Cottage vacation rentals in Province of Siena

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Top-rated cottage rentals in Province of Siena

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Top guest favorite

The historical Villa di Geggiano is surrounded by lush gardens and vineyards, displaying elegant landscaping. Its stone façade and terracotta roof harmonize with the rolling hills in the distance. A gravel driveway leads to the entrance, providing access to the serene countryside ambiance.

Cottage in Geggiano

4.99 out of 5 average rating, 129 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.

Guest favorite

Cottage in Barberino Tavarnelle

4.98 out of 5 average rating, 187 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.

Top guest favorite

Cottage in Monteriggioni

4.96 out of 5 average rating, 233 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.

Top guest favorite

A spacious wooden deck overlooks a panoramic view of rolling hills and distant mountains, with the sea visible on the horizon. Two lounge chairs are positioned for relaxation, surrounded by native plants and trees that enhance the natural setting.

Cottage in Vetulonia

4.96 out of 5 average rating, 120 reviews

La Dolce Vita ~ romantic retreat in quiet nature

Welcome to Il Baciarino! We are a rustic agriturismo in the green hills of Maremma, Toscana's wild and unexplored coastal region. Il Baciarino is a place to come and stay, to escape from the bustle of the city and your busy life, and to unwind in nature; perfect for those who love unspoiled nature, endless views, fresh seafood & good wine. Il Baciarino has various unique rustic cottages nestled in 19 acres of wilderness, on the outskirts of the tiny Etruscan town of Vetulonia.

Guest favorite

A serene private pool is set against a panoramic view of rolling hills and lush greenery. The water reflects the clear sky, while the pool's edge extends into a sunlit patio area, offering an inviting space for relaxation.

Cottage in Pari

4.95 out of 5 average rating, 152 reviews

La Casa del Frantoiano - Pari -

We offer our guests a small apartment in Pari, a charming village in the heart of Tuscany, near the Petriolo Thermal Baths and halfway between Siena and the sea, reachable in about half an hour. Completely and recently renovated, it consists of a kitchen, large bedroom, bathroom, outdoor relaxation space with table available. Equipped with air conditioning and every kind of comfort, it is ideal for 2/3 people, in the kitchen there is a single bed. Private pool by appointment.

Guest favorite

An independent country cottage is framed by lush greenery, with a stone-paved entrance leading to a cozy building. The sunset casts a warm glow, illuminating the surroundings and a fenced garden area. An electronic gate provides access, enhancing privacy and security.

Cottage in Ponte Feccia

4.95 out of 5 average rating, 163 reviews

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.

Superhost

A scenic view of the Orcia Valley is presented, displaying rolling hills adorned with greenery and neatly trimmed cypress trees. The landscape transitions into soft earth tones that blend with the horizon, creating a serene backdrop under a clear sky.

Cottage in Radicofani

4.84 out of 5 average rating, 127 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).

Guest favorite

Cottage in Casole d'Elsa (SI)

4.85 out of 5 average rating, 132 reviews

Eco-house, pool & garden on beautiful olive farm

New independent eco-house in 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.

Guest favorite

An archway adorned with greenery frames a clear view of a spacious pool, surrounded by manicured grass. A variety of lounge chairs are positioned nearby, inviting relaxation under the bright blue sky with scattered clouds.

Cottage in Montagnano

4.93 out of 5 average rating, 125 reviews

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

Superhost

Cottage in Fungaia, Monteriggioni

4.83 out of 5 average rating, 270 reviews

Countryside, 10 min from Siena

Apartment and large garden for exclusive use. It's a must for countryside, peace and relaxation, close to major places of cultural interest, trekking, biking trails. In a hilly area characterized by beautiful oak and holm oak forests, it enjoys a quiet location and a beautiful view of Siena, which is only 7 km away. (2 km are dirt road).

Superhost

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

4.9 out of 5 average rating, 179 reviews

Podere Grignano, beautiful Tuscany

If the calendar indicates no availability, please check our other advert through the Airbnb map (Podere Grignano, beautiful Tuscany with a dot at the end). The other house can still be free. The houses are semidetached, The 2 houses are practically identical. The reviews are of both houses.

Guest favorite

A spacious dining area features rustic stone walls and exposed wooden beams overhead. A long dining table is surrounded by wooden chairs. Decorative elements, such as wall art and floral arrangements, add character. An open doorway provides a view into the kitchen area.

Cottage in Cortona

4.82 out of 5 average rating, 104 reviews

Tuscan Charm of Cottage Roccaio Cortona

The search for a warm and welcoming Tuscan abode is over. Cottage Roccaio is a stone-clad home adjoined to another occupied house on a small family estate encircled by olive groves. Very cool stone environments and with swimming pool with wellness air for your complete comfort and relaxation.