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Holiday rentals in Montelupo Fiorentino

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Top-rated holiday rentals in Montelupo Fiorentino

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, 230 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 rustic dining area features a long wooden table set with linens and decorative items. The space is illuminated by a chandelier and has large windows offering views of the surrounding landscape, with a stone fireplace and traditional frescoes adorning the walls.
Flat in Carmignano
4.97 out of 5 average rating, 273 reviews

Giglio Blu Charming Loft

The accommodation is a portion of a historical noble residence dating back to the 14th century, adorned with frescoes and tastefully restored. It is located on the ground floor of a quiet and safe street, with a private and independent entrance and self check-in. The space is cozy, comfortable, and elegant, perfect for guests seeking an authentic Tuscan experience with modern comfort and technology. It is situated just a few kilometers away from Florence, Pisa, Lucca, Vinci, San Gimignano...

Top guest favourite
A terrace showcases a small table set with glasses and a bottle, complemented by two chairs. A scenic view of the Tuscan countryside can be seen in the background, revealing rolling hills and traditional rooftops under a bright sky.
Flat in San Miniato
4.99 out of 5 average rating, 165 reviews

San Miniato - Panoramic terrace in the historic center

Brand new apartment in the historic center of San Miniato. Recently renovated, it is ideal for those seeking tranquility in the heart of the city, with a beautiful view of the Tuscan countryside thanks to the panoramic terrace perfect for a breakfast in the sun or a special aperitif. Immersed in the historic part of the city, typical restaurants, shops and all the beauties of San Miniato can be easily reached on foot. Thanks to its central location, it is ideal for visiting all of Tuscany.

Guest favourite
Loft in Montelupo Fiorentino
4.9 out of 5 average rating, 157 reviews

Dalla Rossa(A happy place for family)

Ideale per famiglie.Centralissimo e a due passi dalla stazione ferroviaria(100mt),il che lo rende perfetto come base per spostarsi e visitare le città d'arte.Comodi trasferimenti peri Firenze e Pisa. Grande parco a pochi mt di distanza. Quattro posti letto,zona giorno con cucina completa ed accessoriata,,2 Tv,bagno con doccia.Piccolo spazio privato esterno sul retro dove pranzare e rilassarvi.Posto auto gratuito in loco.CHIEDIAMO DI EVITARE RUMORI INUTILI DOPO LE 23.00. Vi aspettiamo!

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, 214 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 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, 174 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.

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 serene outdoor view features olive trees dotting a grassy area. A few lounge chairs are arranged by the pool, which reflects the soft hues of early morning light. A mist envelops the landscape, enhancing the tranquil setting.
Farm stay in Lastra a Signa
4.99 out of 5 average rating, 158 reviews

Flat for 4 with garden & pool in agriturismo

We have created an intimate and exclusive environment, which can accommodate a maximum of 10 guests, where you can find a feeling of tranquility and freedom. The 70 square meter Rasty apartment is located on the ground floor, it is spread over two independent bedrooms and can accommodate up to four people, with four-poster beds, garden view, bathroom, living area and kitchen with fully equipped kitchenette.

Guest favourite
Apartment in Montelupo Fiorentino
4.93 out of 5 average rating, 104 reviews

DA CLOE lovely two-room apartment near Florence

Two-room apartment renovated in 2019, on the first floor of a historic building, with a flight of stairs, without an elevator, located in the center of Montelupo Fiorentino, close to all essential services (train station, bank, post office, supermarket, free parking). The main Tuscan cities of art are easily accessible both by train and car (Florence 20 min. Pisa 40 min. Siena 60 min).

Guest favourite
A serene scene is presented with a stone tower beside a tranquil lagoon. Natural rock formations are reflected in the calm water, while lush greenery surrounds the area, enhancing the peaceful environment. The tower's unique architectural features add historical character to the landscape.
Tower in Fiesole
4.95 out of 5 average rating, 209 reviews

A Big Dream in a Little Tower.

The Tower was created in the late 1800s by an illustrious Englishman, Sir John Temple Leader, in one of the oldest and most important stone quarries belonging to the Medici family. From the same quarry were extracted many important works such as the columns of the Medici chapels, the steps of the Laurenziana library .. all just 5 km from the historic center of Florence.

Guest favourite
A modern bedroom features a comfortable bed with crisp linens and decorative pillows. A large mirror and chic side tables complement the space. A detailed mural adorns one wall, while natural light enters through a window, enhancing the room's ambiance.
Apartment in Montelupo Fiorentino
4.98 out of 5 average rating, 168 reviews

House of Arts ♥

A modern 85 sqm apartment, just renovated, with a large double bedroom, another bedroom with two single beds, living room with sofa bed and 55'' TV, a spacious bathroom and a bright kitchen fully equipped. The balcony, directly connected with the kitchen, offers a nice view on the town of Montelupo. Rooms are decorated with particular paintings made by a local artist.

Top guest favourite
A spacious living area features large arched windows offering panoramic views of the Tuscan hills. A black leather sofa and a rocking chair are arranged around a decorative coffee table, with a subtle light from a chandelier above. A fireplace adds warmth to the serene space.
Townhouse in Scandicci
4.89 out of 5 average rating, 326 reviews

Florence Country Side: Giogoli a place to be!

A lovely antique home located in the Florentine countryside with a wonderful panoramic view overlooking Florence. At only 15 min driving from the centre of Florence, 15 from Chianti and 40 min from Siena. Our home is the perfect location for exploring Tuscany and relaxing while enjoying its beautiful landscape!

Popular amenities for Montelupo Fiorentino holiday rentals

When is the best time to visit Montelupo Fiorentino?

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Frequently Asked Questions

  • Are there family-friendly vacation rentals in Montelupo Fiorentino?

    Montelupo Fiorentino has more than 20 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.

  • How much does it cost to stay in house rentals in Montelupo Fiorentino?

    Experience the best of Montelupo Fiorentino with our house rentals, starting at about $40 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.

  • Are there pet-friendly vacation rentals in Montelupo Fiorentino?

    Four-legged friends are welcome in Montelupo Fiorentino. Choose from more than 20 vacation rentals for guests traveling with pets.

  • Are there vacation rentals with a dedicated workspace in Montelupo Fiorentino?

    Yes! Work meets play with ease at over 30 vacation rentals in Montelupo Fiorentino featuring dedicated workspaces. Stay connected and productive in your home away from home.

  • Do condo rentals in Montelupo Fiorentino have air conditioning?

    Absolutely! We offer over 10 condo rentals with air conditioning in Montelupo Fiorentino. Enjoy a tailored experience with all the comforts you desire.

  • Do condo rentals in Montelupo Fiorentino have a kitchen?

    Absolutely! We offer over 10 condo rentals with a kitchen in Montelupo Fiorentino. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Montelupo Fiorentino have wifi?

    Absolutely! We offer over 20 house rentals with wifi in Montelupo Fiorentino. Enjoy a tailored experience with all the comforts you desire.

  • Do house rentals in Montelupo Fiorentino have free parking?

    Absolutely! We offer over 10 house rentals with free parking in Montelupo Fiorentino. Enjoy a tailored experience with all the comforts you desire.

Quick stats about holiday rentals in Montelupo Fiorentino

  • Total holiday rentals

    Explore 60 holiday rentals in Montelupo Fiorentino

  • Nightly prices starting at

    Montelupo Fiorentino holiday rentals start at $51 SGD per night before taxes and fees

  • Verified guest reviews

    Over 2,360 verified reviews to help you choose

  • Family-friendly holiday rentals

    20 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 20 rentals that welcome pets

  • Rentals with dedicated workspaces

    30 properties have a dedicated workspace

  • Wifi availability

    60 of Montelupo Fiorentino holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Montelupo Fiorentino rentals

  • 4.9 Average rating

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