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Holiday home rentals in San Gimignano

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Top-rated holiday home rentals in San Gimignano

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Guest favourite
A rolling landscape is depicted, featuring neatly arranged rows of olive trees and grapevines. In the background, the towers of San Gimignano are visible against a clear blue sky, complementing the serene atmosphere of the agriturismo.
Holiday home
4.78 out of 5 average rating, 231 reviews

San Gimignano, Montegonfoli SIX

Wonderful apartment in the country side of San Gimignano, at about 3Km and 5min from town center by car, far from noise, but close to all you may need. The apartment is suited for 4 people with 2 bedrooms each one with its en-suite bathroom. Bedrooms have an high privacy, splitted by the living room with kitchen, featured by the huge fireplace where our ancient farmer used to sleep over a FIAT 500 seat. First floor, 20 steps, no elevator. Side view on San Gimignano city and towers on the right

Guest favourite
An aerial view captures a charming Tuscan farmhouse nestled within lush green vineyards and rolling hills. The property features a rustic stone exterior and a terracotta roof, complemented by surrounding greenery and a clear blue sky.
Holiday home
4.95 out of 5 average rating, 187 reviews

Vittoria Chianti Vacations 🍇🍷

Vittoria Chianti Vacations is the ideal solution for those seeking peace and tranquility in the heart of Chianti, close to all comforts. Typical Tuscan farmhouse halfway between Florence and Siena, is located in a strategic position to quickly reach Florence, Siena, San Gimignano, Monteriggioni, Volterra and the Chianti hills. Siena Eye Laser Clinic 2 min. Private parking, two bedrooms, equipped kitchen, private bathroom, Wi-Fi, private garden, barbecue, a wonderful view of the Chianti hills.

Top guest favourite
A private terrace is set against a backdrop of lush greenery, featuring a gravel surface and wooden railing. Two chairs and a small table are arranged for relaxation, with a distant view of rolling hills and valleys under a clear blue sky, creating a serene environment.
Holiday home
4.97 out of 5 average rating, 118 reviews

Vicolo dell'Inferno* @home in San Miniato old town

Welcome to the historic centre of San Miniato! Our holiday home is located in the charming and quiet Vicolo dell'Inferno, right on the main square. San Miniato was once known as “the city of 20 miles”, located right in the middle between Pisa, Florence, Siena and Lucca. It is ideal for day trips without sacrificing the tranquillity of an authentic medieval village. After a day of good food and visiting cities of art, you can relax on your balcony and enjoy the slow pace of Tuscan life.


Top guest favourite
An aerial view captures the historic castle surrounded by lush green hills and vineyards. The impressive structure features tall towers and ornate architecture, set amid manicured gardens and tree-lined pathways, reflecting the beauty of the Chianti landscape.
Holiday home
5 out of 5 average rating, 116 reviews

Chianti Craft House Badia a Passignano

Ancient house in the historic village of Badia a Passignano, completely and finely restored in 2022. The house is located exactly in the center of the village of Badia a Passignano, overlooking the abbey castle and the Chianti vineyards. The house consists of 2 bedrooms air-conditioned: 1 double bedroom with service bathroom and 1 with 2 single beds and the possibility of a third with sofa chair; a full bathroom with shower, a full kitchen with washing machine and dishwasher, dining area

Guest favourite
Holiday home
4.89 out of 5 average rating, 162 reviews

Barrel Suite Tuscany • Hot Tub • Vineyard View

Wooden barrel suite in Tuscany, nestled in an olive grove in Reggello: breathtaking views over hills and vineyards, total peace. One of the largest barrels in the world (3.5 m x 8 m) with a private bathroom, kitchenette, veranda and small courtyard. All barrels have a hot tub pool for your relaxation. Strategic location: Florence ~40 min, Siena and Arezzo for day trips. Private parking on the property and a welcome Tuscan cold cuts and cheese board. Close to The Mall Luxury Outlet.

Top guest favourite
A spacious living area features a green sofa adorned with a colorful blanket. A large artwork depicting food hangs on the wall, complemented by potted plants and a dining table displaying fresh fruit. Natural light streams through an archway, enhancing the inviting atmosphere.
Holiday home
5 out of 5 average rating, 105 reviews

GREEN like hope in Florence

This is a a cozy one-bedroom apartment on a single level, ideal for families. It has a living room with a double sofa bed, a small kitchen with a high chair for children, a bedroom with a double bed, and an additional armchair bed. It features a unique bathroom with a shower and a private courtyard. In shades of green, with soft furnishings and natural fabrics, in respect of its historicity, the ancient wooden coffered ceiling from the 1700s has been preserved in the living room.

Top guest favourite
A bright bedroom features a spacious bed with crisp white linens and a decorative pillow. A vivid landscape painting hangs above, while a window with wooden frames reveals a scenic view of the Tuscan hills, complemented by soft natural light filtering through sheer curtains.
Holiday home
4.98 out of 5 average rating, 144 reviews

Breathe in Tuscany: 180° view of the hills

Please note that the second bedroom is divided from the hallway by a curtain and not by a door. Experience San Gimignano with a splendid view of the Tuscan hills! In the heart of San Gimignano, experience the city with a separate entrance, second floor and breathtaking views of the Tuscan hills. Private parking is available upon request. Entrance, living room, 2 double bedrooms, kitchen and large bathroom. city tax to be added to the price, €2.50 per person per night.

Guest favourite
The image showcases a modern kitchen area featuring sleek white cabinets and stainless steel appliances. A round light fixture hangs above a wooden dining table accompanied by metallic chairs. A staircase with a minimalist design leads to the upper level, and natural light fills the space from a nearby window.
Holiday home
4.92 out of 5 average rating, 169 reviews

House of Poggio al Vico

Portion of a cosy farmhouse, renovated in Tuscan country chic style on the hills of Pratolino, calm and quiet with private parking. Two double bedrooms, kitchen, living room with fireplace and garden. Perfect for 4 people. The apartment is located 20 minutes from the centre of Florence, and can also be reached by bus no. 25 or AT, which is very well connected. Strategic location to stay in a quiet place in the countryside but close to Florence and Mugello, safe.

Superhost
A rustic stone building features a charming entrance adorned with blooming flowers and lush greenery. The structure showcases traditional architecture with arched doorways and a tiled roof, set against a clear blue sky and surrounded by serene natural beauty.
Holiday home
4.91 out of 5 average rating, 218 reviews

Charming farmhouse with garden, views & pool

Agriturismo Timignano is a beautiful farmhouse surrounded by stunning unspoilt countryside. The stone farmhouse has been restored over the years to create 3 totally separate apartments, each with independent entrance , private terraces and garden space. The farm is surrounded by unspoilt countryside with spectacular views and magnificent sunsets. It is a calm, relaxed place, an idyllic retreat away from the crowds ideal for couples.

Guest favourite
A charming rustic farmhouse is set against a dramatic sky, framed by lush green trees. The exterior features warm-toned walls and a tiled roof, while a spacious yard includes seating arrangements for outdoor relaxation, inviting guests to enjoy the serene countryside.
Holiday home
4.92 out of 5 average rating, 217 reviews

Casa al Gianni - Oak

Hi, we're Cristina & Carmelo! We invite you to live an authentic experience in our farmhouse “Casa al Gianni” located 20 minutes from Siena. Our hallmark is simple life in close contact with nature and the animals of our farm. Immersed in the woods and the beautiful Tuscan countryside, you will spend an unforgettable vacation. This slice of paradise will remain in your heart!

Top guest favourite
A paved pathway leads to a charming outdoor seating area under a canopy, surrounded by low shrubs and greenery. The house features a mix of neutral-colored walls with green shutters, providing a cozy retreat in a tranquil setting.
Holiday home
4.98 out of 5 average rating, 150 reviews

Podere Docciolino Vacation Home

In podere docciolino you'll find a stay full of relax! The house, surrounded by the countryside will offer you peace and tranquillity. Join us to try this experience. The house is 3.9 km from the train station; it is not recommended to walk to it as the road is very busy. The bus stop for Pistoia is 450 mt away, and the bus stop for Prato is 1.3 km away

Guest favourite
An outdoor area is presented, featuring a stone-paved patio with several potted plants. The entrance to the house is framed by arched doors, which open to a cozy seating arrangement. Views of the surrounding landscape are visible in the background.
Holiday home
4.93 out of 5 average rating, 126 reviews

Historic apartment Il Prato in Castelfranco

Il Prato is a historic Tuscan farmhouse on the outskirts of Castelfranco di Sopra, finely restored and surrounded by olive trees, orchards and woods. It has a beautiful garden where you can relax and eat. Equidistant from the great cities of art of Siena, Florence and Arezzo.

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Destinations to explore

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