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Cottage holiday rentals in Siena

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Top-rated cottage rentals in Siena

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Guest favourite
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 in a quiet and secluded location, 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 diversity is an ideal starting point 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 favourite
An aerial view of the historic Monteriggioni Castle showcases its medieval architecture surrounded by lush countryside. The fortified walls encircle the village, which is dotted with trees and buildings, while rolling hills extend into the distance under a sunset sky.
Cottage in Monteriggioni

Monteriggioni Castello, holiday house in Tuscany

Our accommodation is a historic building that dates back to the construction of the castle. It has been recently restored and furnished with attention to every detail. It is very welcoming and has all the most modern amenities. Tourists who decide to be our guests will have the advantage of living in the medieval environment of the castle, taking advantage of all the conveniences. They will feel pampered and have the opportunity to return home having lived a unique and unforgettable experience.

4.95 out of 5 average rating, 295 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

PLEASE NOTE THAT BEING IN THE COUNTRYSIDE WITH FEW PUBLIC TRANSPORTATION OTHER THAN TAXI, THE BEST WAY TO ENJOY YOUR STAY AND TO VISIT THE BEAUTIFUL SURROUNDINGS IS TO HAVE A CAR. The 18th century Villa di Geggiano, surrounded by vineyards and lovingly cared gardens, is located in the Chianti area near Siena, one of the most beautiful regions of Italy which will provide an idyllic and enchanting backdrop to your vacation. Our guesthouse is located in one of the garden pavilions of the villa.

4.99 out of 5 average rating, 155 reviews
Top guest favourite
The stone house features a welcoming entrance with large arched windows. A vibrant flower box filled with geraniums complements the lush green lawn. A shaded area with wooden seating offers a place to relax, while the infinity pool and surrounding vineyards are visible in the background.
Cottage in Barberino Tavarnelle

Stone House with Exclusive Pool Codilungo in Chianti

Welcome to your Tuscan dream between Florence & Siena. Perfect for families or romantic getaways. • 360° views of iconic Chianti hills. •Huge Exclusive Infinity Pool (17x9m), lit at night (open from May 1st to October 15th) • Total privacy, yet restaurants/shops are 10-15 mins away. • Comfort for 6: 3 bedrooms (2 double, 1 twin) & 3 full baths. • Modern amenities: Fully equipped kitchen area, Smart TV. • Outdoor bliss: Large dining loggia, professional BBQ, poolside porch & bath.

4.98 out of 5 average rating, 216 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, 115 reviews
Top guest favourite
A stone patio is shown, featuring a small table set with two chairs. The entrance to the cottage is visible, accompanied by wooden shutters. Lush greenery surrounds the area, providing a serene environment.
Cottage in Ponte Feccia

Country cottage C&M surrounded by greenery, love Tuscany

Country stone cottage, independent in the Tuscan countryside in the province of Siena, with large garden, porch and gazebo. Our house is located in the countryside of the municipality of Chiusdino, just 5 minutes from the two main towns of Monticiano and Chiusdino and 10 minutes from the beautiful Abbey of Galgano. 30 minutes from Siena, from Monteriggioni, an hour from Florence and 30/40 minutes from the sea. Just 20 minutes from the beautiful Terme del Petriolo.

4.95 out of 5 average rating, 200 reviews
Top guest favourite
A spacious area of well-kept grass is seen in the foreground, with a rustic Tuscan farmhouse in the background. The building features a tiled roof and multiple windows. Bare trees and some greenery surround the property, under a clear blue sky with scattered clouds.
Cottage in Sovicille

From Simone, podere santi Lucia and Pietro

Recently opened, the property is a section of a Tuscan farmhouse with a separate entrance, set in the Sienese countryside just 10 minutes from the historic centre of Siena. The apartment consists of two double bedrooms with two double beds and a single bed, a bathroom with a shower and a bathtub, a living room and a kitchen. A 60x120 cm cot with safety rails is available on request. There is a shared farmyard outside. Tourist tax €1.50/person

4.94 out of 5 average rating, 240 reviews
Top guest favourite
Cottage in Castellina in Chianti

Leccio Cottage - Masseto In Chianti

MASSETO IN CHIANTI, located in La Piazza, between Panzano and Castellina in Chianti, is a private village where you can relax in the garden and near the pool, play sports, or pivot to visit many surrounding Renaissance towns like Firenze, Siena, San Giminiano, Arezzo, Volterra. Kids can move carefree in the village. We offer four indipendent ancient cottages : Quinto (2 beds), Vittoria (4 beds), Cappero (4 beds), Leccio (6 beds).

4.96 out of 5 average rating, 102 reviews
Guest favourite
Cottage in Sovicille

Lovely apartment with garden and views near Siena

At just 18km from Siena, the apartment is part of a traditional Tuscan farmhouse, Santa Barbara, tucked away in the scenic rolling hills of Tuscany. The uniquely positioned grounds dominate the valley, allowing for stunning views with the most enchanting sunsets, or sunrises for those early birds! The apartment allows for a relaxing and recharging break, as well as being in the perfect location to go out and explore.

4.89 out of 5 average rating, 160 reviews
Guest favourite
Two rattan chairs are positioned on a lush green lawn, overlooking rolling hills dotted with olive trees. The tranquil scene features views of a medieval town with distinctive towers, under a partly cloudy sky.
Cottage in San Gimignano

Countryside Cottage With View - Le Papere apt

The cottage is part of a charming traditional Tuscan farmhouse, built in stone and situated in one of the most beautiful areas of Tuscany. A lovely garden surrounds the house and has magnificent views of the medieval town with its famous towers. Warm and cozy atmosphere that makes you feel instantly at home. For those who wish to live the experience of the Tuscan countryside as it is lived by the locals.

4.88 out of 5 average rating, 137 reviews
Guest favourite
A charming cottage is surrounded by lush green grass and decorative plants. The rustic brick exterior features large windows framed with climbing vines. A cozy seating area on a tiled porch offers a relaxing view of the garden and the inviting countryside.
Cottage in Montagnano

Charming cottage in Tuscany

Charming cottage located on a hill with 360-degree views. An oasis of peace and quiet. Surrounded by greenery. Large swimming pool BBQ Area Inside there is a bedroom with a French bed, a living room with a sofa bed, a bathroom, a kitchenette and an indoor and outdoor dining area. Ideal for couples and families with one/two children. Crib available

4.94 out of 5 average rating, 139 reviews
Guest favourite
An open space design features a vaulted brick arch, creating a warm atmosphere. Two spacious beds are positioned under wooden beams, accompanied by a compact seating area and a desk. Natural light filters through the windows, enhancing the rustic charm of the room.
Cottage in Chiusdino

Open-space rural house in San Galgano

The stylishly restored open space house has a large garden with an orchard and a vine arbor with barbecue and a spectacular view of the valley. Located in a village in the Municipality of Chiusdino near the Abbey of San Galgano.

4.93 out of 5 average rating, 174 reviews

Popular amenities for cottage rentals in Siena

KitchenWifiPoolFree parking on premisesAir conditioning

Cottage rentals with a hot tub

Top guest favourite
A shaded pergola adorned with grapevines provides a relaxing spot for outdoor dining. A colorful table features a floral design, surrounded by wrought iron chairs. A private jacuzzi sits nearby, with lush greenery and rolling hills visible in the background.
Cottage in Castelmuzio

Panoramic view & outdoor jacuzzi - Pienza

5.0 out of 5 average rating, 79 reviews
Superhost
A glass-enclosed veranda offers a view of the private garden and pool area. A round dining table with decorative tiles is surrounded by iron chairs. Light filters through the glass, enhancing the rustic charm of the exposed stone walls.
Cottage in Trequanda

"Rosso Poggiolo" farmhouse with swimming pool.

4.75 out of 5 average rating, 144 reviews
Guest favourite
A stone cottage is surrounded by lush greenery, featuring a rustic facade with wooden accents. Potted plants are placed near the entrance, and the roof is topped with a small chimney. A pathway of stones leads to the door, inviting guests to explore.
Cottage in San Gimignano

Romantic House in Tuscany with jacuzzi

4.96 out of 5 average rating, 84 reviews
Guest favourite
Cottage in Colle di Val d'Elsa

Cottage in the countryside with private jacuzzi and swimming pool

4.87 out of 5 average rating, 79 reviews
Top guest favourite
Cottage in Buonconvento

Hut at S. Carlo in Buonconvento

4.95 out of 5 average rating, 39 reviews
Guest favourite
Cottage in Sarteano

Podere Coreno / Genuine Tuscan tranquillity and relaxation

5.0 out of 5 average rating, 6 reviewsThe two-story villa features a rustic exterior with a tiled roof and brick accents. A private pool is visible in the foreground, surrounded by well-maintained grass. A staircase leads to the upper level, and large windows allow for natural light. Lush greenery frames the property.
Cottage in Montepulciano

Farmhouse with Private Saltwater Pool • Montepulciano

4.52 out of 5 average rating, 21 reviews

Pet-friendly cottage rentals

Guest favourite
A rustic stone building is set amidst a large, green lawn dotted with olive trees. The facade features multiple windows with arched tops, reflecting the characteristic Tuscan architecture. Natural scenery and gentle hills in the background suggest a peaceful, rural atmosphere.
Cottage in Monteriggioni

Countryside, 10 min from Siena

4.84 out of 5 average rating, 287 reviews
Top guest favourite
An outdoor terrace features wooden furniture arranged around a table, surrounded by greenery and potted plants. The wall of the holiday home, painted in a soft hue, is complemented by open wooden shutters and sliding glass doors leading into the interior.
Cottage in San Gimignano

Small Cottage in San Gimignano

4.95 out of 5 average rating, 173 reviews
Guest favourite
A cozy bedroom features a large bed framed by elegant wrought-iron headboards. Textured stone walls complement the cream-colored backdrop. A small table displays travel brochures and decorative elements, providing a homely touch.
Cottage in Pari

La Casa del Frantoiano - Pari -

4.94 out of 5 average rating, 179 reviews
Guest favourite
A wooden terrace offers two reclining chairs facing a scenic view of distant mountains and lush greenery. The space is framed by surrounding foliage, creating a serene setting for relaxation amidst nature.
Cottage in Vetulonia

La Quercia Panoramic Sea-view Cottage. Tuscany

4.89 out of 5 average rating, 104 reviews
Top guest favourite
An aerial view captures the agriturismo's lush green landscape, featuring neatly arranged cypress trees lining the path. A sparkling swimming pool glimmers amidst the foliage, while sprawling fields extend into the background under a clear sky, showcasing the beauty of the Tuscan countryside.
Cottage in Buonconvento

Tuscan Barn Apartment for 6 with panoramic pool

4.89 out of 5 average rating, 99 reviews
Guest favourite
A rustic stone farmhouse with a tiled roof is set against a clear blue sky. Two chimneys rise from the roof, while a spacious outdoor area showcases green grass and a gravel driveway. Small patio furniture is visible near the entrance.
Cottage in Seggiano

Castagnatello Country House – Walnut Cottage

4.91 out of 5 average rating, 11 reviews
Guest favourite
A rustic stone cottage is framed by lush greenery and a sprawling lawn. The structure features green wooden shutters and a chimney, blending harmoniously with the natural surroundings. The landscape is dotted with trees and shrubs, creating a serene atmosphere.
Cottage in Castellina in Chianti

Casa degli ulivi, live Chianti with swimming pool

4.81 out of 5 average rating, 47 reviews
Superhost
A charming stone house is surrounded by lush greenery and a trellis adorned with climbing vines. The structure features rustic wooden doors and a sloped, tiled roof, while the outdoor area includes a shaded seating space. The landscape is serene, highlighting the natural beauty of the countryside.
Cottage in Sogna

House in Sogna

4.7 out of 5 average rating, 33 reviews

Private cottage rentals

Guest favourite
A stone exterior is presented, showcasing a well-maintained garden with various plants and flowers. A staircase leads from the garden to an entrance, while a wrought-iron gate opens onto a pathway. The structure is flanked by a neighboring building visible in the background.
Cottage in Vescovado

Casa Roberta: a beautiful view of the Crete!

4.83 out of 5 average rating, 160 reviews
Guest favourite
The charming cottage is set against a backdrop of lush greenery, featuring a natural stone facade and a tiled roof. A swimming pool is visible in the foreground, accompanied by sun loungers and umbrellas, while well-maintained gardens and trees surround the property.
Cottage in Radicofani

Cottage "Girasole" in Tuscany

4.85 out of 5 average rating, 140 reviews
Guest favourite
A charming stone exterior features large windows and arched details, surrounded by lush greenery. A path lined with lavender leads to the entrance, with outdoor seating visible under shaded umbrellas. The tranquil setting is complemented by nearby trees and rolling hills in the background.
Cottage in Volterra

Podere Grignano, beautiful Tuscany

4.89 out of 5 average rating, 202 reviews
Guest favourite
A modern eco-house features a wooden exterior with slatted design, surrounded by vibrant greenery and blooming flowers. A small patio is visible at the front, furnished with outdoor seating, complemented by a serene natural landscape under a clear blue sky.
Cottage in Casole d'Elsa

Peaceful modern eco house in the Tuscan hills

4.87 out of 5 average rating, 159 reviews
Guest favourite
A spacious living area features a large arched window offering views of the garden. A modern fireplace is centered within the room, complementing a comfortable seating arrangement. Natural light fills the space, enhancing the rustic wooden beams overhead.
Cottage in San Martino in Grania

Crete Senesi - Asciano Cavoni Hut

5.0 out of 5 average rating, 57 reviews
Top guest favourite
A charming stone house showcases a rustic design with wooden shutters and a balcony. The front porch features seating areas, surrounded by lush greenery and well-maintained gardens. An elegant pathway leads to the house, enhancing its countryside appeal.
Cottage in Villa A Sesta

CASA MARIA

5.0 out of 5 average rating, 20 reviews
Guest favourite
Cottage in Casole d'Elsa

Whispering cypresses cottage. Stunning pool view.

4.94 out of 5 average rating, 35 reviews
Superhost
A cozy living area features a unique rattan chair and a floor cushion on warm wooden flooring. A large window offers views of the surrounding greenery. A rustic kitchen bar, illuminated by natural light, separates the space from the kitchen area, enhancing the open layout.
Cottage in Gaiole in Chianti

Old Chianti chapel-style cottage

4.83 out of 5 average rating, 133 reviews

Destinations to explore