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Villa holiday rentals in Gaiole in Chianti

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Top-rated villa rentals in Gaiole in Chianti

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Top guest favourite
A spacious kitchen showcases a large stone fireplace with a wooden mantle as its centerpiece. Light streams through the window, illuminating the wooden beams overhead. A dining table is set for a meal, while traditional utensils adorn the walls, enhancing the inviting ambiance.
Villa
4.94 out of 5 average rating, 249 reviews

Manor House - IlVillinoFarmhouse

Entire upper floor of the newly renovated Manor House in traditional Tuscan style. High ceilings with exposed beams make the place cozy and perfect for families or groups of friends. In the house, there are two large functional fireplaces (in the living room and kitchen). Private, non-shared accommodation. The house has a large covered terrace, garden with sofas, BBQ, fire pit, private parking. The swimming pool among the olive trees and vineyards is ideal for relaxation and has private access to the shared area

Top guest favourite
Villa
4.97 out of 5 average rating, 125 reviews

Villa with View for Family & Friends, in Tuscany

Huge and charming top floor apt in Tuscan Villa with breathtaking view! Visit Montepulciano, Pienza, Siena, explore country side, vineyards and hot springs, hiking or e-biking, strolling or driving! Two roomy suites with top quality beds and bathroom ensuite. Windows walled living room, comfy sofas, professional kitchen at your own use. We can set Winery visits & tasting, Cooking classes and private dinners. NEW Hot tub facing green hilltop! ExperienceTuscany as a local, with your local Host!

Top guest favourite
The villa's exterior is highlighted by a modern structure with large glass doors and a gently sloping roof. It is surrounded by lush greenery and features a patio area with steps leading to the entrance. Soft lighting illuminates the garden, creating a serene evening ambiance.
Villa
4.93 out of 5 average rating, 311 reviews

Amazing Tuscany Villa, FREE parking

Modern villa with panoramic view in Montepulciano, a few steps from San Biagio. The villa is lovingly furnished and equipped with all comforts for a pleasant holiday. Enjoy breathtaking views of the surrounding countryside from the terrace, or relax in the two spacious gardens at your disposal. You will also have at your disposal a large kitchen to dabble in the magnificent art of cooking, something much loved by us Italians!!! Also available: Free Wi-fi Self check-in Reserved car parking

Top guest favourite
A shaded terrace is presented with multiple wooden loungers arranged around a sleek pool. Lush greenery surrounds the space, offering a natural backdrop, while a stone building stands quietly in the distance under a clear sky.
Villa
5 out of 5 average rating, 27 reviews

Casa Faraona, villa with private pool

Imagine the perfect Chianti villa – a secluded house with private pool and fabulous 180-degree views. That’s just what you’ll experience at Casa Faraona.

Set down a lane a few meters away from the "Eroica" road and between the wine towns of Radda and Gaiole, this three-bedroom villa is bound to take your breath away at first sight. Typical Tuscan features include terracotta tiles on the floors and beamed ceilings, while soft pastels and stylish furnishings give a light and modern aspect.

Top guest favourite
A historic tower rises prominently against a blue sky dotted with fluffy clouds. Surrounding greenery complements the stone structure, with trees and small buildings visible along the hillside, collectively conveying a sense of tranquility.
Villa
4.99 out of 5 average rating, 135 reviews

Belforti Tower

Torre dei Belforti is the perfect place for people who love beauty, nature and art. Sleeping at the Tower is like traveling trough the time, between knights and princesses. The wonder of this place is enriched by a big garden, with its swimming pool, the cypresses alleys and the olive trees. The village is also a magic place well preserved and still alive. We are Emilia and Luca, we live here and our mission is to give the best to our guests, to fully enjoy this marvelous place.

Top guest favourite
Bright seating area features two white armchairs and a patterned ottoman, surrounded by large glass arches that open to a lush garden. Natural light floods the space, enhancing the exposed stone walls and wooden ceiling beams, complemented by a large potted plant.
Villa
4.97 out of 5 average rating, 118 reviews

Luxury Villa in the very heart of Chianti

The views, the views, oh my word the VIEWS! Originating in the early 12th century this spectacular home once served as the bakery for the entire village. Now fully renovated, the entrance and ground level have been opened with glass arches allowing natural light to illuminate the exposed walls, 4 large bedrooms, 3 with ensuite baths ( including a jacuzzi ). Only Minutes away from the famous Wineries of Chianti, this is THE Spot for a glass amongst friends.

Top guest favourite
An inviting villa surrounded by lush greenery and vibrant flowers, featuring blooming rose bushes and olive trees. The gravel pathway leads to the entrance, showcasing a two-story structure with balconies. Sunlight highlights the colorful landscape, creating a serene atmosphere.
Villa
5 out of 5 average rating, 178 reviews

The Tower

Ancient Tuscan villa, beautiful, with exclusive private garden, completely renovated, surrounded by the beautiful and gentle Tuscan hills. The villa has a breathtaking view, is very sunny, well furnished and equipped with all amenities, quiet and not isolated. The house is located in Bagnolo, a small hamlet of Impruneta at the gates of Chianti, an area of olive groves, vineyards and peace. The house is about 10 km by car from the center of Florence.

Top guest favourite
A well-maintained garden surrounds a refreshing pool, bordered by manicured grass. A comfortable seating area, featuring two lounger chairs and a shaded umbrella, provides a serene spot for relaxation. Soft greenery and flowering shrubs form a natural backdrop, enhancing the tranquil atmosphere.
Villa
4.96 out of 5 average rating, 200 reviews

Villa Isabella

Villa Isabella is a comfortable Tuscan style villa located in the splendid Chianti hills in Tuscany with a large garden and a spectacular breathtaking panoramic swimming pool for exclusive use where you can experience the Tuscan tradition in full local style with the possibility of organizing private shuttles service for reach the property traditional experiences, services and tours only and exclusively for our guests.

Top guest favourite
Villa
4.98 out of 5 average rating, 140 reviews

Farmhouse on Florence hill

Two levels 800th rustic country house, on the hills surrounding the town with original forniture and a stunning view of the facing valley, a beautiful patio and large garden. 15 min driving from center, well placed for Chianti area, Siena, San Gimignano. 1hr driving to Pisa, Lucca, Volterra, Arezzo, Cortona and much more! Possible to have cooking class or dinners with my personal chefs Mirella and Stefano!

Top guest favourite
Villa
4.95 out of 5 average rating, 165 reviews

"Villa Daisy" overlooking Siena

Wonderful villa with independent entrance inside the "Caggiolo" farm, brought to light with careful and thorough renovation that has kept intact the typical features of a Tuscan farm. Beautiful panoramic view of Siena. Located in Ville di Corsano, just 14 km from the city. An ideal place to spend days in total relaxation and enjoy the wonders that this area offers (Chianti, Val d'Orcia, Crete Senesi etc).

Guest favourite
A stone bungalow is viewed from the poolside, featuring a private pool surrounded by sun loungers and an umbrella. The terrace, equipped with a dining table and chairs, shows lush greenery and elegant flowers in window boxes.
Villa
5 out of 5 average rating, 9 reviews

La Casa di Radda

La Casa di Radda is a welcoming holiday home in the Chianti Classico region, notable for its proximity to the charming village of Radda. Just a short walk separates the house from the delightful restaurants, cafés, and small shops in the town center. It is ideal for a family vacation or a getaway with friends, offering the perfect setting for relaxing days in a rural environment.

Guest favourite
The crystal-clear swimming pool reflects the blue sky, bordered by a well-kept garden. In the background, a stone farmhouse features green shutters and a classic tiled roof. The pool area is complemented by shaded seating, offering a serene and private atmosphere.
Villa
4.92 out of 5 average rating, 83 reviews

Podere il Trebbio

Farmhouse with private equipped pool. Located 1 km from the village, in an optimal position, the farmhouse is divided into two large apartments, there are no shared spaces, except for the patio where there is the entrance to the 'other apartment The parking, pool, relaxation area and garden are for exclusive use.

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