
Monthly Rentals in Madonna di Pietracupa
Discover long-term rentals that feel like home for stays of a month or longer.
Nearby monthly rentals
Top guest favorite

Vacation home in San Donato In Poggio
4.98 out of 5 average rating, 134 reviewsChianti Penthouse with panoramic View & Pool
Jens & KatjaRating, 5 stars2 weeks ago
Our stay in Tuscany was absolutely unforgettable! The peaceful surroundings and stunning views made it the perfect getaway. The small village nearby was charming, with some fantastic restaurants and a supermarket just a short walk away. The scenery all around was simply breathtaking. Giada was super friendly and incredibly responsive — they even helped us rent bikes, which made exploring the area even more special. Everything was clean, well-equipped, and comfortable. We had a wonderful time and would love to come back!
Guest favorite

Apartment in Badia a Passignano
4.91 out of 5 average rating, 123 reviewsChianti, Country house with pool
AlexanderRating, 5 stars6 months ago
Claudios apartment is more a house in house which is part of a former farm of the 19th century. It's located on a hill in the tremendous Chianti region, where we enjoyed the most beautiful sunrises and sets. You need to be aware of the fully off-road track from Badia to the house, taking between 15 and 20 min (4WD not mandatory). Every trip to any restaurant, supermarket or anything else takes time but on the other hand side we enjoyed the privacy, silence and nature of this courtyard. The house itself was super tidy and clean and equipped with love. There was absolutely nothing we missed. And with the horseback riding opportunity since beginning of the season, just 5 min by feet at the next farm, our kids had also a lot to explore. Thanks a lot for the kind hospitality, warmly recommended.
Superhost

Castle in Barberino Tavarnelle
4.87 out of 5 average rating, 106 reviewsSuite in Chianti
AnnRating, 5 stars3 weeks ago
Classic, fairytale stay in Tuscany in the heart of wine country. This place seemed too good to be true – it wasn’t. Combines what-its-like-to-live-in-Italy with European luxury and unique peek into how Italian families are preserving history in a storied land. Parts of this estate date to 1100 and the property has been in the family for many generations. You can see and feel the great care they take of their home and the deep pride they experience sharing it with their guests. Scrumptious interior as modern, luxury amenities embellish this of-the-ages castle -- massive stone fireplace, wood beam ceiling, entry door, handcrafted shutters, pressed-glass interior doors. Extremely private and tucked away, teaming with birds and wildlife. Being in the space was inspiring and of another era! If you get a chance to stay here, don’t pass it up. Next trip, I'm bringing all my friends and family to fill the place up to the top of the ramparts! Thank you Pietro and family for a fabulous stay.
Guest favorite

Condo in San Donato
4.93 out of 5 average rating, 70 reviewsApartment Fiorenza in Chianti Classico
DanielaRating, 5 stars1 month ago
We were very satisfied with our choice. The apartment was perfect and matched the description. It was clean, well decorated, and very comfortable, with all the amenities needed to feel at home. Perfect location - in the heart of San Donato, just a few steps to a pizzaria and a trattoria, but quiet and peaceful. Wonderful hosts - warm, friendly and hospitable.
The comforts of home and great monthly rates
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.*
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*Some exclusions may apply in certain geographies and for some properties.