
Vacation rentals in Montaione
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Top-rated vacation rentals in Montaione
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Garden House
"Casa del giardino" ...... a blooming oasis within the medieval walls.. The owners Mario and Donella would like to offer you a unique vacation in San Gimignano. You can enjoy the wonderful garden, an extraordinary oasis of peace and silence, in the city center, for the exclusive use of those who rent the apartment. Thus, reading a book, relaxing in the sun, sipping an excellent glass of Chianti or having breakfast surrounded by greenery and among the flowers of this garden will be a memorable experience!

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,

Farmhouse with pool in Chianti
Agriturismo Il Colle is located on one of the Chianti hills. The structure has been completely renovated, dominates the Chianti valleys and enjoys a splendid view of the surrounding hills and the city of Florence just 35 minutes by car The apartment is on the first floor of the main farmhouse, with independent access and garden with trees. The rustic furnishings in the classic Tuscan style, with wooden beam ceilings and terracotta floors give a characteristic touch to the environment.

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.

Wonderful Loft in Villa with Pool in Chianti
Located on the second and top floor of the "Suites le Valline" complex, the Piazzale Michelangelo loft offers a unique style in an ideal location for exploring Tuscany, a 15-minute drive from Florence and San Casciano! Treat yourself to a moment of relaxation on the beautiful panoramic terrace overlooking Florence, or cool off in the bio pool among the olive trees... and remember that all the vegetables from the Valline vegetable garden are at your disposal!

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.

Luxury Medieval Tower - Penthouse
Step into the past... San Gimignano Luxury Medieval Tower is right in the heart of the UNESCO town. You will be caught by the sight of San Gimignano's beautiful landscapes and at the same time you will be able to enjoy the luxury amenities of in-town living: walk downstairs to the cafes, bread shop, butcher, restaurants and local shops. Hear the church bells directly from your windows. Walking distance to all of San Gimignano main attractions.

Casa al Gianni - Capanna
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!

Michelangelo: entire space in the heart of Tuscany
Come and take a vacation at our beautiful apartment in Peccioli, Tuscany! Enjoy a renovated space, beautifully decorated, with new appliances and furniture, Air conditioner in all spaces, high-speed internet, and all you need to enjoy your time in Italy. Peccioli is a gem in the heart of Tuscany, near all the big cities and touristic attractions.

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.

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.

Podere Guidi
Apartment in a panoramic villa between Florence and Siena, in the heart of Chianti, in a charming village. Pool open from May until the end of September. From 2026, the pool will be open from 9 a.m. to 1 p.m. with exclusive use for guests at this time.
Popular amenities for Montaione vacation rentals
Other great vacation rentals in Montaione

Villa Via Francigena

Casa Billi

Farmholiday Villino del Grillo in San Gimignano SI

Noble villa·Pool, terrace, fireplaces & chic decor

Villa in Chianti: Swimming Pool and Beach Bar

Podere Tignano, 4-bedroom villa in the Chianti!

Loggia in the Santo Spirito district

The charming cottage in Tuscany with breathtaking views
Quick stats about vacation rentals in Montaione
Total rentals
30 properties
Nightly prices starting at
€ 60 before taxes and fees
Total number of reviews
250 reviews
Family-friendly rentals
20 properties are a good fit for families
Pet-friendly rentals
20 properties allow pets
Rentals with a pool
20 properties have a pool
Frequently Asked Questions
Are there Montaione vacation rentals on Airbnb with pools?
Yes! Dive into the perfect getaway at one of over 20 vacation homes with pools in Montaione, available on Airbnb. Make a splash and soak up the sun in style!
Are there vacation rentals with a dedicated workspace in Montaione?
Yes! Work meets play with ease at over 10 vacation rentals in Montaione featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there pet-friendly vacation rentals in Montaione?
Four-legged friends are welcome in Montaione. Choose from more than 20 vacation rentals for guests traveling with pets.
Are there family-friendly vacation rentals in Montaione?
Montaione has more than 30 family-friendly stays. Amenities on the property may include high chairs, travel cribs, or strollers.
Do apartment rentals in Montaione have wifi?
Absolutely! We offer over 10 apartment rentals with wifi in Montaione. Enjoy a tailored experience with all the comforts you desire.
How much does it cost to stay in apartment rentals in Montaione?
Experience the best of Montaione with our apartment rentals, starting at about $100 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 Montaione have a kitchen?
Absolutely! We offer over 10 apartment rentals with a kitchen in Montaione. Enjoy a tailored experience with all the comforts you desire.
What are the most popular amenities for Apartment Rentals in Montaione?
Enhance your stay in our Apartment Rentals with the most popular amenities: over 10 homes with wifi, over 10 homes with free parking, over 10 homes with a kitchen, and more. Indulge in the ultimate retreat, tailored to your preferences.
Destinations to explore
- Santa Maria Novella
- Duomo di Firenze
- Piazza del Duomo (Pisa)
- Basilica of Santa Maria Novella
- Parco Nazionale delle Foreste Casentinesi, Monte Falterona e Campigna
- Ponte Vecchio
- Cala Violina
- Gulf of Baratti
- Uffizi Gallery
- Mugello Circuit
- Mercato Centrale
- Piazzale Michelangelo
- Fortezza da Basso
- Parco delle Cascine
- Spiagge bianche
- Pitti Palace
- Piazza della Repubblica
- Careggi University Hospital
- Spiaggia Libera
- The Boboli Gardens
- Cantina Winery, Cellar and Farm Fattoria Santa Vittoria
- Spiaggia Marina di Cecina
- Stadio Artemio Franchi
- Medici Chapels