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Vacation rentals in San Gimignano

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Top-rated vacation rentals in San Gimignano

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Top guest favorite
An aerial view captures Podere Vergianoni nestled in the Chianti hills, surrounded by lush vineyards. The property features a clear blue pool, shaded terraces, and carefully landscaped gardens. Rolling hills and rows of grapevines create a serene backdrop, highlighting the natural beauty of the Tuscan countryside.
Condo in Noce
5 out of 5 average rating, 335 reviews

Podere Vergianoni immerso nelChianti con piscina

Podere Vergianoni is an ancient and authentic farmhouse dating back to the 17th century located in the beautiful hills of Chianti in Tuscany. The apartment is impeccably furnished in the traditional local style of old Tuscany: ancient wooden beams, terracotta floors, and unique furniture. In the large outdoor courtyard, you'll find a large swimming pool on a panoramic terrace at your disposal, overlooking the valley with breathtaking views of vineyards and olive groves, where you can enjoy spectacular sunsets.

Top guest favorite
A bright living area showcases large glass doors leading to an outdoor terrace with scenic views. A colorful area rug lies on the wooden floor, complemented by a modern sofa and decorative artwork on the wall. Natural light fills the space, enhancing its openness.
Home in Vaiano
5 out of 5 average rating, 269 reviews

The MOONLIT & SUNNY COTTAGE near Florence

IL COLLE DI FALTUGNANO: immersed in an olive grove on a Tuscan hills and with an amazing view of the valley, the stone cottage has been remarkably recovered a few months ago, a caravanserai a few century ago. In a strategic position close to Florence and Mugello is a good base for exploring Tuscany and be independent at the same time with supermarkets and restaurants just a few minutes away. Close to a farmhouse you can buy fresh local organic ingredients such as bio vegetables, eggs or cheese.

Top guest favorite
The image showcases a view of the Torre del Diavolo framed by lush greenery. Two bottles of wine are positioned in the foreground, enhancing the peaceful garden setting. Historic buildings with textured stone facades are visible, complementing the charming medieval atmosphere.
Apartment in San Gimignano
4.98 out of 5 average rating, 172 reviews

Apartment at ground floor with garden

A refined and very central setting, between Piazza della Cisterna and Piazza del Duomo. The house has the rare value of combining a comfortable ground floor, with independent entrance, to a stunning view of the famous Devil's tower.The exclusive garden, equipped to dine outdoors, read or stay between flowers and towers, is an extraordinary oasis of peace and silence, just around the corner of the two lively main squares.Parking available in a private garage at a cost of €9.00 per day,6 min walk.

Top guest favorite
A stone structure with a tiled roof is framed by greenery, surrounded by rolling hills. A spacious outdoor area features a wooden table, inviting relaxation. Large trees and thriving shrubs enhance the tranquil setting, with a backdrop of a serene sunset illuminating the landscape.
Home in San Casciano In Val di Pesa
4.98 out of 5 average rating, 234 reviews

The Chianti Classico Sunset

Se cercate una location idilliaca nel cuore del Chianti classico, immersi nei vigneti e oliveti delle splendide colline toscane, nel podere di una Villa storica del ‘500, allora venite nel nostro fienile!! Ha una posizione dominante con una vista strepitosa, dove è possibile godersi tramonti mozzafiato. La totale indipendenza della casa, l'accogliente giardino, il grande loggiato permettono di trascorrere soggiorni in totale tranquillità. Le nostre recensioni sono la vostra migliore garanzia.

Top guest favorite
A medieval stone tower stands tall against a clear blue sky, showcasing its historic architecture. The narrow road lined with greenery leads to the entrance, with the texture of the stonework and windows highlighted, inviting guests to explore its unique charm.
Tower in San Quirico d'Orcia
5 out of 5 average rating, 110 reviews

Luxurious Medieval Tower & Private Concierge

It’s rare to find a place that’s not only romantic but also historic & truly one of a kind. La Torretta is part of Toscana a Due—a medieval tower with a huge garden & olive trees, right in the heart of San Quirico, overlooking the Val d’Orcia. The 1000-year-old building has been redesigned as a blend of heritage & antique luxury. With our unique tailored concierge service and a warm welcome into our family’s life, we share our traditions, history, and Tuscany’s hidden treasures with you.

Top guest favorite
An aerial view of the property reveals a charming red house surrounded by lush greenery. Tall cypress trees and vibrant bushes create a tranquil landscape, while an expansive lawn features relaxing loungers, inviting guests to enjoy the serene atmosphere of the Tuscan countryside.
Home in Gambassi Terme
5 out of 5 average rating, 218 reviews

Il Fienile, Luxury Apartment in the Tuscan Hills

‘Il Fienile’ is in an enchanting position immersed in the beauty of the Tuscan hills, with a breathtaking view of the surrounding countryside. It is located in the hamlet of Catignano in Gambassi Terme, just a few kilometres from San Gimignano. The house sits in a protected oasis surrounded by a beautiful private park with olive trees, a pond, pine trees and woods, where you can walk, relax and enjoy the pleasures of unspoilt nature. A unique experience entirely to be enjoyed.

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, 152 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.

Top guest favorite
Farm stay in Simignano
4.92 out of 5 average rating, 269 reviews

Casa al Gianni - Hut

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!

Top guest favorite
A rustic stone staircase leads to a wooden entrance door framed by colorful potted plants. The door, featuring a decorative handle, is set against a textured stone wall, with a lantern placed on the side for soft lighting.
Home in San Gimignano
4.97 out of 5 average rating, 119 reviews

Casa Maurino

"Casa Maurino", in the historic center of San Gimignano, is a delightful apartment nestled in the ancient city walls. Ideal place to spend short stays, immersing yourself in the evocative atmosphere of the medieval village. Located in a quiet and peaceful position with a panoramic terrace overlooking the Tuscan hills to indulge in romantic moments of relaxation. Independent entrance from a characteristic stone staircase, panoramic terrace. Suitable for couples.

Top guest favorite
Apartment in San Gimignano
5 out of 5 average rating, 150 reviews

The Tuscan Dream-modern in the center of San Gimignano

The Tuscan Dream, an exclusive apartment in the historic center of San Gimignano! This 100 m² apartment, located a few steps from the famous medieval towers, is the ideal base for exploring the UNESCO heritage village. The apartment has large bright spaces, a fully equipped kitchen, a living room with panoramic views of the Tuscan hills, two elegant bedrooms and two spacious bathrooms. Enjoy a spectacular view and relax at sunset with a good glass of local wine.

Top guest favorite
Home in San Gimignano
4.99 out of 5 average rating, 209 reviews

Romantic Garden in Historic San Gimignano

Enjoy a romantic stay in the heart of San Gimignano, inside the medieval walls.The apt features a private garden, a rare and peaceful corner where you can have breakfast, relax after exploring the town or enjoy a glass of wine in the evening. Perfect for couples looking for charm, history and quiet retreat in one of Tuscany's most beautiful villages.

Top guest favorite
The aerial view captures the historic structure nestled among rolling green hills, framed by tall trees. The stone walls reflect medieval architecture, while a terrace offers an inviting space below. The surrounding landscape showcases farms and cypress trees against a clear blue sky.
Home in Monticchiello
4.98 out of 5 average rating, 215 reviews

"La Lambarda" tower Suite

In Val d'Orcia there is a small medieval village called Monticchiello, surrounded by walls and protected by four towers; one of these is the "La Lambarda", which stands at the highest point of the country and enjoys a panoramic view across the valley.

Popular amenities for San Gimignano vacation rentals

When is the best time to visit San Gimignano?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. priceG$30,542 GYDG$29,496 GYDG$28,659 GYDG$28,450 GYDG$28,450 GYDG$29,915 GYDG$32,843 GYDG$32,843 GYDG$30,542 GYDG$29,078 GYDG$28,659 GYDG$30,961 GYD
Avg. temp7°C8°C11°C14°C18°C23°C25°C25°C21°C16°C11°C7°C

Frequently Asked Questions

  • What are the best places to stay in San Gimignano?

    San Gimignano has unique stays near its medieval center, countryside villas surrounded by vineyards, and cozy guesthouses within historic stone buildings. Consider choosing a location near Piazza della Cisterna or around the town walls for charming local atmosphere and easy access to main sites.

  • What are the best things to do in San Gimignano with kids?

    Families can explore the medieval towers, climb Torre Grossa for panoramic views, or discover local history at the Museo Civico. Kids often enjoy gelato shops around Piazza della Cisterna and shaded strolls along quiet lanes.

  • What are some of the best things to do in San Gimignano?

    Explore San Gimignano’s medieval towers, tour the Duomo di San Gimignano, and discover art in the Museo Civico. The town also has artisan shops, gelato tasting, and scenic walks around its ancient walls.

  • How is the weather in San Gimignano?

    San Gimignano has mild winters with averages from 36–52°F (2–11°C) and warmer, drier summers that typically reach 65–90°F (18–32°C). Rain is more frequent in autumn and early spring, so packing layers and a light rain jacket is helpful.

  • When is the best time to visit San Gimignano?

    Late spring and early autumn are often recommended for mild temperatures, blooming landscapes, and local events around the medieval town. Summer draws visitors for longer daylight hours and lively piazzas, though streets can become busier during the peak of the season.

  • What are the best places to visit in San Gimignano?

    Popular places include Piazza della Cisterna for local activity, the Duomo di San Gimignano for frescoes, and Torre Grossa for views over terracotta rooftops. Historic lane ways and the Rocca of Montestaffoli are also often suggested.

  • What are some hiking trails in San Gimignano?

    San Gimignano has scenic trails winding through olive groves, cypress-lined paths, and gentle hills around the town. Many hikers enjoy the Via Francigena section, which is known for its countryside panoramas and quiet rural lanes.

  • What are some family activities we can do in San Gimignano?

    Families can participate in hands-on art workshops, sample gelato, or join guided medieval town walks. The Rocca of Montestaffoli has open spaces for kids to explore and picnic with panoramic views.

  • What are some of the best day trip ideas from San Gimignano?

    Day trips often include exploring nearby Tuscan towns, visiting local vineyards for wine and olive oil tastings, or discovering regional markets. The surrounding countryside is known for hilltop villages, medieval castles, and scenic walking trails.

  • Are there any pet friendly accommodations available in San Gimignano?

    Many stays in San Gimignano welcome pets, especially in countryside villas or apartments near the historic center. Look for listings mentioning gardens or nearby trails for convenient walks with your pet.

  • What are some local tips for visiting San Gimignano?

    Visit popular piazzas early or later in the day for a quieter experience, and consider sampling locally grown saffron and white wine. Comfortable shoes help with cobblestone streets, and evenings can be cooler even in summer.

  • What is San Gimignano known for?

    San Gimignano is known for its well-preserved medieval towers, Vernaccia white wine, and local saffron traditions. The skyline and historic center are recognized for their UNESCO World Heritage status.

  • What are the best hidden gems to explore in San Gimignano?

    Wander lesser-known lanes around the town walls, explore artisan workshops for ceramics or woodwork, and relax in the garden of the Rocca of Montestaffoli. Some visitors enjoy small frescoed chapels tucked away from the main sights.

  • What are the best foods to try in San Gimignano?

    Frequently suggested specialties include pappardelle al cinghiale (wild boar pasta), local cheeses, and dishes featuring saffron. Sampling the town’s renowned gelato and Vernaccia di San Gimignano white wine is also popular.

  • What should I bring for a trip to San Gimignano?

    Bring comfortable shoes for cobbled lanes and a light rain jacket for unpredictable spring or autumn showers. A reusable water bottle and a small daypack are helpful while exploring historical sites and local markets.

  • What is the nightlife in San Gimignano like?

    San Gimignano’s nightlife has relaxed wine bars, local cafés, and outdoor seating in central piazzas. Evenings are often spent tasting regional wines or enjoying casual music events in intimate venues around the historic core.

  • What are the most popular events or festivals in San Gimignano?

    San Gimignano hosts medieval festivals in late spring and cultural celebrations featuring traditional music and food. Local events dedicated to Vernaccia wine and saffron are often scheduled throughout the year, drawing visitors to plazas and historic venues.

  • Are there family friendly vacation rentals in San Gimignano?

    Many homes and apartments in San Gimignano are family friendly, often with kitchens and access to outdoor spaces. Accommodations around the town’s center or quieter surrounding areas help families enjoy the local atmosphere together.

Quick stats about vacation rentals in San Gimignano

  • Total vacation rentals

    Explore 950 vacation rentals in San Gimignano

  • Nightly prices starting at

    San Gimignano vacation rentals start at G$6,276 GYD per night before taxes and fees

  • Verified guest reviews

    Over 36,280 verified reviews to help you choose

  • Family-friendly vacation rentals

    510 properties offer extra space & kid-friendly amenities

  • Pet-friendly vacation rentals

    Find 460 rentals that welcome pets

  • Vacation rentals with a pool

    520 properties feature pools

  • Rentals with dedicated workspaces

    350 properties have a dedicated workspace

  • Wi-Fi availability

    910 of San Gimignano vacation rentals include wi-fi access

  • Popular amenities for guests

    Guests love Gym, BBQ grill, and Laptop-friendly workspace across San Gimignano rentals

  • 4.8 Average rating

    San Gimignano stays are highly rated by guests—averaging 4.8 out of 5!

Destinations to explore

  1. Airbnb
  2. Italy
  3. Tuscany
  4. Siena
  5. San Gimignano