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Holiday rentals in Gracciano dell'Elsa

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Top-rated holiday rentals in Gracciano dell'Elsa

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

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Top guest favourite
An outdoor patio area features rustic furnishings and is framed by gracefully draping curtains. The space is adorned with comfortable seating and a communal dining table, set against a backdrop of tall cypress trees and a clear blue sky, inviting relaxation in a serene environment.
Home in Simignano
4.98 out of 5 average rating, 189 reviews

Casa al Gianni - The Simignano Barn

Transformed from a former barn, this luxurious retreat offers 5 bedrooms, 4 bathrooms, a large, fully equipped kitchen, a spacious living room, and a large private garden with parking, a hot tub, a patio with sofas, a BBQ, a fire pit, and an outdoor kitchen. Ideal for those seeking a unique experience, it combines rustic charm with modern comforts. Perfect for families or groups, it promises magical evenings under the stars, including relaxation in the hot tub and outdoor dinners. A memorable getaway awaits you in this slice of paradise!

ValueFamilyDecor

Guest favourite
A spacious bedroom features a large, woven bed with a soft blue quilt, complemented by light-colored walls. A comfortable armchair is situated near the window, allowing natural light to brighten the space. A bedside table holds a lamp and additional textiles are neatly arranged.
Flat in Colle di Val d'Elsa
4.8 out of 5 average rating, 117 reviews

Sentier Elsa and Francigena Apartment

Two-room apartment with a kitchen and a large bedroom, small private bathroom without a bidet. Shared garden and nearby parking. Great location, close to the main road, 5 minutes by car from the historic center of Colle val d'Elsa. Siena, Monteriggioni, Volterra and Florence are easily accessible. We are a few minutes' walk from the entrance to the "Sentier Elsa" park and on the Francigena between San Gimignano and Siena. The property is located in an urban area, and there may be noise from cars during the day.

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Guest favourite
Townhouse in Scandicci
4.88 out of 5 average rating, 337 reviews

Florence Sunset Hills • Giogoli

Escape to the peaceful hills of Giogoli where authentic Tuscan charm meets breathtaking views of Florence.Just 15 minutes from the city center and the Chianti countryside, this elegant home is the perfect base for exploring Tuscany while enjoying quiet mornings, unforgettable sunsets, and the beauty of the surrounding landscape. Surrounded by nature but close to the region's most iconic spots, it's the ideal retreat for anyone looking for comfort, tranquility, and a genuinely Tuscan experience

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Top guest favourite
A well-maintained garden area is visible, featuring lush green grass and small trees. The exterior of the building is constructed with light-colored bricks, while the sky above is partly cloudy, creating a calm atmosphere. Nearby, additional greenery and residential buildings can be seen.
Apartment in Colle di Val d'Elsa
4.94 out of 5 average rating, 105 reviews

La Casina di Piano Colle di Val d'Elsa

In the heart of Tuscany between Siena, Florence, San Gimignano, you will find a welcoming place where you can rest, and share your itinerary with owners who, like you, love to travel. You will have an equipped kitchen with a living room, 2 bedrooms for a total of 4 beds, with the possibility of reaching 5. Bathroom with hairdryer, wifi, air conditioning, garden, luggage and bike storage, free parking. A few meters away are all the useful services, pharmacy, laundromat, refreshments.

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Top guest favourite
An aerial view captures Podere Vergianoni nestled in the Chianti hills, surrounded by lush vineyards. The property features a clear blue pool, shaded terraces, and carefully landscaped gardens. Rolling hills and rows of grapevines create a serene backdrop, highlighting the natural beauty of the Tuscan countryside.
Apartment in Noce
5.0 out of 5 average rating, 344 reviews

Podere Vergianoni nestled in Chianti with a pool

Podere Vergianoni is a family-run, historic property dating back to the 1600s, located in the beautiful hills of Chianti in Tuscany. Our family can arrange a private shuttle and local experiences directly. The apartment is available for 2 adults with the option of adding a sofa bed for 2 children under 12 years of age. In the large outdoor courtyard you'll find a saltwater pool with a relaxation area on a panoramic terrace overlooking the castle and vineyards with unique sunsets.

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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, 228 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.

ValueFamilyGrill

Top guest favourite
A modern kitchen and dining area features a wooden ceiling and a light wooden floor. A dining table with four chairs is positioned near a large window. A counter with kitchen appliances and storage is visible, alongside decorative plants that add a touch of greenery.
Home in Colle di Val d'Elsa
4.99 out of 5 average rating, 132 reviews

The House in the Alley – Colle di Val d'Elsa

Very central location, house completely renovated in 2023, cozy and quiet, equipped with every comfort. Independent entrance. Located 50 meters from Piazza Arnolfo di Cambio and 300 meters from the historic center (reachable on foot or by elevator), for those traveling by bus the stop is only 100 meters away. Strategic location for visiting Siena, Florence, San Gimignano, Volterra, Chianti Hills and for those who want to travel the Via Francigena or visit the Elsa River Park.

ValueFamilyAir conditioning

Guest favourite
Castle in Tignano
5.0 out of 5 average rating, 25 reviews

Luxury Medieval Tower • Exclusive Chianti Stay

Welcome to one of the most exclusive residences in Chianti: a medieval tower transformed into a refined luxury retreat overlooking the Tuscan hills. Contemporary design, iconic furnishings, works of art and luxury comforts come together in a unique experience. An oasis of tranquility with a private garden, glass annex, Wi-Fi, and smart working area. Extra services: private chef, tastings in the cellar, wellness treatments and tours of the most beautiful villages in Tuscany.

LocationFamilyBack garden

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, 103 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.

ValueFamilyComfort

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, 475 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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Top guest favourite
The living area features polished wooden floors and a cozy sofa. A painting is displayed above a brick fireplace, while a television is placed on a small cabinet. A staircase with a wooden handrail leads to the upper level, illuminated by soft wall lights.
Apartment in Colle di Val d'Elsa
4.97 out of 5 average rating, 248 reviews

DorminColle - Tuscan-style apartment

Bright and spacious apartment, consisting of a comfortable double bedroom with TV, portable air conditioner, with bathroom complete with shower and toilet. Third bed located in a characteristic loft area with wooden beams equipped with a bed. Large kitchen equipped with dishwasher, coffee machine, microwave, filtered water dispenser, Living room with TV and sofa, dining room overlooking the Old Village. Free parking 150 meters away from the apartment.

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Top guest favourite
Apartment in Colle di Val d'Elsa
5.0 out of 5 average rating, 25 reviews

Florence & Siena • Terrace • Private Parking • A/C

Imagine waking up to sunlight filling the apartment and enjoying breakfast overlooking the Tuscan hills. Bright top-floor apartment with elevator, panoramic terrace and 180° open views, between Florence and Siena, in a quiet private area with no through traffic. Perfect for families, with parking, air conditioning, fast Wi-Fi, fully equipped kitchen and all the comforts to explore Tuscany’s villages, wineries, art cities and iconic landscapes.

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Popular amenities for Gracciano dell'Elsa holiday rentals