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Holiday rentals in Castelfiorentino

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Top-rated holiday rentals in Castelfiorentino

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

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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

Sunset on Chianti Classico

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
A spacious terrace is surrounded by lush greenery, featuring terracotta pots filled with plants. Comfortable wooden chairs are positioned to invite relaxation, overlooking scenic hills in the distance. A soft canopy provides shade, enhancing the tranquil atmosphere of this outdoor space.
Home in Peccioli
4.99 out of 5 average rating, 134 reviews

House with a breathless view in Tuscany

Halfway between Pisa and Florence this house comes with a large panoramic terrace, equipped with sunchairs and a large table for outdoor dining. Below, an hanging garden on the property overlooks one of the most striking views in Tuscany. The location is strategic, in the beating heart of an ancient medieval village, now home to an open-air contemporary art museum. Peccioli is a great starting point for those who want to visit the art cities of Tuscany, or immerse yourself in local life,

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, 204 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.
Apartment 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, 449 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 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.
Apartment in Gambassi Terme
4.99 out of 5 average rating, 113 reviews

CASA NELLA Apartment in the Historic Center

This charming and cozy apartment is located on the 2nd floor of a historic building, with large bright spaces and a picturesque view of the characteristic Piazzetta della Cisterna. The living room is spacious and has two windows overlooking the square. The kitchenette is fully equipped, including a dishwasher. The double bedroom has a private bathroom with shower and bidet. Guests will have bed linen, towels and bath towels, all included.

Top guest favourite
A charming house is framed by a well-kept garden, featuring large glass panels that offer views of the surrounding landscape. A seating area with two loungers is positioned on the grass, along with a small table. The entrance leads to a welcoming interior space.
Tiny home in Capraia e limite
4.99 out of 5 average rating, 111 reviews

Historic charm with modern comfort, Tuscany

Charming Retreat for Two, 15 Minutes from Vinci Escape to a cozy hideaway perfect for couples seeking relaxation and comfort. Enjoy a private garden and a shared travertine pool with stunning views of the Tuscan countryside—especially magical at sunset. Ideal for romantic, slow-paced weekly stays. We live on the property with discretion and are happy to assist if needed. A car is required to reach the house.

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
4.91 out of 5 average rating, 242 reviews

Casa al Gianni - Hut

Hi, we're Cristina & Carmelo! We invite you to live an authentic experience in our farmhouse “Casa al Gianni” located 20 minutes from Siena. Our hallmark is simple life in close contact with nature and the animals of our farm. Immersed in the woods and the beautiful Tuscan countryside, you will spend an unforgettable vacation. This slice of paradise will remain in your heart!

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, 316 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.

Top guest favourite
An infinity pool reflects the sky, surrounded by olive trees and well-manicured gardens. Comfortable lounge chairs are placed neatly along the pool deck under shaded umbrellas. A gradual elevation creates a seamless transition between the pool area and scenic countryside views.
Farm stay in Palaia
4.98 out of 5 average rating, 179 reviews

Countryside Dream farm in Tuscany

Great place in the middle of Tuscan Hills, you will be surrounded 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.

Guest favourite
A charming exterior of a building is presented, featuring a small basketball hoop mounted on the wall. Colorful potted plants adorn the entrance, enhancing the inviting aspect of the facade. An outdoor space is marked by a gravel surface, providing a relaxed atmosphere.
Flat in Montespertoli
4.88 out of 5 average rating, 113 reviews

La casa del Poggio

New studio apartment, located in a small village in the municipality of Montespertoli among vineyards and olive groves. It is located in a strategic location a short distance from Florence, Pisa, Siena, Volterra and San Gimignano. The tourist accommodation tax is included in the price.

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 $77 SGD per night before taxes and fees

  • Verified guest reviews

    Over 390 verified reviews to help you choose

  • Wifi availability

    10 of Castelfiorentino holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Castelfiorentino rentals

  • 4.9 Average rating

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