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, 115 reviews

Old Chianti chapel-style cottage

EevaRating, 5 stars1 week ago
We spent 10 days at Pieros lovely chapel cottage in Gaiole in Chianti with our small family of two adults and a small baby. The cottage had all the amenities one would need when traveling with a baby! The cottage was really peaceful and quiet, and it had a small private garden to enjoy those lazy mornings in the countryside. The location was great for making small daytrips to sights and wineries around Tuscany. The inside of the house was really cute and the house had a unique atmosphere, but we found some parts of the kitchen and bathroom slightly untidy. Communication with Piero and Ivana worked really well - both were friendly and ready to help at all times. Special thanks to Ivana for making our very late check-in possible! I would definitely recommend Piero’s cottage! Great value for money.
Guest favourite
Villa in Gaiole in Chianti
5 out of 5 average rating, 6 reviews

Casanova of Bricciano

PeterRating, 5 stars1 week ago
What a fabulous setting and location. Perfect to explore the Chianti region and beyond. It’s roomy, everything you need is there, beautiful pool and a view to cherish. Dining on the terrace is a wonderful experience and with a vinyard with lovely wines available right next door what more do you need from a Tuscan holiday. All hosted perfectly by Fabio and Andrea. Very highly recommended.
Guest favourite
Guest suite in Gaiole in Chianti
4.98 out of 5 average rating, 44 reviews

Independent cottage surrounded by nature

CarlosRating, 5 stars2 weeks ago
Tommaso’s place is such a gem. Hidden in the woods of Chianti in Tuscany, the place brings immaculate views, a cottage that is part of a beautiful estate and a pool that we had to ourselves. Renting a car is necessary because there is nothing walkable from the Airbnb but driving through the hills and wineries of Tuscany is absolutely amazing. Tommaso and Simone ensured that we had absolutely everything we needed. Could not suggest this Airbnb more.
Top Guest favourite
Villa in Gaiole in Chianti
4.93 out of 5 average rating, 27 reviews

Sestuccina

EmmaRating, 5 stars2 weeks ago
We had a lovely stay at this beautiful villa. The photos do not do it justice at all! From the infinity pool overlooking the vineyard to the hot tub with views of a castle, it was stunning and jaw dropping scenery. Brigittia made sure we were prepared to have a great trip - from helping us with reservations and arranging transportation for us with her husband (who was wonderful) she was a fantastic host. We would love to visit again sometime and would recommend for anyone wanting to spend time in the countryside.

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.*

Book with confidence

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

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.

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