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Family-friendly vacation rentals in Montemerano

Find and book unique family-friendly homes on Airbnb

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Popular amenities for Montemerano family-friendly rentals

Family-friendly home rentals with a hot tub

Superhost
A terrace features a simple table set with two white chairs, offering a view of the lush greenery beyond. An awning provides shade, while a blue sky with scattered clouds creates a serene atmosphere.
Apartment in Principina a Mare
5 out of 5 average rating, 6 reviews

Romantic Studio with Park View

ClaudiaRating, 5 stars3 days ago
My husband and I stayed for a week and we had a great time. The area is quiet, great for resting, and it is close to the beach. Clean accommodation and with everything you could need. The girls were all always very helpful and welcoming. I recommend it to those who want to enjoy days to recover, without the chaos of tourism.
Top guest favorite
A rustic stone farmhouse is surrounded by lush green lawns and vibrant flower beds. Large glass doors lead to the garden, offering a view of the inviting outdoor space. Trees and natural vegetation enhance the serene countryside setting under a clear blue sky.
Farm stay in Pari
4.8 out of 5 average rating, 89 reviews

la Casa between Siena and Grosseto

RobertRating, 5 stars3 months ago
Lorenzo's farm is a wonderful hide-a-way! A great place to escape the world! It is about a 10–15 minute drive from Pari, but for us this was exactly what we wanted. The surroundings are spectacularly beautiful. The vineyard was beautiful but expect to get a little muddy walking through it. The town of Pari is also idyllic. The views over the surrounding valleys are awe inspiring. There is only 1 grocery and a couple of restaurants in town, but there are many more if you are willing to drive an additional 15-20 minutes. We spent one day going to the Bagni di Petriolo hot springs. We paid the fee to go in the building, although if you stay outside, it is free. It was well worth the money, and it was a very relaxing experience. It was about a 15-minute drive from Lorenzo's farm. Lorenzo was a very responsive host. He always answered quickly on What'sApp. He provided great recommendations for what to do in the local area. We had dinner one evening and it was delectable!
Guest favorite
The villa showcases a charming stone facade, complemented by a covered terrace that features stylish outdoor seating. Lush green grass surrounds the property, while vibrant planters add a touch of color. The expansive view of the countryside is visible against a backdrop of clear blue skies.
Villa in Allerona
5 out of 5 average rating, 34 reviews

Vakantievilla Farmhouse Dolci Hills

JeffRating, 5 stars1 month ago
This was the finest AirBNB home that we've ever stayed in. Every room was immaculate, the views were incredible (private and among vineyards, you can see for miles), every appliance and fixture seemed new. Everything was anticipated to make the stay perfect.....a refrigerator, bathroom and shower at the beautiful pool, pool towels in each bedroom, etc. As soon as you walk into this house, you are going to go "wow", and for good reason. Francesca came and cooked us a delicious local dinner and did some light grocery shopping for us.....all for an unreasonably LOW fee. We had another chef team come in on another night. We also visited a local winery where we had a fantastic, private wine tasting tour and lunch (Tenuta Vitalonga) and followed that up with touring Orvieto and having dinner at a very unique restaurant (Le Grotte del Funaro). Make sure you have a car or are using a bus/limo service for your transportation, nothing is walkable from this beautiful private house.
Guest favorite
The villa is set against a backdrop of rolling hills and gardens. A large pool is visible in the foreground, featuring a circular shape and steps leading into the water. The stone structure with a tiled roof complements the natural surroundings.
Villa in Montepulciano
4.91 out of 5 average rating, 126 reviews

Villa in Montepulciano with a Pool

SantiagoRating, 5 stars1 week ago
We just checked out of this wonderful villa today, and it has truly been one of the most special places we’ve ever stayed. We arrived with my husband’s parents, my husband, and our toddler, and from the moment we got there, everything exceeded our expectations. Alex greeted us warmly, gave us a tour of the villa and the property, and provided detailed printed information about nearby restaurants, supermarkets, cafés, bakeries, and wine tours. The property also produces its own wine, which was available for purchase and could be conveniently delivered to our villa during our stay. Alex shared his contact number and made himself available in case we needed anything—which we really appreciated. One of the highlights of the property was the stunning infinity pool overlooking the vineyard and offering breathtaking views. It was the perfect setting to disconnect and truly live in the moment. The air conditioning and hot water worked perfectly. Thank you Alex!
Top guest favorite
An ancient stone well is positioned in the foreground, showcasing intricate carvings and a circular top. In the background, an impressive stone building features a tower and windows, accented by flags. The scene captures the historical charm of Montepulciano's central square under a clear blue sky.
Apartment in Montepulciano
4.92 out of 5 average rating, 142 reviews

Charming House in Montepulciano

KirstenRating, 5 stars3 months ago
Our family loved staying in Fernanda’s apartment! My husband and I had visited Montepulciano two years ago, stayed at Fernanda’s place and loved it so much we came back with our three boys. Everything is so lovely and welcoming and Fernanda is the best hostess. She even made local dinner reservations for us. Thank you for everything, Fernanda!!
Superhost
The stone villa is framed by lush greenery and overlooks a tranquil swimming pool. Large glass doors reflect the natural surroundings, enhancing the connection to the outdoors. The serene atmosphere is complemented by the native plants situated throughout the landscaped grounds.
Vacation home in Saturnia
4.79 out of 5 average rating, 14 reviews

Tuscan country villa with private swimming pool

MadeleineRating, 5 stars3 weeks ago
What an amazing and beautiful home! We loved our stay here with our family and enjoyed a delicious meal prepared by Susanna and Tiziano for my sisters birthday dinner. Gorgeous location, great pool, really fun art all over the entire house that’s been restored but full of character. Plus it’s just 5 mins and your at the hot springs or restaurants. We can’t it to go back!
Top guest favorite
An outdoor terrace features a glass dining table set for four, complemented by green chairs. A bottle of wine and glasses rest on the table, with vibrant red flowers adding a pop of color. A scenic valley view showcases rolling hills and a distant mountain.
Condo in Chiusi
4.95 out of 5 average rating, 148 reviews

La Terrazza su Chiusi - panoramic apartment

DianneRating, 5 stars1 month ago
Chiusi may not be a major hilltop town but it is very special because it lacks the tourists. We had plenty of restaurants to visit in the week we stayed, and lots of historic sights to see. You do need a car to visit surrounding towns but the peacefulness of Chiusi makes it delightful. Rafaels place is perfect with the balcony and sublime views. He was an exceptional host who did not impose on our privacy but always friendly and helpful. I would highly recommend this place and town.
Guest favorite
A refreshing swimming pool is surrounded by lounge chairs on a deck. Lush greenery lines the fence, providing privacy. A stone wall with a traditional roof is visible in the background, contrasting with the bright blue sky overhead.
Townhouse in San Quirico
4.92 out of 5 average rating, 59 reviews

Tuscan Countryside Retreat with Heated Pool

GiancarloRating, 5 stars3 weeks ago
Amazing 2 levels house with private pool and everything and anything you might need. Brand new appliances, beautifully furnished, plenty of bathrooms, quiet area. The hosts are extremely friendly and helpful. Plenty to do in the surroundings. We highly recommend it!!

Family- and pet-friendly home rentals

Guest favorite
The bedroom features light-colored walls and wooden flooring. A spacious bed is paired with a smaller bed suitable for a child. Natural light enters through a window adorned with light curtains. A mirror and dark wooden furniture complement the room's decor.
Home in Bagnore
4.93 out of 5 average rating, 177 reviews

La Casa del Valle

MattiaRating, 5 stars3 days ago
The accommodation is wonderful, comfortable, very clean, and the host was very kind also with regard to the flexibility of the check-in! A magnificent place and 100% recommended
Top guest favorite
A warm living space features wooden beams and stone walls. A cozy sitting area is arranged with soft seating, and a dining table is placed nearby. The fireplace adds character, while large windows offer views of the surrounding landscape and invite natural light.
Vacation home in Bolsena
4.98 out of 5 average rating, 172 reviews

The view with a room - Piazza dei Monaldeschi

EricaRating, 5 stars2 weeks ago
Our stay at Giulio & Emanuela’s place was truly magical. Giulio was very proactive and responsive with giving us directions and instructions on how to get there. They were always there for us if needed and extremely friendly, welcoming, and helpful. Could not rave about this gem more. The place and the surrounding neighborhood are something special, and I hope to be back again someday!
Top guest favorite
An aerial view highlights a stone farmhouse nestled within lush greenery, surrounded by mature trees. The structure features a terracotta-tiled roof and a charming porch. A pathway leads to a smaller stone building, providing a sense of harmony with the natural landscape.
Villa in Sarteano
4.97 out of 5 average rating, 125 reviews

Stone farmhouse in the Val d'Orcia

Theng JuhRating, 5 stars2 weeks ago
Stefania was super nice to wait for us despite we were later for 3 hours. Her house was very beautiful and lots of space for 10 of us. Everyone can have their own space on the balcony or terrace. Can have BBQ too. House was very well equipped with everything that we expected. Had a wonderful time. Thank you.
Guest favorite
A hammock hangs gently between trees in a spacious garden, surrounded by large volcanic rocks. Sunlight filters through the lush greenery, creating a serene outdoor space ideal for relaxation. Wooden stools and natural landscaping enhance the tranquil atmosphere.
Home in Vivo d’Orcia
4.95 out of 5 average rating, 139 reviews

At the Sassone Holiday Home, Val d'Orcia, Tuscany

DianeRating, 5 stars3 weeks ago
We loved our time at Luca's place. We visited Tuscany with our college aged kids. Luca's house was comfortable and welcoming. We went out for a few meals, but also enjoyed preparing foods in the wonderful kitchen. We ate dinners together and played board games on the spacious kitchen table. It was homey. We called it "cucina magica" because all of the foods we cooked came out so perfectly. This is a wonderful home in a lovely setting with hiking trails from the backyard. We spent several mornings at the nearby hot springs. What a treat! Luca was communicative and helpful with all of our questions.
Guest favorite
An aerial view captures the agriturismo's spacious grounds, featuring a inviting swimming pool surrounded by sun loungers. Lush green lawns and well-maintained gardens frame the rustic stone buildings, which offer a peaceful retreat amidst scenic farmland.
Farm stay in Pienza
4.94 out of 5 average rating, 172 reviews

Agriturismo Palazzi del Papa Val d 'Orcia Pienza

EleanorRating, 5 stars1 month ago
We had an amazing week long stay!! Sabrina is a fantastic host! The apartment was SO clean and comfortable and had everything we needed. Breakfast each morning was very yummy and fresh! We did the dinner one night and it was so amazing! Location is great too. Easy drive to many close by towns, grocery stores, and restaurants. The property is beautiful with lots of flowers. A little too cold for the pool during our stay but our kids loved the swing set and teeter totter. Absolutely recommend staying here!
Top guest favorite
A panoramic terrace is depicted, featuring two rattan chairs and a small round table. A pitcher and cups are placed on the table, with vibrant flowers adorning the railing. A clear sky and rolling hills are visible in the background, enhancing the serene outdoor setting.
Condo in Montepulciano
4.98 out of 5 average rating, 320 reviews

Residence In cerca d'Autore

WilliamRating, 5 stars2 weeks ago
We absolutely loved our week stay here and couldn't have been happier. It was spacious, beautifully furnished and steps away from nearby restaurants and shops. Best of all was the huge terrace –it had insanely gorgeous views of the Tuscany landscape which never got old. Looked forward to our morning coffee and early evening aperitivo with the views of the Tuscan landscape. The views were fabulous (including a nice sunrise if you're an early riser)! We didn't have reservations for dinner one night and wandered just across the street to Rosso Rubino Trattoria. The owners could not have been nicer, and the food was delicious. Berardino graciously held us a spot in the coveted "Parcheggio 7" and drove our luggage up the hill upon arrival. He gave us a tour of the apartment and several great recommendations. It was a very welcoming start to our stay. It was the perfect base for exploring Tuscany and hope to return soon.
Top guest favorite
A wooden deck is surrounded by colorful flower pots and offers a table set for outdoor dining. The area is shaded by a pergola, providing a relaxed space to enjoy views of rolling hills and greenery in the distance.
Apartment in Montepulciano
4.92 out of 5 average rating, 157 reviews

Romantic apartment in a quite place

MelissaRating, 5 stars1 week ago
We had such a lovely stay at Paolo's place in Montepulciano! The location was beautiful and the pool was a highlight! They also had a little playground which was great for our toddler. Paolo was very welcoming and gave great recommendations for places to eat. They grow olive trees on the property, so they provided a little bottle of homemade olive oil in the kitchen, which was delicious! Thanks for having us and we hope to come back in the future!
Guest favorite
An inviting living space features a cozy fireplace framed by a rustic stone wall. Natural light filters through floral-patterned curtains, illuminating a spacious sitting area with a two-seater sofa. A four-poster bed draped in sheer fabric enhances the room's charm, complemented by decorative lanterns.
Apartment in Caminino
4.91 out of 5 average rating, 168 reviews

Pieve di Caminino Historic Farm

ChrisRating, 5 stars1 month ago
Emy was a friendly and accommodating host. The home far exceeded our expectations. Thank you very much Emy!

Family-friendly home rentals with a pool

Superhost
A rustic stone house is set against a backdrop of lush trees, featuring a terrace with sun loungers arranged around a central swimming pool. The building's earthy tones complement the natural surroundings, while a chimney adds a touch of charm to the exterior.
Cottage in Roccalbegna
4.91 out of 5 average rating, 77 reviews

Small cottage, swimming pool entirely private use

MilliRating, 5 stars1 week ago
What a fabulous place - if you want to escape from it all, this is the place to come! Love the private pool too! Air conditioning in the bedroom was very good and appreciated. Olga and Max were very accommodating and answered questions very quickly. Maybe consider installing a BBQ outside the house otherwise could not fault it and we cannot wait to return!
Superhost
A serene hillside retreat is set amidst lush vineyards, showcasing a rustic building adjacent to a sparkling pool. The landscape features rolling hills and a vibrant sky at dusk, providing a tranquil backdrop that emphasizes the peaceful surroundings.
Farm stay in Castelnuovo dell’Abate
4.88 out of 5 average rating, 68 reviews

CasaVIOLA Brunello vineyards

IhorRating, 5 stars2 weeks ago
This is an incredible villa in Tuscany, my girlfriend and I are excited about our vacation here! It’s a pity that we booked for only two days, next time we will book for a longer period. Definitely recommend!
Top guest favorite
A hammock is gently suspended between wooden posts, surrounded by a lush green lawn and trees. Colorful flower pots are positioned nearby, and charming rustic buildings are visible in the background under a clear blue sky.
Farm stay in Magliano in Toscana
5 out of 5 average rating, 31 reviews

agriturismo Torribasse

SophieRating, 5 stars9 months ago
The property is very nicely located in the middle of the countryside, the sea can be reached in about 20 minutes by car. Enrico gives many tips for excursions and activities nearby upon arrival. The place itself was clean and well equipped, you have everything you need.
Superhost
Villa in Seggiano
5 out of 5 average rating, 8 reviews

Case Bianchi

JulianeRating, 5 stars3 weeks ago
We had a great time! Super clean and spacious house with a nice outdoor area. Constanze was always super helpful and responded quickly. But be aware, you need a car and restaurants and supermarkets are not in walking distance. Thanks a lot for having us.
Guest favorite
The outdoor area features a serene swimming pool surrounded by a natural landscape. Lush greenery and blooming flowers enhance the setting, while a wooden deck offers space for relaxation. In the distance, hills create a tranquil backdrop, emphasizing the beauty of the surrounding nature.
Cottage in Santa Fiora
4.86 out of 5 average rating, 22 reviews

Il Seccatoio – a stone house with a panoramic view

FrancescaRating, 5 stars1 month ago
My husband and I stayed two nights in the Chestnut Dryer of the Podere di Maggio. What can I say? A real paradise: nestled in a wonderful valley with Mount Amiata in front of it and the beautiful medieval village of Santa Fiora. We could not ask for more: wonderful structure, well cared for, in detail, priceless peace. The hosts were great, hospitable, and really made us feel at home. In short, everything is perfect, nothing is missing, of course you have to love bucolic life like us ! The only downside? Two nights were too short and we'll definitely be back . Thanks Peter , Rita and sweet Noemi. See you soon
Guest favorite
A private swimming pool is surrounded by lush greenery and flowering plants, offering a serene retreat with expansive views of the rolling hills and mountains beyond. Two lounge chairs are positioned by the pool, inviting relaxation in a tranquil outdoor setting.
Cottage in San Casciano dei Bagni
5 out of 5 average rating, 17 reviews

Toscana, Country house with exclusive pool

ThomasRating, 5 stars1 month ago
The view is stunning. The place is very private. Leonardo is very responsive. Definitely worth visiting La Pace, a lovely restaurant 5 mins walk away. 10/10 recommend
Guest favorite
A heated swimming pool is framed by a tiled apron, set against a backdrop of lush greenery and a partially shaded pergola. The clear blue water contrasts with the earthy tones of the surrounding landscape, inviting relaxation in a tranquil outdoor setting.
Villa in San Casciano dei Bagni
4.98 out of 5 average rating, 64 reviews

Luxury Tuscan countryside villa with pool/WiFi/AC

Devon And DavisRating, 5 stars1 week ago
I cannot say enough about our trip to Martino’s villa. What a lovely villa in the cute town of San Casciano dei Bagni. We had a great family vacation, enjoying some of the smaller towns and a visit to Montepulciano . We enjoyed Eleanor’s cooking for us two nights- what an amazing chef! Martino was very responsive and helpful when we needed something. I hope we can return one day!
Top guest favorite
A stone house is observed in the background with a sloped roof and a covered patio area. In the foreground, a rectangular swimming pool reflects the sky, surrounded by a grassy area and lounge chairs. Trees are visible, adding greenery to the serene setting.
Villa in Sorano
4.98 out of 5 average rating, 97 reviews

Poggio Bronzino, Montebuono – Sorano (Gr)

MarleneRating, 5 stars9 months ago
Very nice and quiet place to stay, perfect for families. The pool was great, the house large enough for 4 adults + toddler, everything very clean, very well equipped kitchen. The pizzeria in the village is very good, the other larger places are a bit far away. All in all, a beautiful place to stay

Quick stats about vacation rentals that are family-friendly in Montemerano

  • Total rentals

    10 properties

  • Nightly prices starting at

    G$16,737 GYD before taxes and fees

  • Total number of reviews

    540 reviews

  • Wifi availability

    10 properties include access to wifi

  • Popular amenities

    Kitchen, Wifi, and Pool

  • Local attractions

    Vecchia Osteria Cacio e Vino, Trattoria Ristorante Enoteca La Cascia, and Osteria Passaparola Nell'Antico Frantoio

Destinations to explore