Holiday home rentals in San Gimignano

An aerial view captures the scenic landscape surrounding an ancient farm complex nestled within lush greenery. A swimming pool is visible at the center, surrounded by sun loungers, while rolling hills stretch into the distance under a soft evening light.

4.93 out of 5 average rating, 118 reviews

Podere La Castellina - No. 2 LECCETO

Stone and brick apartment inside the "Podere la Castellina" (former 13th century convent), in the magnificent natural park of Montagnola Senese. The apartment located on the ground floor can comfortably accommodate 2 people and includes: - living room with TV - kitchen with oven and electric stove - master bedroom - bathroom with large shower - private outdoor table Available to guests is a panoramic swimming pool, solarium and terrace with breathtaking views, equipped with a wood-burning oven and barbecue.

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.

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

A stone-paved courtyard features a rustic house with weathered yellow walls and green shuttered windows. A small table with chairs is set under the sun, surrounded by potted plants, creating an inviting outdoor space for guests to enjoy the fresh air.

4.88 out of 5 average rating, 102 reviews

[Florence Hills] Borgo Le Palaie

Il nostro bnb vuole offrire un angolo di pace e tranquillità, facile e veloce da raggiungere, in una caratteristica casa toscana ristrutturata a soli 7 km (25 minuti) dal parcheggio nel centro storico di Firenze. A Borgo Le Palaie è possibile immergersi nel paesaggio delle colline fiorentine tra cipressi e ulivi, gustare il panorama e a poca distanza visitare vigneti e cantine importanti. Si arriva comodamente con l'auto (incluso un posto riservato agli ospiti) o con l'autobus a 300 metri.

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.

4.95 out of 5 average rating, 184 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.

A modern kitchen space features a marble countertop with two wooden stools. Large windows showcase a scenic view of Florence's rooftops, including the iconic dome, while natural light fills the room. A fruit bowl and coffee maker are included on the counter.

4.95 out of 5 average rating, 450 reviews

Breathtaking view from romantic nest in citycenter

Unique and charming attic in the middle of historic center with amazing breathtaking view on the city center. Perfect for a romantic stay in the heart of Florence. Fully windowed on 3/4 walls. Completely renewed with modern design furniture. Powerful A/C, fast wi-fi, fully equipped kitchen. Going downstairs you will immediately be absorbed in the most beautiful area of city center. Attention! Only for young-soul people: 5th FLOOR, NO LIFT, last 2 flights of stairs in a narrow spiral stair.

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.

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.

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.

4.92 out of 5 average rating, 216 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!

The rustic kitchen area features exposed stone walls and a warm, earthy tone. A small wooden table with two chairs sits adjacent to a red cabinet. A sink with a vintage faucet and decorative items can be seen, complemented by soft lighting from an overhead fixture.

4.93 out of 5 average rating, 378 reviews

Romantic stay at a bio-agritourism in Florence

Escape the crowd of Firenze and be ready for an authentic rural Tuscan lifestyle experience ... The deers graze the fields near the house, you can hear the wild boars grunting and the crickets singing. Healthy food, good wine, a bio sauna and a jacuzzi in the olive grove; a real re-charge and re-connection in Nature in an eco-friendly and cozy accommodation .

4.89 out of 5 average rating, 224 reviews

A spacious living area features a light-colored sofa with a decorative throw, complemented by wooden beams overhead. The open kitchen with modern appliances is visible in the background, alongside large windows that provide natural light and a view of the exterior.

Holiday home in Peccioli

Michelangelo: entire space in the heart of Tuscany

Come and take a vacation at our beautiful apartment in Peccioli, Tuscany! Enjoy a renovated space, beautifully decorated, with new appliances and furniture, Air conditioner in all spaces, high-speed internet, and all you need to enjoy your time in Italy. Peccioli is a gem in the heart of Tuscany, near all the big cities and touristic attractions.

A terrace is showcased, featuring a wooden table accompanied by white chairs. The scene includes expansive views of rolling hills and vineyards, framed by tall cypress trees. The sky reveals warm sunset hues, creating a serene atmosphere.

4.91 out of 5 average rating, 115 reviews

Stunning Tuscan apartment for 2

This apartment - tucked away privately and enjoying a stunning view from its terrace - is part of an 'agriturismo' farm which produces organic Chianti Classico. Spacious and light, it has 1 double bedroom, 1 sitting room, 1 bathroom and a kitchen.

Holiday home in San Gimignano

The image captures the twelfth-century towers of San Gimignano, framed by lush greenery. The buildings exhibit a blend of rustic stone and earthy tones, with various trees partially obscuring the view, offering a glimpse of the historic skyline of the UNESCO World Heritage Site.

4.8 out of 5 average rating, 106 reviews

San Gimignano, Tuscany

Set inside the walls of historic San Gimignano, this medieval (but fully refurbished) apartment will stir your senses. San Gimignano is right at your door. Step out into a World Heritage City 45 minutes from Florence, 35 minutes from Siena. Enjoy

The image captures a serene outdoor setting featuring a swimming pool surrounded by a well-maintained lawn. Several sun loungers positioned around the pool invite relaxation, while the rustic house and lush greenery complete the idyllic scene.