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Holiday rentals in Pestello

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Top-rated holiday rentals in Pestello

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Guest favourite
A shaded garden area features a hammock suspended from a tree and a round table with chairs, set against a backdrop of lush greenery and rolling hills. The panoramic view extends under a partly cloudy sky.
Home in Poggio San Marco
4.97 out of 5 average rating, 305 reviews

Charming converted Hayloft overlooking the Chianti Hills

Inspired by the rustic Tuscan style, this gorgeously refurbished hayloft features ceilings with exposed beams and bricks and thoughtful touches for a stylish and comfortable decor. From the relaxing hammock and the stone made barbecue in a panoramic garden to the cozy fireplace, every space feels open and inviting. Immersed in total peace and tranquillity with a breathtaking view over the Chianti hills, halfway between Florence, Arezzo and Siena, the barn is a perfect homebase to visit Tuscany. The accommodation has 2 floors. The upper floor spaces 2 double bedrooms with wonderful views of the olive trees and a bathroom with window and large masonry shower. On the ground floor a cozy and spacious living area with fireplace and a kitchenette with gas stove a large fridge and oven. The barn has ceilings with exposed beams and bricks. Outside there is a panoramic garden set on its own where, in the shade of a walnut trees, you can relax on a hammock or grill your meal (included an authentic local Fiorentina steak :-) on the stone made barbecue. A garden table is there for romantic dinners 'al fresco'. Immersed in total peace and tranquility halfway between Florence, Arezzo and Siena the barn is a perfect homebase to visit Tuscany. To find the exact location of the house type the following code in GMaps: 8FMHGG25+QV The house is in the countryside. The closest towns are Cavriglia and the small Medioeval villages of Moncioni and Montegonzi. In each town you can find great local restaurants and a small grocery shop. Moncioni is 3 km far away. A big supermarket is located in Montevarchi and you can reach it in 8 minutes by car ( exactly 7 km far away). In Montevarchi you can also find one of the best farmer markets in Tuscany! The station of Montevarchi is 8 km away from the barn. From there you can take train to Florence and Arezzo. Siena can be reached in 30 minutes by car. The easy access to the motorway A1/E35 Milan-Florence-Rome (the Valdarno exit is only at 13 km) allows you to reach numerous interesting spots within a short time, both in Tuscany and Umbria, while few kilometres south of Cavriglia you enter the suggestive territory of the Crete Senesi. Out in the countryside, the home offers an authentic experience of Tuscany. Small towns and villages are a short drive away providing acces to exceptional local restaurants and fantastic farmers markets. A big supermarket is located in Montevarchi (7 km far away). The railway station is 8 km away from the barn. From there you can take train to Florence and Arezzo. Cities of interest like Siena, Montepulciano, Pienza and Monteriggioni can be reached in 40 minutes by car The only way to reach the house is by car. A taxi service is active from Montevarchi You will be provided of blankets and towels. The kitchen is equipped with and kind of pots, pans, bowl, plates and silverware. You are welcome to use them. Free Netflix available

Top guest favourite
An outdoor patio area features rustic furnishings and is framed by gracefully draping curtains. The space is adorned with comfortable seating and a communal dining table, set against a backdrop of tall cypress trees and a clear blue sky, inviting relaxation in a serene environment.
Home in Simignano
4.97 out of 5 average rating, 194 reviews

Casa al Gianni - The Simignano Barn

Converted from an old barn, this luxurious retreat offers 5 bedrooms, 4 bathrooms, a large, fully equipped kitchen, a spacious living room, and a large private garden with parking, a hot tub, a patio with sofas, a BBQ, a fire pit, and an outdoor kitchen. Ideal for those looking for a unique experience, it combines rustic charm with modern comforts. Perfect for families or groups, it promises magical evenings under the stars, with relaxation in the hot tub and al fresco dinners. A memorable getaway awaits you in this little slice of paradise!

Top guest favourite
Home in Greve in Chianti
4.99 out of 5 average rating, 113 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.

Top guest favourite
The entrance of Villa Piandarca is framed by lush greenery and decorative pots. A rustic wooden door stands partially open, revealing a white curtain gently flowing in the breeze. The building's warm yellow exterior adds to the inviting atmosphere of the property.
Home in Terranuova Bracciolini
4.98 out of 5 average rating, 57 reviews

Villa Piandarca - Tuscany - WIFI - private pool

The Villa Piandarca is, situated in a panoramic place, immersed among the vineyards of the Tuscan countryside, and in a strategic position between Firenze, Siena and Arezzo. It consists of two apartments with separate entrance from the garden. The villa has a total capacity for 10 people and each apartment has a kitchenette with dish washer and air-conditioning in all rooms, wifi and veranda. The villa has also large outdoor areas and a beautiful salt water swimming pool where guests can relax.

Top guest favourite
The charming farmhouse features a warm yellow exterior and traditional terracotta roof. Tall cypress trees and verdant olive trees surround the property, which sits among rolling hills. A covered patio extends from the house, providing outdoor seating space with a view of the scenic landscape.
Farm stay in Bucine
4.91 out of 5 average rating, 88 reviews

Feriale I. Petrolo Winery. Pool, wi-fi, vineyards

Charming farmhouse of the Petrolo winery in the heart of Tuscany. 5 bedrooms and 4 bathrooms, for 10 guest +2 on sofa bed. Panoramic views over the Valdarno valley, next to Chianti Classico. The house is placed among vineyards and olive trees with the medieval watchtower of Galatrona nearby. The house has wi-fi, private garden with bbq and easy access to the swimming pool shared with 2 of our houses. To access the house climb 20 steps to the first floor, landing on a cute panoramic terrace.

Top guest favourite
The exterior of a charming villa is surrounded by lush greenery, with vines climbing along the walls. A gravel pathway leads to the entrance, framed by well-kept gardens. Sunlight filters through the trees, creating a peaceful atmosphere ideal for relaxation and outdoor gatherings.
Villa in Pergine Valdarno
4.96 out of 5 average rating, 101 reviews

La Vignaccia (Farmhouse) - villa w/private pool

Nestled amidst the rolling hills of Tuscany, La Vignaccia beckons you to experience the true essence of Italian living. This enchanting villa, set within a sprawling estate, offers a haven of tranquility, where you can unwind and immerse yourself in the beauty of the Tuscan countryside. A secluded garden awaits, providing a serene setting for relaxation and alfresco dining. Take a refreshing dip in the sparkling pool, surrounded by breathtaking views of the Tuscan landscape.

Top guest favourite
Farm stay in Greve in Chianti
4.99 out of 5 average rating, 510 reviews

Farmhouse in Chianti with Swimming Pool

Agriturismo Il Colle is located on one of the Chianti hills. The structure 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 The apartment is located on the ground floor of the main farmhouse, with independent access and private space. The care taken in the restoration and furnishing make the house particularly welcoming, respecting the rural style.

Guest favourite
Home in Pogi
5.0 out of 5 average rating, 10 reviews

Private Cottage with Plunge Pool in Tuscan Estate

A private cottage with garden and plunge pool, set within Borgo Iesolana Estate. Perfect for up to 6 guests, yet equally special for couples. Enjoy total privacy, a fully fenced garden (ideal for dogs), stunning views and an exclusive plunge pool — with breakfast included and full access to the Borgo’s pools, restaurant and bar just a short walk away. Private parking, Wi-Fi, TV, air conditioning, heating and a fully equipped kitchen complete the experience.

Guest favourite
A spacious bedroom features a comfortable bed, with natural light flowing in through a window that offers a glimpse of the surrounding greenery. Soft linens and a minimalist decor contribute to a serene and relaxing environment.
Cottage in Massa Sabbioni
4.95 out of 5 average rating, 57 reviews

Private Country House with swimming pool -Chianti

In the heart of Tuscany, at the gateway to Chianti Classico, Amoliv is a private retreat with 5 bedrooms, each featuring en-suite bathrooms and separate entrances. A professional kitchen and living room open onto a panoramic terrace with stunning views of Valdarno and Pratomagno. Surrounded by olive groves and woodlands, the property offers a private pool and BBQ area, ideal for families and groups seeking Tuscany's beauty.

Superhost
A modern studio space features a comfortable sleeping area with a spacious bed, harmoniously positioned next to a flat-screen television. A round dining table surrounded by four chairs occupies one corner, while a compact kitchen with essential appliances is visible on the left side of the image.
Flat in Montevarchi
4.8 out of 5 average rating, 122 reviews

La Casina in the Center

Modern, centrally-located studio apartment. 5 minutes from Montevarchi-Terranuova station. Ideal for reaching Florence, Arezzo, Siena, and Chianti. Distances: FLORENCE - 35 min by train / 40 min by car SIENA - 55 min by car AREZZO - 25 min by train / 30 min by car RADDA IN CHIANTI - 31 min by car GAIOLE IN CHIANTI - 27 min by car

Guest favourite
Home in Moncioni
4.9 out of 5 average rating, 30 reviews

Private Tuscan hilltop farmhouse with pool

On a secluded hilltop near picturesque Moncioni this 1700's farmhouse offers all charms of Tuscany with the twist of designer, timeless contemporary interiors, air conditioning ❄️, panoramic pool treehouse and separate renovated barn. The house has been featured in many interior magazines.

Top guest favourite
Home in Terranuova Bracciolini
4.97 out of 5 average rating, 159 reviews

Villa Lolù with private heated swimming-pool

Charming villa with private heated pool, and outdoor hot tub. Very large 175 sqm house with kitchen, dining room, living room with fireplace, 3 double bedrooms, 1 bedroom with 2 single beds, 1 double sofa bed, 3 bathrooms, one of which is en suite. Starting this year, there is also a gym

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