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Family-friendly vacation rentals in Santa Fiora

Find and book unique family-friendly homes on Airbnb

Quick stats about vacation rentals that are family-friendly in Santa Fiora

  • Total vacation rentals

    Explore 20 vacation rentals in Santa Fiora

  • Nightly prices starting at

    Santa Fiora vacation rentals start at ﺩ.ﺇ 257 per night before taxes and fees

  • Verified guest reviews

    Over 140 verified reviews to help you choose

  • Pet-friendly vacation rentals

    Find 10 rentals that welcome pets

  • Wi-Fi availability

    10 of Santa Fiora vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi, and Pool across Santa Fiora rentals

  • 4.7 Average rating

    Santa Fiora stays receive an average rating of 4.7 out of 5 from guests

Top-rated family-friendly rentals in Santa Fiora

Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

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Top guest favorite
A rustic building is seen under a starry night sky, with a partial roof providing shelter. Soft light glows from the interior, illuminating the entrance. Lush greenery and trees surround the scene, adding depth to the serene nighttime landscape.
Farm stay in Simignano

Casa al Gianni - Hut

Hi, we’re Cristina and Carmelo! We look forward to welcoming you to “Casa al Gianni,” our agritourism property in the woods of the Montagnola Senese, just 20 minutes from Siena. Here, life slows down: just the scent of the earth, the song of the birds, and the warmth of our animals. It is an invitation to rediscover the beauty of the little things, surrounded by the greenery of the most authentic Tuscany. It’s not just a vacation; it’s a return to our roots. This peaceful haven will stay in your soul. We look forward to welcoming you!

4.93 out of 5 average rating, 288 reviews
Top guest favorite
A rustic stone farmhouse is nestled in a lush green landscape, surrounded by rolling hills and tall cypress trees. The sun casts a warm glow on the exterior, highlighting the charming architecture. An open courtyard with a small pool can be seen in the foreground.
Farm stay in Campiglia D'orcia

Poggio Bicchieri Holiday Farm - Memoria apartment

Relax with the whole family in this accommodation. The holiday farm consists of two independent apartments with a living room, kitchen, bedroom, and bathroom. You won't have to share anything with other guests, as we have taken care to organize everything so that everyone has their own space and everything is separate. Outside there is a barbecue, table with chairs and deck chairs. In the vicinity are Pienza, San Quirico d'Orcia, Bagno Vignoni, Montalcino, and Bagni San Filippo. To reach us, there is 1.5 km of dirt road!

4.92 out of 5 average rating, 620 reviews
Top guest favorite
A wooden dining table is positioned beneath shelves holding decorative items and books. A plant in a vase adds a touch of greenery. A staircase is visible in the background, along with a cabinet displaying more books and decor on nearby shelves.
Apartment in Castel del Piano

Casa Cecilia Farm

Apartment in a house surrounded by greenery, near the village of Castel del Piano. It overlooks the chestnut grove of the property and beyond the view is lost along the valley of the Ente river until you can see the Brunello vineyards and the centuries-old olive trees. The apartment consists of a living room, a kitchen, and a bedroom. Possibility to use the wood-burning oven and barbecue as well as the garage for bicycles and motorcycles ideal for discovering the wonders of Monte Amiata. Tourist tax to be paid on-site

4.99 out of 5 average rating, 288 reviews
Top guest favorite
A spacious rooftop terrace is showcased, featuring a black chair and a table positioned near flowering red plants. Sunlight casts shadows on the tiled floor, highlighting the surrounding terracotta rooftops and greenery in the distance, offering a scenic view of the medieval town.
Home in Abbadia San Salvatore

La Casetta di Alice - with panoramic terrace -

The house is in the heart of the medieval historic center of Abbadia S. S. Distributed over several levels, it has two independent entrances, and a large roof terrace, equipped solarium, from which you can admire a beautiful view. Recently renovated, it offers a unique and welcoming atmosphere. TV in the living room and in the bedroom. Ultra-fast FASTWEB Wi-Fi. For a couple with a child, there is also the option to add a single bed in the room with the parents. Self check-in is available.

4.98 out of 5 average rating, 174 reviews
Top guest favorite
A charming cottage is shown with a terracotta facade and a tiled roof. A small table with two chairs is set on a patio, surrounded by potted plants. Lush greenery and trees can be seen in the background under a clear blue sky.
Guesthouse in Macciano

Tuscan cottage with an heavenly view

Heaven's Window takes your breath away. As our only guests, you will be surrounded by infinite views, endless tranquility, sounds of singing birds and calling deer. Down the valley and on your walks you may spot foxes ferrets and wild boar. Collect porcupine quills. Breathe! Halfway between Rome and Florence. Close to Siena, Val d’Orcia and countless hot springs . A private paradise surrounded by divine dining and hilltop jewels of antiquity like Montepulciano and Montalcino of sublime wines.

4.97 out of 5 average rating, 246 reviews
Top guest favorite
A serene landscape features rolling green hills under a vibrant sunset sky, casting soft colors across the horizon. A stone wall is adorned with lush greenery and flowers, providing a tranquil viewpoint for someone contemplating the picturesque view of the valley and distant hills.
Home in Cetona

Casa Dolce Toscana | Panoramic Suite with a View

CASA DOLCE TOSCANA 🖼️ Hi! I'm Jolanta 😊 Welcome to our beloved Tuscan accommodation, with panoramic views, nestled in the hills of Tuscany. A perfect oasis of peace for those who want to relax and enjoy an authentic experience. Located a few kilometers from Siena and Florence, our accommodation combines rustic charm with all modern comforts. It is located in the heart of the historic center of the famous village of Cetona, below the castle, overlooking the valley and the scent of Tuscany.

4.99 out of 5 average rating, 178 reviews
Guest favorite
A serene outdoor pool area is surrounded by lush greenery and rustic stone pathways. Lounge chairs are positioned beside the pool, creating a space for relaxation. The picturesque villa can be seen in the background, framed by trees and gentle hillside.
Villa in Castiglione d'Orcia

Wp Relais Borgo Vignalunga

Discover Borgo Vignalunga by WP Relais, an charming hamlet set in a 46-hectare estate in the heart of the Val D'Orcia, a UNESCO World Heritage Site. Surrounded by woodland, pastures, a lush vegetable garden, cultivated fields and three olive groves with 1,500 olive trees, Borgo Vignalunga is the ideal place to experience the true essence of Tuscany. The property is close to historical villages, evocative architecture, unspoilt natural landscapes and renowned restaurants, bars and wineries.

4.94 out of 5 average rating, 145 reviews
Top guest favorite
The villa's exterior is highlighted by a modern structure with large glass doors and a gently sloping roof. It is surrounded by lush greenery and features a patio area with steps leading to the entrance. Soft lighting illuminates the garden, creating a serene evening ambiance.
Villa in Montepulciano

Amazing Tuscany Villa, FREE parking

Modern villa with panoramic view in Montepulciano, a few steps from San Biagio. The villa is lovingly furnished and equipped with all comforts for a pleasant holiday. Enjoy breathtaking views of the surrounding countryside from the terrace, or relax in the two spacious gardens at your disposal. You will also have at your disposal a large kitchen to dabble in the magnificent art of cooking, something much loved by us Italians!!! Also available: Free Wi-fi Self check-in Reserved car parking

4.92 out of 5 average rating, 331 reviews
Guest favorite
A modern stone house is surrounded by lush greenery, nestled against a hillside. Large glass windows provide ample natural light, showcasing the inviting interior. The roof has a gentle slope, reflecting a blend of traditional and contemporary architecture.
Cottage in Seggiano

EcoLodge – modern design in a peaceful panoramic location

The modern, ecological and comfortable EcoLodge is quiet and secluded, surrounded by olive groves, chestnut and fruit trees, vines and meadows. In front of you are the hills of the Val d'Orcia; behind you is Monte Amiata. Three worlds meet here: Val d'Orcia, Monte Amiata, and Maremma. The Vielfältigkeit is an ideal base for culture, wine, hiking, mountain biking, hot springs and the sea – and at the same time a place to enjoy Tuscan country life away from the crowds of tourists.

4.94 out of 5 average rating, 110 reviews
Top guest favorite
An aerial view showcases a charming stone cottage surrounded by lush greenery and mature trees. The roof is partially covered with natural foliage, blending the structure harmoniously into the landscape. The area features rocky outcrops and dense vegetation, highlighting the peaceful rural setting.
Farm stay in Seggiano

Terra Delle Sidhe, Seggiano, Tuscany

Terra delle Sidhe is a small organic farm located in southern Tuscany overlooking a beautiful valley located on the slopes of Monte Amiata, between the medieval towns of Castel del Piano and Seggiano. A 250 year old chestnut dryer stone house in use till 30 years ago, the holiday cottage we offer is surrounded by an organic chestnut forest and olive trees that are hundreds of years old. This charming cozy house it has now been lovingly renovated with taste and simplicity.

4.99 out of 5 average rating, 290 reviews
Top guest favorite
An aerial view highlights a stone farmhouse nestled within lush greenery, surrounded by mature trees. The structure features a terracotta-tiled roof and a charming porch. A pathway leads to a smaller stone building, providing a sense of harmony with the natural landscape.
Villa in Sarteano

Stone farmhouse in Val D'Orcia

19th-century Tuscan farmhouse with exposed stones immersed in the wonderful Tuscan countryside with a splendid view of the Val di Chiana. It is surrounded by a 6-hectare park with an olive grove of 300 plants. It is located in Sarteano, in the village, an ancient medieval village with a dream castle, known for the Music and Jazz Festival that takes place at the end of summer. We are in the beautiful Val d'Orcia, a UNESCO World Natural Heritage Site since 2004.

4.97 out of 5 average rating, 158 reviews
Top guest favorite
A rustic stone farmhouse is surrounded by colorful flower pots, adding charm to the entryway. The structure features a mix of wooden shutters and terracotta accents. A gravel driveway leads to the entrance, framed by lush greenery and vibrant blooms.
Apartment in Castiglione d'Orcia

Mimosa Apartment - Poggio al Vento

Private apartment in a farmhouse from the 1600s. The same consists of kitchen, double bedroom and bathroom. It has everything you need for a pleasant stay. From the terrace, the breathtaking view, overlooking Mount Amiata, Rocca D'Orcia an ancient fortress and the Castle of Ripa D'Orcia. The swimming pool overlooks the Montalcino side. We are an organic farm, we produce high quality wine and oil. We offer, for a fee, tastings of our red wines. Winery tour etc

4.99 out of 5 average rating, 112 reviews

Popular amenities for Santa Fiora family-friendly rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Family-friendly home rentals with a hot tub

Top guest favorite
A traditional stone casale is set among lush greenery, featuring wooden shutters on the upper windows. Olive and fruit trees frame the home, enhancing its natural setting. A well-maintained lawn extends around the property, inviting relaxation in this peaceful environment.
Cabin in Cetona

Poggio dell'orso.Traditional Casale. Amazing views

4.96 out of 5 average rating, 167 reviews
Top guest favorite
The exterior of a charming stone villa is surrounded by a lush garden featuring vibrant lavender plants. Stairs lead to a welcoming entrance adorned with potted flowers and a shaded seating area. The rustic façade reflects traditional Tuscan architecture against a clear blue sky.
Villa in Chianciano Terme

Charming Tuscan Villa with View forFamily&Friends

4.97 out of 5 average rating, 128 reviews
Top guest favorite
Villa in Montepulciano

Wine Experience Villa in Montepulciano

4.97 out of 5 average rating, 125 reviews
Guest favorite
Home in Asciano

Palazzo Monaci - Pool in the Crete Senesi

4.96 out of 5 average rating, 138 reviews
Top guest favorite
A serene garden area features a lounging chair with a folded towel placed neatly on it. Stone planters and lush greenery surround a small hot tub, complemented by flowering plants and trees. The backdrop includes rustic architecture under a clear sky.
Villa in Monticchiello

Villa unesco heritage, Jacuzzi & garden. BB Daria

4.98 out of 5 average rating, 182 reviews
Top guest favorite
A rustic stone house is set on a green hillside, surrounded by trees. A large pool reflects its surroundings, with steps leading into the water. The garden features well-maintained lawns and a wooden deck nearby, inviting outdoor relaxation.
Home in Poggi del Sasso

LECCIONE RESIDENCE

4.93 out of 5 average rating, 144 reviews
Top 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

Your Private Tuscan Retreat

4.99 out of 5 average rating, 162 reviews
Guest favorite
Villa in Montepulciano

Villa a Montepulciano con Piscina

4.92 out of 5 average rating, 146 reviews

Family- and pet-friendly home rentals

Guest favorite
Farm stay in Pienza

Agriturismo Palazzi del Papa Val d'Orcia Pienza

4.94 out of 5 average rating, 194 reviews
Top guest favorite
A rustic agriturismo is framed by vibrant greenery and blooming flowers. Outdoor seating is provided by several light-colored chairs and a patterned table. The stone building showcases large windows, which invite natural light into the space, while a welcoming atmosphere is suggested by the well-maintained garden.
Farm stay in Pienza

Spedaletto Castle, Val d'Orcia, Pienza

4.97 out of 5 average rating, 181 reviews
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

Pink like the sunset sky

4.99 out of 5 average rating, 233 reviews
Top guest favorite
Aerial view of a serene agriturismo surrounded by lush vineyards and golden fields. The property features a pool set amidst well-kept gardens and tall cypress trees. Rolling hills in the background extend towards the horizon, contributing to the peaceful landscape.
Farm stay in Montepulciano

Tuscan farmhouse stay with restaurant and pool

4.94 out of 5 average rating, 107 reviews
Top guest favorite
A spacious room features a double bed with an orange bedspread, complemented by two wooden nightstands. Natural light floods in through a large window with orange curtains, while a wooden beam ceiling adds character. Vintage decor elements are showcased on the walls.
Farm stay in Chiusi

Breeder's Room - Triple room breakfast included

5.0 out of 5 average rating, 107 reviews
Superhost
An open door reveals a scenic view of historic buildings on a hillside. Light floods the room, highlighting the wooden furniture and stone flooring. A subtle contrast between the interior and the vibrant landscape can be seen in the background.
Earthen home in Pitigliano

The cave

4.86 out of 5 average rating, 1008 reviews
Top guest favorite
The illuminated village of Pitigliano is captured at dusk, showcasing its distinct stone buildings and rooftops. The historic tower stands prominently in the background, while soft lights line the streets, creating a serene atmosphere in the valley below.
Condo in Pitigliano

Panoramic penthouse in the ancient village

4.94 out of 5 average rating, 463 reviews
Top guest favorite
A charming outdoor seating area is set against a backdrop of rolling green hills. Two green metal chairs and a matching table are surrounded by flowering plants, with cypress trees rising in the distance under a partly cloudy sky.
Condo in Pienza

Tuscan rural home in Mascagni Farmhouse Pienza

5.0 out of 5 average rating, 159 reviews

Family-friendly home rentals with a pool

Top guest favorite
A wooden dining table is set in a lush green garden, surrounded by blooming flowers. Sun loungers and umbrellas line the pool area, with a distant view of rolling hills under a clear blue sky.
Farm stay in Pienza

Piandimaggio family and friends

4.87 out of 5 average rating, 322 reviews
Top guest favorite
A scenic view of the Tuscan hills is framed by clusters of pink roses in the foreground. The rolling landscape features layers of green and gold fields, softly fading into the horizon under a clear sky.
Apartment in Montalcino

Panoramic Country Suite Montalcino

4.9 out of 5 average rating, 404 reviews
Top guest favorite
A spacious living area features a comfortable gray sofa adorned with colorful cushions. Natural light fills the room through large arched windows. A rustic dining table and wooden chairs are positioned nearby, while a staircase leads to the upper floor.
Home in Orvieto

Vineyards Paradise

4.99 out of 5 average rating, 243 reviews
Guest favorite
The image depicts a serene swimming pool surrounded by sun loungers and umbrellas, set against a backdrop of lush greenery and the distant Monte Amiata. The clear water reflects the sky, offering a tranquil atmosphere for relaxation and enjoyment.
Farm stay in Montepulciano

Unique view 3 bdr villa with pool & A/C in Pienza

4.95 out of 5 average rating, 102 reviews
Top guest favorite
Aerial view of the agriturismo surrounded by lush green hills and fields. The property includes a swimming pool, framed by rows of tall cypress trees that create a natural boundary. The rural landscape extends into the distance, illustrating the serene environment.
Condo in Asciano

Loggiato 3 apartment in Tuscany near Siena

4.93 out of 5 average rating, 201 reviews
Top guest favorite
A person interacts with a falcon, demonstrating the connection between humans and raptors. The background features a natural landscape with greenery, and additional animals can be seen grazing in the distance. The setting showcases an engaging outdoor experience in a tranquil environment.
Vacation home in Chianciano Terme

The Eagle and the Olive Tree

5.0 out of 5 average rating, 127 reviews
Guest favorite
An ancient stone farmhouse is viewed from a garden, surrounded by lush greenery. A wooden pergola stretches alongside the building, adorned with blooming plants. The sun sets gently behind the mountains, casting a warm glow over the peaceful landscape.
Farm stay in Pescina

Luca's Farmhouse Brezza Apartment

4.86 out of 5 average rating, 105 reviews
Guest favorite
Villa in San Casciano dei Bagni

Podere la Piscina Termale – RestArt

4.92 out of 5 average rating, 24 reviews

Destinations to explore