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Holiday houses in Pergine Valdarno

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Top-rated holiday rentals in Pergine Valdarno

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top Guest favourite
A rustic building is seen under a starry night sky, with a partial roof providing shelter. Soft light glows from the interior, illuminating the entrance. Lush greenery and trees surround the scene, adding depth to the serene nighttime landscape.
Farm stay in Simignano
4.93 out of 5 average rating, 292 reviews

Casa al Gianni - Hut

Hi, we’re Cristina and Carmelo! We look forward to welcoming you to ‘Casa al Gianni’, our farm stay in the woods of the Montagnola Senese, just 20 minutes from Siena. Here, life slows down: just the scent of the earth, the song of the birds and the companionship of our animals. It’s an invitation to rediscover the beauty of the little things, surrounded by the greenery of the most authentic Tuscany. It’s not just a holiday; it’s a return to our roots. This haven of peace will stay with you in your heart. We look forward to welcoming you!

Guest favourite
A sunny dining area is presented with a wooden table at the center, accompanied by a cozy sofa adorned with blue and yellow cushions. Fresh flowers are arranged in a vase on the table. Large doors allow natural light to fill the space, complemented by wooden beams on the ceiling.
Apartment in Pergine Valdarno
4.82 out of 5 average rating, 116 reviews

Detached cottage with pool

Independent apartment surrounded by the greenery of the Tuscan countryside near Pergine Valdarno, in the hills of Chianti Aretino, among olive groves and vineyards, in the middle of the triangle formed by Arezzo, Siena and Florence, on the left bank of the Arno River. Large panoramic swimming pool and fully fenced park shared with two other apartments. Enchanting panoramic location, maximum tranquility, privacy and relaxation. It is possible to have a guide for trekking bikes for interesting routes upon request.

Top Guest favourite
A charming outdoor dining area features a round table set with delicate dishware and a pink tablecloth. Surrounding the table are intricately designed white chairs. A gazebo provides shade, and lush greenery is visible in the background, creating a serene setting for leisurely meals.
Farm stay in Ruscello
4.99 out of 5 average rating, 531 reviews

Farmhouse Fattoria La Parita

Provencal-style apartment nestled between vineyards and olive trees. You will enjoy the tranquility of the countryside 10 km from the city and 4 km from the highway. The song of jays and cuckoos will be the soundtrack to the stay while the roe deer graze among the olive trees. A basic Italian breakfast is included (coffee, tea, milk, biscuits, etc.), but if you prefer a richer breakfast served at the table, the cost is €15 per person (€10 from 5 to 15 years, free under 5 years). EV wallbox available.

Top Guest favourite
A spacious piazza is surrounded by elegant medieval architecture, featuring a central hexagonal area with open-air seating. Stone pathways lead to various shaded spots, while umbrellas provide shelter for patrons. Beautiful clouds drift overhead, enhancing the vibrant scene of daily life in the historical center.
Apartment in Arezzo
5.0 out of 5 average rating, 155 reviews

Piazza Grande Boutique Apartment

Overlooking the most beautiful square in the historic center of Arezzo, where the re-enactment of the Giostra del Saracino takes place, the Piazza Grande Boutique Apartment is located on the second floor of a medieval building, overlooking the beautiful palaces and the Vasari Loggias and is a unique location of its kind. The decor, the work of Countess Cesaroni Venanzi, was created with beautiful antique furniture reinterpreted in a modern way and enriched with contemporary influences.

Guest favourite
The exterior of the stone building is captured in warm evening light, showcasing its rustic charm. A small seating area is visible, with potted plants enhancing the welcoming atmosphere. The surrounding village ambiance and nearby structures add to the quaint setting.
Home in Pergine Valdarno
4.94 out of 5 average rating, 50 reviews

CASA DI VIGNOLO - Medieval Tuscan House

CASA DI VIGNOLO is a beautiful centuries' old building that will enchant you with its local traditional features: the original authentic fireplace, or the original stone sink, or the stone and bricks staircase... you will be captured by the fusion of antique and modern style and mostly you will fall in love with the atmosphere of this small Tuscan village. Non touristic, Pergine Valdarno, will show you the normal everyday life of a small Tuscan town. You will soon feel part of it!

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, 102 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.

Superhost
A charming stone house is shown surrounded by greenery, highlighting its rustic architecture. The warm sunlight illuminates the exterior, revealing wooden shutters and a small covered porch. A well-maintained garden area features potted plants and tidy paths, creating an inviting outdoor space.
Home in Pergine Valdarno
4.89 out of 5 average rating, 37 reviews

Loggetta: farmhouse with garden and pool

Splendid two-storey house in the ancient village of Montozzi Castle, Loggetta has been restored in the rustic Tuscan style, with wooden ceilings and terracotta floors. It consists of a living room, dining area, kitchen, two double bedrooms and two bathrooms. Heating excluded: cost according to consumption. The house has its own private garden with barbecue, table, chairs and a splendid view over the Valdambra. Access to the village's shared swimming pool. DOGS ARE WELCOME!

Top Guest favourite
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, 107 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 favourite
An outdoor dining area is presented on a spacious terrace, featuring a large table set with plates and glasses. A bottle of sparkling wine and a bowl of grapes are positioned at the center. Lush greenery and distant mountains are visible in the background.
Villa in Pergine Valdarno
4.83 out of 5 average rating, 23 reviews

​Private Pool Villa | A/C & Panoramic Views

Welcome to Villa Chiara – Your Countryside Escape ​Spacious 210 sqm villa, built almost on one level. ​Living & Dining: Large living room with fireplace + dining area. ​Cozy Nooks: Studio + den with a second fireplace. ​Bedrooms & Baths: 3 doubles, 2 singles, and 3 full bathrooms. ​Kitchen: Large & fully equipped. ​Outdoors: Private pool and a west-facing covered terrace with sweeping sunset views—ideal for alfresco dining under the stars.

Guest favourite
Home in Pergine Valdarno
4.94 out of 5 average rating, 35 reviews

Apartment in a villa with a jacuzzi and gym

Experience an unforgettable stay in the heart of the Tuscan hills! This elegant and cozy apartment is located in a villa surrounded by greenery, ideal for those looking for tranquility, privacy and comfort. The apartment combines Tuscan style with modern elegance, offering well-kept and bright environments. Outside you can relax in the garden, dine under the stars or immerse yourself in the Jacuzzi surrounded only by the sounds of nature.

Guest favourite
A sparkling swimming pool is surrounded by sun loungers and umbrellas, offering a relaxing space for guests. The rustic farmhouse, with its stone exterior, is visible in the background, amidst lush greenery and trees under a partly cloudy sky.
Holiday home in Castelnuovo Berardenga
4.91 out of 5 average rating, 100 reviews

PIERFANTINI private Chianti house ♿️ 🏊‍♂️ 🐶

Pierfantini is a rustic farmhouse. It is located on a hill in the middle of a natural park. Isolated from the vitta, the nearest town is the medieval village of San Gusmè. The house is renovated and the ground floor adapted for disabled people or wheelchair users There are three apartments but I never rent them separately. The house rent is for all the property

Guest favourite
Villa in Arezzo
5.0 out of 5 average rating, 67 reviews

Coaching House

The Villa is situated in an ancient country building located in Arezzo, twenty minutes walk from the historic center and surrounded by shops, supermarkets, restaurants within a few minutes walk. By car you reach the downtown and the treain station in about 10 minutes; moreover, the structure is close to places of interest such as the Equestrian Centre.

Popular amenities for Pergine Valdarno holiday rentals