Monthly Rentals in Gaiole in Chianti

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

Nearby monthly rentals

Guest favorite
Cottage in Gaiole in Chianti
4.84 out of 5 average rating, 112 reviews

Old Chianti chapel-style cottage

ThiloRating, 5 stars2 weeks ago
We had a wonderful stay in Pietro's house. We felt very comfortable at all times and the view is marvellous. The house is a good starting point for exploring the Chianti region and for hiking in the surrounding area.
Superhost
Home in Rietine
4.85 out of 5 average rating, 207 reviews

Gaiole in Chianti Poggio Casabianca

MonicaRating, 5 stars6 months ago
What a great getaway!! We hope to make it back soon!
Guest favorite
Villa in Gaiole in Chianti
4.89 out of 5 average rating, 66 reviews

Podere il Trebbio

BarbaraRating, 5 stars4 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
Guest suite in Gaiole in Chianti
5 out of 5 average rating, 40 reviews

Independent cottage surrounded by nature

MariellaRating, 5 stars7 months ago
Really secluded location on top of a hill - just what we were looking for. Atmosphere in and around the cottage is calm and immensely beautiful. The pool is also great - we were lucky to have it to ourselves for most of the week. Highly recommend!

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

Capannelle4 locals recommend
Enoteca La Cantinetta Del Chianti S.A.S. Di Azzato Riccardo Michele4 locals recommend
Lo Sfizio4 locals recommend
Coop Informa3 locals recommend
Gaiole station5 locals recommend
Castello di Vertine4 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