Holiday rentals with a pool in San Gimignano

La Casetta

“La Casetta”, is a new restored enchanting apartment immersed in the splendid Tuscan countryside, only 2 kms from the medieval village of Casole d'Elsa in Siena province. Situated in a old farm complex with private entrance, large private garden, and access to the communal swimming pool. Furnished with utmost care down to the finest detail. Ideal for a relaxing, regenerative week with family or friends, emerged in an uncontaminated natural landscape. Possibility of excursions on foot and by bicycle in an evocative natural setting of lush forests and gentle hills of rare beauty. One can enjoy local dishes of the wonderful Tuscan tradition in many of the nearby restaurants or organize splendid home-cooked meals with the barbecue in the garden. Ideally situated for visits the many nearby towns and cities rich in art and beauty: 30 mins to Siena, 1 hour to Florence ,30 mins to San Gimignano and Volterra, 45 mins to the Chianti area. La Casetta is the ideal place to regenerate your body and mind. (We are the same owners of “La Senesina" apartment near Siena check out our rating on the web! Our 5 stars ratings are your warranty for a great stunning vacation)

Family · Location · Cleanliness

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Relaxation and charm in the Chianti hills

Beautiful stone farmhouse, detached, surrounded by olive trees and the Chianti hills, with private garden and panoramic swimming pool. Ground floor with large living rooms, antique fireplace and wood-burning oven, bright living room and fully equipped kitchen. On the first floor, three suites consisting of a bedroom, study and private bathroom. Access via gate and white road on private property just 500 meters from the village of Strada in Chianti. Ideal for peace and relaxation. Convenient location for visiting Tuscany.

Location · Family · Comfort

Montegonfoli 5 apartment in farmhouse, 4+2 guests

Comfortable apartment for 4 adults and 2 babies under 12yo, in San Gimignano countryside, in a resort/farmhouse. Here in Montegonfoli you can spend a vacation in absolute relax, in an enchanted natural context, far from the noise but at the same time very close to the most beautiful attractions of the world. First floor with amazing views on San Gimignano and Chianti Hills. No aircon, but every bedroom has a large fan for the few hot nights we are getting in July/August. We usually have 15°C!

Value · Location · Amenities

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Stone House with Exclusive Pool Codilungo in Chianti

Welcome to your Tuscan dream between Florence & Siena. Perfect for families or romantic getaways. • 360° views of iconic Chianti hills. •Huge Exclusive Infinity Pool (17x9m), lit at night (open from May 1st to October 15th) • Total privacy, yet restaurants/shops are 10-15 mins away. • Comfort for 6: 3 bedrooms (2 double, 1 twin) & 3 full baths. • Modern amenities: Fully equipped kitchen area, Smart TV. • Outdoor bliss: Large dining loggia, professional BBQ, poolside porch & bath.

Family · Value · Long stay

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Villa Gourmet Food, Pizza, Chef, Pool and Nature

Villa Gourmet Typical farmhouse in the heart of Tuscany with 6 bedrooms that can comfortably accommodate up to 14 guests. - Exclusive saltwater infinity pool - Gourmet cuisine - Large garden with private parking - Two Free Charging Station (3,75 KW) - Veranda with table and Weber barbecue by the pool - Children's play area and table tennis - Football pitch - Home Restaurant service available - Cooking class and pizza workshop using a wood-fired oven - Shuttle Services

Location · Value · Beach

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Podere Vergianoni nestled in Chianti with a pool

Podere Vergianoni is a family-run property dating back to the 1600s, located in the beautiful hills of Chianti in Tuscany. Our family can organise 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.

Value · Family · Condition

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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.

Location · Family · Breakfast

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Farmhouse in Chianti with Swimming Pool

Agriturismo Il Colle is located on one of the Chianti hills. The structure has been completely renovated, dominates the Chianti valleys and enjoys a splendid view of the surrounding hills and the city of Florence just 35 minutes by car The apartment is located on the ground floor of the main farmhouse, with independent access and private space. The care taken in the restoration and furnishing make the house particularly welcoming, respecting the rural style.

Value · Location · Amenities

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Poggio Massiccioli

Cosy apartment for 4 people, furnished in Tuscan style with exposed beams, nestled among the rolling hills of the Tuscan countryside. Guests have access to a fully equipped garden, free Wi-Fi, a shared swimming pool with facilities, a wood-fired oven and barbecue, and a washing machine. The apartment is housed in a charming 19th-century stone farmhouse that has recently been renovated in the Tuscan style and divided into three comfortable apartments.

Value · Family · Pool

Il Castro Luxury San Gimignano. Michelangelo Suite

Il Castro is a group of apartments finely recovered from a careful renovation, which has left the signs of the past unchanged. The classic furnishings, meticulously decorated by local artisans, blend in perfect harmony with elements of fine design, giving a minimalist and refined effect. The finishes of the bathrooms are extraordinary, where the search for detail and the quality of the materials transform the environment into something unique.

Family · Location · Pool

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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.

Location · Family · Long stay

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Cercis - La Palmierina

The apartment is part of a completely fenced estate of 60 hectares of unspoiled nature: more than 1000 olive trees, countless cypresses and fragrant forests create an idyllic environment for those seeking tranquility and silence. The Palmierina estate is near Castelfalfi (a true jewel of medieval architecture) and close to Florence (50 Km), Siena (50 Km), and Pisa (50 Km). There are two golf courses nearby.

Family · Location · Checkout