Monthly Rentals in Gaiole in Chianti

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

Nearby monthly rentals

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.
Top guest favorite
Apartment in Cavriglia
4.97 out of 5 average rating, 144 reviews

ABOVE the HAZE tourist rental

SusanneRating, 5 stars1 week ago
We had a wonderful stay at Laura’s apartment! The place is beautifully located with an incredible view – even better than in the pictures. Everything was perfectly clean and well prepared, and Laura gave us such a warm and kind welcome. We felt at home from the very first moment. Highly recommended – we’d love to come back one day!
Guest favorite
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.
Guest favorite
Home in Gaiole in Chianti
4.93 out of 5 average rating, 28 reviews

Casina del Chianti

PaulaRating, 5 stars1 week ago
Wow stunning location. Cool place, really sociable and so relaxing. I am sorry I am not still there and will definitely return. The whole region is a dreamscape. This place encapsulates the Chianti style. Loved every moment!

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 vacation rentals and a single monthly payment without additional charges.*

Book with confidence

Reviewed by our trusted community of guests and 24/7 support during your extended stay.

Work-friendly spaces for digital nomads

Traveling professional? Find a long-term stay with high-speed wifi and dedicated working spaces.

Looking for serviced apartments?

Airbnb has fully furnished apartment homes ideal for staffing, corporate housing, and relocation needs.

Stay near Gaiole in Chianti's top sights

Eroica 13 locals recommend
Capannelle9 locals recommend
Enoteca La Cantinetta Del Chianti S.A.S. Di Azzato Riccardo Michele8 locals recommend
Lo Sfizio6 locals recommend
I'GALLETTO BRIACO6 locals recommend
Coop Informa6 locals recommend

Destinations to explore

*Some exclusions may apply in certain geographies and for some properties.
  1. Airbnb
  2. Italy
  3. Tuscany
  4. Province of Siena
  5. Gaiole in Chianti
  6. Monthly Rentals