Vacation home rentals in San Gimignano

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, 249 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

LocationFamilyBeach

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, 165 reviews

Respira la Toscana: vista a 180° sulle Colline

Please note that the second bedroom is divided from the hallway by a curtain and not by a door. inVivi la tua esperienza a San Gimignano con una splendida vista sulle colline toscane! Nel cuore di San Gimignano, vivi la città con ingresso indipendente, primo piano e panorama mozzafiato sulle colline toscane. Disponibile su richiesta il posto auto privato. Ingresso, salotto, 2 camere matrimoniali, cucina e ampio bagno. city tax da aggiungere al prezzo, 2,5€ per ogni persona per ogni notte.

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Vacation home in Poggibonsi

The kitchen features a warm design with wooden cabinetry and a rustic tiled countertop. Equipped with modern appliances, it includes a dining table surrounded by chairs, offering natural light from large windows with view of the garden.

4.92 out of 5 average rating, 101 reviews

Cozy Tuscany base - 10 min San Gimignano

“CASA DONELLA” a corner of Tuscan history, just a few minutes from San Gimignano. FREE PARKING & EASY ACCESS TO CHIANTI Hello, I'm Cristina and together with my sister Claudia we would be delighted to welcome you to our charming flat located on the outskirts of Poggibonsi in a typical Tuscan rural village, next to the provincial road that leads to: the Chianti area, the important art cities of Florence, Siena, Pisa and Lucca, and just a 10-minute drive from the famous town of San Gimignano.

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Vacation home in Badia a Passignano

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.

5.0 out of 5 average rating, 122 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

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Vacation home in Poggibonsi

4.91 out of 5 average rating, 113 reviews

Sangi Chianti Vacations

Sangi Chianti Vacations is the ideal solution for those seeking peace and tranquility in the heart of Chianti, near San Gimignano. 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 5 min. Private parking, two bedrooms, equipped kitchen, private bathroom, Wi-Fi, private garden, barbecue, a wonderful view of the Chianti hills.

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Vacation home in Sovicille

An aerial view captures the serene layout of the estate, surrounded by lush greenery and rolling hills. The inviting pool is situated centrally, accompanied by sun loungers. Stone buildings harmonize with the natural landscape, reflecting the tranquil beauty of the Montagnola Senese.

4.97 out of 5 average rating, 161 reviews

Podere La Castellina - N°1 COTTAGE

Cottage indipendente in pietre e mattoni all'interno del "Podere la Castellina" (ex convento 13° secolo), nel magnifico parco naturale della Montagnola Senese. Il cottage può ospitare comodamente 5 persone e comprende: - ampio soggiorno con tv e camino - cucina abitabile con forno - camera matrimoniale - camera con tre letti singoli - bagno con doccia A disposizione degli ospiti piscina panoramica, solarium e terrazza con vista mozzafiato, dotata di forno a legna e barbecue.

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Vacation home in loc. Simignano

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.

4.93 out of 5 average rating, 244 reviews

Casa al Gianni - Quercia

Ciao, siamo Cristina e Carmelo! Vi aspettiamo a "Casa al Gianni", il nostro agriturismo tra i boschi della Montagnola Senese a soli 20 minuti da Siena. Qui la vita rallenta: Solo il profumo della terra, il canto degli uccelli e la simpatia dei nostri animali. È un invito a riscoprire la bellezza delle piccole cose, immersi nel verde della Toscana più vera. Non è solo una vacanza, è un ritorno alle origini. Questo angolo di pace vi resterà nell'anima. Vi aspettiamo!

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Vacation home in Rosennano

An expansive window offers a breathtaking view of rolling hills and valleys, extending into the distant horizon. A small table with a laptop is positioned in front, accompanied by a white chair. Soft light fills the inviting space, emphasizing the serene landscape outside.

4.99 out of 5 average rating, 103 reviews

La Loggia. House with pool and stunning view

LA LOGGIA House, renovated in 2015, is a large independent apartment, ideal to be rented by those who love nature, tranquility and peace of these uncontaminated places immersed in nature. The apartment is characterized by a huge window overlooking the valley where you can enjoy one of the most spectacular views in the region. The view that can be admired from LA LOGGIA spans more than 60 km on the Chianti and the Crete Senesi.

LocationFamilySleep quality

4.96 out of 5 average rating, 142 reviews

La Casa dei Ricordi -car/motorcycle garage at 650m

Welcome to La Casa dei Ricordi, a 17th-century home full of soul: this is where I was born and raised. Today, it opens its doors to offer you an authentic experience. Located in an incredibly quiet and peaceful area, it’s the perfect place to relax just steps away from Piazza del Duomo and Piazza della Cisterna. A charming retreat in the heart of the historic center, where history meets the peace of a true family home.

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Vacation home in Castelnuovo Berardenga

A sparkling swimming pool is surrounded by sun loungers and umbrellas, offering a relaxing space for guests. The rustic farmhouse, with its stone exterior, is visible in the background, amidst lush greenery and trees under a partly cloudy sky.

4.91 out of 5 average rating, 100 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

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Vacation home in Peccioli

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.

4.87 out of 5 average rating, 262 reviews

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.

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Vacation home in Monteroni d'Arbia

A bright bedroom features a spacious bed with light linens and a decorative throw. Natural light enters through open double windows, revealing a private terrace. A television and a small desk with a chair are present, while two bedside tables with lamps offer soft lighting.

4.92 out of 5 average rating, 113 reviews

White lily con vista su Siena

Caggiolo è un podere completamente ristrutturato composto da più appartamenti, con vista panoramica su Siena. Situato ad 1 km da Ville di Corsano, a soli 14 km dalla città. Luogo ideale per trascorrere giorni in totale relax e godere delle meraviglie che questa zona offre (Chianti, Val d'Orcia, Crete Senesi..).

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Popular amenities for San Gimignano vacation home rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly vacation home rentals

Vacation home in Panzano in Chianti

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.

4.98 out of 5 average rating, 174 reviews

Fienile Santa Teresa

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Vacation home in Casole d'Elsa

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.

4.92 out of 5 average rating, 233 reviews

Charming farmhouse with garden, views & pool

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Vacation home in Fucecchio

4.83 out of 5 average rating, 211 reviews

Appartamento - Fattoria del Turricchio

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A rustic stone exterior features an arched entrance framed by a wooden awning. Two windows, one with a grille and the other with an open curtain, complement the weathered brick facade.

4.91 out of 5 average rating, 32 reviews

1-Casa Corallo con parcheggio di proprietà

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4.95 out of 5 average rating, 96 reviews

Tuscan House with Private Jacuzzi in Chianti

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Superhost

A traditional stone well is positioned in the foreground, framed by a brick terrace. In the background, a historic village with medieval towers rises against a clear blue sky, complemented by lush greenery and terracotta planters lining the area.

4.83 out of 5 average rating, 42 reviews

The Cottage

ValueFamilyComfort

An inviting living area features rustic wooden beams and terracotta tiles. A round ottoman is centered on a patterned rug, surrounded by a sofa, dining table, and chairs. Large arched windows provide ample natural light, while a decorative chest and artwork accent the walls.

4.94 out of 5 average rating, 50 reviews

Apartment La Roccaia

LocationFamilyHospitality

5.0 out of 5 average rating, 28 reviews

Appartamento Lo Scrigno Dei Sogni San Gimignano

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Vacation home rentals with a patio

Vacation home in Bagno A Ripoli

A charming kitchen area is highlighted by wooden cabinetry and a white tiled backsplash. A dining table with chairs is positioned prominently, accompanied by a decorative tray. Kitchen appliances, including a stove and sink, are present, alongside various utensils and cookware.

4.9 out of 5 average rating, 270 reviews

I Rosai appartamento sulle colline fiorentine

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Vacation home in Greve in Chianti

4.93 out of 5 average rating, 106 reviews

Il toscano - Nuovo con terrazza in centro a Greve

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Vacation home in Ulignano

The outdoor area features a sparkling swimming pool surrounded by lush greenery, tall trees, and comfortable lounge chairs. Umbrellas provide shade, and a stone wall frames the space, enhancing the serene atmosphere of this inviting garden retreat.

4.86 out of 5 average rating, 22 reviews

★ Romantic apartment & stunning view of Tuscany ★

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Vacation home in Monteroni d'Arbia

An elegant dining area is centered around a large wooden table surrounded by soft, upholstered chairs. Beams of natural light filter through skylights and windows, highlighting the warm wooden ceiling and contemporary kitchen space in the background.

5.0 out of 5 average rating, 35 reviews

Tuja

LocationFamilyAccuracy

Vacation home in Radda in Chianti

The historic farmhouse is surrounded by tall, ancient cypress trees and lush greenery. A gravel patio with outdoor seating is visible in the foreground, leading to an inviting garden area. The sky is clear with scattered clouds, creating a bright and welcoming ambiance.

4.98 out of 5 average rating, 46 reviews

Tuscany Country House, Central Chianti, Pano Views

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Vacation home in Barberino Tavarnelle

A tranquil swimming pool is set within a lush green garden, surrounded by neatly arranged sun loungers and shaded by tall trees. Umbrellas provide additional shade, and the serene landscape complements the inviting blue water of the pool.

5.0 out of 5 average rating, 6 reviews

Glicini 1, holiday home and pool 30' from Florence

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Vacation home in Poggibonsi

4.98 out of 5 average rating, 41 reviews

Podere le Fonti- Pet Friendly-15 min San Gimignano

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Vacation home in Montaione

4.93 out of 5 average rating, 15 reviews

Casa Camelia - Your authentic Tuscan getaway

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Vacation home rentals with a washer and dryer

4.92 out of 5 average rating, 148 reviews

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.

Vacation home in Fiesole

[Colline di Firenze] Casa toscana con posto auto

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Vacation home in Montespertoli

A panoramic view captures a hillside town featuring a historic tower, surrounded by lush greenery and rolling vineyards. The landscape displays a blend of trees, fields, and distant hills under a clear sky, showcasing the natural beauty of the Tuscan countryside.

4.95 out of 5 average rating, 146 reviews

Chianti Panorama | House with 3 En-Suite Bathrooms

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Vacation home in Santo Spirito

4.97 out of 5 average rating, 144 reviews

4BR • Luxury Palazzo • Iconic Views • Pitti Palace

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Vacation home in Florence

An inviting living space features a terracotta sofa alongside a wooden dining table with four white chairs. A television is mounted on the wall, and natural light illuminates the room. Decorative elements include a hanging light and a plant in the corner.

4.94 out of 5 average rating, 101 reviews

Zen Island downtown Florence, new apartment for 6

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4.95 out of 5 average rating, 310 reviews

A bright kitchen-living room features wooden cabinetry and a traditional stove. A dining table with white chairs is set beside two windows that offer natural light. Traditional tiles adorn the walls, complementing the rustic charm of the wooden beams on the ceiling.

Vacation home in Sorana

Tuscan Nature Views From Casa Gave

ValueFamilyGetting around

4.98 out of 5 average rating, 166 reviews

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.

Vacation home in Pistoia

Podere docciolino casa vacanze

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Vacation home in Florence

A spacious living area is highlighted by large windows, allowing natural light to fill the room. Elegant furnishings include a comfortable gray sofa, a round dining table with four chairs, and a cozy reading nook, creating a welcoming atmosphere for relaxation and socializing.

4.91 out of 5 average rating, 357 reviews

Melarancio Residence

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