Monthly Rentals in San Regolo

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

Nearby monthly rentals

Superhost
Home in Rietine
4.85 out of 5 average rating, 209 reviews

Gaiole in Chianti Poggio Casabianca

AlexRating, 5 stars1 month ago
Valeria and Simone have a super nice and clean apartment! We felt very comfortable right from the beginning. The apartment offers a great starting point for numerous hikes and excursions. During our stay, we always got good tips and advice from the two. Our dog also felt very comfortable and since the property is completely fenced, he was able to move freely. We would come back back. It was an incredibly beautiful time!
Top guest favorite
Villa in Gaiole in Chianti
5 out of 5 average rating, 5 reviews

Citerna's Hut

CyrillRating, 5 stars1 month ago
From first contact to departure, communication went absolutely smoothly. The house is beautifully, stylishly decorated and fantastically located on a winery. The view over Tuscany is simply wonderful – a real highlight! We felt very comfortable from the first moment. Excursions by mountain bike are also possible directly from the house, which was a big plus for us. For those looking for a relaxing and comfortable holiday in fantastic surroundings, this accommodation is absolutely recommended. We'll be happy to come back on occasion!
Guest favorite
Vacation home in Castelnuovo Berardenga
4.9 out of 5 average rating, 78 reviews

PIERFANTINI private Chianti house ♿️ 🏊‍♂️ 🐶

KellyRating, 5 stars1 day ago
The home is beautiful, clean, peaceful. We loved the pool! The location was a bit challenging to get to, things that are close in kilometers take a long time to get to because of narrow, twisty roads. The upstairs apartment had AC, but the bottom one did not. We stayed cool anyway with all the windows open! All five of us loved the water pressure in the showers! eating our breakfast out on the pergola each morning, watching the birds swoop in for drinks in the pool was delightful! It felt safe and peaceful!
Superhost
Condo in Castelnuovo Berardenga
5 out of 5 average rating, 5 reviews

San Rocco – Bellavista – Castello di Bossi

GaiaRating, 5 stars10 months ago
The property is wonderful, surrounded by greenery and with a pool with an incredible view. The room was super clean and with all possible comforts. We interacted a lot with a very kind lady at the reception, very friendly and helpful. The wine we tasted was also exceptional , it's worth staying there for just one night! Extremely recommended

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.
*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