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Holiday rentals in Il Cipresso

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Top-rated holiday rentals in Il Cipresso

Guests agree: these stays are highly rated for location, cleanliness and more.

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Top guest favourite
A rustic building is seen under a starry night sky, with a partial roof providing shelter. Soft light glows from the interior, illuminating the entrance. Lush greenery and trees surround the scene, adding depth to the serene nighttime landscape.
Farm stay in Simignano
4.93 out of 5 average rating, 285 reviews

Casa al Gianni - Hut

Hi, we're Cristina and Carmelo! We look forward to welcoming you to 'Casa al Gianni', our farmhouse in the woods of the Montagnola Senese, just 20 minutes from Siena. Here, life slows down: just the scent of the earth, the song of the birds, and the companionship of our animals. It's an invitation to rediscover the beauty of the little things, surrounded by the greenery of the most authentic Tuscany. It's not just a holiday; it's a return to our roots. This peaceful haven will stay in your heart. We look forward to welcoming you!

Guest favourite
An aerial view captures the serene layout of the estate, surrounded by lush greenery and rolling hills. The inviting pool is situated centrally, accompanied by sun loungers. Stone buildings harmonize with the natural landscape, reflecting the tranquil beauty of the Montagnola Senese.
Holiday home in Sovicille
4.97 out of 5 average rating, 160 reviews

Podere La Castellina - No. 1 COTTAGE

Independent stone and brick cottage inside the "Podere la Castellina" (former 13th century convent), in the magnificent natural park of Montagnola Senese. The cottage can comfortably accommodate 5 people and includes: - large living room with TV and fireplace - kitchen with oven - master bedroom - bedroom with three single beds - bathroom with shower Guests have access to a panoramic swimming pool, solarium and terrace with breathtaking views, equipped with a wood-burning oven and barbecue.

Guest favourite
Flat in Volterra
5.0 out of 5 average rating, 5 reviews

Olive Harmony Tuscan Escape with Pool

Discover the authentic charm of Tuscany at Olive Harmony, a peaceful villa nestled in the countryside near Volterra. Surrounded by olive groves and rolling hills, it offers beautiful views, two bedrooms, two bathrooms, and welcoming interiors. Relax in your private outdoor area, enjoy dinner under the stars, or unwind by the shared swimming pool. The perfect retreat for families and friends looking to experience Tuscany surrounded by nature, tranquillity, and timeless medieval towns.

Guest favourite
An open layout reveals a cozy living area with a light blue couch and a wall-mounted television. The space is complemented by warm wooden flooring and a stone wall, creating a harmonious blend of modern design and traditional elements. A glass partition separates the sleeping area.
Loft in Volterra
4.85 out of 5 average rating, 259 reviews

LOFT with a view located in the heart of Volterra

Small loft with independent entrance located in the heart of Volterra, ideal for a couple who decides to enjoy the magical atmosphere of the city for a few days. Every choice inside is designed to give guests a precious setting. The view of the sunsets over the sea of the Tuscan archipelago offers the romantic canvas on which to imprint unique memories. The warmth of the wood, the solidity of the stone and the brilliance of the crystal perfectly describe the owner's concept of Home.

Top guest favourite
A wooden dining table is centered in the room, surrounded by four chairs. A vase of sunflowers adds a touch of color. A shelf with clear glass doors displays kitchen appliances and tableware. A TV is visible in the background, alongside a framed artwork.
Apartment in Volterra
4.89 out of 5 average rating, 511 reviews

Piazzetta N20 Apartment

Positioned in one of the most suggestive locations of Volterra, the apartments is a wonderful place, full of natural light and surrounded by a breathtaking landscape. Placed in the old part of the town, inside the medieval walls, the property is one of two apartment that lie within the same building; it’s composed by a large open space with cooking facilities completely equipped and a living room, a double bedroom, a bathroom with shower. Clima is present. Free Wi-Fi Is available

Top guest favourite
A historic tower rises prominently against a blue sky dotted with fluffy clouds. Surrounding greenery complements the stone structure, with trees and small buildings visible along the hillside, collectively conveying a sense of tranquility.
Villa in Montecatini Val di Cecina
4.99 out of 5 average rating, 137 reviews

Belforti Tower

Torre dei Belforti is the perfect place for people who love beauty, nature and art. Sleeping at the Tower is like traveling trough the time, between knights and princesses. The wonder of this place is enriched by a big garden, with its swimming pool, the cypresses alleys and the olive trees. The village is also a magic place well preserved and still alive. We are Emilia and Luca, we live here and our mission is to give the best to our guests, to fully enjoy this marvelous place.

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
5.0 out of 5 average rating, 229 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 bright bedroom features a spacious bed with a patterned quilt and decorative pillows. Natural light enters through windows, which are adorned with soft curtains. A comfortable armchair sits in one corner next to a bedside table, and a folding stool is positioned at the foot of the bed.
Apartment in Volterra
4.96 out of 5 average rating, 98 reviews

FREE Parking - with awesome view

You will be staying in an apartment suitable for travelers from all over the world. Located in a strategic position just below the walls, it is just a few meters away from one of the major points of interest in the city (Porta all'arco) and about 400 meters from Piazza dei Priori. You will also find 3 supermarkets nearby. The apartment offers a beautiful view of the surrounding countryside, with the sea visible on the horizon, which is approximately 50 km away from Volterra.

Top guest favourite
A spacious living area features exposed brick walls, wooden beams, and warm lighting. A comfortable sofa and a mid-century modern coffee table sit invitingly, while a dining table and chairs are positioned nearby. Large windows enhance the natural light, which complements the earthy tones of the room.
Apartment in San Gimignano
5.0 out of 5 average rating, 63 reviews

AnticaVista, Luxury Apartment with Tower Views

A hidden gem nestled within the ancient walls of a 14th-century tower house, right in the heart of San Gimignano, a UNESCO World Heritage Site. This one-of-a-kind apartment is where history meets contemporary elegance. Look out the window and you’ll feel like you can almost touch the medieval towers. The view is breathtaking: unforgettable glimpses of the majestic Torre Grossa, framed by the iconic skyline that earned San Gimignano its nickname, the “Medieval Manhattan.”

Top guest favourite
A large swimming pool surrounded by a brick patio and manicured lawns is highlighted in this image. Sun loungers are positioned along the pool's edge, with lush greenery and trees creating a serene backdrop. The villa's charming structure is visible in the distance under a partly cloudy sky.
Villa in Barberino Tavarnelle
4.98 out of 5 average rating, 104 reviews

Podere Tignano, 4-bedroom villa in the Chianti!

Nestled among the rolling hills of Chianti between Florence and Siena, Podere Tignano offers breathtaking views over vineyards, olive groves, and golden grain fields. This charming Tuscan stone villa blends authentic rural character with modern comfort and welcomes up to 8 guests in 4 bedrooms. Surrounded by peaceful countryside and featuring a private swimming pool, it is the perfect retreat for those seeking relaxation, nature, and the true spirit of Tuscany.

Top guest favourite
Home in Barberino Tavarnelle
5.0 out of 5 average rating, 85 reviews

Charming Country Tuscan House with Fantastic View

An incredible experience between flavor, nature and relax in the heart of Chianti. Situated between Barberino Tavarnelle, San Gimignano, Greve in Chianti, and Florence, Belvedere 27/A overlooks the Santa Maria Novella Castle, amidst olive groves and vineyards with an amazing view. A countryside Tuscan home, surrounded by olive’s fields and greenery, equipped with every comfort. Reconnect in this serene, one-of-a-kind stay, for a relaxing and peaceful holiday.

Top guest favourite
A charming stone building surrounded by lush greenery features a wooden terrace with a parasol and flower pots. Two loungers are placed on the well-maintained lawn, providing a relaxing outdoor space.
Farm stay in Greve in Chianti
4.99 out of 5 average rating, 476 reviews

Old hayloft on the Chianti hills

Agriturismo Il Colle is located on one of the Chianti hills. The property has been completely renovated, overlooking the Chianti valleys and enjoying splendid views of the surrounding hills and the city of Florence. The apartment is completely independent, on two internally connected floors, and features a private garden lined with centuries-old oaks and Tuscan cypresses. The restoration maintained the original Tuscan architectural style of rural barns.

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