
Holiday houses 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.

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, complete with relaxation in the hot tub and al fresco dining. A memorable getaway awaits you in this slice of paradise!
FamilyValueBathroom
4.97 out of 5 average rating, 194 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.
ValueFamilyCondition
4.8 out of 5 average rating, 117 reviews
Il Fienile del Borgo – Monteriggioni
This delightful, finely renovated barn combines modernity and Tuscan tradition. It is located in the countryside near Monteriggioni, a short distance from Siena, San Gimignano, and Colle Val d'Elsa. The house is an oasis of peace and tranquility: it has a large private garden with a swimming pool for exclusive use, a barbecue for outdoor dinners under the porch; inside there is a large living room with an equipped kitchen, a double bedroom, a bathroom, and a loft with two single beds and a double bed.
FamilyLocationPool
4.96 out of 5 average rating, 26 reviews
Casa Lida [Garden+Parking]
Welcome to Casa Lida, your peaceful retreat in the heart of Tuscany. Independent two-story apartment on Via Francigena, in Colle di Val d'Elsa: a base for discovering Siena, San Gimignano, Monteriggioni, Volterra, and the Chianti vineyards. Two bedrooms and two bathrooms, equipped kitchen, fireplace, and heating. Outside, there is a large private garden with a terrace for outdoor breakfasts and dinners, and parking. Fast Wi-Fi. Ideal for couples, families, and those seeking peace and authenticity.
LocationValueCondition
5.0 out of 5 average rating, 83 reviews
Villa of the 2 Olive Trees (Abbadia Isola)
FULLY AIR CONDITIONED, modern 6BR/4BA VILLA on Via Francigena: an enchanted paradise for friends & families with kids (trampoline, basketball area, soccer & volley/beach tennis nets, fossball, table tennis) & w. pets (fenced garden). Located in the small village Abbadia Isola in the shadow of the medieval castle of Monteriggioni, right on the path the ancient road & pilgrim route running from France to Rome (via Francigena) A.k.A FAMILY GROUPS KIDS FRIENDS dream VILLA Siena 12mn (ABB)
FamilyValueCheckout
4.97 out of 5 average rating, 174 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.
LocationFamilyCheck-in
4.94 out of 5 average rating, 105 reviews
Siena, House in the heart of Tuscany
Holiday home in the medieval village of Colle di Val d'Elsa, at 115 Via Gracco del Secco in Tuscan style on 2 floors, 3 bedrooms, 3 bathrooms, fireplace and wood-burning oven. Voucher from 5 euros per person per day for breakfast at Mario Barone bakery. Recently renovated and furnished with care and value. Wifi and air conditioning. Next to the Spa Hotel San Lorenzo. Ample nearby public parking. At 15 minutes from San Gimignano, 20 fm Volterra, 40 fm Florence, 25 fm Siena.
ValueLocationWi-Fi
4.95 out of 5 average rating, 22 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.
ValueLocationAir conditioning
4.99 out of 5 average rating, 133 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.
FamilyLocationCheck-in
5.0 out of 5 average rating, 25 reviews
The Bottom
A newly built apartment with a private entrance and a small outdoor garden, located in a residential complex of only four apartments in the heart of Via Francigena, a short distance from the SentierElsa River Park and the Caldane. It is located 24 km from Siena, 45 km from Florence, 10 km from Monteriggioni, and 15 km from San Gimignano. Ideal as a base for those who want to visit Tuscany's most iconic places and are looking for a dynamic and convenient vacation.
FamilyLocationTV
4.96 out of 5 average rating, 25 reviews
CANONICA 43 Luxury villa in the heart of Tuscany
CANONICA 43 Spacious and modern apartment, immersed in the Tuscan countryside. In an unspoiled nature, you will spend a vacation in an atmosphere of peace and relaxation. It is an excellent starting point for visiting small villages, famous cities of art, for walks in the woods or for beautiful bike rides pedaling through the rolling hills that surround it. You can taste Tuscan dishes in the typical restaurants of the area or organize a barbecue in the garden
FamilyLocationParking
5.0 out of 5 average rating, 78 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.
ValueLocationAmenities
4.98 out of 5 average rating, 105 reviewsPopular amenities for Gracciano dell'Elsa holiday rentals
Other great holiday rentals in Gracciano dell'Elsa

The independent Cottage on the Tuscan hills
LocationFamilyView
4.91 out of 5 average rating, 23 reviews
I Melograni del Chianti - Focolare Apartment
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Casa del Contadino
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Cipressini 2 - pool and amazing views
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5.0 out of 5 average rating, 65 reviews
NonnAnnita Rooms
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4.91 out of 5 average rating, 55 reviews
Tuscany jem: The Chianti Farmer's House
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4.98 out of 5 average rating, 84 reviews
AnticaVista, Luxury Apartment with Tower Views
ValueLocationDecor
5.0 out of 5 average rating, 64 reviews
App. Poggiarello
FamilyLocationWalkability
4.96 out of 5 average rating, 57 reviewsDestinations to explore
- Cathedral of Santa Maria del Fiore
- Santa Maria Novella
- Santa Maria Novella
- Ponte Vecchio
- Basilica of Santa Maria Novella
- Piazza del Duomo (Pisa)
- Cala Violina
- Stazione Santa Maria Novella
- Mugello Circuit
- Mercato Centrale
- Spiagge Bianche
- Parco Nazionale delle Foreste Casentinesi, Monte Falterona e Campigna
- Pisa Centrale Railway Station
- Uffizi Gallery
- Gulf of Baratti
- Fortezza da Basso
- Piazza della Repubblica
- Parco delle Cascine
- Del Chianti
- Piazzale Michelangelo
- Palazzo Vecchio
- Piazza della Signoria
- Pitti Palace
- Boboli's Garden





