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Family-friendly vacation rentals in Massa Marittima

Find and book unique family-friendly homes on Airbnb

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Popular amenities for Massa Marittima family-friendly rentals

Family-friendly home rentals with a hot tub

Guest favorite
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 favorite
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.
Top guest favorite
Home in Figline e Incisa Valdarno
4.96 out of 5 average rating, 105 reviews

Torretta Apartment

DebbieRating, 5 stars1 week 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 favorite
Cottage in Radicondoli
4.93 out of 5 average rating, 137 reviews

Beautiful renovated barn in Tuscany

PhilippRating, 5 stars4 weeks ago
We had a wonderful week in Gloria's house. Our four-legged friend also felt totally comfortable in nature. The house is small but nice and has everything you need. The property is a nice size and is perfect for eating outside, relaxing in the hot tub or just lying in the sun. The way to the house is a little challenging, but with a normal car and a little driving experience it can be mastered. Gloria was always available to us and gave us good excursion tips for the area in advance. Even with any inquiries, she always responded very quickly and helped us. To just get out and enjoy the nature and tranquility of Tuscany, it is perfect. We will be happy to come back!
Guest favorite
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 favorite
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.
Guest favorite
Apartment in Florence
4.89 out of 5 average rating, 339 reviews

Apartment with garden and parking

ClaudeRating, 5 stars2 weeks ago
Our hosts welcomed us with great kindness and gave us all the information to direct us to Florence. The very cute and fresh apartment has a very nice flowery and peaceful garden. We had a great time
Guest favorite
Villa in Chianciano Terme
4.92 out of 5 average rating, 107 reviews

Cottage in Val d'Orcia, Jacuzzi & HotTub with view

MadisonRating, 5 stars1 week ago
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

Top guest favorite
Apartment in Pratovecchio - Stia
4.99 out of 5 average rating, 100 reviews

Podere La Quercia

MariaRating, 5 stars1 week ago
We immediately loved our place. Serena's house is located on a very large property surrounded by beautiful trees, an exceptionally beautiful terrace with sun loungers, a large dining table and an oak tree that provides shade. The property is very well maintained and laid out with a lot of respect for nature. From the house you can start hiking directly, Serena's husband knows his way around and can give great hiking tips. If you drive only a few kilometers, you are already at an altitude of over 1000 m. Even if it is very hot, you can take great hikes from there in pleasant temperatures, which have always inspired us. The apartment, a former stable, has been designed with a lot of love and taste. We felt like at home from the first moment. Serena and Paolo are perfect hosts, always friendly, always available and helpful. We were there for 12 days and would have liked to have stayed longer. We'd be happy to come back. Thank you!!
Top guest favorite
Farm stay in Arezzo
4.97 out of 5 average rating, 230 reviews

Explore nature in the center of Vigneti Chianti

BaileyRating, 5 stars1 week ago
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.
Guest favorite
Guest suite in Greve in Chianti
4.97 out of 5 average rating, 395 reviews

Selvabella in Chianti B&B Il Riccio

Ann KristinRating, 5 stars1 week ago
We had an amazing stay! Very nice and warm people and cute dogs. Amazing views, green and lush garden. Delicious food and drinks. Fun with pasta course! I recommend this place! Fantastic experience!
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 immediately fell in love with this property. Everything here makes up the image that can be made 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 there, the energy is beneficial, nature, animals, everything is in harmony! The welcome, Oscar's cooking, the superb swimming pool, the shaded terrace, the hearty homemade breakfasts! It's more than a favorite, this place is a gem! We'll be back!
Top guest favorite
Apartment in Montepulciano
5 out of 5 average rating, 118 reviews

Stuart White Tea Central Panoramic & Garden

MarkRating, 5 stars1 month ago
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!
Top guest favorite
Apartment in La Presura
4.93 out of 5 average rating, 147 reviews

Country house 9 km to Florence-2+1g,free parking

TimRating, 5 stars1 week ago
Very nice quiet place to stay with Tuscan flair. Great complex also with a pool and a view. Quickly in Florence and on the streets to the excursion destinations. Definitely recommend! We'll be back. :)
Top guest favorite
Apartment in Montepulciano
4.97 out of 5 average rating, 392 reviews

A view from the top, Montepulciano

AliciaRating, 5 stars1 month ago
We had a wonderful stay at Luca’s and the view cannot be beat! Luca went above expectations by meeting us at checkin to show us where to park and taking our luggage to and from the unit. Hope to stay here again one day!
Guest favorite
Villa in Castagneto Carducci
4.94 out of 5 average rating, 121 reviews

La Conchetta – Bolgheri

JanRating, 5 stars1 month ago
We were here for the second time and we are thrilled again. We love the house and the surroundings are perfect for us. We'd love to come back :-)

Family-friendly home rentals with a pool

Top guest favorite
Apartment in Montalcino
4.9 out of 5 average rating, 359 reviews

Panoramic Country Suite Montalcino

BernhardRating, 5 stars2 days ago
We stayed at Aleksandra's in Montalcino in the heart of Brunello, a breathtakingly beautiful area, for a week. The large property is fantastic and with the tranquility and the view just the right thing to relax and unwind. An unforgettable experience for the whole family. This is how you imagine a Tuscan holiday. We highly recommend the place.
Guest favorite
Home in Montaione
4.94 out of 5 average rating, 104 reviews

Cercis - La Palmierina

JenniferRating, 5 stars1 week ago
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!
Superhost
Vacation home in Casole d'Elsa (SI)
4.89 out of 5 average rating, 227 reviews

Studio in Tuscan farmhouse with pool & views

KarolinaRating, 5 stars1 day ago
We had a great week at Fabio's. The place is exactly like the photos. Beautiful garden with herbs and views of the surroundings. The apartment has several different seating areas (by the grill, garden bench and sunset seating) and is closest to the pool of all 3 apartments. The pool pleasantly surprised with its size. Fabio is very friendly, helpful and speaks great English. It offers the possibility of buying your own excellent olive oil and red wine, we recommend. We worked from the apartment all week and the wi-fi was trouble-free even for video calls.
Guest favorite
Apartment in Casole D'Elsa
4.93 out of 5 average rating, 103 reviews

Girasoli apartment with pool in farmhouse

RichardRating, 5 stars1 month ago
Beautiful rustic stay in the heart of Tuscany. Manuela was very friendly and helpful. The farm at night with the fireflies lighting up the bushes and nightingale singing in the trees was absolutely enchanting.
Top guest favorite
Apartment in Castellina in Chianti
4.97 out of 5 average rating, 113 reviews

Visit Chianti, Siena, S.Gimignano, Florence

CarlyRating, 5 stars1 month ago
The perfect place to explore Chianti each day. We stayed 5 nights and it was just perfect. Great amenities, beautiful pool, bbqs and lovely areas to sit and enjoy the views and the sunset. Always fabulous to come home to. Our upstairs apartment was spacious, comfortable and all we required with a lovely view. We had great recommendations from Silvia which we followed up on. Great to have restaurants nearby. Reasonable- highly recommend.
Top guest favorite
Villa in Tavarnelle Val di Pesa
4.93 out of 5 average rating, 148 reviews

GUIDI POWER

TerryRating, 5 stars1 week ago
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.
Guest favorite
Farm stay in San Gimignano
4.89 out of 5 average rating, 209 reviews

Oleandro double room with pool in San Gimignano

EricaRating, 5 stars1 week ago
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.
Guest favorite
Apartment in San Gimignano
4.89 out of 5 average rating, 126 reviews

Apartment Ortensia

DanielaRating, 5 stars2 months ago
Great place! We loved it!

Quick stats about vacation rentals that are family-friendly in Massa Marittima

  • Total rentals

    40 properties

  • Nightly prices starting at

    G$6,276 GYD 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

  • Wifi availability

    30 properties include access to wifi

Destinations to explore