
Family-friendly holiday rentals in Massa Marittima
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Top-rated family-friendly rentals in Massa Marittima
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Family-friendly home rentals with a hot tub

Art-Design Fienile in the heart of Tuscany
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.

Il Fienile, Cottage in the country with Jacuzzi
Massimo beschreibt den Weg zur Unterkunft sehr gut, das Häuschen liegt etwa 20 min südlich von Florenz mitten in den Weinbergen, sehr ruhig und malerisch in den toskanischen Hügeln. Wir waren zu dritt bei Massimo und uns hat es an nichts gefehlt! Ob Stadtbesichtigung von Siena& Florenz, Weinverkostung oder einfach die Ruhe am Haus genießen: für alles das perfekt geeignet! Das Haus ist typisch toskanisch, Massimo und Beatrice haben viel Arbeit reingesteckt um ihren Gästen einen authentischen Aufenthalt zu bieten: trotzdem aber modern mit Klimaanlage- im Sommer geht’s auch kaum ohne! Vielen Dank für die tolle Zeit!

Torretta Apartment
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!

Country house La Meria
Als je hier verblijft, waan je je in een schilderij, zo mooi is dit huisje gelegen in de bergen! Lucca is echt super aardig en grappig. Hij verteld een hoop. Het restaurant wat ze runnen is ook prima, en goed eten! Het ontbijt is uitgebreid. Wij raden dit huisje zeker aan!

Your Private Tuscan Retreat
We had such a great time at this AirBnB. It is a very peaceful and private place, perfectly to disconnect and relax. The hot tub and sauna are a great addition and invite to enjoy the surroundings. Location wise you need a car and prepare to drive a bit more in case you wanna explore Tuscan cities. I would still argue it is worth it as you get a great place to stay.

La Casetta
Können wir absolut empfehlen ! Ist alles so wie im Text beschrieben und auf den Foto´s zu sehen. Liegt ca 2 km außerhalb vom total schnuckeligen Örtchen Casole de Elsa. Von Andrea + Barbara gab´s alle nötigen Infos zur Anreise und viele tolle Tipps vor Ort, immer mit den dazugehörigen Links. Zum Beispiel verzögerte sich unsere Anreise verkehrsbedingt auf ca. 22:15 Uhr. War kein Problem, wir standen in Kontakt und als wir ankamen, hat uns Andrea persönlich in Empfang genommen. Und wenn wir während unseres Aufenthaltes eine Frage hatten, kam immer sehr zügig eine Antwort. (Wo man in Siena am Besten parken kann, wie gelangt man am Besten nach Florenz, ...)

Domus Nannini - Loggia Salimbeni SPA
这是住过最好的最有特色的民宿,像宫殿一样的房间,四面墙加顶都是湿壁画,叹为观止,设施也非常齐全,最最关键是房东态度很好,入住时帮我们提东西,入住后一直在关心我们,给我们准备了很多水和零食,问候入住的体验感,告诉我们哪里吃东西比较方便也推荐了很多当地比较好的餐厅。强烈推荐!

Cottage in Val d'Orcia, Jacuzzi & HotTub with view
Fulvia’s apartment is a true Tuscan gem—beautifully decorated with charm and character, and equipped with everything you need. The property offers stunning views and a peaceful sense of seclusion, and it’s even more beautiful than in the photos. Fulvia is right nearby and always available if you need anything. She and her husband are both warm, thoughtful, and made us feel genuinely welcome. Fulvia even arranged dinner at a local restaurant, which turned out to be one of the best meals of our trip. This is a special place and our only regret is not staying longer.
Family- and pet-friendly home rentals

Casa del Giardino
My husband and I, plus our French Bulldog, had the pleasure of staying here for just over 3 weeks. Immediately felt like home, and host family had everything to do with that! Highly recommend. stunning views, fabulous location and some of the most gracious people I've ever met.

Esplora la natura al centro di Vigneti Chianti
Staying at Agrigreen La Lama was hands down the best Airbnb experience I’ve ever had. From the moment we arrived, Rita welcomed us with such warmth and hospitality that we felt at home. The property is peaceful, beautifully maintained, and full of charm—surrounded by nature and the kind of quiet that soothes the soul. One of the most memorable parts of our stay was getting to cook in Rita’s own home, which she generously opened to us. It was such a unique and personal experience that made us feel truly connected to the space and the spirit of the farm. If you’re looking for a place to slow down, feel grounded, and enjoy genuine hospitality, Rita’s space is an absolute gem. I’m already looking forward to the day I can return.

PODERE GUIDI
Giuliani is a wonderful host who made us feel as if this slice of paradise was our home, too. The location, the meticulously restored home, the views all make for the ultimate Tuscan experience. But Giuliani and her husband bring it all together with their warmth and attentiveness. It was a tough place to say goodbye to — for now. If you are looking for a Tuscan experience, this is it. And remember to ask for the hosts’ home-cooked meal. It is a culinary experience in the very best sense.

Casa Al Poggio & Chianti view
Hands down our favorite part of our two weeks in Italy! Casa Al Poggio was our Tuscan home away from home. We went and did all the things… Florence, Cinque Terre, San Gimignano, Montepulciano, etc. But coming “home” to this place was the best. So peaceful and picturesque looking across the valley at the Badia Di Passignano. We cooked many meals in the well stocked kitchen and my husband loved the rustic BBQ. Fresh herbs in the garden and the smell of jasmine blooming on the patio. Book yourself extra time here…you won’t want to leave! Emanuele & Tamara are the kindest people. Take them up on all of their restaurant recommendations. Everyone one was a hit! We can’t wait to go back.

House between Firenze, Arezzo, chianti e Siena
Nous avons été de suite sous le charme de cette propriété. Tout ici compose l'image qu'on peut se faire de la belle campagne Toscane. Tout en haut de la colline surplombant la vallée, la vue y est splendide et romantique. La propriété a été renovée avec le confort d'aujourd'hui tout en conservant son âme d'autrefois. On s'y sent de suite bien, l'energie est bienfaisante, la nature, les animaux, tout est en harmonie! L'accueil, la cuisine d'Oscar, la superbe piscine, la terrasse ombragée, les petits-dejeuners copieux fait maison! C'est plus qu'un coup de coeur, cet endroit est une pépite! Nous reviendrons!

Stuart White Tea Central Panoramic & Garden
My wife, brother-in-law, and I had an incredible time in Montepulciano, and Giacomo’s apartment was the perfect place from where we started out daily adventures, took afternoon naps, and then headed out for fantastic dinners. Giacomo’s apartment was excellent, making it easy to get settled after a long day of travel. Giacomo guided us into the temporary parking spot when we got lost for a few minutes, and was quick to assist with any questions we had during our stay. The restaurant recommendations were all excellent, as well as the other activities he suggested. We will definitely stay here again when we visit Montepulciano!

agriturismo il poderuccio monolocale
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!

Suite in Castello di Valle
We come from Hong Kong, and a building like this is not often seen there. We are very happy to have had the chance to stay at the house. Some of the details in the house really impressed us, especially the antique furniture! Pietro is a great host—very friendly and responsive. I had some pleasant conversations with him. Thanks again!
Family-friendly home rentals with a pool

Panoramic Country Suite Montalcino
Zeer attente communicatie en service!! Accommodatie overtreft de beschrijving. Grandioos uitzicht, een tuin zo groot als een park en een charmant ingerichte woning. Goede uitvalsbasis voor naburige steden of om in alle rust bij te komen.

Cercis - La Palmierina
We had an absolutely amazing time at Daniela’s place - it was clean, had stunning views and was quick access to Pisa, Florence & Siena. Beautiful pool and lovely terrace with amazing views and sunsets. The kitchen also had everything we needed, including local olive oil and pasta & local wine as a welcoming gift. Daniela went above and beyond providing us with lilos and a pump for the pool too. Overall, 10/10 stay!

Studio in Tuscan farmhouse with pool & views
Il podere di Fabio e Sarah è una vera oasi di pace e tranquillità! Siamo stati accolti amichevolmente e fin da subito ci siamo sentiti a casa! È stato un soggiorno estremamente piacevole all’insegna della natura e degli splendidi paesaggi circostanti. La piscina, con veduta sulla valle, è davvero splendida! L’alloggio messo a disposizione è ben curato e arredato con gusto! Fabio è stato molto disponibile e gentile: ci è stato di grande aiuto per risolvere un inconveniente che abbiamo avuto appena arrivati! Torneremo sicuramente in questo paradiso..un luogo stupendo dove si rallenta e ci si riappropria della bellezza della natura 💚 Grazie Fabio e Sarah!

Countryside Dream farm in Tuscany
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! 🌿🍷☀️

Oleandro double room with pool in San Gimignano
While Paolo was away, our check-in and communication with Bruno went very smoothly. The property is absolutely stunning. The view of Sam Gimignano as you swim in the pool was something out of a movie scene. The property has surrounding olive trees and vineyards seen right from the window of the airbnb. This particular room is in a tucked away corner of the property and feels very private. Bed was comfy. Washing machine and drying racks, as well as a grill were plusses. Many agriturismos offer a dinner for an added fee, and we were a little disappointed that the dinner (in the past offered by Paolo’s neighbors) was closed during our stay. However, in fending for ourselves, we did appreciate the mini fridge and microwave, and loved eating our dinner right on the private table outside the room door. Also, you do have to clean out your trash at the end of the stay. Price felt right. Overall, would happily stay again and will be forever dreaming of the view.

Appartamento nel Chianti al Mulino dell'Argenna
Wir waren nun schon zum zweiten Mal in der Unterkunft von Elisa und Alessandro – und es war wieder einfach wunderschön und absolut erholsam! Der Ort ist eine richtige Oase, in der man perfekt abschalten kann. Elisa und Alessandro sind äußerst hilfsbereit und herzlich. Sie haben uns mit tollen Tipps für Unternehmungen und Restaurants versorgt, sodass wir unseren Aufenthalt rundum genießen konnten. Wir kommen sehr gerne wieder und können diese Unterkunft nur wärmstens empfehlen!

Colonica in pietra, piscina privata in esclusiva
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!

Paluffo Stillo House
Don’t hesitate to book this beautiful Airbnb which was thoughtfully restored to reflect the history of the area. You won’t want to leave. We explored Certaldo Alto and Montefioralle- both amazing sites. The pool area was perfection and we couldn’t get enough of the landscape! Couldn’t stayed a week!!!
Quick stats about holiday rentals that are family-friendly in Massa Marittima
Total rentals
40 properties
Nightly prices starting at
$46 AUD before taxes and fees
Total number of reviews
680 reviews
Pet-friendly rentals
20 properties allow pets
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Wi-Fi availability
30 properties include access to Wi-Fi
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- Elba
- Giglio Island
- Feniglia
- Gulf of Baratti
- Cala Violina
- Marina di Grosseto beach
- Kite Beach Fiumara
- Spiaggia di Capo Bianco
- Spiaggia Di Sansone
- Spiaggia di Marina Di Campo
- Cavallino Matto
- Spiaggia di Patresi
- Spiaggia Libera
- Cala Di Forno
- Spiaggia Marina di Cecina
- Santa Maria della Scala
- Casa Barthel
- Spiaggia di Seccione - Portoferraio (li)
- Spiaggia Di Barbarossa
- Spiaggia Zuccale
- CavallinoMatto
- Cala del Leone
- Spiaggia della Padulella
- Spiaggia di Cavo