a studio, and a formal and tastefully decorated dining room. The property can welcome up to twelve guests, featuring six elegant bedrooms with en-suite bathrooms. In addition, it offers a double bedroom for staff. All the rooms boast beautiful frescos. The subtle attention to details provides a sumptuous and luxurious atmosphere. This historic villa is a dream waiting to be realized: a Renaissance villa with all modern luxuries that overlooks the hills surrounding Florence. It is a luxurious Tuscan escape indeed.

Circled by the green forests of Chianti, Dream Estate is an exclusive retreat for those seeking peace of mind, tranquillity and privacy. The estate consists of beautiful gardens, olive groves, vineyards, and stunning centuries-old stone farmhouses. The Estate is made up of four main structures all lovingly restored by local craftsmen combining modern luxury with the rustic charm of Tuscan farmhouses: the Villa , an exquisitely renovated two-storey residence available for everyone at the Estate; the Fienile, spacious and airy one bedroom villa with fireplace and opulent bedroom suite; the Scuderia, secluded two bedroom villa with fireplace and private terrace; and the Colombaia, elegant and cozy one bedroom villa with private terrace. Dream Estate offers an abundance of wonderful experiences for every moment of the day. Contemplate Tuscany's timeless beauty from your private gazebo by the pool, feel healthy and enthralled after a match of tennis, beach volley or soccer; interact with the land, its people and history or just simply celebrate life in your own way. A playground and Jungle gym are also available for children. The estate is not only an exclusive Tuscan retreat but also a working farm. The organic wine, olive oil and honey production is carried out with the utmost care for quality and respect of the environment and the surrounding landscape. Guests are welcomed to visit the cellars, learn about wine, share experiences, and discover the true spirit of Tuscany. Dream Estate is your private retreat in the heart of Tuscany.

An Architectural Masterpiece is situated in the Ancaiano district near the historic city of Siena. Designed by the architect Carlo Fontana in the Roman Baroque style, the villa was built in 1680 for Pope Alexander VII. The grounds surrounding the villa are considered among the most exquisite gardens in Italy. The estate is ideally situated for sightseeing, shopping, eating out or just relaxing in the beautiful Tuscan landscape. It's just 14 kilometers from the cultural and artistic city of Siena, 15 kilometers from the famous hilltop town of Monteriggioni, 44 kilometers to breath-taking San Gimignano, while the Chianti region and Florence are an hour drive from the villa. Many fascinating local cultural excursions can be organised, such as local trekking, yoga courses, horse riding, mountain biking, wine tasting and town tours. Within the property, there is also ample entertainment, including a cinema room, exclusive use of the famous private garden, an outdoor, heated swimming pool, a tennis court, and a games room in the Limonaia, with table tennis and table football. The estate was a farmhouse built upon the ruins of a 9th century B.C. Etruscan settlement. This aristocratic property is decorated with elegance, in a traditional style honoring its heritage, but also with consideration to modern sensibilities. The villa features traditional Tuscan fireplaces, terracotta tiled floors, vaulted and beamed ceilings, beautifully frescoed walls, classical paintings, and renowned statues around the estate to greet its guests. The villa is developed over several floors. On the ground floor there is a loggia for dining, a bathroom, a fully-equipped kitchen, and a double bedroom with en-suite bathroom. On the first mezzanine floor we find a bathroom, a double bedroom with access to another double bedroom, and a shared bathroom. On the first and main floor we find one bathroom; three double bedrooms (the beds' dimensions are 185cm, 195cm large, and 145cm), two of which include en-suite bathrooms; a dining room; and a spacious and elegant living room with fireplace and direct access to the exterior kitchen. The second mezzanine floor provides one single bedroom, a bedroom for four children (the bed's dimensions are 80cm), and two bathrooms. On the second main floor we find two double bedrooms, with en-suite bathrooms, a double and a twin bedroom, which share a bathroom, and a twin bedroom, with a private bath. This historic and gorgeous estate, situated just five kilometers from the charming town of Sovicille, is the perfect space to host a large family, multiple families, or a large group of friends. It offers spacious and luxurious facilities in the heart of the gorgeous hills that surround Siena, allowing guests to enjoy privacy as well as each others' company. It is an exclusive paradise in Tuscany.