Monthly Rentals in Montegrossi

Discover long-term rentals that feel like home, for stays of a month or longer.

Nearby monthly rentals

Enter dates and number of guests to see the total trip price including additional fees and taxes, and rounded up to the nearest integer.

Superhost
Cottage in Gaiole in Chianti
4.84 out of 5 average rating, 111 reviews

Old Chianti chapel-style cottage

JoshRating, 5 stars3 months ago
Piero and Ivana were excellent hosts with the most welcoming home that we’ve ever stayed in. We had such a lovely time spending time amongst the peaceful olive trees and coziness of the house, we couldn’t have asked for a better place to stay.
Guest favourite
Cottage in Cavriglia
4.84 out of 5 average rating, 68 reviews

Il Fienile, characteristic stone cottage for 2

DexterRating, 5 stars5 months ago
Marina was the perfect host. She was unbelievably flexible when, due to our rental company, we were many hours late to check-in. She was always responsive when we messaged her before and during the stay and even helped us to get a reduce what we had to pay her. I 100% recommend the place as it is beautiful and very peaceful.
Guest favourite
Villa in Gaiole in Chianti
4.89 out of 5 average rating, 66 reviews

Podere il Trebbio

BarbaraRating, 5 stars3 months ago
We loved staying at Bernardino’s villa. It was a fabulous place for our two families to meet up and spend some time together in Tuscany. Bernardino is an experienced and responsive host. The location was great, the immediate town (Gaiole in Chianti) was sweet and we could easily get to Florence, Siena, and Arezzo. The 20 minutes or so leading up to the town are best driven for your first time in daylight hours, as the roads are fairly windy along the hills. The 400 metres leading up to the villa are a little steep. Our rented mid sized SUV took it fine, but our friends had a lower slung car them at found it a bit trickier. This is not a reason to avoid this lovely place, just noting it fyi.
Home in Montegrossi
4.63 out of 5 average rating, 8 reviews

House Relax in Chianti

FabioRating, 5 stars6 months ago
Great location surrounded by greenery and with a beautiful view. Spacious and with all the necessary comforts in the home. She was employed at the Eroica event and was found to be in a key location. Thanks to Giulia and her sister for her availability and friendliness

Amenities and perks for longer stays

Furnished rentals

Fully furnished rentals include a kitchen and the amenities you need to live comfortably for a month or longer. It’s the perfect alternative to a sublet.

Flexibility you need

Choose your exact move-in and move-out dates and easily book online, without any additional commitment or paperwork.*

Simple monthly prices

Special rates for long-term holiday rentals and a single monthly payment without additional charges.*

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Work-friendly spaces for digital nomads

Travelling professional? Find a long-term stay with high-speed Wi-Fi and dedicated working spaces.

Looking for serviced apartments?

Airbnb has fully furnished apartment homes ideal for staffing, corporate housing and relocation needs.
*Some exclusions may apply in certain geographies and for some properties.
  1. Airbnb
  2. Italy
  3. Tuscany
  4. Province of Siena
  5. Montegrossi
  6. Monthly Rentals