
Holiday houses in Guistrigona
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Top-rated holiday rentals in Guistrigona
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Domus Nannini - Loggia Salimbeni SPA
Apartment of 200 sqm furnished with precious classical furniture and very spacious rooms: 13 windows overlooking the old town, each window offers a unique view of the city. Big and spacious lounge with peerless view on the begin of Banchi di Sopra, Piazza Salimbeni and the headquarter of the Monte dei Paschi, formed by the noble palaces Tantucci, Salimbeni and Spannocchi. Second lounge with library, sofa-bed and the same exclusive view. 2 large bedrooms with city-views and king-size beds. 3 bathrooms one with jacuzzi and one with shower. A long corridor that crosses the apartment, spacious entrance and private terrace on the internal courtyard. Third lounge with sofa-bed and city-view. Dining room with panoramic views of the Duomo of Siena and Basilica of San Domenico which stand out over the medieval roofs of Siena a few meters from us. Fully equipped kitchen with laundry area. It occupies the entire second floor our 1600's palace and offers unique and privileged views of Siena and its architectural wonders. We are on Banchi sopra Sopra, the main course of the historical center of Siena, below the house you will find the best shops in the center with all the brands of high fashion, lots of restaurants; Wineries, Bars and Supermarkets with typical Tuscan products.
LocationValueAir conditioning
4.96 out of 5 average rating, 156 reviews
Casa al Gianni - The Simignano Barn
Transformed from a historic barn, this luxurious retreat offers 5 bedrooms, 4 bathrooms, a large, fully equipped kitchen, a spacious living area, 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 looking for a unique experience, it combines rustic charm with modern comforts. Perfect for families or groups, it promises magical evenings under the stars, with relaxation in the hot tub and outdoor dinners. A memorable getaway awaits you in this little slice of paradise!
LocationFamilyCleanliness
4.97 out of 5 average rating, 198 reviews
Apartment in a Tuscan farmhouse at Le Pietre Vive
Small, cosy apartment with independent access, consisting of charming bedroom with a beautiful view, equipped with ample closet space, a comfortable canopy bed and private bathroom and pretty living room / breakfast area, with sofa-bed. A delicious breakfast is included in the price and from April through October guests also have the option of dining on-site in our traditional farm restaurant. If dates are not available the property includes other rooms in charming cottage also on Airbnb.
ValueLocationCheckout
4.92 out of 5 average rating, 359 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.
LocationValueView
4.99 out of 5 average rating, 155 reviews
Bed and Breakfast Casa Cernano
- 5 Double or Triple rooms each with its own bathroom/WC, with individual entrances from the outside area - Rooms are also individually rented -The price of your stay is based on 1 double room each 2 guests ( also with separate beds upon request ) - Garden - Car park - Free Wi-Fi - Barn with sitting aerea, games for children, coffee machine, ping ong table - Breakfast sweet or savory upon request ( 5 or 7 euro a person/day ) - Dogs are welcome ( 15 euro the entire stay )
FamilyValueWalkability
4.92 out of 5 average rating, 215 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.
FamilyLocationDecor
4.98 out of 5 average rating, 107 reviews
Farmhouse Pacinina – Casa Rosa
The farmhouse Pacinina is the agriturismo of the organic farm Pacina. Pacina counts a total of 60ha including vineyards, olive and fruits trees, forest and fields. Pacinina counts three indipendent apartments surrounded by a beautiful garden full of plants and fruit trees. On the ground floor, an indoor swimming pool, a pool table and common rooms. The Casa Rosa has on the first floor a large kitchen, and on the second floor, four bedrooms and three bathroom.
LocationValueOutdoor spaces
4.93 out of 5 average rating, 42 reviews
The Chianti window
A wonderful place to spend a few days in pleasant company. A large living room with fireplace where you can relax after returning from beautiful walks, bike rides, and excursions. The independent apartment is 15 km from Siena, 20 km from the Thermal Baths and 40 minutes from the villages of San Gimignano and Monteriggioni. Overall, there is a farm that produces wines and oil with the possibility of guided tours and tasting of our products with themed dinners.
LocationFamilyQuiet
4.9 out of 5 average rating, 136 reviews
Sosta Eroica • Panoramic View & Quiet Pool Retreat
Imagine waking up in the hills of the Crete Senesi, spending the day exploring Siena, Montalcino, Pienza, Montepulciano, Val d'Orcia and Chianti, and returning in the evening to a peaceful place with a beautiful view of the hills. Sosta Eroica is a detached house in Asciano, in the heart of Tuscany, perfect for alternating culture, nature, good food and relaxation, with a swimming pool and large green spaces. 📍 The ideal base for exploring Tuscany.
FamilyLocationCondition
4.97 out of 5 average rating, 36 reviews
Luxury frescoed apartment in the historical center
The Palazzo Pannilini Superior apartment is composed of a bright entrance enriched by an elegant coffered ceiling, a large fully frescoed lounge, a large foyer, a kitchen equipped with a terrace, a dining room topped with a frescoed vault, four bedrooms, three bathrooms, a wardrobe room, and a panoramic terrace where you can sunbathe and relax. The apartment is located at the second floor with no elevator. The apartment has air conditioning.
FamilyValueAccuracy
4.97 out of 5 average rating, 116 reviews
Villa Capanna, Private Pool, Breathtaking Views
Ancient restored barn with up to 6 bedrooms and 6 bathrooms, immersed in a historic wine estate, just 6 km from Siena. One of the most beautiful views that the Tuscan panorama can offer, airconditioned bedrooms, exclusive swimming pool, large triple garden, BBQ, poolside table, terrace to enjoy the sunset over the medieval towers on the horizon while sipping the organic wines of the estate, fireplace, parking free, WI-FI internet.
FamilyLocationShared spaces
4.89 out of 5 average rating, 309 reviews
PIERFANTINI private Chianti house ♿️ 🏊♂️ 🐶
Pierfantini is a rustic farmhouse. It is located on a hill in the middle of a natural park. Isolated from the vitta, the nearest town is the medieval village of San Gusmè. The house is renovated and the ground floor adapted for disabled people or wheelchair users There are three apartments but I never rent them separately. The house rent is for all the property
LocationFamilyHospitality
4.91 out of 5 average rating, 100 reviewsPopular amenities for Guistrigona holiday rentals
Other great holiday rentals in Guistrigona

Luxury penthouse with a view of Piazza del Campo
ValueFamilyDecor
5.0 out of 5 average rating, 21 reviews
GuestHost - Top of hill with Siena & Chianti view
ValueLocationWi-Fi
4.88 out of 5 average rating, 89 reviews
Charming Residence Castello di Orgiale near Siena
ValueLocationAir conditioning
4.97 out of 5 average rating, 88 reviews
Pool Escape Just Outside Siena
FamilyLocationBathroom
5.0 out of 5 average rating, 20 reviews
Villa marielena chianti farmhouse with hot tub - v
LocationFamilyCheck-in
5.0 out of 5 average rating, 10 reviews
Incredible Views & Pool in the Tuscan Hills
ValueFamilyView
4.85 out of 5 average rating, 26 reviews
HOUSE ABOVE THE CHIANTI. WITH GARDEN AND POOL
ValueLocationLong stay
4.99 out of 5 average rating, 78 reviews
Tuscany jem: The Chianti Farmer's House
LocationFamilyAir conditioning
4.98 out of 5 average rating, 87 reviewsDestinations to explore
- Lake Trasimeno
- Cathedral of Santa Maria del Fiore
- Santa Maria Novella
- Santa Maria Novella
- Ponte Vecchio
- Basilica of Santa Maria Novella
- Stazione Santa Maria Novella
- Cala Violina
- Mugello Circuit
- Parco Nazionale delle Foreste Casentinesi, Monte Falterona e Campigna
- Mercato Centrale
- Fortezza da Basso
- Uffizi Gallery
- Piazza della Repubblica
- Parco delle Cascine
- Piazzale Michelangelo
- Palazzo Vecchio
- Del Chianti
- Piazza della Signoria
- Pitti Palace
- Boboli's Garden
- Mount Amiata
- Cascate del Mulino
- Stadio Artemio Franchi





