Monthly Rentals in Castellina in Chianti

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

Nearby monthly rentals

Guest favourite
Flat
4.85 out of 5 average rating, 52 reviews

Gelsomino

IlariaRating, 5 stars3 months ago
Warm, cozy, clean place in a great location with a view of the Tuscan hills. Super helpful host and quick to respond, highly recommend!
Top guest favourite
Barn
5 out of 5 average rating, 19 reviews

Cipressini 2 - pool and amazing views

WilliamRating, 5 stars2 weeks ago
Absolutely stunning Tuscan Barn renovation with an incredible view, stunning sunsets, and an at home feel! The Barn was beautiful with hardwood doors and cabinets, marble countertops, a large wood burning fireplace (was one of the highlights), updated bathroom, and very comfortable bed! The ideal place to explore Tuscany from, surrounded by Wineries and Local restaurants, and stunning views. Only a 40 minute drive to Florence or San Gimignano, and 25 minutes from Sienna, makes this place the ideal location to explore this beautiful part of the country! A car is highly recommend if staying here. Maria is absolutely lovey and had so many wonderful recommendations, from day trips, to wineries, and restaurants in the local town to the surrounding countryside. Take her recommendations, as we tried to visits as many as time allowed and were never disappointed! Would highly recommend a stay here if you’re looking for that perfect Tuscan getaway! Will be back!
Guest favourite
Barn
4.97 out of 5 average rating, 34 reviews

Apartment T3

RoryRating, 5 stars1 month ago
Great location if you are looking for a little solitude, close enough to the town to walk if you wanted where there were a few dining options even in the off season.
Guest favourite
Flat
4.86 out of 5 average rating, 14 reviews

At the Poggio della Capannina in Castellina in Chianti

MaureenRating, 5 starstoday
we had a lovely stay here. Very comfortable beds, and well stocked with tea and coffee and some treats. Thanks Stephania e Laura

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 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 Castellina in Chianti's top sights

Antica Trattoria la Torre20 locals recommend
Coop Castellina11 locals recommend
Rental Chianti 50011 locals recommend
Gelateria di Castellina10 locals recommend
Il Fondaccio Dai Dottori9 locals recommend
Ristorante Albergaccio di Castellina9 locals recommend

Destinations to explore

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