Monthly Rentals in San Regolo

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

Nearby monthly rentals

Enter dates and number of guests to see the total trip price including additional fees and taxes, and rounded up to the nearest integer.

Top Guest favourite
Apartment in Villa a Sesta
4.93 out of 5 average rating, 208 reviews

At Paola's in Chianti

RyannRating, 5 stars2 weeks ago
Paola’s place was an incredible getaway for the two of us - we played fetch with Nilde in the garden, had a night where Paola taught us to make pasta and tiramisu, and enjoyed the best sunsets. If you get a chance, definitely check out Osteria Alla Villa for dinner. We will definitely be back! Thank you Paola for the hospitality and making our first trip to Tuscany so special.
Top Guest favourite
Apartment in San Gusmè
4.99 out of 5 average rating, 377 reviews

Beautiful medieval village!!!

AliRating, 5 stars3 days ago
Wow what a fabulous stay ! San Gusme and its surrounding area is beautiful and we felt so lucky to be able to stay in San Gusme itself . Elvira was super helpful and had great local recommendations for wine tasting etc .
Guest favourite
Holiday home in Castelnuovo Berardenga
4.89 out of 5 average rating, 75 reviews

PIERFANTINI private Chianti house ♿️ 🏊‍♂️ 🐶

KellyRating, 5 stars1 week ago
Exceptional property! Epitome of a Tuscan villa. Spacious, beautiful grounds, great pool and so many amenities! Absolutely everything you could ask for in the kitchen, incredible bathrooms - one with a sauna. Three apartment layout was perfect for our larger group - three couples had privacy and a large common space for gathering. Short drive to several cute towns with grocery shopping and restaurants. Pierfantini is a great base for exploring the Toscana region.
Guest favourite
Home in Rietine
5 out of 5 average rating, 12 reviews

House in the Small Village

MarcelloRating, 5 stars4 weeks ago
Everything is perfect. Spacious apartment and located in a very quiet hamlet

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. San Regolo
  6. Monthly Rentals