
Pet-friendly vacation rentals in Montalcino
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Top-rated pet-friendly home rentals in Montalcino
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Pet-friendly house rentals

Casa Fattore - Tuscan countryside house
The stay at the Capocontro estate was very satisfying. The entire ancient hamlet is a jewel set in the countryside, with spectacular views of the woods of Val di Chiana. The accommodation is tidy and clean, picturesque and elegantly retro. Piero and Lella were very helpful in communications and suggestions for places to visit and where to eat. We loved the peace and quiet of the place, as well as the pool with a view. We stopped for a short time and the weather was a bit capricious, otherwise we would have enjoyed the farm's outdoors more. The only small flaw: the dishes and the fridge were not exactly immaculate, but nothing that can't be solved with a sponge. Super recommended for both a short and a long stay, so you can enjoy the quiet of the place and visit the surrounding area.

Holiday in the Chianti Senese
We were six adults, two children (3-year-olds) and one infant staying at the house for a week. It’s located in a secluded spot with a large garden and beautiful views of the Tuscan landscape. We used all of the five bedrooms upstairs and they were dark and cool. The kitchen and living room downstairs also stayed cool. Right outside the kitchen there’s a really nice spot that’s in the shade for the most part of the day, where we had most of our meals. This is a great place to relax and enjoy a dip in the pool. However, you definitely need a car to get around. The gardener came around several times a day to maintain the pool etc. We appreciated this, but might be good to know if you’re looking for complete privacy. We also had some issues with the bathrooms; one toilet and a shower didn’t work properly but were fixed within a day and this didn’t affect our experience. The washing machine didn’t work despite repeated attempts by the host to fix it. The barbecue is in the trash room.

Siena house with private garden 300m from the center
we had a great time in the private garden, then a gem ....our son was very happy with the separate room...in the center in 15 minutes on foot and a fantastic location to visit the area ...in the kitchen there are a lot of things from breakfast to a plate of pasta in case you arrive late...really great thanks carlo

Monte Regio
I was in Castiglione della Pescaia for a week with my family and dog. I had a really good time at Flavia's place, very clean, very nice location and well-kept garden. I have to say that it is the ideal place to relax and enjoy the tranquility of a vacation.

Farmhouse on a winery
Piero was very responsive. The property was very well equipped and located on beautiful land - surrounded by vineyards and open space across a valley. It was centrally located for our daily trips around Umbria and surrounding regions. It was very easy to get there from Rome airport. Loved the ability to buy / taste their wine which was wonderful. We would definitely stay there again in our travels through Italy.

[15 min da Montepulciano] Villa Chiara
Great location and the 2 full size bathrooms were nice!

Romantic cosy flat - Toscana Italy
This was exactly what we were looking for. Very peaceful and private with beautiful views. Lots of wonderful villages to visit and explore within a 30 minute drive. Norma made some great reservations for our anniversary dinner as well as a couple of great wine tours. She also gave us recommendations of which villages were best to visit and what to do there. We highly recommend doing the cooking lessons with her family. They are such a nice family and were very eager to show us how to cook a traditional Tuscan meal. Grandma really is an amazing cook. They even sat with us as a family to share what we had cooked. We have been to many AirBnB’s and Norma has been our best host by far. We would go back the next time we visit Tuscany. Dave and Liz

Typical stone farmhouse
Rossella's accommodation is comfortable, spacious, well structured and with everything you need. There were 6 of us and we had a great time, the rooms are very large, a nice garden that is very well maintained, as well as the fireplace and barbecue. We can certainly only recommend Rossella's place.
Pet-friendly home rentals with a pool

Ulivo - Charming apartment in the countryside
Staying at Simona's in Castiglione del Lago was magical!! The apartment, back yard, terrace and most of all the view were amazing!! Simona and Yens made us feel very comfortable and for me, Nahil and Cooper (their pups) added another level of warmth. Simona was always available if we had any questions, and we had many, and also made lots of suggestions for places to visit in the area and graciously willing to help us when we needed it. Grazie Simona, arriderci a più presto!!

Villa Piandarca "Glicine"-Tuscany-Chianti-pool
We had a great stay at Piandarca. Davide met us at check-in and showed us to our apartment. After check-in offered welcome drinks which we enjoyed in the nearby veranda. The entire property is beautiful, with plenty to explore. Very pet friendly as well (a few dogs, cats, chickens, etc.). Plenty of amenities available, including optional extra's. We took advantage of a cooking class on-site one rainy afternoon, which was led by Anna and Davide in their on-site kitchen. As a group of Americans who can't speak any Italian, taking a cooking class led by the lovely Anna who can't speak English, was a very entertaining evening (it's all in the hand movements!). Luckily we had Davide to translate for us when needed. Our stay was the first week in October, and while the pool was open, it was too cold to use.

Oleandro real farm house in the Tuscan countryside
Great family run place! Welcomed and greeted by Robert’s mother with a glass of wine that Robert made himself. Robert’s mom doesn’t speak any English but she was just so sweet and welcoming. The view is gorgeous and this place is a true agritiursimo with active vineyard and olive farms. Highly recommend.

CountryHouse: Romantic Studio Apt AirCo and pools
This is a jewel of a property. We were looking for a restful and relaxing place in the Italian countryside and this is it!! The amenities are great, Ilario and his wife and their son, Ricardo are lovely people and they are so grateful for your business and make you feel right at home! Our rental unit was spotless and the kitchen has everything you need to cook meals in house of which we did. The bed is very comfortable!! Even though you are out in the country you are still close enough for many of the beautiful sights of this part of Italy. We will definitely return!!

La Manonera Farmhouse "La Casa Rosa for families"
The only thing I could say negative is the lack of lighting for the kitchen and dining room. For the rest everything is perfect if you like the countryside decor:-)

Palazzi del Papa Farmhouse in Val d'Orcia, Pienza
Sabrina and her family were very accommodating and amazing host! The whole stay was superb In every way and my whole family as well as myself noted it couldn’t have been a better experience. From the amazing home cooked breakfast, to the cleanliness of the house, and the well thought out and led cooking class/dinner we enjoyed every aspect. Sabrina was very welcoming and made you feel like family :) I would highly recommend to anyone looking for a peaceful farm style stay that wants to experience Tuscany.

Vacation home Il piccolo rifugio
We had a lovely stay at Annalisa's. She had lovely attention to us and we thank her. She is also very responsive.

Villa Scianellone
We had an excellent time staying at this family home with an amazing view of Torrita di Siena. Great access to many popular hill towns (Cortona, Montepulciano, Pienza, Montalcino, etc). The house and property are beautiful, very private and populated with song birds and olive trees. The hosts are charming and very welcoming. They provided us with all the recommendations we needed and were readily available whenever we wanted to communicate with them. The house is well appointed and has multiple ways to cook from gas range to pizza oven and wood fired grill. I really liked using the giant pinecones as fire starter. We would definitely return and hope to. Such a precious slice of paradise.
Private, pet-friendly home rentals

Medieval Cottage near Cortona
Words can’t describe how beautiful this little restored village is - if you are seeking for a tasteful arranged place where you are all by yourself, surrounded by pure nature and a few other guests (that respect your privacy) this is where you should go. Highly recommended!!

La Palazzinetta bike and motorcycle
Everything is fine.

Back Home - Apartment in Pienza
Had all necessities needed. Helpful neighbors with check in and check out. Good location with free parking!

Robin - Rifugium
*Super super nice and relaxing* We had a great time and, above all, the relaxation we were longing for. The view was even more beautiful than we expected from the photos. Daniele was a perfect and very nice host. The accommodation inside and outside was also 100% what we had hoped for. Highly recommended!

Boggina. Private villa with pool, walk to village
Boggina was such a beautiful setting for our two families. There is no air conditioning, but the house kept beautifully cool by using the shutters in the day and using fans at night. The bedrooms were dreamy, full of trinkets from families past. The pool was fantastic and we enjoyed a lovely wine tasting tour! We basically didn’t want to leave! Many thanks team Marco 😊

Cozy house in the vineyard -Fogliadalloro-
quiet place both for us and for our dog who immediately made friends with the host's 2 dogs (Bretta and Charly)❤️❤️❤️, we will return as soon as possible!!!

VILLA ANNA, relax between Umbria and Tuscany
Great place as pictured. We had trouble finding it at first, but it was our GPS issues. Giulio was responsive when I contacted him. Unfortunately it rained every day we were there. So we didn’t get to enjoy the beautiful outdoor areas.

Pompana Rustic Charm Casale
One of the best places we have been at! so quite and relaxing. the house is so beautiful 😍 🤩
Quick stats about vacation rentals that are pet-friendly in Montalcino
Total rentals
530 properties
Nightly prices starting at
$55 CAD before taxes and fees
Total number of reviews
14K reviews
Family-friendly rentals
300 properties are a good fit for families
Rentals with a pool
250 properties have a pool
Rentals with dedicated workspaces
220 properties have a dedicated workspace
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- CavallinoMatto
- Marina di Grosseto beach
- Avignonesi Winery Fattoria Le Capezzine
- Santa Maria della Scala
- Cavallino Matto
- Kite Beach Fiumara
- Casa Barthel
- Tenuta Le Velette
- Podere La Marronaia, Sosta alle Colonne
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- Cantina Stefanoni
- Madonna del Latte
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- Cala Di Forno
- Riva del Marchese
- Ugolino Golf Club
- Cantina di Montefiascone Soc.Coop.Agr. - Punto di Vendita
- Cantina Contucci
- Pubblico Palace
- Cantina Winery, Cellar and Farm Fattoria Santa Vittoria
- Castiglion del Bosco Winery
- Podere Il Cocco
- Golf Club Toscana
- Casa Del Cioccolato Perugina
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