
Villa holiday rentals in San Gimignano
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Top-rated villa rentals in San Gimignano
Guests agree: These villas are highly rated for location, cleanliness and more.

The Farmhouse Cottage
Entire upper floor of the newly renovated Manor House in traditional Tuscan style. High ceilings with exposed beams make the place cozy and perfect for families or groups of friends. In the house, there are two large functional fireplaces (in the living room and kitchen). Private, non-shared accommodation. The house has a large covered terrace, garden with sofas, BBQ, fire pit, private parking. The swimming pool among the olive trees and vineyards is ideal for relaxation and has private access to the shared area

Poggio del Fattore-Villa with pool, hilltop, Chianti
Poggio del Fattore is situated at the eastern edge of the Chianti region in Valdambra, a green valley that joins the lands of Florence, Siena and Arezzo. The farmstead is on the top of an hill and lies at the end of a long private road through a large olive growing estate; therefore you absolutely need a car. The breathtaking landscapes and the location of the villa offer the privacy needed for a peaceful and relaxing holiday and a perfect departure point from which to explore central Tuscany.

Virgi House
Virgi House is a 160 sqm villa, located 3 km far from Siena’s hystorical center. The villa is distributed over three floors. On the first one there is a double bedroom with bathroom and terrace, a large open space living room, a modern kitchen and a bathroom. Downstairs a double bedroom (or 2 single beds), a large bathroom, a study and a bright living room with a loggia from which you can access the private car park and the garden. The property also provides free wifi, air conditioning.

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.

San Giovanni in Poggio, Villa Meriggio 95 sqm
Detached house, two double bedrooms, two bathrooms with shower, living room with fully equipped kitchen (dishwasher, washing machine, oven, microwave), double sofa bed, private garden with equipped pergola. Satellite TV and free Wi-Fi. Additional services at the property, upon reservation, include Focus brand Jarifa2 6.7 pedal-assisted bicycles and a wellness area with a Forest outdoor Finnish sauna and a heated mini-pool with hydromassage and chromotherapy with panoramic views.

Luxury Villa in the very heart of Chianti
The views, the views, oh my word the VIEWS! Originating in the early 12th century this spectacular home once served as the bakery for the entire village. Now fully renovated, the entrance and ground level have been opened with glass arches allowing natural light to illuminate the exposed walls, 4 large bedrooms, 3 with ensuite baths ( including a jacuzzi ). Only Minutes away from the famous Wineries of Chianti, this is THE Spot for a glass amongst friends.

The Tower
Ancient Tuscan villa, beautiful, with exclusive private garden, completely renovated, surrounded by the beautiful and gentle Tuscan hills. The villa has a breathtaking view, is very sunny, well furnished and equipped with all amenities, quiet and not isolated. The house is located in Bagnolo, a small hamlet of Impruneta at the gates of Chianti, an area of olive groves, vineyards and peace. The house is about 10 km by car from the center of Florence.

Farmhouse in Chianti
Beautiful portion of a farmhouse immersed in Chianti with a beautiful swimming pool, surrounded by vineyards and olive trees, perfectly furnished with a large garden and parking spaces. It is located 20 minutes from Florence, 40 from Siena and 50 from Pisa, in a few minutes you can reach Certaldo (birthplace of Boccaccio) and Vinci (birthplace of Leonardo Da Vinci). The house is halfway between Montespertoli and San Casciano (7km).

Villa Isabella
Villa Isabella is a comfortable Tuscan style villa located in the splendid Chianti hills in Tuscany with a large garden and a spectacular breathtaking panoramic swimming pool for exclusive use where you can experience the Tuscan tradition in full local style with the possibility of organizing private shuttles service for reach the property traditional experiences, services and tours only and exclusively for our guests.

Villa La Doccia, Greve in Chianti
Villa la Doccia is located 8 minutes by car from the center of Greve in Chianti, Casole, The Villa in a quiet and peaceful area is located within a small farm surrounded by vineyards and olive groves. ➡️ We would like to inform you that for this emergency we are doing everything possible to help and protect our guests by adopting a detailed and strict cleaning, We disinfect and sanitize all parts of the house.

"Villa Daisy" overlooking Siena
Wonderful villa with independent entrance inside the "Caggiolo" farm, brought to light with careful and thorough renovation that has kept intact the typical features of a Tuscan farm. Beautiful panoramic view of Siena. Located in Ville di Corsano, just 14 km from the city. An ideal place to spend days in total relaxation and enjoy the wonders that this area offers (Chianti, Val d'Orcia, Crete Senesi etc).

Il Leccio - Tuscany home near San Gimignano
Tuscan farmhouse with beamed ceilings and large living area with fireplace. 3 bedrooms, 2 bathrooms and an outdoor area for lunches and dinners in the company. Hilly and windy landscape with panoramic views of the Tuscan countryside. 12 km from San Gimignano, 30 from Volterra, 30 from Siena and 2 km from the medieval village of Certaldo Alto.
Popular amenities for San Gimignano villa rentals
Private villa rentals

Amazing Chianti villa with pool for 12

Stalla - Villa with garden in the historic center

Charming villa 15' walk to center stunning view

La Cipresseta Estate | Cipresso House

Sestuccina

Private villa in Chianti · Pool and nature

Poggio Novoli 6, Emma Villa

Villa Giorgia 10 people
Luxury villa rentals

Casale del timignano, private villa with huge gard
Le Maggioline Your Tuscany country house

Chianti Villa in Tuscany near Siena and Arezzo

Riecine Capanna 4

Villa Poggialto: breathtaking views and luxury spa

Farmhouse , pool, 13 px. Lucca 10km

Villa Capanna, Private Pool, Breathtaking Views

Casa Faraona, villa with private pool
Villa rentals with a pool

Villa Gelsomino, your dream in Tuscany

La Capannina Di Pillo

Villa San Martino 6-8 people

Luxury Tuscany Villa on the hill with private pool

The Lazy Oak

Montemarcoli

Near San Gimignano and Volterra-villa with pool

Private Villa with semi-Olympic pool and Tennis
Quick stats about villa rentals in San Gimignano

Total holiday rentals
Explore 70 holiday rentals in San Gimignano

Nightly prices starting at
San Gimignano holiday rentals start at $86 AUD per night before taxes and fees

Verified guest reviews
Over 1,470 verified reviews to help you choose

Family-friendly holiday rentals
70 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 20 rentals that welcome pets

Holiday rentals with a pool
60 properties feature pools

Rentals with dedicated workspaces
30 properties have a dedicated workspace

Wi-Fi availability
70 of San Gimignano holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wi-Fi and Pool across San Gimignano rentals

4.8 Average rating
San Gimignano stays are highly rated by guests—averaging 4.8 out of 5!
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- Santa Maria Novella
- Piazza della Signoria
- Mercato Centrale
- Strozzi Palace
- Ponte Vecchio
- Santa Maria Novella
- Great Synagogue of Florence
- Basilica Di San Miniato A Monte
- Cathedral of Santa Maria del Fiore
- Marina di Cecina
- Del Chianti
- Porta Elisa
- Basilica of Santa Maria Novella
- Spiagge Bianche
- Cala Violina
- Siena Cathedral
- Eremo Di Camaldoli
- Piazza del Duomo (Pisa)
- Uffizi Gallery
- Parco Nazionale delle Foreste Casentinesi, Monte Falterona e Campigna
- Fortezza da Basso
- Piazza della Repubblica
- Piazzale Michelangelo
- Pitti Palace
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