Monthly Rentals in Castiglion del Bosco

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

Nearby monthly rentals

Guest favourite
Condo in Castelnuovo dell’Abate
4.91 out of 5 average rating, 288 reviews

La Casetta di Brunello, very panoramic with terrace

JannineRating, 5 stars2 weeks ago
Francesco was the perfect host very communicative and responsive when needed - the unit was spotless and nice decor - loved being in the little town walking to the 3 lively restaurants, grocery and coffee shop not to mention the fabulous vineyards that surrounded the flat - we did some wonderful walks and did side trips to cute little towns - Would recommend highly
Top Guest favourite
Farm stay in Murlo
4.97 out of 5 average rating, 164 reviews

Country house near Siena

SeleenRating, 5 stars1 month ago
My best friend and I LOVED our stay here! The location provided an excellent base for all the places we wanted to visit during our 10-day trip to Tuscany. It was so quiet, peaceful, and relaxing! We also appreciated the option of requesting meals, and the host even surprised us with a special 50th birthday meal for my friend and me - totally unexpected and so thoughtful! The space was clean, comfortable, and had everything we could have needed. The private patio space was also great - we spent several evenings out there eating, relaxing, and enjoying a glass of wine. We also did a cooking class with Michela's brother, Emanuel, which was a lot of fun! I love to cook, so that was special for me. Every person we encountered on this property was so kind and warm and inviting. I will absolutely come back someday! Thank you, Michela & Emanual, for your hospitality!
Guest favourite
Villa in Buonconvento
4.95 out of 5 average rating, 57 reviews

Bellagatta, an Enchanting spot in Val d'Orcia

MartinRating, 5 stars8 months ago
We had an amazing four weeks staying at Bellagatta, using it as a base to explore Tuscany & surrounds, and it met all our expectations and more. Bellagatta is a positioned on a hilltop with stunning 360 degree panoramic views, more beautiful than the photos. The annexe that we stayed in was exceptionally clean and comfortable and well fitted out. Air con was useful on the first few days of our stay which were very hot. The property is well situated, 10 minute drive into Buonconvento (not quite an easy return walk up the hill!) which was convenient for restaurants & shopping. Gaetano was a most delightful host, very welcoming, & always taking interest in which towns we were travelling to and providing useful tips for our visits. His property manager, Susil, was also readily available and looked after us with anything we needed , even providing fresh eggs, vegetables & olive oil from the property. Highly recommended!
Top Guest favourite
Home in Montalcino
5 out of 5 average rating, 125 reviews

Montalcino Townhouse with Private Garden & Spa

JenniferRating, 5 stars3 days ago
We thoroughly enjoyed our stay in Lisa’s Montalcino Townhouse!! She met us upon arrival and gave great recommendations for wineries and restaurants. Attention to details in the home made it perfect and relaxing! Loved the back yard/patio in the evenings especially. She left us 2 bottles of wine, breakfast items, a basket of EU chargers and cords, and robes for the hot tub! It felt like home away from home and we hope to have a return visit! Thanks for thinking of everything we could need for our comfort and stay!

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.*

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Work-friendly spaces for digital nomads

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