
Holiday houses in Montespertoli
Find and book unique accommodation on Airbnb
Quick stats about holiday rentals in Montespertoli

Total holiday rentals
Explore 30 holiday rentals in Montespertoli

Nightly prices starting at
Montespertoli holiday rentals start at $120 NZD per night before taxes and fees

Verified guest reviews
Over 1,630 verified reviews to help you choose

Family-friendly holiday rentals
20 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 10 rentals that welcome pets

Holiday rentals with a pool
10 properties feature pools

Rentals with dedicated workspaces
10 properties have a dedicated workspace

Wi-Fi availability
30 of Montespertoli holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Montespertoli rentals

4.9 Average rating
Montespertoli stays are highly rated by guests—averaging 4.9 out of 5!
Top-rated holiday rentals in Montespertoli
Guests agree: these stays are highly rated for location, cleanliness and more.

Podere Vergianoni nestled in Chianti with a pool
Podere Vergianoni is an ancient and historic property dating back to the 1600s, located in the beautiful hills of Chianti in Tuscany, with the possibility of organizing a shuttle service and exclusive experiences tailored to you. The apartment is available for 2 adults with the option of adding a sofa bed for 2 children under 12 years of age. In the large outdoor courtyard you'll find a saltwater swimming pool with a relaxation area on a panoramic terrace overlooking the castle, hills, and vineyards with unique sunsets.

Florence Sunset Hills • Giogoli
Escape to the peaceful hills of Giogoli where authentic Tuscan charm meets breathtaking views of Florence.Just 15 minutes from the city center and the Chianti countryside, this elegant home is the perfect base for exploring Tuscany while enjoying quiet mornings, unforgettable sunsets, and the beauty of the surrounding landscape. Surrounded by nature but close to the region's most iconic spots, it's the ideal retreat for anyone looking for comfort, tranquility, and a genuinely Tuscan experience

FORNO apartment with garden for 4 people
In Montespertoli, among the rolling hills of Chianti, there is Podere Paglieri, a small family-run farm where wine and oil have been produced for generations. We are located halfway between Florence and Siena, in a perfect position to discover San Giminiano, Volterra, Siena, Lucca, and the Tyrrhenian coast, which are just a few kilometers away. The farm is surrounded by vineyards, olive groves and woods where you can walk freely, has a large and well-kept garden and a beautiful shaded terrace.

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...

La Chicchera, ground floor apt with panoramic view
La Chicchera è un appartamento recentemente rinnovato e curato nei minimi dettagli in una via molto tranquilla del centro di Montespertoli, un paesino nel cuore del Chianti e a breve distanza da Firenze e da tutte le altre città d'arte della Toscana. Facilmente raggiungibili a piedi minimarket, bar, farmacie, ristoranti, negozi, banche; a pochi passi anche le fermate dell’autobus. Saremo felici di accogliervi e poter far parte del vostro soggiorno in Toscana con consigli e suggerimenti!

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.

I Limoni Apartment in Tuscany
In the Chianti hills between Florence Siena rich in history and evocative natural sceneries, the cradle of civilizations that have left an artistic and cultural heritage of unparalleled value, surrounded by unspoiled nature luxuriant vineyards cultivated as gardens, centuries-old olive groves, imposing cypresses, is the "VillaBassa" farm is located. easily accessible Florence 30 min Pisa 50 min Siena 50 min S.Gimignano 30 min Monteriggioni 45 min

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.

Tower Penthouse in small castle near Florence
900 year old tower-penthouse apartment in Chianti Villa, spacious & super-scenic historical home that combines magical atmosphere with space, light, character, convenience. Painting-like 360° views of Tuscan Hills all the way to Florence; sun-filled, private grounds. Perfect location for an unforgettable family stay. Ample private property (including forest). Walking distance from village shops. Convenient location, Florence in sight.

Farmhouse in Chianti
Beautiful portion of a farmhouse immersed in Chianti with a beautiful swimming pool, surrounded by vineyards and olive trees, perfectly furnished with a large garden and parking spaces. It is located 20 minutes from Florence, 40 from Siena and 50 from Pisa, in a few minutes you can reach Certaldo (birthplace of Boccaccio) and Vinci (birthplace of Leonardo Da Vinci). The house is halfway between Montespertoli and San Casciano (7km).

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.

CASA DI CARLA spacious apartment in Chianti
Spacious and bright Tuscan-style apartment located in a characteristic village near Tavarnelle Val di Pesa. Quiet and peaceful, in the heart of the Chianti hills, in an excellent location for reaching Florence and other Tuscan cities of art. Private garden, with gazebo, sofas and barbecue, adjacent to the apartment. Public parking is available nearby.
Popular amenities for Montespertoli holiday rentals
Other great holiday rentals in Montespertoli

Villa la scuderia quiet luxury private garden pool

Tuscan Farmhouse – Private Pool & Chianti Views

Villa i Lecci 2

Church of the Vaioni

Rondini Blu Vacation Home - Torretta Apartment

Luxury Medieval Tower • Exclusive Chianti Stay

Happy Stay in a Tuscany Home with Stunning Views

Villa of the Hydrangeas
Frequently Asked Questions
Are there pet-friendly vacation rentals in Montespertoli?
Four-legged friends are welcome in Montespertoli. Choose from more than 10 vacation rentals for guests traveling with pets.
Are there vacation rentals with a dedicated workspace in Montespertoli?
Yes! Work meets play with ease at over 10 vacation rentals in Montespertoli featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there Montespertoli vacation rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 10 vacation homes with pools in Montespertoli, available on Airbnb. Make a splash and soak up the sun in style!
Are there family-friendly vacation rentals in Montespertoli?
Montespertoli 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 apartment rentals in Montespertoli?
Experience the best of Montespertoli with our apartment rentals, starting at about $70 per day, before taxes and fees. Embrace comfort and style while staying within your budget in your home away from home.
Do apartment rentals in Montespertoli have air conditioning?
Absolutely! We offer over 10 apartment rentals with air conditioning in Montespertoli. Enjoy a tailored experience with all the comforts you desire.
Do apartment rentals in Montespertoli have a kitchen?
Absolutely! We offer over 10 apartment rentals with a kitchen in Montespertoli. Enjoy a tailored experience with all the comforts you desire.
Do apartment rentals in Montespertoli have wifi?
Absolutely! We offer over 10 apartment rentals with wifi in Montespertoli. Enjoy a tailored experience with all the comforts you desire.
Do apartment rentals in Montespertoli have free parking?
Absolutely! We offer over 10 apartment rentals with free parking in Montespertoli. Enjoy a tailored experience with all the comforts you desire.
What are the most popular amenities for Apartment Rentals in Montespertoli?
Enhance your stay in our Apartment Rentals with the most popular amenities: over 10 homes with air conditioning, over 10 homes with wifi, over 10 homes with a kitchen, over 10 homes with free parking, and more. Indulge in the ultimate retreat, tailored to your preferences.
Destinations to explore
- Cathedral of Santa Maria del Fiore
- Santa Maria Novella
- Santa Maria Novella
- Ponte Vecchio
- Basilica of Santa Maria Novella
- Piazza del Duomo (Pisa)
- Mugello Circuit
- Mercato Centrale
- Stazione Santa Maria Novella
- Pisa Centrale Railway Station
- Uffizi Gallery
- Fortezza da Basso
- Parco Nazionale delle Foreste Casentinesi, Monte Falterona e Campigna
- Spiagge Bianche
- Piazza della Repubblica
- Parco delle Cascine
- Piazzale Michelangelo
- Del Chianti
- Pitti Palace
- Boboli's Garden
- Palazzo Vecchio
- Piazza della Signoria
- Medici Chapel
- Basilica of Santa Croce





