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Vacation rentals in San Polo in Chianti

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Top-rated vacation rentals in San Polo in Chianti

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Top guest favorite
Home in Greve in Chianti
4.99 out of 5 average rating, 111 reviews

Relaxation and charm in the Chianti hills

Beautiful stone farmhouse, detached, surrounded by olive trees and the Chianti hills, with private garden and panoramic swimming pool. Ground floor with large living rooms, antique fireplace and wood-burning oven, bright living room and fully equipped kitchen. On the first floor, three suites consisting of a bedroom, study and private bathroom. Access via gate and white road on private property just 500 meters from the village of Strada in Chianti. Ideal for peace and relaxation. Convenient location for visiting Tuscany.

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Townhouse in Scandicci
4.88 out of 5 average rating, 338 reviews

Florence Sunset Hills • Giogoli

Escape to the peaceful hills of Giogoli where authentic Tuscan charm meets breathtaking views of Florence.Just 15 minutes from the city center and the Chianti countryside, this elegant home is the perfect base for exploring Tuscany while enjoying quiet mornings, unforgettable sunsets, and the beauty of the surrounding landscape. Surrounded by nature but close to the region's most iconic spots, it's the ideal retreat for anyone looking for comfort, tranquility, and a genuinely Tuscan experience

Top guest favorite
A dining area features a dark wooden table with black chairs, adorned with a floral centerpiece. Light-colored stone walls and wooden beams create a rustic charm. A blue sofa with floral cushions is positioned against a large window, allowing natural light to fill the space.
Cottage in Quarate
4.92 out of 5 average rating, 158 reviews

FAETOLE typical Tuscan country house near FLORENCE

My cottage is hidden in Tuscan countryside among olive groves, vineyards and woodland. Nevertheless, downtown Florence is only 16km away! While away, spend your time by relaxing in the garden, where you will find a barbecue and an outdoor shower to cool down while sunbathing. Discover the beauty of surrounding countryside with a hike and unwind with a view of picture-perfect vineyards! One can also easily go for day trips to many tiny medieval towns scattered on the hills of Tuscany from here!

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A rustic wooden door with intricate carvings is the focal point of the entrance. A wicker basket and a decorative arrangement of dried plants are positioned nearby, adding a touch of warmth to the inviting space. Natural light filters in from a high window.
Condo in San Polo in Chianti
4.9 out of 5 average rating, 111 reviews

Il Conventino Amazing 19th Cent. Tuscan Farmhouse

Amazing 19th cent. tuscan farmhouse in the Chianti Classico Area. Private house with a separate access and a living area with kitchen, dining table and one sofa bed. One tuscan style master bedroom with cozy atmosphere and a large wardrobe. Fully equipment kitchenette with fridge, stove and coffee machine. Private bathroom with shower. A cozy private terrace & garden with dining table and stone bbq are available. The large and quiet garden of the main villa surrounds the house.

Top guest favorite
A large swimming pool surrounded by a brick patio and manicured lawns is highlighted in this image. Sun loungers are positioned along the pool's edge, with lush greenery and trees creating a serene backdrop. The villa's charming structure is visible in the distance under a partly cloudy sky.
Villa in Barberino Tavarnelle
4.98 out of 5 average rating, 104 reviews

Podere Tignano, 4-bedroom villa in the Chianti!

Nestled among the rolling hills of Chianti between Florence and Siena, Podere Tignano offers breathtaking views over vineyards, olive groves, and golden grain fields. This charming Tuscan stone villa blends authentic rural character with modern comfort and welcomes up to 8 guests in 4 bedrooms. Surrounded by peaceful countryside and featuring a private swimming pool, it is the perfect retreat for those seeking relaxation, nature, and the true spirit of Tuscany.

Guest favorite
A tranquil outdoor pool area is enclosed by greenery, featuring sun loungers and umbrellas. Clear blue water reflects the surrounding hills under a sunny sky. A rustic shower stands to one side, inviting guests to refresh after enjoying the scenic landscape.
Home in Bagno A Ripoli
5.0 out of 5 average rating, 8 reviews

Casa Spiano

14 km from Florence, Casamaggio is the ideal place to also enjoy the natural beauty of the Florentine countryside. Located at the end of the village of San Donato in Collina, where essential services are also available on foot, it is ideal for those who want to visit Florence with local transport/buses. Casamaggio is a characteristic rural building, which directly overlooks the olive grove, and whose terrace facing east enjoys a panoramic view of the Valdarno.

Top guest favorite
A spacious outdoor area features a swimming pool surrounded by lush green lawns and dotted with comfortable sun loungers. Umbrellas provide shade, and the serene landscape is framed by tall trees and gentle hills in the background.
Farm stay in Greve in Chianti
4.99 out of 5 average rating, 429 reviews

Typical Tuscan country house

Agriturismo Il Colle is located on one of the Chianti hills. The property has been completely renovated, dominates the Chianti valleys and enjoys a splendid view of the surrounding hills and the city of Florence just 35 minutes by car This apartment is one level, totally independent with private garden. Restored and furnished with great care to make the guest's stay as comfortable and relaxing as possible, in the full respect of the Tuscan rural style.

Top guest favorite
The historic tower-penthouse villa is surrounded by lush greenery and trees. The three-story structure is characterized by its earthy facade and wooden shutters. Well-maintained gardens with various plants create a serene outdoor environment, enhancing the villa's tranquil charm and historical significance.
Castle in Bagno A Ripoli
4.96 out of 5 average rating, 138 reviews

Tower Penthouse in small castle near Florence

900 year old Tower-Penthouse apartment in Chianti Villa, spacious & super-scenic historical home that combines magical atmosphere with space, light, history, convenience. (AC throughout). Painting-like 360° views of Tuscan Hills all the way to Florence; sun-filled, private grounds. Perfect location for an unforgettable family stay. Ample private property (including forest). Walking distance from village shops. Convenient location, Florence in sight.

Guest favorite
A serene pool area is highlighted by lounge chairs set along a stone terrace. The water reflects a golden sunset, providing a tranquil atmosphere. Surrounding greenery adds to the natural beauty, creating a peaceful environment for relaxation.
Apartment in La Presura
4.86 out of 5 average rating, 274 reviews

Countryhouse 9 kms to Florence-3+2,free park, wine

We are a Farmhouse at only 9 km from Florence in the beautiful Chianti hills with gorgeous pool and free private parking We are a small organic farm producing our own wine Chianti Classico and extra virgen olive oil Only 1 hour driving to the most important city of Tuscany such as Pisa, Siena, San Gimignano, Pienza, Monteriggioni, Lucca and Arezzo. Public transportation to Florence and Greve in Chianti (bus stop at only 200 mt from us)

Top guest favorite
The image showcases a rustic stone farmhouse surrounded by lush vineyards and olive trees. The building features a classic roof with terracotta tiles, set against a clear blue sky. Green grass frames the scene, emphasizing the natural beauty of the countryside.
Villa in Impruneta
4.99 out of 5 average rating, 120 reviews

Agriturismo Podere Scaluccia Chianti, Florence

The farmhouse is located 15 minutes (8 km) from the center of Florence, a city rich in art and culture, and is surrounded by beautiful panoramic views of the hills, at the entrance to Chianti. The house is old: traditional materials such as stone, wood and terracotta are the main features. The outdoor garden is available to everyone! To learn more, search for Podere Scaluccia

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A spacious living area features a modern design, with a prominent stone fireplace and minimalist furniture. Large glass doors open to a serene outdoor view, while natural light brightens the room, highlighting the soft tones of the walls and furnishings.
Tower in Fiesole
4.95 out of 5 average rating, 219 reviews

A Big Dream in a Little Tower.

The Tower was created in the late 1800s by an illustrious Englishman, Sir John Temple Leader, in one of the oldest and most important stone quarries belonging to the Medici family. From the same quarry were extracted many important works such as the columns of the Medici chapels, the steps of the Laurenziana library .. all just 5 km from the historic center of Florence.

Top guest favorite
The exterior view features a rustic stone house surrounded by greenery, including trees and flowering plants. Sun loungers are positioned on the lawn, creating a space for relaxation. A spacious terrace extends from the house, providing access to the inviting garden area.
Home in Bagno A Ripoli
4.99 out of 5 average rating, 184 reviews

Tuscany .Countryhouse on the Florence's hills

Recently renovated house in 19th century Tuscan farmhouse surrounded by hills, vineyards and olive groves located in the Chianti area and 1 km from the village (Antella) and 20 minutes by car from Florence center. The property is equipped with cooling for the summer months, although the very thick stone walls ensure a pleasant temperature even in summer.

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