Monthly Rentals in Tregole

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

Nearby monthly rentals

Top Guest favourite
Cottage in Monteriggioni
4.96 out of 5 average rating, 239 reviews

Monteriggioni Castello, holiday house in Tuscany

JakeRating, 5 stars1 week ago
It’s hard to put into words. Monteriggioni was the perfect place for my fiancé and I to go. I proposed there, we had the most amazing food there, and everyone was extremely friendly. The best part was coming back after a long day and eating at one of there restaurants or grabbing a panini and just sitting waiting for the sun to go down while staring out into Tuscany. We couldn’t have envisioned a more spectacular place and experience. Now I have everyone asking where I went and stayed and that they want to follow suit. It’s absolutely perfect and the buses are extremely easy to navigate. We couldn’t have been more pleased with our stay and with our hosts. This is going to be our forever Tuscan home. So grateful and pleased.
Guest favourite
Apartment in Castellina in Chianti
4.91 out of 5 average rating, 11 reviews

The Farmer's House in Chant

HugoRating, 5 stars2 months ago
We had a lovely stay at Liza and Filippo's, the apartment is very well renovated, we slept very well and has everything you need. We were very well hosted. It feels like home. A little more smell of humidity related to the period surely! The location is ideal for moping in this beautiful area. Thanks!
Top Guest favourite
Apartment in Castellina in Chianti
4.84 out of 5 average rating, 301 reviews

Relax Chianti. Apartment with pool and garden

CédricRating, 5 stars1 month ago
Amazing home with a breathtaking view of the Tuscan landscape of Chianti. A relaxing calm with the complicity of the birdsong. A privilege to share with family. Our child was very happy to discover their room with new games. Cinzia is a wonderful host. A "high level" home!
Guest favourite
Apartment in Castellina in Chianti
4.81 out of 5 average rating, 21 reviews

At the Poggio della Capannina in Castellina in Chianti

StephanRating, 5 stars2 days ago
We enjoyed staying in Laura's place.

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