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Vacation home rentals in San Gimignano

Find and book unique vacation home rentals on Airbnb

Top-rated vacation home rentals in San Gimignano

Guests agree: these vacation home rentals are highly rated for location, cleanliness, and more.

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Guest favorite
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.
Vacation home in Simignano
4.92 out of 5 average rating, 227 reviews

Casa al Gianni - Oak

Hi, we’re Cristina and Carmelo! We look forward to welcoming you to “Casa al Gianni,” our agritourism property in the woods of the Montagnola Senese, just 20 minutes from Siena. Here, life slows down: just the scent of the earth, the song of the birds, and the warmth of our animals. It is an invitation to rediscover the beauty of the little things, surrounded by the greenery of the most authentic Tuscany. It’s not just a vacation; it’s a return to our roots. This peaceful haven will stay in your soul. We look forward to welcoming you!

Top guest favorite
A person interacts with a falcon, demonstrating the connection between humans and raptors. The background features a natural landscape with greenery, and additional animals can be seen grazing in the distance. The setting showcases an engaging outdoor experience in a tranquil environment.
Vacation home in Chianciano Terme
5 out of 5 average rating, 119 reviews

The Eagle and the Olive Tree

At Aquila e l'Ulivo, an ancient renovated farmhouse from the 1200s, you will not only find all the necessary comforts for a wonderful stay, but you will also experience the thrill of feeling free and immersed in the unspoiled nature of Val D'Orcia. Here you'll have the opportunity to walk with the two falcons Ayga and Sayen and interact with the eagles, and why not sip an excellent aperitif by the pool. We are waiting for you in our world, made up of animals, relaxation, nature and even a touch of Magic.

Top guest favorite
An aerial view of a rustic complex surrounded by lush greenery. A swimming pool is visible at the center, accompanied by sun loungers. The surrounding landscape features rolling hills and fields, creating a serene atmosphere.
Vacation home in Sovicille
4.96 out of 5 average rating, 102 reviews

Podere La Castellina - No. 4 FICO

Appartamento in pietre e mattoni all'interno del "Podere la Castellina" (ex convento 13° secolo), nel magnifico parco naturale della Montagnola Senese. L'appartamento situato al primo piano può ospitare comodamente 4 persone (2+2 bambini) e comprende: - ampio soggiorno con tv, divano e 2 letti singoli - cucina abitabile con forno - camera matrimoniale - bagno con doccia A disposizione degli ospiti piscina panoramica, solarium e terrazza con vista mozzafiato, dotata di forno a legna e barbecue.

Guest favorite
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.
Vacation home in Poggibonsi
4.94 out of 5 average rating, 193 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 favorite
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.
Vacation home in Badia a Passignano
5 out of 5 average rating, 118 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

Top guest favorite
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.
Vacation home in San Gimignano
4.98 out of 5 average rating, 151 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 favorite
Vacation home in Reggello
4.89 out of 5 average rating, 193 reviews

Barrel Suite Tuscany • Hot Tub • Vineyard View

Sleep inside a wine barrel in Tuscany — one of the largest in the world (3.5 m × 8 m) — nestled in an olive grove in Reggello, with panoramic views over the hills and vineyard. Private bathroom, kitchenette, veranda, private courtyard and exclusive hot tub: everything for a total escape from the world. 40 min from Florence, with Siena, Arezzo, The Mall Luxury Outlet and Vallombrosa all within easy reach. Free private parking included.

Top guest favorite
An outdoor seating area features a small table surrounded by two chairs, adorned with a light breakfast setup. The stone facade of the house is complemented by climbing vines and a bright flower arrangement, inviting guests to enjoy the fresh air.
Vacation home in Monticchiello
4.97 out of 5 average rating, 128 reviews

In Tuscany Rooms

**Your Dream Retreat in the Heart of Val d'Orcia** Welcome to In Toscana Camere, a charming holiday home located in the historic center of Monticchiello, a Tuscan village full of charm and authenticity. Surrounded by stone walls and enhanced by modern, comfortable interiors, this home offers the perfect balance between tradition and contemporary style. Wake up every morning to a breathtaking view of the stunning Val d'Orcia.

Top guest favorite
A stone pathway leads up to the entrance, flanked by a lush wisteria in bloom, cascading purple flowers enhancing the garden's vibrant greenery. A bench offers a spot to relax and enjoy the peaceful surroundings.
Vacation home in Vaglia
4.93 out of 5 average rating, 107 reviews

THE WINE CELLAR OF THE WISTERIA

The apartment is an annex of the main house – originally the winery of the nearby 19-century villa –composed of sitting room, kitchen, double bedroom with attached bathroom. In the living area there is a French-size sofa bed, only suitable for family or close friends (no independent access to the bathroom). Uncovered private parking. About 300 mt of dirt road from the main road. Tourist tax: 1,5 Euros per person per night.

Guest favorite
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.
Vacation home in Peccioli
4.89 out of 5 average rating, 240 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.

Top guest favorite
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.
Vacation home in Monteroni d'Arbia
4.93 out of 5 average rating, 101 reviews

White lily with a view of Siena

Caggiolo is a completely renovated farm consisting of several apartments, with a panoramic view of Siena. Located 1 km from 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).

Guest favorite
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.
Vacation home in Greve in Chianti
4.91 out of 5 average rating, 124 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.

Popular amenities for San Gimignano vacation home rentals

When is the best time to visit San Gimignano?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceﺩ.ﺇ 408ﺩ.ﺇ 411ﺩ.ﺇ 595ﺩ.ﺇ 533ﺩ.ﺇ 488ﺩ.ﺇ 555ﺩ.ﺇ 599ﺩ.ﺇ 650ﺩ.ﺇ 646ﺩ.ﺇ 518ﺩ.ﺇ 400ﺩ.ﺇ 650
Avg. temp7°C8°C11°C14°C18°C23°C25°C25°C21°C16°C11°C7°C

Destinations to explore

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  3. Tuscany
  4. Siena
  5. San Gimignano
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