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Family-friendly holiday rentals in Trequanda

Find and book unique family-friendly homes on Airbnb

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Popular amenities for Trequanda family-friendly rentals

Family-friendly home rentals with a hot tub

Guest favourite
Farm stay in Figline e Incisa Valdarno
4.92 out of 5 average rating, 325 reviews

Bioagriturism hills Florence 3p

JayRating, 5 stars4 days ago
Our stay was a dream to be in. Francesca and Francesco have created a wonderful place, are likeable people and great hosts. We were warmly welcomed and received all the necessary information. From the first moment, we felt at home and were able to freely explore the lovingly designed grounds and also enjoy them in privacy. The contact with other guests was also pleasant and respectful. The rooms are rustic and tastefully furnished and exude a special charm. The view will take your breath away. The journey to Poderracio is correspondingly adventurous (switchbacks and narrow, bumpy road). All products, such as the breakfast basket, are super delicious and of high quality. In addition, we received freshly harvested vegetables (zucchini, beetroot, onions and garlic) from Francesca. During the stay, we were invited to bake pizza together in the private rooms and enjoyed a wonderful evening. THANKS!
Top Guest favourite
Cottage in San Casciano In Val di Pesa
4.95 out of 5 average rating, 147 reviews

Il Fienile, Cottage in the country with Jacuzzi

BethanyRating, 5 stars3 weeks ago
If I could move in here permanently, I would. What a gorgeous stay with responsive and respectful hosts. Everything was as described, the hot tub was glorious, and we loved looking through the binder of photos of painstaking restoration over the years.
Guest favourite
Condo in Montevarchi
4.95 out of 5 average rating, 192 reviews

Art-Design Fienile in the heart of Tuscany

AlisterRating, 5 stars2 weeks ago
Incredible trip. Paola and Michele were so friendly and welcoming. Always there to give advice and make sure you had everything you needed. The little converted hay barn was just beautiful and lovely. Location wise it just couldn’t be beaten. The garden was amazing and we ate outside morning and night, easy access to amazing Tuscany countryside and also a short trip on the train to Florence from Montevarchi. Loved every minute we were there and we were sorry to leave. Would highly recommend.
Top Guest favourite
Home in Figline e Incisa Valdarno
4.96 out of 5 average rating, 105 reviews

Torretta Apartment

DebbieRating, 5 stars2 weeks ago
I can not say enough about Alessandra and her amazing land! It was the most magical place we have ever been to. We are taking a 3 month trip, hitting up 21 cities in Europe and this is BY far the best! She was so kind and took us shopping and back to our train! She was always there when we needed her.thank you Alessandra we will see you next year!
Guest favourite
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!
Guest favourite
Home in Gaiole in Chianti
4.86 out of 5 average rating, 264 reviews

Charming estate with views

AndrewRating, 5 stars1 week ago
Incredible stay and Bernardino and his family were incredibly welcoming and pleasant. They helped us check in later and were there to help us with any questions we had. Absolutely would recommend to anyone looking for a peaceful Tuscan retreat.
Superhost
Villa in Baschi
4.87 out of 5 average rating, 176 reviews

VILLALADOLCEVITA

SimonRating, 5 stars2 weeks ago
Very nice stay for a few days relaxing in summer. Beautiful olive gardens around the house, nice collection of wine. Everything clear, super big house, will come back next year!
Top Guest favourite
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.

Family- and pet-friendly home rentals

Guest favourite
Apartment in Pienza
4.9 out of 5 average rating, 170 reviews

Back Home - Apartment in Pienza

CharmaineRating, 5 stars2 weeks ago
Valeria was a very helpful host, always responds to any questions we had. The house is close to Pienza's city centre while being in a cozy neighbourhood so really enjoyed the location. It was really close to the bus stop as well. The rooms in the were also spacious and beds were clean.
Top Guest favourite
Castle in Montecatini Val di Cecina
4.99 out of 5 average rating, 118 reviews

Belforti Tower

JoyRating, 5 stars3 days ago
What a wonderful week we had with Luca and Emilia at the tower! It was amazing to see all the pictures in real life - it was even more amazing in person. And the garden is just magical. I had no idea the beauty of the pool area. Laying by the pool and listening to nature we felt transported to a simpler time. To top it off Luca was so delightful. We enjoyed his company and hearing more about the story of the tower and the town. I would recommend this as a stop on anyone’s vacation to Italy. Wonderful hosts in a magical setting!
Top Guest favourite
Villa in Sarteano
4.97 out of 5 average rating, 125 reviews

Stone farmhouse in 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.
Superhost
Condo in Castelfranco di Sopra
4.83 out of 5 average rating, 252 reviews

House between Firenze, Arezzo, chianti e Siena

Sylvie & AlainRating, 5 stars1 week ago
We were immediately enchanted by this property. Everything here makes up the image that one can have of the beautiful Tuscan countryside. At the top of the hill overlooking the valley, the view is splendid and romantic. The property has been renovated with today's comforts while retaining its soul of yesteryear. You feel good right away, the energy is beneficial, nature, animals, everything is in harmony! The welcome, Oscar's cooking, the superb pool, the shaded terrace, the hearty homemade breakfasts! It's more than a favorite, this place is a gem! We'll be back!
Superhost
Farm stay in Roccatederighi
4.92 out of 5 average rating, 136 reviews

Holiday in antique farm, Belvedere

MauriceRating, 5 stars2 weeks ago
What tranquility and what a view. Beautiful estate and super friendly people who try to make you feel comfortable. Also a nice and pleasant swimming pool for when it is very hot.
Superhost
Farm stay in Castiglione d'Orcia
4.89 out of 5 average rating, 229 reviews

il poderuccio farmhouse studio apartment

RachelRating, 5 stars3 weeks ago
Great stay! Initially the place was a bit further out of town than we had anticipated but we still found it very accessible to lots of the things we hoped to do! The view was amazing! So peaceful to sit on the terrace!
Guest favourite
Farm stay in Pienza
4.94 out of 5 average rating, 172 reviews

Palazzi del Papa Farmhouse in 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 favourite
Farm stay in Montepulciano
4.95 out of 5 average rating, 244 reviews

Pescaia Montepulciano Farmhouse Apartment 1

MelanieRating, 5 stars1 month ago
We were welcomed by Sabrina's dad. He's a very nice man. He even shows us the way to the grocery store. The accommodation is very clean with lots of amenities. And what about the view is quite beautiful. This is a place to stay that I would recommend without hesitation. Thanks to Sabrina and her family.

Family-friendly home rentals with a pool

Top Guest favourite
Farm stay in Pisa
4.99 out of 5 average rating, 298 reviews

Tenuta Chiudendone in Tuscany

KarenRating, 5 stars1 week ago
Wonderful place for a family and to recharge in our busy trip to Italy. Sign up for the farm to table experience when you stay. The hosts could not have been more helpful and wonderful. Beautiful property and accommodation.
Superhost
Home in Asciano
4.88 out of 5 average rating, 144 reviews

A Charming House in Asciano - Siena

CristinaRating, 5 stars8 months ago
Very nice place with a great view, very quiet and relaxing. The apartment was clean and cozy. The only inconvenience were the squeaky doors.
Top Guest favourite
Farm stay in Palaia
4.98 out of 5 average rating, 169 reviews

Countryside Dream farm in Tuscany

MercedesRating, 5 stars1 week ago
We had the most magical stay at this Tuscany farm! The property is absolutely stunning — nestled among rolling vineyards and olive groves, with postcard-perfect views in every direction. Our apartment was spacious, charming, and had everything we needed for a comfortable stay. The hosts were incredibly kind and welcoming, sharing local recommendations. Our kids loved meeting the animals, exploring the grounds, and especially swimming in the beautiful pool overlooking the hills — it was a total dream! Evenings on the terrace with a glass of wine and the Tuscan sunset were unforgettable. This was a once-in-a-lifetime experience for our family, and we can't wait to return. Highly recommend to anyone looking for a peaceful, authentic Tuscan escape! 🌿🍷☀️
Superhost
Apartment in Montepulciano
4.84 out of 5 average rating, 99 reviews

La Casa delle Querce - "Belvedere" (The House of Oaks - "Belvedere")

JiachengRating, 5 stars2 months ago
Great house, stayed here for four days. We don't have a car so can only choose a place with good transport links.It is close to the train station and the view is the best place for us! The landlord was very friendly and came to the train station to pick us up and drop us off. Friends without a car can report a day or rent an e-bike/tram to get around. The room on the second floor has a good view, you can see the beautiful Tuscan pastoral scenery by pushing the window, the natural scenery is accompanied by birds, the whole person is quiet, it is so relaxing. There is a kitchen where you can go to the nearby supermarket to buy your own cooking (30 minutes on foot). The room was clean and tidy, the bed was soft and hard, everything was very satisfactory.The only regret is that the pool is only open in May. I hope I can come back next time!
Top Guest favourite
Home in Asciano - Chiusure - Monte Oliveto Maggiore
4.96 out of 5 average rating, 182 reviews

Country House in the Crete Senesi

CharlotteRating, 5 stars1 month ago
We feel so lucky to of found Guido and his beautiful house. Firstly Guido could not be more helpful, so responsive, friendly and has the best recommendations! He made sure the house was spotless for our arrival, even the pool is so clean it was perfect. The house itself is stunning, stays lovely and cool in the heat but the garden is just drenched in sunshine. Guido has made sure you can bask in the sunshine by the pool or chill out in shade in the height of the afternoon. There are so many comfortable spots to sit in! The pool was lovely and refreshing when it was hot mid afternoon and looked beautiful in the evening. Tuscany is stunning, there's so much to explore - would heavily recommend a car for that. In walking distance there are a couple of very delicious restaurants and if you're feeling adventurous you can walk to the monostary nearby which is definitely worth visiting. Thank you Guido!
Top Guest favourite
Apartment in Barberino Val d'Elsa
4.99 out of 5 average rating, 122 reviews

Apartment in Chianti at Mulino dell 'Argenna

MarkusRating, 5 stars1 week ago
We have now been to Elisa and Alessandro's accommodation for the second time – and it was simply beautiful and absolutely relaxing again! The place is a real oasis where you can switch off perfectly. Elisa and Alessandro are extremely helpful and warm. They provided us with great tips for activities and restaurants, so we could enjoy our stay all around. We'd love to come back and highly recommend this place!
Top Guest favourite
Farm stay in Reggello
4.96 out of 5 average rating, 163 reviews

Stone farmhouse, exclusive private pool

MeganRating, 5 stars2 weeks ago
We absolutely loved our stay at this property in Reggello! The hosts were so warm and communicative—they greeted us upon arrival and gave us a full walkthrough of the home! The view was stunning, and the pool was beautiful and very clean. Aldo even came by each morning to clean it before we used it, which was such a thoughtful touch. Everything in the house worked perfectly—the Wi-Fi was fast, all the appliances and lighting functioned well, and we had no issues during our stay. The drive from Florence was easy (we had a rental car), and it made exploring nearby wineries and towns super convenient. We also LOVED their on-site farmers market. It was their own personal setup with wines, olive oil, jams, and other homemade goods -- plus fresh produce like eggs, garlic, artichoke, & shallots, which they generously offered free of charge. We’d definitely stay here again and highly recommend this property to anyone looking for a peaceful and scenic escape in the Tuscan countryside!
Guest favourite
Guesthouse in Antria
4.92 out of 5 average rating, 130 reviews

A charming Tuscan retreat

janeRating, 5 stars2 weeks ago
A very peaceful retreat in a beautiful garden with lots of private places to sit or eat and an extended view over the valley towards Arezzo and mountains beyond. Caroline was helpful but did not intrude. The cottage has an authentic Tuscan style and furniture to match and although quite dark there are big windows looking out onto the garden and view. We enjoyed using the private pool and exploring the local area as well as a National Park to the north (lovely beech forest) and Siena. The TV isn’t ‘smart’ and there is no dishwasher but this is reflected in the price (however there’s a large book collection including lots of guidebooks). It was a very relaxing stay for us, thank you.

Quick stats about holiday rentals that are family-friendly in Trequanda

  • Total rentals

    180 properties

  • Nightly prices starting at

    $117 NZD before taxes and fees

  • Total number of reviews

    1.6K reviews

  • Pet-friendly rentals

    120 properties allow pets

  • Rentals with a pool

    150 properties have a pool

  • Rentals with dedicated workspaces

    60 properties have a dedicated workspace

Destinations to explore

  1. Airbnb
  2. Italy
  3. Tuscany
  4. Province of Siena
  5. Trequanda
  6. Family-friendly rentals