Holiday houses in Matassino

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Top-rated holiday rentals in Matassino

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Top Guest favourite

Home in Greve in Chianti

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.

ValueLocationCheck-in

4.99 out of 5 average rating, 113 reviews

Guest favourite

Townhouse in Scandicci

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

ValueLocationOutdoor spaces

4.88 out of 5 average rating, 338 reviews

Top Guest favourite

The rustic farmhouse is set against a clear blue sky, featuring a textured stone façade with wooden window shutters. A gravel courtyard is visible, adorned with potted plants and outdoor seating, offering a welcoming entrance to the tranquil countryside surroundings.

Farm stay in Reggello

Stone farmhouse, exclusive private pool

Podere Montebono is located in the hills of Reggello, just 30 km from Florence. Ideal for getting to cities of art and natural sites. The farmhouse is secluded on a hill, immersed in nature, surrounded by olive trees, a garden and woods. The guest house is a separate wing of the large two-storey farmhouse: 3 bedrooms, kitchen, living room, bathroom. The private pool is exclusively for those who rent the house (max 4 people). We do not rent single rooms. Barbecue area. Total privacy.

LocationValueBreakfast

4.96 out of 5 average rating, 193 reviews

Top Guest favourite

A dining table is set on a balcony, featuring decorative plates, a coffee pot, and colorful mugs. Potted plants adorn the railing, complemented by a view of the lush countryside and distant hills under a clear sky.

Apartment in Montalpero

[Tuscany Home] Garden Retreat w/ Parking & BBQ

Enchanting apartment in the heart of the Tuscan countryside, strategically located between Chianti, Florence and Arezzo. ✔ Up to 6 guests ✔ Welcome Book with professional tips and recommendations ✔ Private parking on site ✔ Just 5 min by car to Figline Valdarno train station · 35 min to Florence ✔ 2 double bedrooms + 1 bedroom with bunk beds · Spacious living room ✔ 50" UltraHD 4K Smart TV, fast Wi-Fi, air conditioning and heating ✔ Brick barbecue for unforgettable outdoor meals

ValueLocationTV

4.97 out of 5 average rating, 119 reviews

Top Guest favourite

An open window reveals a captivating view of Piazza Marsilio Ficino, featuring historic buildings and a clock tower. The square is lined with parked cars and inviting outdoor seating, creating a vibrant atmosphere in the heart of Figline Valdarno.

Condo in Figline Valdarno

[Beatrice's Dream] Luxury & Design Penthouse 5*

Charming Luxury and Design Penthouse located in the Heart of Figline Valdarno with stunning views of the Square. ✔ Suitable for hosting up to 4 PEOPLE ✔ 5 minutes walk from Figline Valdarno station and 30 minutes drive from Florence ✔ Professional Welcome Book with recommendations on restaurants and places to visit ✔ 2 double beds, 2 bathrooms, Jacuzzi ✔ Cinema Room with Smart TV 4K 55", Fiber Wifi ✔ Underfloor heating on the ground floor, air conditioning system with Fan Coil

ValueFamilyKitchen

4.98 out of 5 average rating, 88 reviews

Top Guest favourite

The exterior of the castle is showcased at sunset, with vibrant orange and purple skies providing a dramatic backdrop. Stone towers rise from the landscape, surrounded by greenery and colorful flora, reflecting the historic charm of the property.

Castle in Ferrano

The Castle of Ferrano - Castle in Tuscany

Try the experience of staying in a real Castle! Il Castello di Ferrano offers to its hosts the chance of living an unforgettable experience: you will be the only guests in the castle, and everything will be for you (private pool from June to September, gardens etc..). Historical building, surrounded by nature, finely decorated, frescoes/moulding on the ceiling, ample terrace w/ stone and terracotta floor, private outdoor pool.. Good position. Preferably come by car.

FamilyValueHiking

4.99 out of 5 average rating, 226 reviews

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

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.

FamilyValueBackyard

4.98 out of 5 average rating, 105 reviews

Top Guest favourite

Farm stay in Greve in Chianti

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.

FamilyValueBarbecue

4.99 out of 5 average rating, 510 reviews

Top Guest favourite

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

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.

LocationFamilyIndoor spaces

4.96 out of 5 average rating, 138 reviews

Top Guest favourite

The kitchen features modern appliances, including a coffee machine and refrigerator. A wooden countertop separates the cooking area from two white bar stools. Light wood floors enhance the spacious feel, while decorative wall tiles add a subtle touch of elegance.

Apartment in Figline Valdarno

[Harmony Home] Cozy and Comfort Retreat

Charming apartment in the heart of Figline Valdarno, in a strategic location between Chianti, Florence, and Arezzo. ✔ Accommodates up to 4 GUESTS ✔ Professional Welcome Book with tips on restaurants and places to visit ✔ 5-minute walk from Figline Valdarno train station and 30-minute drive from Florence ✔ 2 Double bedrooms with dedicated workspaces ✔ 1 Full bathroom and 1 half bathroom ✔ Smart TV, Fiber Wi-Fi, A/C heating & cooling, washing machine

LocationFamilyLaundry

4.98 out of 5 average rating, 81 reviews

Guest favourite

Farm stay in Castelfranco di sopra

Romantic apartment in the Tuscan village

The house is located in an ancient medieval village that has been completely renovated while maintaining the charm of its history. In the village you will find two swimming pools, a restaurant, many gardens and much more... It is in a strategic position to be able to reach the main attractions such as the Chianti Region, Florence, Arezzo and Siena!

FamilyValueTV

4.89 out of 5 average rating, 339 reviews

Top Guest favourite

The exterior of a rustic yellow barn is displayed, featuring a large wooden door and a balcony above with decorative lattice work. Surrounding greenery and a gravel pathway enhance the natural setting.

Barn in Ontaneto

Typical Renovated Barn

Stay in an authentic late 19th-century Tuscan barn, completely renovated in 2022, where the charm of tradition meets modern comfort. We have created a cosy 35 sqm loft, perfect for couples looking for romance, families with a child and international tourists who want to experience the real Tuscany.

LocationValueGetting around

4.9 out of 5 average rating, 168 reviews