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House holiday rentals in Bolgheri

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Top-rated house rentals in Bolgheri

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Top guest favourite
An outdoor patio area is featured, showcasing a spacious covered space with large, light curtains that gently sway in the breeze. Comfortable seating options consist of bean bags and a dining table, all surrounded by lush greenery and tall cypress trees.
Home in Simignano
4.98 out of 5 average rating, 162 reviews

Casa al Gianni - The Simignano Barn

Transformed from an old barn, this luxurious retreat offers 5 bedrooms, 4 bathrooms, large equipped kitchen, large living room and a large private garden with parking, hot tub, patio with sofas, BBQ, fire pit and 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, between relaxation in the hot tub and outdoor dinners. A memorable getaway awaits you in this slice of paradise!

Top guest favourite
A charming pathway leads to the entrance of the house, surrounded by lush greenery. Flower pots are positioned along the stone walkway, with a seating area visible to the side, inviting guests to enjoy the serene landscape of rolling hills in the background.
Home in Greve in Chianti
4.98 out of 5 average rating, 199 reviews

Love in Chianti

Welcome to the delightful cottage of Riccardo and Pauline, a small corner of love where colors and details are designed to give peace and quiet. You will find yourself immersed in the green Tuscan hills, in a breathtaking landscape where the renowned Chianti Classico wine is born. The area is ideal for walking and cycling. You will be close to the cities of art, such as Florence, Siena and Arezzo. Upon request and according to availability, we offer a paid shuttle service. We look forward to seeing you ❤️

Top guest favourite
A shaded terrace offers panoramic views of rolling hills and lush greenery, with terracotta rooftops visible in the foreground. The clear sky enhances the vibrant landscape, highlighting the rich textures of the countryside.
Home in Impruneta
4.98 out of 5 average rating, 173 reviews

Tiny romantic tower on the hills of Florence

Think of a tiny charming ancient tower, embedded in a time into a small XIX century tuscan villa on the florentine hills. Think of a romantic place for a couple, with a bedroom and a living room which opens onto a breathtaking terrace in the countryside, with a bathroom and a tiny kitchen. Also think that in 20 minutes drive you are into Florence downtown. Well, this is the place! To get all this you have to climb three flights of stairs with no lift. But you'll see it surely worth the effort.

Top guest favourite
A stone structure with a tiled roof is framed by greenery, surrounded by rolling hills. A spacious outdoor area features a wooden table, inviting relaxation. Large trees and thriving shrubs enhance the tranquil setting, with a backdrop of a serene sunset illuminating the landscape.
Home in San Casciano In Val di Pesa
4.98 out of 5 average rating, 221 reviews

Sunset on Chianti Classico

Se cercate una location idilliaca nel cuore del Chianti classico, immersi nei vigneti e oliveti delle splendide colline toscane, nel podere di una Villa storica del ‘500, allora venite nel nostro fienile!! Ha una posizione dominante con una vista strepitosa, dove è possibile godersi tramonti mozzafiato. La totale indipendenza della casa, l'accogliente giardino, il grande loggiato permettono di trascorrere soggiorni in totale tranquillità. Le nostre recensioni sono la vostra migliore garanzia.

Guest favourite
A charming stone cottage is surrounded by lush greenery and tall trees. Two white lounge chairs are positioned on the manicured lawn, accompanied by a small round table. A sun umbrella offers shade, while large windows reflect natural light, showcasing the inviting interior.
Home in Montescudaio
4.96 out of 5 average rating, 124 reviews

Open space surrounded by nature

Casa Namaste is a small stone cottage with well-kept interiors 1 km from the medieval village of Montescudaio. The house is completely surrounded by woods and centuries-old oaks. 150 meters away flows the Cecina river. In the 5000 square meter garden there is a natural spring with a large stone tub to cool off and an outdoor hot shower surrounded by greenery. We have a Vodafone adsl line with download 33 and upload 1.4. Smart TV and air conditioning are also available starting this spring

Top guest favourite
An aerial view of the property reveals a charming red house surrounded by lush greenery. Tall cypress trees and vibrant bushes create a tranquil landscape, while an expansive lawn features relaxing loungers, inviting guests to enjoy the serene atmosphere of the Tuscan countryside.
Home in Gambassi Terme
5 out of 5 average rating, 204 reviews

Il Fienile, Luxury Apartment in the Tuscan Hills

‘Il Fienile’ is in an enchanting position immersed in the beauty of the Tuscan hills, with a breathtaking view of the surrounding countryside. It is located in the hamlet of Catignano in Gambassi Terme, just a few kilometres from San Gimignano. The house sits in a protected oasis surrounded by a beautiful private park with olive trees, a pond, pine trees and woods, where you can walk, relax and enjoy the pleasures of unspoilt nature. A unique experience entirely to be enjoyed.

Top guest favourite
A lush green garden is framed by a rustic pergola made of wooden beams. Grassy paths lead deeper into the garden, where vibrant flowers and trees provide a natural backdrop. Rolling hills and a clear blue sky are visible in the distance, creating a serene outdoor setting.
Home in Castellina in Chianti
4.98 out of 5 average rating, 127 reviews

Private Chianti Cottage, Garden & Vineyard Views

Set in a picturesque hamlet, overlooking the Chianti hills, this charming country house is just 10 minutes from Siena and Castellina in Chianti. Recently renovated, it blends authentic Tuscan charm with modern comforts. The house features two bedrooms, two bathrooms, a cozy living area and a fully equipped kitchen with a dishwasher, two fridges, and a washing machine. Outside, enjoy a beautiful garden and relax in the outdoor marble hot tub, soaking in the breathtaking views.

Top guest favourite
The image showcases a refreshing pool surrounded by lounge chairs and umbrellas, enhancing the outdoor relaxation area. The pool is framed by lush greenery and a stone wall, with the charming rustic house visible in the background under a clear blue sky.
Home in Barberino Tavarnelle
5 out of 5 average rating, 122 reviews

Infinity pool in Chianti area

On the Chianti hills, portion of an old stone farmhouse from the 1800s, located in S. Filippo, a small hamlet of Barberino Tavarnelle, halfway between Florence and Siena, a 30-minute drive from Florence airport, 1 hour from Pisa airport. Three bedrooms, two bathrooms, large living room with fireplace, eat-in kitchen and dining room. Magnificent view of the hills from every window! Beautiful infinity pool with whirlpool area, unheated and open from April to October.

Top guest favourite
A spacious terrace is surrounded by lush greenery, featuring terracotta pots filled with plants. Comfortable wooden chairs are positioned to invite relaxation, overlooking scenic hills in the distance. A soft canopy provides shade, enhancing the tranquil atmosphere of this outdoor space.
Home in Peccioli
4.99 out of 5 average rating, 135 reviews

House with a breathless view in Tuscany

Halfway between Pisa and Florence, this dreamy Tuscan house is your perfect escape. Lounge on the panoramic terrace with sun-kissed views, sip your morning coffee, or enjoy al fresco dinners under the golden sunset. Nestled in the heart of a charming village turned open-air contemporary art museum, every corner feels like a picture-perfect moment. Peccioli is your gateway to Tuscany’s art cities or a serene hideaway to savor the magic of authentic local life.

Top guest favourite
A winding driveway is lined with tall cypress trees on either side. The green landscape stretches into the distance, revealing rolling hills and a distant rustic building surrounded by nature, creating a serene and inviting setting.
Home in Montaione
4.95 out of 5 average rating, 126 reviews

Cercis - La Palmierina

E' un appartamento facente parte di una tenuta completamente recintata di 60 ettari di natura incontaminata: più di 1000 ulivi, innumerevoli cipressi e foreste profumate creano un ambiente idilliaco per coloro che ricercano tranquillità e silenzi. La tenuta Palmierina è in prossimità di Castelfalfi (un vero gioiello di architettura medievale) e nelle vicinanze di Firenze (50 Km), Siena (50 Km), Pisa (50 Km). Nelle vicinanze ci sono due campi da golf.

Guest favourite
A spacious freestanding bathtub is filled with water, adorned with floating flowers and candles. A small wooden table beside it holds a bucket of champagne and two glasses. Soft towels and a decorative rose are also visible, contributing to a relaxing ambiance.
Home in Fiesole
4.99 out of 5 average rating, 284 reviews

"La limonaia" - Romantic Suite

Romantic Suite immersed in the enchanting hills of Fiesole. It is the ideal place fot those looking for unique and exclusive experience of its kind characterized by suggestive views and unforgettable sunsets. The accommodation is part of an old 19th century Tuscan farmhouse surrounded by its own olive groves and woods. This is an ideal place for a relaxing holiday and privileged base for visiting the major centers of interest in Tuscany.

Guest favourite
A charming stone exterior reveals a rustic villa surrounded by greenery. The entrance features a wooden door and terracotta roof tiles. Potted plants add color, while seating areas are positioned on a patio, inviting relaxation in the scenic surroundings under a clear blue sky.
Home in Radda in Chianti
4.92 out of 5 average rating, 157 reviews

Casa Dante - Authentic Chianti Stay | Views&Relax

Wake up to breathtaking views over the rolling hills of Chianti and enjoy a glass of wine at sunset from your private terrace. This peaceful home offers the perfect mix of privacy, comfort, and authentic Tuscan charm. Located just minutes from the center of Radda in Chianti, the house is ideally positioned to explore wineries, charming villages, and the surrounding countryside—while still feeling quiet.

Popular amenities for house rentals in Bolgheri

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