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Cottage vacation rentals in Siena

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Top-rated cottage rentals in Siena

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Top guest favorite

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

4.99 out of 5 average rating, 135 reviews

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.

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

4.97 out of 5 average rating, 199 reviews

Stone House with Exclusive Pool Codilungo in Chianti

Spend a holiday in the heart of the Tuscan countryside in this cozy stone house with terracotta floors and beamed ceilings in solid oak, furnished with paintings of author , equipped with all comforts. Enjoy yourself by swimming in the large infinity pool (18m X 9m, open from May 1st to October 15th for guests of Stone house use only) or relax in an armchair under the loggia, tasting a glass of Chianti wine in front of the rolling hills of vineyards, olive groves, woods and medieval villages.

The rustic stone cottage is set in a verdant landscape, surrounded by trees. A spacious outdoor patio with a table and chairs invites relaxation and dining in the sun. The clear blue sky enhances the serene, inviting atmosphere of this countryside retreat.

Cottage in La Cetina

4.96 out of 5 average rating, 106 reviews

Eleutherìa: Cozy Cottage in the heart of Tuscany

Eleutherìa is a recently refurbished cottage, located on the top of the hill surrounded by the stunning Tuscan countryside. It is right in the middle of trekking tracks crossing centuries-old woods and wild nature, those who walk along can feel nature and discover to belong to it.. Offering a 75 sqm (800 sqft) area with patio overlooking the garden to unwind your senses. Just about 18 Km (11 Mi) from the medieval city of Siena, it’s a strategic location to the major Tuscan’s attractions.

Top guest favorite

A serene scene captures the rolling hills of Tuscany at sunrise, enveloped in soft mist. A pergola adorned with vines frames the view, while lush greenery and bushes create a natural border. The sky displays a gradient of warm hues as the day begins.

Cottage in Castellina in Chianti

4.98 out of 5 average rating, 101 reviews

Cottage Cappero - Masseto In Chianti

MASSETO IN CHIANTI è un villaggio privato dove potrete rilassarvi nel vostro giardino privato e in piscina, fare sport, o utilizzare come base per visitare città rinascimentali: Firenze, Siena, San Gimignano, Arezzo, Volterra. Offriamo altri tre cottage con accesso indipendente e giardinetto privato: Quinto (2 letti), Vittoria (4 letti), Leccio (6 letti). La piscina è condivisa dai 4 cottage, ciascuno dispone di un gazebo privato, con distanze garantite e sanificazione a norma Covid-19.

Top guest favorite

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

4.96 out of 5 average rating, 252 reviews

Monteriggioni Castello, holiday house in Tuscany

Il nostro alloggio è un edificio storico che risale alla costruzione del castello. È stato recentemente restaurato e arredato con cura in tutti i dettagli. È molto accogliente e dispone di tutti i più moderni servizi. I turisti che decideranno di essere nostri ospiti, avranno il vantaggio di vivere nell' ambiente medievale del castello, usufruendo di tutti i confort. Si sentiranno coccolati e avranno l'opportunità di tornare indientro vivendo un' esperienza unica e indimenticabile.

A wooden deck offers a serene view of rolling green hills extending into the distance. Two sun loungers are placed on the deck, inviting relaxation amid the natural surroundings. Trees frame the scene, creating a peaceful atmosphere, ideal for enjoying the landscape.

Cottage in Vetulonia

4.96 out of 5 average rating, 122 reviews

La Dolce Vita Romantic Sea-view Cottage. Tuscany

Welcome to Il Baciarino, a rustic agriturismo in the green hills of Maremma, Tuscany’s wild and less-traveled coastal region. Our property offers unique, handcrafted cottages with sea views, privacy, and direct contact with nature. Set within 19 acres of hillside wilderness in the charming Etruscan town of Vetulonia, Il Baciarino is the perfect place to escape the city, slow down, and enjoy unspoiled landscapes, fresh seafood, and good wine.

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

4.94 out of 5 average rating, 176 reviews

Country cottage C&M immerso nel verde love Tuscany

Country cottage in pietra , indipendente nella campagna Toscana in provincia di Siena ,con ampio giardino, portico e gazebo. La nostra casa e' situata nella campagna del comune di Chiusdino, a soli 5 minuti dai due paesi principali Monticiano e Chiusdino e 10 minuti dalla splendida Abbazia di.Galgano . 30 minuti da Siena , da Monteriggioni , un'ora da Firenze e 30/40min minuti dal mare. Soli 20 minuti dalle belle Terme del Petriolo .

A modern eco-house is nestled among vibrant wildflowers and lush greenery. The exterior features a wooden façade with a sloped roof, surrounded by colorful blooms in shades of purple and yellow, set against a backdrop of blue sky and fluffy white clouds.

Cottage in Casole d'Elsa (SI)

4.86 out of 5 average rating, 143 reviews

Peaceful modern eco house in the Tuscan hills

A thoughtfully designed low impact house in a rural setting, away from the crowds between Florence and Siena. This is an annex building on a family run olive farm surrounded by unspoilt Tuscan countryside. Plenty of shaded outdoor space, barbecue, stunning views, fantastic sunsets and big night skies. We are an official agriturismo, there are two other independent apartments on the olive farm that share the pool and private parking.

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

4.85 out of 5 average rating, 134 reviews

Cottage "Girasole" in Tuscany

A lovely cottage in the old farmhouse "Podere Maltaia" that overlooks the Unesco's Heritage protected area Orcia Valley, surrounded by large farmyards and 3 hectares of private land that includes an outdoor swimming pool (opened seasonally, based on outside temperature - please ask to know the dates for the upcoming or ongoing summer season), garden, outdoor dining area, BBQ and parking area (not-covered, free of charge).

The garden features a shaded dining area with a large umbrella and a wooden table set with chairs. A brick barbecue stands nearby, surrounded by greenery and well-maintained grass. The entrance to the house is visible through elegant wrought iron doors.

Cottage in La Piazza

4.96 out of 5 average rating, 103 reviews

Casa La Misura nel cuore del Chianti

La Misura house is part of Borgo Montecastelli, a beautiful rural complex located right on the border between the provinces of Siena and Florence. Due to its strategic position, straddling two valleys, Borgo Montecastelli enjoys a magnificent panorama from its summit towards the villages that surround it: Panzano, Radda in Chianti, Castellina in Chianti, as well as farmhouses, churches, and towers.

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

4.93 out of 5 average rating, 130 reviews

Affascinante cottage in Toscana

Affascinante cottage situato su collina con vista a 360 gradi . Oasi di pace e tranquillità. Immersa nel verde. Ampia piscina Area barbecue All'interno camera con letto francese, salotto con divano letto, bagno, cucinino e spazio pranzo interno ed esterno . Ideale per coppie e famiglie con uno / due figli . Disponibilità culla

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Popular amenities for Siena cottage rentals

Free parking on premises

Air conditioning

Cottage rentals with a hot tub

Top guest favorite

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

4.97 out of 5 average rating, 72 reviews

Romantic House in Tuscany with jacuzzi

A modern villa is surrounded by lush green grass, showcasing a sparkling swimming pool that reflects the evening sky. Lounge chairs are arranged by the poolside, with two shaded areas offering protection from the elements. The villa features multiple large windows, providing a welcoming glow.

Cottage in Foiano della Chiana

Luxury Cottage Spaccasole - Pool W/Cortona

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

4.96 out of 5 average rating, 93 reviews

EcoLodge – modernes Design in ruhiger Panoramalage

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

5 out of 5 average rating, 63 reviews

Panoramic view & outdoor jacuzzi - Pienza

An aerial view of the cottage reveals a spacious patio featuring a hot tub and seating area. Surrounding greenery and olive trees provide a natural backdrop, while a gravel driveway leads to the entrance of the home. The rustic roof complements the charming landscape.

Cottage in Campiglia D'orcia

4.93 out of 5 average rating, 40 reviews

Val D’Orcia Eco Cottage - Exclusive Retreat

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

4.75 out of 5 average rating, 143 reviews

"Rosso Poggiolo" casale con piscina.

The 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

4.65 out of 5 average rating, 17 reviews

Tuscany Villa Girasole

Pet-friendly cottage rentals

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

4.93 out of 5 average rating, 224 reviews

Da Simone, podere santi Lucia e Pietro

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 Fungaia, Monteriggioni

4.84 out of 5 average rating, 277 reviews

Countryside, 10 min from Siena

Two lounge chairs with cushions are positioned beside a private pool, overlooking rolling hills at sunset. A small table holds a bottle of sparkling beverage, enhancing the serene atmosphere. Lush greenery and trees frame the view, creating a sense of tranquility.

Cottage in San Casciano dei Bagni

5 out of 5 average rating, 19 reviews

Toscana, Country house with exclusive pool

An exterior view of a rustic farmhouse features weathered stone walls and dark wooden shutters. Lavender flowers bloom nearby, adding a touch of color to the scene. Two doors offer access to the home, and a small potted plant is visible in the ground floor window.

Cottage in Sovicille

4.89 out of 5 average rating, 146 reviews

Apartment for 2 with super views+pool near Siena

A rustic two-story building constructed from warm brick is surrounded by lush greenery. Large windows invite natural light, while wooden shutters add charm. The exterior features a gravel path leading to lounge chairs, creating a serene outdoor space for relaxation.

Cottage in Buonconvento

4.84 out of 5 average rating, 64 reviews

QuarterApartment for 6P Agriturismo Quarantallina

Top guest favorite

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

5 out of 5 average rating, 98 reviews

Your Tuscan oak tree house, enchanting Val d'Orcia

A bright living area features large glass doors, inviting natural light and showcasing views of the garden. Wooden furniture, including a dining table with chairs and a cozy sofa, is accentuated by soft, light-colored curtains that gently frame the windows.

Cottage in Pienza

4.95 out of 5 average rating, 42 reviews

Cottage San Lorenzo

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

4.95 out of 5 average rating, 160 reviews

Affittacamere La Casa del Frantoiano -Pari-

Private cottage rentals

A charming independent home is set amidst greenery, featuring a stone exterior and terracotta roof. Large windows framed in green provide a view of the surrounding landscape. The entrance is covered by a small porch, adding to the inviting appeal of the exterior.

Cottage in Bucine

4.84 out of 5 average rating, 153 reviews

Cottage in campagna toscana

A charming villa stands surrounded by greenery and vibrant flowers, showcasing a rustic facade with a tiled roof and a central chimney. A wooden fence frames the property, enhancing the serene countryside setting under a clear blue sky.

Cottage in Cinigiano

5 out of 5 average rating, 7 reviews

Cottages in Tuscan Country (Spazzacamino)

A charming exterior of La Casetta is visible, featuring a blue wooden veranda with a railing. Various terracotta pots are arranged along the entrance, showcasing a mixture of plants. The surrounding greenery adds to the serene atmosphere of the natural setting.

Cottage in Castiglione della Pescaia

4.96 out of 5 average rating, 50 reviews

The Cottage

An exterior view of a rustic stone structure is presented, featuring a covered porch with a wooden table and benches. Olive trees surround the area, providing shade. A barbecue station is visible nearby, with a pathway leading through the outdoor space.

Cottage in Sinalunga

4.87 out of 5 average rating, 84 reviews

Rustico sulle colline toscane

The exterior of a rustic apartment is visible, featuring a covered porch supported by wooden beams. Lush greenery surrounds the structure, with a well-maintained lawn and flowering plants in the garden. The building shows a blend of stone and stucco, reflecting traditional architecture.

Cottage in Villa Parigini

4.75 out of 5 average rating, 4 reviews

Restored Barn in Chianti property, pool, terrace

The cottage's exterior is characterized by a rustic stone façade, complemented by wooden shutters and a sloped tiled roof. Flowering plants are situated in terracotta pots around the entrance, while the surrounding landscape features green trees and a clear blue sky.

Cottage in Chiusi

4.96 out of 5 average rating, 51 reviews

Cottage in the south of Tuscany

The living/dining area features exposed wooden beams on the ceiling and a terracotta tiled floor. A modern kitchen with wooden cabinetry is complemented by a dining table set for four. Natural light enters through red-framed windows, enhancing the cozy ambiance.

Cottage in Cennina

4.83 out of 5 average rating, 165 reviews

The Five Oaks Cottage

A charming stone cottage is displayed, featuring a welcoming entrance and large wooden windows. A round table with green chairs is set in a gravel courtyard surrounded by potted plants. Soft shadows from trees offer a refreshing contrast to the sunlit surroundings.

Cottage in Cortona

4.79 out of 5 average rating, 116 reviews

Tuscan Charm of Cottage Roccaio Cortona

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