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Holiday rentals in Castelfalfi

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Top-rated holiday rentals in Castelfalfi

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Top guest favourite
Aerial view showcases the rustic property nestled among the lush vineyards. Sunlight casts a warm glow over the hills, while a sparkling pool is situated near the residences, surrounded by greenery. The tranquil landscape includes gently rolling hills and rows of grapevines.
Apartment
5 out of 5 average rating, 308 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
Holiday home
4.94 out of 5 average rating, 52 reviews

Tuscan countryside apartment with pool | Relax

Apartment set in the Tuscan countryside, surrounded by olive trees and quiet, with garden, panoramic pool and free parking. Ideal for couples, small families and remote work thanks to fast Starlink internet. King-size bed, equipped kitchen, air conditioning, TV with Netflix & Disney+. Private terrace with table, barbecue and deckchairs. Direct access to nature trails. Close to Peccioli, Volterra, Pisa, Firenze,San Gimignano and the sea (45 min). Here you’ll find space, calm and the real Tuscany.

Superhost
A charming two-story building is set against a backdrop of lush greenery. The exterior features earthy tones with green window shutters and a partially covered entrance. A spacious grassy area is visible in front, with a few lounge chairs arranged for relaxation.
Loft
4.57 out of 5 average rating, 7 reviews

In the heart of Tuscany

The apartment is in a renovated medieval village with elegant shops, swimming pools and golf near the estate of Castelfalfi. In the heart of Tuscany at the intersection of the provinces Florence, Pisa and Siena; in the proximity you can find historical places like San Gimignano and Volterra, San Vivaldo and the via Francigena. The studio is at the first floor, a few steps from the Castle. You can enjoy the panorama of the beautiful Tuscan hills from the common garden at the ground floor.

Top guest favourite
Home
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
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.

Guest favourite
Holiday home
5 out of 5 average rating, 8 reviews

Casa Camelia - Your authentic Tuscan getaway

Escape to our authentic Tuscan home, situated in a 65 acre estate with over 1.000 olive trees. The perfect retreat for families seeking a tranquil getaway. Nestled in the heart of Tuscany - near San Gimignano and Volterra - our charming holiday home features two beautifully appointed bedrooms, offering a cozy and inviting atmosphere. Enjoy leisurely days by the shared swimming pool, taking in the wonderful views of the rolling hills and lush olive orchards.

Top guest favourite
An inviting swimming pool is surrounded by sun loungers and umbrellas, set against a backdrop of lush greenery and rolling hills. The clear blue water reflects the sky, offering a serene atmosphere for relaxation.
Holiday home
4.96 out of 5 average rating, 52 reviews

Peaceful tuscan house with pool in Tuscany

An oasis of peace located in the heart of Tuscany and on the wine roads! -A strategic area between Certaldo, San Gimignano, Siena and Florence. -Casa Valentina is hidden in a grove where you will enjoy fresh air, a stream with the chirping of birds and a wonderful swimming pool where you can enjoy our breathtaking views -A newly renovated house that meets the historicity of the property, the comfort and the contemporaneity that makes it unique in its style.

Top guest favourite
A serene outdoor pool area is framed by lush green grass, featuring several sun loungers and umbrellas. The clear water in the pool reflects the blue sky, while tall cypress trees provide a natural backdrop to the tranquil setting.
Farm stay
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
Home
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
A charming house is set amidst a verdant landscape, featuring a two-story design with blue shutters. A patio area is visible, furnished for outdoor dining, with flowering wisteria cascading nearby, enhancing the garden's natural beauty.
Flat
4.96 out of 5 average rating, 124 reviews

Podere Le Murella "Sunset"

A cozy retreat for two, set among the green Tuscan hills. Enjoy a private patio for outdoor dining, large garden, free Wi-Fi, fully equipped kitchen, coffee machine, washing machine, dryer, barbecue area, and linens included. Private parking. Ideal for a romantic escape or relaxing stay near Pisa, Florence, Volterra, and charming villages. A perfect base to explore nature, art, and local life—all year round.

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
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
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.

Popular amenities for Castelfalfi holiday rentals

  1. Airbnb
  2. Italy
  3. Tuscany
  4. Castelfalfi