Family-friendly vacation rentals in Trequanda

4.97 out of 5 average rating, 194 reviews

An outdoor patio area features rustic furnishings and is framed by gracefully draping curtains. The space is adorned with comfortable seating and a communal dining table, set against a backdrop of tall cypress trees and a clear blue sky, inviting relaxation in a serene environment.

Home in Simignano

Casa al Gianni - The Simignano Barn

Converted from an old barn, this luxurious retreat offers 5 bedrooms, 4 bathrooms, a large fully equipped kitchen, a spacious living room, a large private garden with parking, a hot tub, a patio with sofas, a BBQ, a fire pit, and an outdoor kitchen. Ideal for those looking for a unique experience, it combines rustic charm with modern comforts. Perfect for families or groups, it promises magical evenings under the stars, including relaxation in the hot tub and outdoor dinners. A memorable getaway awaits you in this slice of paradise!

Farm stay in Campiglia D'orcia

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.

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

4.99 out of 5 average rating, 233 reviews

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

The apartment is located on the 2nd floor, consisting of 2 bedrooms (possibility of making double or single beds depending on the needs of the customer), a bathroom, large living room and kitchen equipped for cooking. TV, (for those who request it, a washing machine is available from 9 a.m. to 8 p.m. in our laundry room). To come to us, a car is recommended, to be independent, and to visit the Tuscan countryside. Convenient location for visiting Tuscany I look forward to showing you the real Tuscany!

4.97 out of 5 average rating, 125 reviews

Wine Experience Villa in Montepulciano

🏡 Villa Talosa is immersed in the vineyards of the Fattoria della Talosa, a historic winery in Montepulciano that produces Vino Nobile. An authentic place, ideal for relaxing with the magic of the Tuscan countryside and an enchanting view from every window. Just 1.5 km from the historic center, which can also be reached on foot, you can visit our Historic Winery from the 1500s under Piazza Grande: a unique experience between history and passion for wine. Heating and air conditioning are included.

4.96 out of 5 average rating, 138 reviews

Home in Asciano

Palazzo Monaci - Pool in the Crete Senesi

Welcome to Palazzo Monaci! An oasis of nature and unique beauty, in the heart of the Crete Senesi, in Tuscany. A residence with a pool and a breathtaking view of the Crete Senesi. Perfect for couples or families looking for a relaxing vacation. The location is perfect for exploring the surrounding areas. You can hike in the Tuscan countryside, visit the characteristic medieval villages, taste the delicious local wines, and immerse yourself in the culture and history of this fascinating region.

Farm stay in Castelnuovo Berardenga

Apartment in Tuscan farm house.

Small, cosy apartment with independent access, consisting of charming bedroom with a beautiful view, equipped with ample closet space, a comfortable canopy bed and private bathroom and pretty living room / breakfast area, with sofa-bed. A delicious breakfast is included in the price and from April through October guests also have the option of dining on-site in our traditional farm restaurant. If dates are not available the property includes other rooms in charming cottage also on Airbnb.

4.92 out of 5 average rating, 357 reviews

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.

4.92 out of 5 average rating, 331 reviews

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

Farm stay in Monte San Savino

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.

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, 113 reviews

Farm stay in Montepulciano

Aerial view of a scenic agriturismo surrounded by vineyards and rolling hills. The property features a pool and is framed by tall cypress trees, enhancing the natural landscape of lush green and golden fields under a partly cloudy sky.

Rural Tuscany | Family farmstay with restaurant

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.

4.96 out of 5 average rating, 115 reviews

Cottage in Osteria delle Noci

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.

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, 115 reviews

4.97 out of 5 average rating, 158 reviews

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, 181 reviews

Home in Scrofiano

Jenny's Barn

The ancient barn, now finely restored, is located in the heart of the Valdichiana a few steps from the characteristic medieval village of Scrofiano. From the house you can enjoy a breathtaking view of the green Sienese hills where centuries-old olive trees and vineyards alternate from which the prestigious Chianti is obtained. Ideal for 2 people looking for a relaxing stay away from the chaos of the city. On request it is possible to add a baby bed and a cot.

Popular amenities for Trequanda family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

4.98 out of 5 average rating, 182 reviews

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

Villa in Chianciano Terme

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.

Charming Tuscan Villa with View forFamily&Friends

4.97 out of 5 average rating, 128 reviews

Villa in Castiglion Fiorentino

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.

Tuscan charm of villa - countryside - Villa Senaia

4.9 out of 5 average rating, 240 reviews

4.99 out of 5 average rating, 177 reviews

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

4.96 out of 5 average rating, 167 reviews

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

4.92 out of 5 average rating, 146 reviews

Villa a Montepulciano con Piscina

4.99 out of 5 average rating, 155 reviews

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

Farm stay in Gaiole in Chianti

A warm living area is presented, featuring a comfortable sofa adorned with soft pillows and a round dining table. The space is illuminated by wall sconces, while an arched entryway leads to another room. Large windows allow natural light to fill the area.

La Pieve - the house next to the church

4.97 out of 5 average rating, 115 reviews

Family- and pet-friendly home rentals

Vacation home in Monticchiello

An outdoor seating area features a small table surrounded by two chairs, adorned with a light breakfast setup. The stone facade of the house is complemented by climbing vines and a bright flower arrangement, inviting guests to enjoy the fresh air.

In Toscana Camere

4.96 out of 5 average rating, 137 reviews

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.

4.96 out of 5 average rating, 166 reviews

A paradise in Montepulciano...

Home in Foiano della Chiana

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.

La Lisa: country house surrounded by fields

4.94 out of 5 average rating, 135 reviews

4.97 out of 5 average rating, 246 reviews

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

Apartment in Monticchiello

Two comfortable chairs are positioned on a lush green lawn, complemented by a small wooden table. A basket of vibrant yellow flowers is nearby, set against a backdrop of rolling hills and cypress trees under a clear blue sky.

Casa Bonari - a paradise for the eyes

4.97 out of 5 average rating, 187 reviews

Farm stay in Montepulciano

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.

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

4.95 out of 5 average rating, 102 reviews

Superhost

The exterior of a cottage is surrounded by lush greenery and large trees, providing a natural frame. The stone structure features an archway entrance, with a chimney visible above the roof, blending harmoniously into the tranquil landscape.

Farm stay in Siena

Spigo - Indipendent Cottage Zampugna

4.85 out of 5 average rating, 128 reviews

Apartment in Montepulciano

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.

Under the sunset, Montepulciano

4.98 out of 5 average rating, 163 reviews

Family-friendly home rentals with a pool

4.96 out of 5 average rating, 122 reviews

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

4.99 out of 5 average rating, 117 reviews

The outdoor pool area features a light blue water surface complemented by three tiered fountains. A small white table with a glass is placed on the wooden deck, surrounded by two white chairs. The rustic stone buildings create a charming backdrop, adorned with greenery.

Apartment in Montalcino

Castel Brunello - 2 doublebed rooms + terrace

Home in Abbey of Monte Oliveto Maggiore

The image showcases a serene swimming pool with crystal-clear water reflecting the blue sky. In the background, a rustic two-story house with brick exterior is framed by lush greenery and flowering plants, creating a tranquil setting.

Country House in the Crete Senesi

4.97 out of 5 average rating, 206 reviews

Home in Foiano della Chiana

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.

Conca d'Oro villa with private pool, sleeps 4

4.92 out of 5 average rating, 172 reviews

4.94 out of 5 average rating, 18 reviews

A spacious living area features a striped sofa with soft cushions, complemented by a wooden coffee table and a vase of fresh flowers. The warm terracotta flooring and rustic beams enhance the inviting ambiance. Steps lead to additional rooms, visible in the background.

Condo in Montisi

Apartment in ancient house + pool and terrace

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

4.9 out of 5 average rating, 21 reviews

Home in San Giovanni d'Asso

Country chic house in a village,private pool,wiFi

5.0 out of 5 average rating, 81 reviews