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Family-friendly holiday rentals in Sinalunga

Find and book unique family-friendly homes on Airbnb

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

  • Total holiday rentals

    Explore 20 holiday rentals in Sinalunga

  • Nightly prices starting at

    Sinalunga holiday rentals start at €62 per night before taxes and fees

  • Verified guest reviews

    Over 250 verified reviews to help you choose

  • Pet-friendly holiday rentals

    Find 10 rentals that welcome pets

  • Holiday rentals with a pool

    10 properties feature pools

  • Rentals with dedicated workspaces

    10 properties have a dedicated workspace

  • Wifi availability

    20 of Sinalunga holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Sinalunga rentals

  • 4.7 Average rating

    Sinalunga stays receive an average rating of 4.7 out of 5 from guests

Top-rated family-friendly rentals in Sinalunga

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

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Top guest favourite
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 farmhouse 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 companionship of our animals. It's an invitation to rediscover the beauty of the little things, surrounded by the greenery of the most authentic Tuscany. It's not just a holiday; it's a return to our roots. This peaceful haven will stay in your heart. We look forward to welcoming you!

4.93 out of 5 average rating, 294 reviews
Superhost
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, 627 reviews
Top guest favourite
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.
Guest house 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, 252 reviews
Top guest favourite
The exterior of a charming farmhouse is visible, featuring stone walls adorned with climbing greenery. Large windows reflect natural light and overlook the landscaped garden. A gravel path leads to the entrance, surrounded by greenery and trees under a clear blue sky.
Home in Rigomagno

House Rigomagno Siena

Apartment with beamed ceilings and terracotta floors, this apartment is set in a 19th-century farmhouse located in the hills of Siena in Rigomagno Toscana. From the solarium next to the swimming pool in the middle of the olive trees, you can admire the panorama of the Sienese hills and the medieval village of Rigomagno ... all this characterizes the ideal holiday for couples or families who want to relax. Solarium, garden, terrace, swimming pool are exclusively for guests of the apartment.

4.96 out of 5 average rating, 125 reviews
Top guest favourite
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 Suites & Views

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.

4.98 out of 5 average rating, 187 reviews
Top guest favourite
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, 338 reviews
Top guest favourite
A serene pool area is showcased with two sun loungers positioned beside a tranquil salt-water pool. The expansive view of the valley and distant cityscape adds to the peaceful ambiance, while greenery surrounds the space, enhancing the sense of privacy and relaxation.
Farm stay in Monte San Savino

LUXURY VILLA SALTWATER POOL 35 min FROM CORTONA

ID Code: 051025 AAT 0017 Wisely renovated 1600 exclusive original tuscanian stone house, superbly positioned up on a hill in total privacy. This villa is placed in a real postcard with a 360˚ view. Just 30 minutes drive from Cortona and less than 10 minutes drive from A1 Monte San Savino motorway exit, the villa is reachable through a boulevard flanked by secular trees and it boasts a stunning view on the Valdichiana valley with its towns and villages such as Monte San Savino and Cortona.

4.99 out of 5 average rating, 116 reviews
Top guest favourite
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

Via della Stella is a charming agriturismo with a housing surface of 530m², divided over nine separate apartments. Each apartment has its own living room, kitchen and one or more bath & bedrooms. The farmhouse has a wonderful panoramic swimming pool. Its great position with view over the hills heading up to Montepulciano create a serene atmosphere. The farmhouse has been carefully decorated in rural Tuscan style. Activities such as wine tastings and cooking classes are available onsite.

4.94 out of 5 average rating, 109 reviews
Top guest favourite
A charming stone cottage is set within lush greenery, featuring a covered porch with outdoor seating. Olive trees surround the area, enhancing the natural beauty. A bicycle leans against the wall, inviting exploration of the peaceful countryside.
Cottage in Osteria delle Noci

Your Tuscan oak tree house, enchanting Val d'Orcia

The house enjoys a rare and enchanting view of the Val d’Orcia and Monte Amiata, ensuring maximum privacy. The interiors mirror the charm of the Tuscan style, with antique furniture and finishes made by local artisans. It is equipped with a double bedroom, a large living room with a big table, a fully equipped kitchenette, a double sofa bed in front of the fireplace, in the living room. Outside, the patio will allow you to eat with the colors of the sunset as a backdrop.

5.0 out of 5 average rating, 116 reviews
Top guest favourite
A modern kitchenette is equipped with essential appliances, including a microwave and coffee maker. A glass dining table is surrounded by four black chairs. A wooden bunk bed occupies one corner, with light filtering through the window providing a view of the greenery outside.
Flat in Sinalunga

Panoramic Resort - Private Terrace & Parking

New apartment, Wi-Fi, SMART TV, private bathroom, air conditioning, private kitchen, laundry room, free private parking, private terrace. Breathtaking panoramic view . A few minutes from the motorway, but surrounded by greenery, 800 meters from the center of the village, with restaurants, bars and supermarkets. Strategic for visiting major towns in Tuscany : Montalcino , Pienza , Siena , Arezzo , Terme , Montepulciano . City tax to be paid at the property.

4.98 out of 5 average rating, 173 reviews
Top guest favourite
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.

4.98 out of 5 average rating, 160 reviews
Guest favourite
A charming stone house with a terracotta roof features a welcoming entryway, shaded by umbrellas and surrounded by colorful flowers. In the background, a serene saltwater infinity pool is framed by landscaped greenery, complementing the tranquil rural setting.
Home in Foiano della Chiana

Conca d'Oro villa with private pool, sleeps 4

Just 2 km from the village, cozy typical Tuscan farmhouse, tastefully furnished and equipped. The farmhouse is located in a panoramic position immersed in the peaceful Tuscan countryside. Guests have access to a beautiful infinity pool for their exclusive use, equipped with sun loungers, and a lovely garden with a patio furnished for outdoor dining and enjoying fantastic sunsets. A strategic location for tourists. Free high-speed satellite Wi-Fi

4.92 out of 5 average rating, 173 reviews

Popular amenities for Sinalunga family-friendly rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Family-friendly home rentals with a hot tub

Top guest favourite
Villa in Montepulciano

Wine Experience Villa in Montepulciano

4.97 out of 5 average rating, 126 reviews
Top guest favourite
Villa in Chianciano Terme

Charming Tuscan Villa in Val d'Orcia with a view

4.97 out of 5 average rating, 130 reviews
Guest favourite
Home in Asciano

Palazzo Monaci - Pool in the Crete Senesi

4.96 out of 5 average rating, 142 reviews
Guest favourite
A stone villa surrounded by greenery is featured under a clear blue sky. A large swimming pool reflects the sunlight, complemented by sun loungers and colorful potted flowers along the edges. The outdoor area is perfect for relaxation with scenic views of the Tuscan hills.
Villa in Castiglion Fiorentino

Tuscan charm of villa - countryside - Villa Senaia

4.9 out of 5 average rating, 240 reviews
Guest favourite
Villa in Castiglione d'Orcia

Wp Relais Villa Vignalunga

4.93 out of 5 average rating, 117 reviews
Top guest favourite
An aerial view showcases the expansive grounds of La settecentesca Villa di Geggiano, surrounded by manicured gardens and lush vineyards. The main villa is prominent, with a circular driveway leading to it, while gentle hills extend into the background.
Cottage in Geggiano

Villa di Geggiano – Guesthouse

4.99 out of 5 average rating, 155 reviews
Guest favourite
Villa in Montepulciano

Villa in Montepulciano with a Pool

4.92 out of 5 average rating, 149 reviews
Guest favourite
A sparkling swimming pool is surrounded by sun loungers and umbrellas, offering a relaxing space for guests. The rustic farmhouse, with its stone exterior, is visible in the background, amidst lush greenery and trees under a partly cloudy sky.
Holiday home in Castelnuovo Berardenga

PIERFANTINI private Chianti house ♿️ 🏊‍♂️ 🐶

4.91 out of 5 average rating, 100 reviews

Family- and pet-friendly home rentals

Guest favourite
The image showcases a rustic stone building surrounded by a gravel courtyard. Flower pots with vibrant geraniums decorate the area, and a large tree provides shade. Sunlight illuminates the brick facade, creating a warm and inviting atmosphere in the outdoor space.
Home in Foiano della Chiana

La Lisa: country house surrounded by fields

4.94 out of 5 average rating, 135 reviews
Top guest favourite
A large, rectangular swimming pool is set within a green lawn, surrounded by tall trees and blooming shrubs. Sun loungers are placed around the pool, providing a space for relaxation. The lush Tuscan countryside stretches into the distance under a clear blue sky.
Villa in Montepulciano

A paradise in Montepulciano...

4.96 out of 5 average rating, 169 reviews
Top guest favourite
Home in Scrofiano

Jenny's Barn

4.96 out of 5 average rating, 187 reviews
Guest favourite
Farm stay in Castelnuovo Berardenga

Apartment in a Tuscan farmhouse at Le Pietre Vive

4.92 out of 5 average rating, 359 reviews
Top guest favourite
A dog sits in a grassy area, observing the expansive vineyard landscape that unfolds beyond, featuring rolling hills and rows of grapevines under soft morning light.
Farm stay in Montepulciano

Separate room, between Cortona and Montepulciano

4.95 out of 5 average rating, 229 reviews
Guest favourite
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, 104 reviews
Top guest favourite
An inviting interior features exposed brick walls and a blend of modern and rustic design elements. A staircase leads to the upper floor, while large doors open to reveal a view of the outdoors. A wooden table and a cozy chair enhance the living space.
Flat in Montepulciano

Under the sunset, Montepulciano

4.98 out of 5 average rating, 165 reviews
Top guest favourite
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.
Apartment in Asciano

Pink like the sunset sky

4.99 out of 5 average rating, 236 reviews

Family-friendly home rentals with a pool

Top guest favourite
An aerial view captures Podere Vergianoni nestled in the Chianti hills, surrounded by lush vineyards. The property features a clear blue pool, shaded terraces, and carefully landscaped gardens. Rolling hills and rows of grapevines create a serene backdrop, highlighting the natural beauty of the Tuscan countryside.
Apartment in Noce

Podere Vergianoni nestled in Chianti with a pool

5.0 out of 5 average rating, 352 reviews
Top guest favourite
An outdoor pool area is surrounded by olive trees and vineyards, with sun loungers and shaded umbrellas arranged on the deck. Soft sunlight bathes the scene, highlighting the peaceful setting. A gravel path leads around the pool, inviting relaxation amid the natural landscape.
Flat in Monteriggioni

Comfort Apartment in the Chianti Vineyards

4.93 out of 5 average rating, 455 reviews
Top guest favourite
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.
Flat in Montalcino

Panoramic Country Suite Montalcino

4.9 out of 5 average rating, 406 reviews
Top guest favourite
The exterior of a charming villa is surrounded by lush greenery, with vines climbing along the walls. A gravel pathway leads to the entrance, framed by well-kept gardens. Sunlight filters through the trees, creating a peaceful atmosphere ideal for relaxation and outdoor gatherings.
Villa in Pergine Valdarno

La Vignaccia (Farmhouse) - villa w/private pool

4.96 out of 5 average rating, 102 reviews
Top guest favourite
Flat in Castiglione del Lago

Farmhouse close to Montepulciano

4.88 out of 5 average rating, 145 reviews
Top guest favourite
A two-story villa with terracotta roof tiles is surrounded by lush greenery and trees. A welcoming entrance is framed by climbing plants. The property is set against a scenic backdrop of rolling hills and vineyards, creating a serene atmosphere.
Farm stay in Sinalunga

Villa Panorama near Siena Tuscany

5.0 out of 5 average rating, 55 reviews
Superhost
The expansive view captures rolling hills and lush greenery, framed by a scattering of trees. Charming farmhouses dot the landscape, reflecting a serene countryside ambiance under a partly cloudy sky. Mountains can be seen in the distance, adding depth to the scenic horizon.
Apartment in Sinalunga

Geranium Apartment with Pool

4.68 out of 5 average rating, 19 reviews
Superhost
The exterior of a rustic stone villa features a large, multi-level structure with a sloping roof and a shaded terrace. Comfortable seating areas with sun loungers are positioned on the grassy lawn, surrounded by low greenery and tall trees, under a clear blue sky.
Home in Sinalunga

Perfect Large Family Villa in Tuscany

4.91 out of 5 average rating, 23 reviews

Destinations to explore