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Holiday rentals in Monteriggioni

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Top-rated holiday rentals in Monteriggioni

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Guest favourite
A rustic stone farmhouse showcases a charming facade with a mix of arched and rectangular windows. Lush greenery surrounds the entrance, creating a natural frame. The building features a mix of warm tones and textures, typical of traditional Tuscan architecture.
Farm stay
4.83 out of 5 average rating, 162 reviews

Podere Casalino – La Pergola

Set in the peaceful countryside near the Monteriggioni Castle, Il Casalino is the result of our love for restoring an old Tuscan farmhouse. My husband and I have carefully created two apartments for our guests: Il Gatto and La Pergola. We want you to feel at home from the very first moment. If you have any questions, feel free to message me: I will reply as quickly as possible. We truly look forward to welcoming you to Il Casalino and sharing this special place with you! Warm regards, Laura

Top guest favourite
The image showcases a vibrant town square surrounded by historic buildings, including the prominent Torre Salvucci Maggiore. The sky is expansive, featuring soft clouds scattered across a blue backdrop. The texture of the stone architecture provides a glimpse into the medieval influence of the area.
Tower
4.94 out of 5 average rating, 124 reviews

Medieval Tower experience with Panoramic Rooftop

If you are looking for a memorable experience, this is the right place for you! With its 42 mt high, the Salvucci Tower is one of the famous towers of San Gimignano and today the only one turned into a vertically-spread apartment divided into 11 floors, for a total of 143 steps. A unique and timeless place, ideal to experience something never tried before. The tower can hosts couples or small groups up to 3 people. Its panoramic rooftop boasts an incredibly breathtaking view all over the town.

Guest favourite
An expansive outdoor deck offers a serene view of rolling hills under a clear sky. An infinity pool transitions seamlessly into the landscape, with two soft seating cushions placed nearby, inviting relaxation and contemplation of the stunning panoramic scenery.
Home
4.88 out of 5 average rating, 189 reviews

Infinity view

Completamente ristrutturata posizione con vista mozzafiato sul Valdarno. Il piano terra è composto da soggiorno con due vetrate che danno sul patio, camino, divano letto, bagno con grande doccia e cucina moderna con isola in acciaio, con tre porte finestre per accedere alla zona pranzo esterna con bbq. Il primo piano è composto da due camere matrimoniali ognuna dotata del proprio bagno con doccia. Giardino è moto curato,ci sono vari angoli relax, prendisole è una piscina infinity ad idrolisi

Guest favourite
A green metal table is set with a bouquet of fresh flowers, surrounded by two matching chairs. In the background, a rustic brick building with barred windows is partially concealed by lush greenery, creating a serene, natural setting.
Farm stay
4.79 out of 5 average rating, 157 reviews

Capannacce more than a Farmhouse: La Casetta

Capannacce is a special place for us. Farm, but not only. It is home. For us and for the animals that live here, horses, chickens, cows, felines and canids. Indeed, the heart of the farm is the breeding of racehorses, English thoroughbreds. And of the Pontremolese cow, a native heritage breed. We are immersed in the Crete Senesi, where every summer sunset is a delight. The countryside made of quietness that soothes, but not far from the town of Rapolano Terme and all related comforts.

Top guest favourite
Cottage
4.95 out of 5 average rating, 273 reviews

Monteriggioni Castello, holiday house in Tuscany

Il nostro alloggio è un edificio storico che risale alla costruzione del castello. È stato recentemente restaurato e arredato con cura in tutti i dettagli. È molto accogliente e dispone di tutti i più moderni servizi. I turisti che decideranno di essere nostri ospiti, avranno il vantaggio di vivere nell' ambiente medievale del castello, usufruendo di tutti i confort. Si sentiranno coccolati e avranno l'opportunità di tornare indientro vivendo un' esperienza unica e indimenticabile.

Top guest favourite
The image showcases a refreshing pool surrounded by lounge chairs and umbrellas, enhancing the outdoor relaxation area. The pool is framed by lush greenery and a stone wall, with the charming rustic house visible in the background under a clear blue sky.
Home
5 out of 5 average rating, 122 reviews

Infinity pool in Chianti area

On the Chianti hills, portion of an old stone farmhouse from the 1800s, located in S. Filippo, a small hamlet of Barberino Tavarnelle, halfway between Florence and Siena, a 30-minute drive from Florence airport, 1 hour from Pisa airport. Three bedrooms, two bathrooms, large living room with fireplace, eat-in kitchen and dining room. Magnificent view of the hills from every window! Beautiful infinity pool with whirlpool area, unheated and open from April to October.

Top guest favourite
A historic villa is situated amidst lush, rolling hills, surrounded by vineyards. The exterior features a traditional stone facade, large windows, and terracotta roof tiles. Manicured gardens with circular patterns enhance the property's charm, complemented by tall cypress trees framing the serene landscape.
Flat
4.94 out of 5 average rating, 171 reviews

Villa di Geggiano - Perellino Suite

The 700 years old Villa di Geggiano, surrounded by our working vineyard and lovingly maintained gardens, is located in Chianti in Tuscany which is one of the most beautiful regions of Italy. Our guesthouse is located in one of the original garden pavilions of the villa. PLEASE NOTE THAT WE ARE IN THE COUNTRYSIDE WITH VERY FEW PUBLIC TRANSPORT OTHER THAN TAXI SO THE BEST WAY TO ENJOY YOUR STAY AND TO VISIT THE BEAUTIFUL SURROUNDINGS IS TO HAVE A RENTAL CAR.

Top guest favourite
A charming outdoor seating area is set against a backdrop of rolling green hills. Two green metal chairs and a matching table are surrounded by flowering plants, with cypress trees rising in the distance under a partly cloudy sky.
Apartment
5 out of 5 average rating, 137 reviews

Mascagni Farmhouse in Val d'Orcia, Pienza

Climb the iconic Tuscan hills to Mascagni Organic Farm, an organic farm where your new home awaits: a finely restored 16th-century barn nestled among olive trees and wheat fields. Relax with a cup of tea, pick rosemary and lavender in the garden with breathtaking views of the Val d'Orcia. Rediscover your true nature among the pristine fields and olive trees: here, walks and bike rides have no limits! Ready to create memories that will last a lifetime?

Top guest favourite
The countryside property is nestled among lush greenery, featuring rustic architecture and terracotta roofs. Surrounded by rolling hills and trees, the natural landscape creates a peaceful setting. A gravel path leads to the house, enhancing the connection to the serene outdoor environment.
Farm stay
4.93 out of 5 average rating, 163 reviews

House at Gianni - Olmo

Hi, we're Cristina & Carmelo! We invite you to discover the rustic charm and authenticity of "Casa al Gianni," our farmhouse in the heart of the Tuscan countryside, 20 minutes from Siena. After a recent renovation, our accommodations are ready to welcome you with all modern comforts without losing the essence of tradition. In the Olmo Apartment, brand new beds await you, a promise of peaceful and regenerating sleep, a new kitchen and a new bathroom.

Guest favourite
Apartment
4.86 out of 5 average rating, 140 reviews

Fattoria Lornano Winery- villa ''Trebbiano''

4 villas with private garden, private parking, large swimming pool (OPEN FROM 1ST MAY TO 15TH OCTOBER) and park, located within the historic complex of the Fattoria Lornano, immersed in the Chianti hills. Trebbiano is an apartment for two within one of the houses, accessed either from the main piazza or its private garden patio. It is a lovely retreat for a couple wishing to enjoy the wine estate with a touch more privacy.

Top guest favourite
A stone facade is viewed from a well-maintained garden, featuring lush green grass and neatly trimmed hedges. A wooden door is visible, leading into a charming interior, while the house's rustic architecture complements the serene landscape under a clear blue sky.
Home
4.98 out of 5 average rating, 111 reviews

Explore Chianti from a Charming Stone House

Awaken in a bedroom with beamed ceilings, open doors to a private garden, and take an early morning dip in the pool. Return to a classically designed house with terra cotta floors, wood-burning fireplace, and bathrooms with exuberant tile work. Casa Marinella is the perfect place to discover Chiantishire. Fully equipped kitchen, AC in each bedroom, private garden and barbecue.

Top guest favourite
A charming garden area features a round table surrounded by four wrought iron chairs. Vibrant flowers bloom in planters, and lush greenery adds to the tranquil environment. A rustic stone wall and traditional rooftops provide a picturesque backdrop, enhancing the sense of privacy.
Home
4.99 out of 5 average rating, 202 reviews

Romantic Garden in Historic San Gimignano

Enjoy a romantic stay in the heart of San Gimignano, inside the medieval walls.The apt features a private garden, a rare and peaceful corner where you can have breakfast, relax after exploring the town or enjoy a glass of wine in the evening. Perfect for couples looking for charm, history and quiet retreat in one of Tuscany's most beautiful villages.

Popular amenities for Monteriggioni holiday rentals

  1. Airbnb
  2. Italy
  3. Tuscany
  4. Siena
  5. Monteriggioni