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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 bright living area features a wooden table with a wine bottle and glass in the foreground. Large glass doors open to a patio, revealing countryside views and two outdoor chairs facing the tranquil landscape.
Apartment in San Giovanni d'Asso
5 out of 5 average rating, 20 reviews

Podere Ferranino #Cimabue Townhouse

CoreyRating, 5 stars2 weeks ago
Amazin relaxation! Great space, gorgeous view, and they even have an electric charging station!
Guest favorite
A charming corner of the property is adorned with bright pink flowers and framed by the rustic building. The view extends to rolling hills in the distance under a clear blue sky, with greenery surrounding a stone patio area in the foreground.
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!
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, 144 reviews

Charming House in Montepulciano

AngieRating, 5 stars6 days ago
We had the most lovely stay at Fernanda’s and definitely want to come back someday! It was the best of our 3 week trip. From the moment of booking she was super responsive and helpful. The place was large and felt like home—great for us and adult son. Of course the views were the best and wish we could have just sat in front of the window for 3 days. It’s in quiet and peaceful part of village which was also perfect after busy Rome and Florence.. Grazie Mille Fernanda for your kindness.
Superhost
The image displays a stone villa set against a clear blue sky, with a spacious pool in the foreground. Lush greenery surrounds the pool area, while a covered outdoor seating space is visible to the side, providing a view of the serene landscape.
Vacation home in Saturnia
4.79 out of 5 average rating, 14 reviews

Private villa with swimming pool in Tuscany

MadeleineRating, 5 stars4 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, 60 reviews

Tuscan Countryside Retreat with Heated Pool

MarkRating, 5 stars1 week ago
We had a wonderful stay. Our hosts were available and responsive, but gave us privacy. Perfect! If you want to visit Italy and be away from tourists, this is the perfect place. The house was exactly as described. Even though the outside temperature was in the low 30s, we chose not to use the a/c. The house stayed comfortably cool. The outdoor pool was perfect. Some of the local towns were spectacular, Pitigliano in particular. Worth staying, just to visit this one town! A day trip to Porto Ecole is also worth the effort. Perhaps our only disappointment was that some of the village restaurants were closed during all of our (4 night) stay, including the one that I had an online reservation at for our final evening.

Family- and pet-friendly home rentals

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, 173 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!
Superhost
A bright and spacious bedroom is shown, featuring a large bed with light-colored bedding. Two bedside tables hold lamps, providing a soft glow. A vase with dried flowers sits on a wooden dresser. Light pours in through a window covered by dark curtains, and a large pendant lamp hangs overhead.
Apartment in Montemerano
4.65 out of 5 average rating, 205 reviews

Casa delle Mura

SusanRating, 5 stars1 week ago
We had a wonderful stay at this Airbnb! The space was spotlessly clean, cozy, and incredibly quiet—perfect for relaxing. The view from the third floor was beautiful and well worth the stairs. The host was very responsive and helpful throughout our stay, which made everything easy and stress-free. Only a few minutes drive to the lovely Le Cascate di Saturina (Hot Springs). Highly recommend for anyone looking for a peaceful and comfortable place to stay!
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.
Superhost
The exterior of a cottage is surrounded by lush greenery and large trees, providing a natural frame. The stone structure features an archway entrance, with a chimney visible above the roof, blending harmoniously into the tranquil landscape.
Farm stay in Provincia di Siena
4.87 out of 5 average rating, 118 reviews

Spigo - Indipendent Cottage Zampugna

FilipRating, 5 stars6 days ago
Beautiful place, everything ready with refreshments, accommodation quiet and clean ... Air conditioning functional, but almost not needed, because it was a beautiful classic Tuscan accommodation, where we definitely were not the last
Top guest favorite
A small staircase leads up, surrounded by textured white walls and terracotta tiles. A window with wooden frames allows natural light to enter, offering a view of greenery outside. The décor includes a rustic light fixture and an ornamental mirror, enhancing the inviting atmosphere.
Apartment in Sorano
4.73 out of 5 average rating, 108 reviews

Romantic apartment for two in beautiful Sorano

BethRating, 5 stars3 weeks ago
This place was magical. I fell asleep every night listening to the waterfall in the ravine. Town was a fairytale spot. I never got tired of exploring the beautiful, twisting old streets. Property was just as promised. Rikke went so far above and beyond to make me feel welcome, even arranging a money saving ride to the train station for me. Great experience!
Superhost
An outdoor area features a stone patio with a small dining table and chairs shaded by a large umbrella. Potted plants surround the space, while a swimming pool reflects the blue sky, offering scenic views of the hills and greenery in the distance.
Home in Sorano
4.8 out of 5 average rating, 128 reviews

Lovely home in villa with garden and pool

JoshRating, 5 stars2 weeks ago
A beautiful stay in Tuscany perfect for relaxing on the property and visiting towns.
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!
Guest favorite
The spacious kitchen and living area features a central island counter with a wine bottle and glasses. Natural light floods the space through multiple windows, illuminating the dining table and a cozy seating area with a sofa. A rustic ceiling enhances the homey ambiance.
Condo in Pienza
4.91 out of 5 average rating, 100 reviews

Amazing view of Val d'Orcia Pienza

IndiaRating, 5 starstoday
Absolutely fantastic! Will be returning!

Family-friendly home rentals with a pool

Superhost
A spacious living area is characterized by high wooden beams and terracotta tiles. A comfortable sofa and a wooden dining table with chairs are present, alongside a cozy fireplace featuring a natural stone surround. Soft lighting fixtures enhance the room's welcoming atmosphere.
Apartment in Pienza
5 out of 5 average rating, 3 reviews

Rocca, elegance in Sorbelle d'Orcia, Pienza

Eva MariaRating, 5 stars6 days ago
We had a wonderful time in this fantastically located apartment! The house is wonderfully quiet with a Tuscan postcard view – especially at the pool, a real highlight. After a small start-hopala (not that bad and quickly clarified) we got exactly the apartment we had booked – and it absolutely matched the description. The hosts were super warm, helpful and always trying to make our stay as comfortable as possible. We especially enjoyed the optional Italian breakfast – delicious, lovingly made and with a lot of charm. Perfect location for exploring the surrounding area, from small villages to larger cities, everything was easily accessible. A great place to relax and enjoy – we will be happy to come back!
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!
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
The villa sits gracefully on a lush green landscape, with a serene swimming pool positioned nearby. Sun loungers are arranged around the pool, and the rustic architecture features large windows and a traditional tile roof. Rolling hills and a clear sky complete the scenic setting.
Home in Buonconvento
4.88 out of 5 average rating, 17 reviews

Il Fienile - Pool Villa with 4 Bdrs and Sauna

SadieRating, 5 stars4 days ago
This place is a dream! Everything is stunning. I loved every room and every view. Everything is thoughtfully put together with comforts like an ice machine and AC on when you arrive. The staff are friendly and go above and beyond. I loved the wine available for purchase. Pietro was a great communicator and helpful with fabulous suggestions and support. I would come back in a heartbeat.
Superhost
A rectangular swimming pool reflects the vibrant yellow facade of the villa, surrounded by lounge chairs. Lush greenery and tall cypress trees frame the scene, while clear blue skies enhance the serene atmosphere of the outdoor space.
Villa in Chiusi
4.89 out of 5 average rating, 9 reviews

Villa Febea - Villa Febea 16

HelenaRating, 5 stars1 month ago
Villa Febea is the most magical place, perfect for a large family gathering and celebration. It is gorgeous, comfortable, practical and in a great location. We were given first-class treatment and felt at home and well taken care of. We were given guidance and advice on the planning of our stay over the course of many months, so when we arrived at the villa, everything fell into place perfectly. The owners offer a large selection of services and excursions and can help with just about anything. We had fantastic dinners organized for us at the villa, and we highly recommend the pasta making class followed by dinner, which was one of many highlights. We loved the place, the staff and our whole experience. A holiday and celebration to remember forever!
Superhost
An inviting saltwater pool is surrounded by landscaped gardens featuring native greenery. Lounge chairs are placed nearby, offering a comfortable spot to relax. A rustic stone farmhouse is visible in the background, complementing the serene countryside setting.
Villa in Castiglione d'Orcia
5 out of 5 average rating, 11 reviews

#1 Luxe Farmhouse, Hilltop Views, Saltwater Pool

MiaRating, 5 stars1 month ago
We were looking for a villa that had plenty of space for my husband and I with our 3 adult kids and this villa was perfect! We all had our own bedrooms and private bathrooms. The villa was in the idyllic peaceful Tuscan countryside surrounded by rolling hills, wine vineyards and olive trees with distant views of castles. It is absolutely gorgeous! Alessandro, the owner of the villa met us upon check in. The property has been in his family for hundreds if years. He was incredibly kind and generous, leaving an abundant amount of fruit, several bottles of wine from his vineyard and beautiful fresh flowers in every room. He was always available to answer any questions and make recommendations. Anke, the property manager, was excellent and responsive. Promptly answering my questions prior to the trip and proactively giving us wonderful recommendations. Highlights were truffle hunting Il Podere Castle, Umbria Olive oil tour and Banfi Castle wine tasting. Memories to last a lifetime! ❤️
Guest favorite
A stone farmhouse surrounded by lush greenery is visible, with a private pool in the foreground. Tall cypress trees line the property, enhancing the natural setting. The open landscape features well-maintained grass and shrubs, contributing to a peaceful outdoor space.
Apartment in Castiglione d'Orcia
4.96 out of 5 average rating, 47 reviews

La Tana del Bianconiglio - Girasole Apartment

FenuRating, 5 stars1 week ago
Amazing location, was exactly what we were looking for. Host is very responsive and flexible
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!

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

  • Total rentals

    10 properties

  • Nightly prices starting at

    G$16,728 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