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Family-friendly vacation rentals in Santa Fiora

Find and book unique family-friendly homes on Airbnb

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Popular amenities for Santa Fiora family-friendly rentals

Family-friendly home rentals with a hot tub

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, 121 reviews

Villa in Montepulciano with a Pool

LindaRating, 5 stars1 week ago
We had a wonderful time in Tuscany! We were able to make use of the pool on the first day with our two boys, 7 and 4. We visited Pienza, Montepulciano and Montelccino. We also purchased two of the wines from the estate. Alex made everything very easy and was a great host!
Guest favorite
A ground-level countryside dwelling is presented with natural stone pathways and wooden shutters. Potted plants are positioned near the entrance. The exterior is complemented by expansive windows, providing views of the surrounding landscape under a clear blue sky.
Home in Catabbio
4.89 out of 5 average rating, 158 reviews

Country house La Meria

DamonRating, 5 stars6 months ago
We are an American and Italian family traveling through Italy and we highy recommend this special spot in the mountains. The landscape was beautiful and the breakfast was wonderful. We ended up arriving very late in the evening as their was a crash on the autostrada and Luca was very accommodating and communicative. We would stay here again.
Guest favorite
An outdoor wood-fired hot tub is surrounded by lush green grass, offering a scenic view over the expansive landscape. A stone pathway leads to the hot tub, while the rustic stone cottage is visible in the background under a partly cloudy sky.
Cottage in Castell'Azzara
4.99 out of 5 average rating, 134 reviews

Your Private Tuscan Retreat

EliyahRating, 5 stars2 days ago
We had a wonderful stay at Riccardo and Kate’s beautiful hide‑away in Tuscany. The place was spotless, thoughtfully equipped and felt both spacious and cosy at the same time. It’s perfectly located, only a five‑minute drive to the lovely town of Castell​e Azzara. Waking up to birdsong, spending slow afternoons in the sauna and spa and falling asleep to absolute silence left us completely relaxed. Riccardo and Kate were the perfect hosts - welcoming, attentive and responsive. They really have thought of everything. If you’re looking for peace, comfort, and a real Tuscan escape, this is the place. We 100% recommend to future guests. Grazie mille!
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 stars1 month 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!!
Top guest favorite
Home in Simignano
4.97 out of 5 average rating, 115 reviews

Casa al Gianni - The Simignano Barn

RebeccaRating, 5 stars1 week ago
Cristina’s villa was the perfect Tuscan escape for our family. There is much to love…the sweet pigs, the village dogs, the breathtaking views, the peaceful and quiet evenings and mornings, delicious food and beer produced on the farm, AND the most lovely and kind family/hosts. I could honestly go on and on about how much we loved this villa and location. 5 stars all the way! We had our 6 yr old daughter with us and she says it was her favorite place she has stayed on a holiday because of the pigs, ping pong table, swing, and because she had so much fun with the host family children and other guests whom stayed in the other available villas. Also, the big dinner hosted on the last night of our stay was the highlight of our trip! (Tip: make sure to buy some of their products made on the farm….so delicious!)
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, 147 reviews

La Terrazza su Chiusi - panoramic apartment

AshleyRating, 5 stars2 months ago
Beautiful views and Raffaele was a great host! It was off season so there wasn't much to do in the neighborhood but that was perfectly fine with me and the peacefulness was exactly what I wanted.
Guest favorite
A functional kitchen area is complemented by a light blue sofa and a dining table. Two wine glasses are placed on the table alongside brochures. The kitchen features white cabinetry, a gas stove, and a countertop, creating an inviting space for meal preparation.
Condo in Cortona
4.82 out of 5 average rating, 55 reviews

Tuscany Seen in a Fabulouse House

PeterRating, 5 stars4 months ago
Very nice and clean appartment in a very quiet area. Only Met Gaston shortly since we were out all day visiting Tuscany with friends, But he was very Friendly. Will definitely come back
Top guest favorite
A spacious living area features a large wooden dining table surrounded by chairs, complemented by a cozy seating arrangement with armchairs and a sofa. A bookshelf filled with various books stands against the wall, and warm lighting enhances the relaxed atmosphere.
Apartment in Orvieto
4.94 out of 5 average rating, 104 reviews

Apartment B&B Casadarte

HeidiRating, 5 stars8 months ago
Where do I start? If you’re thinking of traveling to Orvieto, stay here. This is the most unique and charming Airbnb we’ve ever stayed at. Sylvia and Aldo made us feel like we were old friends coming to visit, welcoming us into their cozy family home and sharing with us their favorite restaurants, coffee shops, and gelaterias. Aldo picked us up and returned us to the train station; the fridge was stocked with yogurt, milk, juice, and butter; they left breakfast sweets for us and a bottle of wine. We loved reading about Sylvia’s father, Valentini, and enjoyed his artwork throughout the house. The beds were comfy, the kitchen is small but has what you need to cook. And Orvieto, ahhh, what a wonderful little town. We visited in August and there were many tourists but it didn’t feel crowded. We loved our stay and want to go back!

Family- and pet-friendly home rentals

Top guest favorite
An open living space features a colorful polka-dotted sofa and a small dining table surrounded by vibrant chairs. The kitchen area is organized with shelves displaying kitchenware and appliances, with a warm wooden ceiling enhancing the cozy atmosphere.
Apartment in Pienza
4.9 out of 5 average rating, 163 reviews

Back Home - Apartment in Pienza

MorganRating, 5 stars1 month ago
Had all necessities needed. Helpful neighbors with check in and check out. Good location with free parking!
Top guest favorite
A tranquil garden space is visible, featuring a large, white umbrella providing shade over two reclining chairs. Lush green grass surrounds the area, complemented by potted greenery and flowering plants, creating a serene outdoor escape.
Apartment in Siena
4.93 out of 5 average rating, 108 reviews

Casa Borgianni at Villa Caprera

TroelsRating, 5 stars6 months ago
We had the most amazing time at this beautiful Tuscan house! The location is stunning– nestled in the rolling hills, surrounded by olive groves. Waking up to such breathtaking views every morning was a dream come true. The house itself is full of charm and character, with traditional stone walls, beautiful windows, wooden beams, and cozy, comfortable furnishings. It was immaculately clean and had everything we needed for a relaxing stay. We especially loved the ‘tower bedroom’ with view to Siena ‘skyline’. Only downside is that you can hear the ‘Autostrada’ when the wind is ‘set wrong’.
Top guest favorite
A rustic farmhouse is shown, featuring a spacious outdoor patio with wooden furniture. Surrounding greenery includes trees and manicured shrubs. The background reveals rolling hills under a partly cloudy sky, enhancing the rural charm of the property.
Home in Località LeCoste
4.95 out of 5 average rating, 203 reviews

Borgo Petroio

SiriRating, 5 stars6 months ago
Alex is an amazing host. She made us feel so welcome. The apartment was very Tuscan quaint and the location was wonderful for driving around Tuscany.
Guest favorite
A serene bedroom features a wrought iron bed with white linens and a soft brown quilt. Natural light filters in through a partially open door, revealing an outdoor area. A small wooden table holds a vase with flowers, complementing the rustic decor.
Home in Pievescola
4.93 out of 5 average rating, 124 reviews

Antico Borgo Ripostena – n. 5 Garage

KeriRating, 5 stars6 months ago
Marina's place is one of the most beautiful places I've ever seen. The attention to details, the amenities and her communication made our stay very relaxing and enjoyable. Thanks Martina for a great stay in Tuscany.
Superhost
The exterior of a rustic stone building features a welcoming facade adorned with red shutters and vibrant flower boxes. A gravel path leads to the entrance, bordered by pots of blooming flowers. The surrounding greenery enhances the tranquil atmosphere of the property.
Apartment in San Quirico d'Orcia
4.5 out of 5 average rating, 6 reviews

Oleandro real farm house in the Tuscan countryside

JackyRating, 5 stars6 months ago
Great family run place! Welcomed and greeted by Robert’s mother with a glass of wine that Robert made himself. Robert’s mom doesn’t speak any English but she was just so sweet and welcoming. The view is gorgeous and this place is a true agritiursimo with active vineyard and olive farms. Highly recommend.
Superhost
An orange exterior structure features green shutters and a sloped roof. A small garden area with a table and chairs is visible, offering a space for outdoor meals. Surrounding trees provide shade and contribute to the serene landscape.
Farm stay in Montepulciano
4.82 out of 5 average rating, 115 reviews

La Manonera Farmhouse "La Casa Rosa for families"

SylvanaRating, 5 stars7 months ago
The only thing I could say negative is the lack of lighting for the kitchen and dining room. For the rest everything is perfect if you like the countryside decor:-)
Top guest favorite
An aerial view reveals a charming country house nestled among rolling hills. Olive trees and vineyards extend across the landscape, while a winding road leads to the property, which is framed by tall cypress trees and lush greenery.
Condo in Asciano
4.99 out of 5 average rating, 176 reviews

Pink like the sunset sky

JingmingRating, 5 stars6 days ago
Very lovely place, clean and beautiful. Lucia is very friendly and responsive for everything. Thank you
Superhost
A large swimming pool is surrounded by well-maintained grounds, featuring clear blue water under a bright sky. Loungers and parasols are positioned around the pool area, with lush greenery in the background and distant hills visible.
Condo in Pian di Marte
4.67 out of 5 average rating, 6 reviews

Nerone Apartment

GiuliaRating, 5 stars9 months ago
The accommodation is a small paradise of tranquility. No noise pollution. Wonderful view. Careful environment and a beautiful pool where you can relax and cool off. Antonella and her family are exquisite, kind, and extremely discreet people. strategic location to visit both the villages of Lake Trasimeno and to visit Perugia, Assisi and many other places. The nearby village is enchanting and you can shop for local products. For a more complex shopping just reach the lake village (Passignano) and you can find coop and Conad. the only thing that should be considered is that the area is totally devoid of a mobile network. The house is equipped with wifi, but as soon as you leave the house, even just to go to the pool, you have no way to access the network. For those like us who wanted to disconnect from everything, it was a no problem. If instead you needed to work or be available, it should be considered. overall for us it was a beautiful week of relaxation. It's worth it.

Family-friendly home rentals with a pool

Guest favorite
Farm stay in Sovicille
5 out of 5 average rating, 23 reviews

Tuscan Villa:Pool,Hot Tub,A/C,wi-fi,7bd near Siena

TimRating, 5 stars9 months ago
Cannot recommend more highly. A fantastic experience from start to finish. Helpful from the moment we booked to the moment left, including helping us organise lunches and wine tours. The villa itself is spectacular with stunning views of the Tuscan countryside. The villa was clean, spacious and charming with a bathroom for every room, fully equipped kitchen, games room, TV room and laundry. The pool is fantastic, as is the hot tub and the outdoor dining area and BBQ was perfect for everyone to eat, drink and laugh around. A truly memorable holiday at an unforgettable place
Top guest favorite
An aerial view captures the rustic charm of a farmhouse complex surrounded by lush greenery and neatly arranged olive groves. A rectangular swimming pool is visible near the buildings, with sun loungers positioned around it, offering a serene outdoor space.
Farm stay in Sovicille
5 out of 5 average rating, 62 reviews

Panoramic farmhouse with pool - Big Apartment

TiffanyRating, 5 stars2 weeks ago
This place was gorgeous! We loved the apartment and it was great for our family of 5. The grounds were gorgeous and the house charming! We also loved the full breakfast and were sad we didn’t sign up for it for the whole time. Rebecca and Paola were both so kind and helpful. We couldn’t have asked for anything more for our time in Tuscany. We will stay here again and hopefully get to try the pool.
Guest favorite
A neatly arranged outdoor dining table is set with various glassware and tableware. A vibrant bouquet of flowers is positioned in a vase at the center. In the background, a swimming pool reflects the sunlight, with vineyards and a historic church visible in the distance.
Apartment in Monteroni d'Arbia
4.94 out of 5 average rating, 17 reviews

Cottage by the pool, Siena

JonasRating, 5 stars7 months ago
amazing view, amazing location, thanks for everything! WiFi is good enough to work remotely including video calls etc.
Guest favorite
A sparkling pool is set in a well-maintained lawn, surrounded by tall trees and cypress plants. Comfortable lounge chairs are positioned beside the water, with a shaded area provided by an umbrella. The rustic villa can be seen in the background against a clear blue sky.
Villa in Asciano
4.95 out of 5 average rating, 75 reviews

Podere on the Crete Senesi

ChulaRating, 5 stars6 months ago
We spent a glorious and relaxing week at Sarchianello and could not recommend it more. The location was perfect for day trips to local places like Siena and Montalcino, and it was the ideal place to return to for an evening of eating and drinking. We loved our stay and were sorry to leave! It truly felt like a home away from home.
Guest favorite
A well-maintained pool area features a clear swimming pool in the foreground. Sun loungers are positioned beside the pool, shaded by umbrellas. In the background, the farmhouse with blue shutters is surrounded by lush gardens and trees, offering a serene outdoor space.
Home in Asciano
4.96 out of 5 average rating, 45 reviews

Tuscan farmhouse near Siena + Cortona, heated pool

RobRating, 5 stars6 months ago
We absolutely loved the home and location! There were nine of us and everyone had their own space and bathroom. The home was very clean and decorated beautifully. Amanda was a fabulous host. She was very responsive with all communication and helpful with places to see in the region. The location was excellent for traveling all around Tuscany and it was very peaceful. We can't wait to go back!
Superhost
Cottage in Paciano
4.71 out of 5 average rating, 21 reviews

Casetta Di Pietra 2-bed cottage with private pool.

DawidRating, 5 stars5 months ago
Fiona is a great host. She was really friendly and always eager to help. The house is super cosy and well equipped. The kitchen is great, there was everything we needed to cook delicious Italian dishes. We loved the fire burner. I can highly recommend this quiet place to anyone willing to rest from the bustling city life. The internet connection could be better but this is a very remote location so there’s probably nothing the host can do to improve it. The pool closes in October. It was too cold there to use it but it could have been mentioned in the offer. The quite high (300 eur) deposit for electricity was required and this should have been mentioned as well. It hasn’t been returned to us yet so I can’t say how high the bill for electricity could be. Anyway, this is a really nice place and we had a great time there.
Guest favorite
A tranquil pool with clear blue water reflects the sky, surrounded by lush greenery and colorful flowers. Rolling hills and a scenic landscape are visible in the background, enhancing the serene environment of the property.
Apartment in Sovicille
4.9 out of 5 average rating, 131 reviews

Apartment for 2 with super views+pool near Siena

JanRating, 5 stars7 months ago
Mario was very warm and a very very great host. We would always come back!
Superhost
The image features an aerial view of a spacious rural property, showcasing manicured gardens and a swimming pool surrounded by lounge chairs. In the background, hills and olive trees are visible, with charming structures dotting the landscape, enhancing the serene atmosphere of the Tuscan countryside.
Villa in Poderi di Montemerano
4.98 out of 5 average rating, 41 reviews

Fonte dei Frati - Private Villa and Pool

KelvynRating, 5 stars7 months ago
Perfect spot for a Tuscany experience. Nicely located between two friendly villages with fantastic restaurants and any supplies that you may need. The swimming pool was well maintained by Luciano and was used by us multiple times a day, for our group it was a highlight of the property. We all came away very happy with our stay and would totally recommend staying at this property.

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