
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
my partner and I stayed 2 weeks during the Christmas holidays. The apartment was very clean , cozy and related to all the comforts. Perfect location for a couple near Piazza del Campo, a 10 12-minute walk away. Carlo and Maria Teresa were two perfect hosts and made our stay perfect

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!

Comfortable house Greve in Chianti
Our stay here was perfect! It is such a lovey Tuscan place that made us feel right at home. It is a short 10 minute walk from the center of Greve and it provides lovely views of the surrounding areas. Luana is very kind and quick to respond to our questions. We highly recommend this place for future guests! The only advice we can give for guests staying anywhere in Tuscany is to pick up some mosquito spray - they are everywhere.

Potentino Garden
Quiet place surrounded by nature. Quiet owners and always ready to give info. I recommend a visit to the surroundings of Monte Amiata
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.

Casa al Fiume - Villa with exclusive pool
We thoroughly enjoyed our stay and highly recommend. Barbara was gracious and great to work with. The house was charming and just as great as it looks on the listing. The property and grounds are amazing. The town nearby was fun to visit with everything you need and lots to see. You are also in easy driving range of the other main Tuscany towns. Overall an excellent experience. Thank you Barbara!

Castellin di Bocco Tuscan countryhouse with pool
We absolutely loved our stay at Castellina Di Bocco and were sad to leave! The house was extremely clean, well furnished and inviting whilst Giulia was a generous host. From the moment we set foot on the property, we were warmly welcomed by three wonderful dogs (Thor, Pagnotta and Menta) that would become best friends with our children for the entirety of our stay. The house was great for our family of four with two living areas. Set high up on a hill, overlooking the township of Castiglion Fibocchi, you’re spoiled by a view that rivals the nearby Big Bench tourist attraction! The town itself is accessible by foot but as a family we needed to drive everywhere - Google maps guides the way perfectly. We had intended on visiting vineyards across Chianti but this was a challenge. We opted for close by wineries instead and a stop over in nearby Montepuliciano which did not disappoint. We missed out on using the pool due to bad weather but it looks perfect for warmer weather!

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!!

Holiday Home in Umbria with shared pool
Very peaceful place, just what we needed. Paolo was very friendly and helpful.

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:-)
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!!

3bdr deLux Villa in Montepulciano Tuscany,Top View
When you stay with Fulvia you feel like you are a long lost relative coming for a visit! The surroundings are calming and picturesque and the home has a wonderful history as a restaurant. The house is very warm and inviting and spacious but maybe not good for those who crave minimalism. The AC works well and although there is no pool, the hot tub became a nice cool soak at night. She gave us a cooking class which was a wonderful experience and she arranged the menu around our likes and dislikes. She also had great recommendations for towns to visit and places to eat and also organized a wine tour close by. She and her family live on the ground floor, but it still feels private in the outdoor areas. We stayed there after a few days in Florence on our way to Rome and it was half way in between, so it was great location to visit towns on the way in and on the way out.

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 😊

Vacation in tuscan hills.
Stefano was a great host during our stay, extremely helpful and attentive. Her vacation home is a dip in the heart of Tuscany, it allowed us to return at slower pace and punctuated by the wonderful nature that surrounds it. The location is strategic, just minutes from Cortona and the main streets to reach Tuscany at every point. We highly recommend Stefano and his home.

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.

Stunning Villa with heated pool
Alina was extremely helpful and always willing to help. The house was perfect for our family of 10. The kitchen was well equipped and the house was very clean. We would definitely recommend it and looking forward to staying here again in the future.
Quick stats about vacation rentals that are pet-friendly in Montalcino
Total rentals
510 properties
Nightly prices starting at
$56 CAD before taxes and fees
Total number of reviews
14K reviews
Family-friendly rentals
290 properties are a good fit for families
Rentals with a pool
240 properties have a pool
Rentals with dedicated workspaces
210 properties have a dedicated workspace
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- CavallinoMatto
- Avignonesi Winery Fattoria Le Capezzine
- Tenuta Le Velette
- Riva del Marchese
- Cantina de' Ricci
- Cantina di Montefiascone Soc.Coop.Agr. - Punto di Vendita
- Pubblico Palace
- Cantina Stefanoni
- Cantina Winery, Cellar and Farm Fattoria Santa Vittoria
- Santa Maria della Scala
- Podere Il Cocco
- Cantina Contucci
- Madonna del Latte
- Ugolino Golf Club
- Golf Club Toscana
- Podere La Marronaia, Sosta alle Colonne
- Marina di Grosseto beach
- Cala Di Forno
- Kite Beach Fiumara
- Cavallino Matto
- Castiglion del Bosco Winery
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