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Holiday houses in Castelfiorentino

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Top-rated holiday rentals in Castelfiorentino

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Top Guest favourite
An aerial view captures Podere Vergianoni nestled in the Chianti hills, surrounded by lush vineyards. The property features a clear blue pool, shaded terraces, and carefully landscaped gardens. Rolling hills and rows of grapevines create a serene backdrop, highlighting the natural beauty of the Tuscan countryside.
Condo in Noce
5 out of 5 average rating, 300 reviews

Podere Vergianoni nestled in Chianti with a pool

Podere Vergianoni is an ancient and authentic farmhouse dating back to the 17th century located in the beautiful hills of Chianti in Tuscany. The apartment is impeccably furnished in the traditional local style of old Tuscany: ancient wooden beams, terracotta floors, and unique furniture. In the large outdoor courtyard, you'll find a large swimming pool on a panoramic terrace at your disposal, overlooking the valley with breathtaking views of vineyards and olive groves, where you can enjoy spectacular sunsets.

Top Guest favourite
A spacious bedroom is presented with a neatly arranged bed featuring soft linens. A large mirror hangs above a wooden bench, reflecting the natural light from the window. Fresh towels are neatly folded on the bed, and an indoor plant adds a touch of greenery.
Condo in Gambassi Terme
4.99 out of 5 average rating, 113 reviews

CASA NELLA Apartment in the Historic Center

Questo affascinante e accogliente appartamento si trova al 1^ piano di un edificio storico, con ampi spazi luminosi e una vista pittoresca sulla caratteristica Piazzetta della Cisterna. Il soggiorno è spazioso e dotato di due finestre che affacciano sulla piazza. L'angolo cottura è completamente attrezzato, incluso un lavastoviglie. La camera matrimoniale dispone di bagno privato con doccia e bidet. Gli ospiti avranno a disposizione biancheria da letto, asciugamani e teli bagno, tutti inclusi.

Top Guest favourite
A stone structure with a tiled roof is framed by greenery, surrounded by rolling hills. A spacious outdoor area features a wooden table, inviting relaxation. Large trees and thriving shrubs enhance the tranquil setting, with a backdrop of a serene sunset illuminating the landscape.
Home in San Casciano In Val di Pesa
4.98 out of 5 average rating, 220 reviews

The Chianti Classico Sunset

Se cercate una location idilliaca nel cuore del Chianti classico, immersi nei vigneti e oliveti delle splendide colline toscane, nel podere di una Villa storica del ‘500, allora venite nel nostro fienile!! Ha una posizione dominante con una vista strepitosa, dove è possibile godersi tramonti mozzafiato. La totale indipendenza della casa, l'accogliente giardino, il grande loggiato permettono di trascorrere soggiorni in totale tranquillità. Le nostre recensioni sono la vostra migliore garanzia.

Top Guest favourite
An aerial view of the property reveals a charming red house surrounded by lush greenery. Tall cypress trees and vibrant bushes create a tranquil landscape, while an expansive lawn features relaxing loungers, inviting guests to enjoy the serene atmosphere of the Tuscan countryside.
Home in Gambassi Terme
5 out of 5 average rating, 203 reviews

Il Fienile, Luxury Apartment in the Tuscan Hills

‘Il Fienile’ is in an enchanting position immersed in the beauty of the Tuscan hills, with a breathtaking view of the surrounding countryside. It is located in the hamlet of Catignano in Gambassi Terme, just a few kilometres from San Gimignano. The house sits in a protected oasis surrounded by a beautiful private park with olive trees, a pond, pine trees and woods, where you can walk, relax and enjoy the pleasures of unspoilt nature. A unique experience entirely to be enjoyed.

Top Guest favourite
An outdoor space features a large swimming pool surrounded by lush greenery and olive trees. Sun loungers are arranged around the pool, and striped umbrellas provide shade. The view includes gently rolling hills, contributing to a serene environment.
Farm stay in Castelfiorentino
4.91 out of 5 average rating, 136 reviews

Apartment in Agriturismo with pool and great view

L'appartamento, facente parte di un agriturismo è arredato in stile tipico , tutto interamente rinnovato , composto da camera matrimoniale, cucina , bagno e divano letto doppio nella cucina; situato nel centro della Toscana è un ottimo punto di partenza per poter visitare la regione; a 20 minuti da San Gimignano e 35 da Firenze. E' adatto ad una coppia o ad una famiglia con figli piccoli avendo come soluzione per la terza e la quarta persona un unico divano letto matrimoniale.

Guest favourite
The kitchen features wooden cabinetry and granite countertops, with modern appliances including a refrigerator and oven. A wooden dining table seats four and is adorned with a decorative centerpiece. Soft lighting highlights the warm tones of the space, creating an inviting cooking and dining area.
Condo in Castelfiorentino
4.87 out of 5 average rating, 104 reviews

Casa Tilli

Cozy apartment located in the historic center of Castelfiorentino, equipped with a kitchen, living room with fireplace, double bedroom loft, 2-seater sofa bed, bathroom with shower. It is a five-minute walk from the train station and the bus station. You can reach the art cities of Florence, Siena, Pisa in about an hour. Less than an hour's drive away you can reach the medieval villages of S. Gimignano and Volterra. Pisa and Florence airports are an hour away.

Top Guest favourite
A charming stone building surrounded by lush greenery features a wooden terrace with a parasol and flower pots. Two loungers are placed on the well-maintained lawn, providing a relaxing outdoor space.
Farm stay in Greve in Chianti
4.99 out of 5 average rating, 446 reviews

Old hayloft on the Chianti hills

Agriturismo Il Colle is located on one of the Chianti hills. The property has been completely renovated, overlooking the Chianti valleys and enjoying splendid views of the surrounding hills and the city of Florence. The apartment is completely independent, on two internally connected floors, and features a private garden lined with centuries-old oaks and Tuscan cypresses. The restoration maintained the original Tuscan architectural style of rural barns.

Top Guest favourite
A winding driveway is lined with tall cypress trees on either side. The green landscape stretches into the distance, revealing rolling hills and a distant rustic building surrounded by nature, creating a serene and inviting setting.
Home in Montaione
4.95 out of 5 average rating, 126 reviews

Cercis - La Palmierina

E' un appartamento facente parte di una tenuta completamente recintata di 60 ettari di natura incontaminata: più di 1000 ulivi, innumerevoli cipressi e foreste profumate creano un ambiente idilliaco per coloro che ricercano tranquillità e silenzi. La tenuta Palmierina è in prossimità di Castelfalfi (un vero gioiello di architettura medievale) e nelle vicinanze di Firenze (50 Km), Siena (50 Km), Pisa (50 Km). Nelle vicinanze ci sono due campi da golf.

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 in Impruneta
5 out of 5 average rating, 163 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.

Guest favourite
The exterior of a two-story, Tuscan-style apartment is visible, featuring light-colored walls and traditional wooden shutters. A welcoming staircase leads to a balcony adorned with potted plants, providing access to the upper level. Greenery surrounds the entrance, adding to the tranquil ambiance.
Condo in Gambassi Terme
4.89 out of 5 average rating, 246 reviews

A View Over Tuscany's Countryside

A quite and peaceful apartment in the middle of Tuscany countryside, ideal for 3 people also, is about 60 squares meters with bath , double bed , living room with a sofa' bed, kitchen and a beautiful terrace overlooking the vineyards.There is, also, a private parking inside the condominium and a nice bar near by. It is located near the main tourist attractions, this apartment is ideal for travelers who wants to explore Tuscany.

Top Guest favourite
The image features a serene infinity pool reflecting the surrounding trees and villa during sunset. Sun loungers are positioned beside the pool, and the well-maintained outdoor area offers a tranquil ambiance enhanced by the natural landscape.
Farm stay in Pisa
4.99 out of 5 average rating, 314 reviews

Tenuta Chiudendone in Tuscany

Great place in the middle of Tuscan Hills, you will be sorrounded by nature but close to all the beautiful cities of Tuscany! We rent two apartments, one on the upper floor called Balla and one on the ground floor called Modigliani. Tell us which one you prefer. PLEASE NOTE YOU WILL NEED A CAR DURING YOUR STAY.

Superhost
An open-plan kitchen and dining area is showcased, featuring wooden beams overhead. A dining table is surrounded by four chairs, and a cozy seating area includes a gray armchair. Various plants adorn the space, enhancing its warm and inviting ambiance.
Home in Tavarnelle Val di Pesa
4.88 out of 5 average rating, 182 reviews

Nada Home

My house is immersed in the Tuscan countryside among olive trees and vineyards in the heart of Chianti, wonderful views, relaxation, I offer cooking schools and exclusive dinners, my garden can be the perfect setting for a wonderful candlelit dinner prepared exclusively for my guests 🤗

Popular amenities for Castelfiorentino holiday rentals

Quick stats about holiday rentals in Castelfiorentino

  • Total holiday rentals

    Explore 10 holiday rentals in Castelfiorentino

  • Nightly prices starting at

    Castelfiorentino holiday rentals start at $104 NZD per night before taxes and fees

  • Verified guest reviews

    Over 390 verified reviews to help you choose

  • Wi-Fi availability

    10 of Castelfiorentino holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wi-Fi and Pool across Castelfiorentino rentals

  • 4.9 Average rating

    Castelfiorentino stays are highly rated by guests—averaging 4.9 out of 5!