
Vacation rentals in San Gimignano
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Top-rated vacation rentals in San Gimignano
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Il Sogno Toscano-moderno in centro a San Gimignano
Il Sogno Toscano, appartamento esclusivo nel centro storico di San Gimignano! Questo appartamento di 100 m²,situato a pochi passi dalle celebri torri medievali, è la base ideale per esplorare il borgo patrimonio UNESCO. L’appartamento dispone di ampi spazi luminosi, una cucina completamente attrezzata, soggiorno con vista panoramica sui colli toscani, due camere da letto eleganti e due bagni spaziosi. Godetevi una vista spettacolare e rilassatevi al tramonto con un buon bicchiere di vino locale.

Casa Irene
Casa Irene è un delizioso appartamento in stile Toscano, situato al secondo ed ultimo piano di una palazzina a soli 5 minuti a piedi dal centro,50 mt per porta San Matteo ed altri 50 mt per la via Francigena. Data la posizione defilata si raggiunge facilmente in auto per parcheggiare nell'immediato parcheggio libero. L'appartamento dotato di wifi ed aria condizionata si suddivide in sala/cucina openspace,camera e bagno con doccia ed un terrazzo abitabile con affacci sulle mura di San Gimignano

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.Possibility of parking in a private box for a fee at a cost of € 9.00 x day.

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.

Podere Vergianoni immerso nelChianti con piscina
Podere Vergianoni è un antica e autentica casa colonica risalente al 1600 situata nelle splendide colline del Chianti in Toscana . L'appartamento è arredato in perfetto stile tradizionale locale dell'antica Toscana : antiche travi in legno, pavimenti in cotto e arredamenti unici. Nel grande cortile esterno troverete a vostra disposizione una grande piscina con terrazza panoramica che si affaccia su una valle con vista mozzafiato su vigneti e oliveti dove godersi tramonti spettacolari.

casa del giardino
"Casa del giardino" ......un oasi in fiore tra le mura medievali.. I proprietari Mario e Donella , vorrebbero offrirvi una vacanza irripetibile a San Gimignano. Potrete godere del meraviglioso giardino, straordinaria oasi di pace e silenzio, nel centro città, ad uso esclusivo di chi affitta l'appartamento. Così, leggere un libro, rilassarsi al sole, sorseggiare un ottimo calice di Chianti o fare colazione immersi nel verde e tra i fiori di questo giardino sarà un'esperienza memorabile!

Casa Maurino
"Casa Maurino”, nel centro storico di San Gimignano, è un delizioso appartamento incastonato nelle antiche mura di cinta della città. Luogo ideale in cui trascorrere brevi soggiorni, immergendosi nella suggestiva atmosfera del borgo medioevale. Situato in posizione tranquilla e silenziosa con terrazzo panoramico sulle colline toscane per concedersi romantici momenti di relax. Ingresso indipendente da caratteristica scalinata in pietra, terrazzo panoramico. Adatto per coppie.

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.

Cozy Apt overlooking the Duomo, San Gimignano
Super central apartment located right in the main Piazza of San Gimignano overlooking the Duomo. Great location in the vibrant heart of the town with all services at your doorstep: chemist, cafés, restaurants, groceries, museums, tourist information office.. Walking out through Porta San Giovanni you'll find the Coop supermarket and the bus stop to Poggibonsi railway station (12km away). Car parks are also located outside the city walls, just a few minutes' walk away.

Old hayloft on the Chianti hills
Agriturismo Il Colle is located on one of the Chianti hills. The property has been completely renovated, overlooking the Chianti valleys and enjoying splendid views of the surrounding hills and the city of Florence. The apartment is completely independent, on two internally connected floors, and features a private garden lined with centuries-old oaks and Tuscan cypresses. The restoration maintained the original Tuscan architectural style of rural barns.

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

Countryside Cottage With View - Le Rondini apt
The cottage is part of a charming traditional Tuscan farmhouse, built in stone and situated in one of the most beautiful areas of Tuscany.A lovely garden surrounds the house and has magnificent views of the medieval town with its famous towers.
Popular amenities for San Gimignano vacation rentals
San Gimignano house rentals

StageROOM03 - Idyllic Chianti cottage near Siena

Infinity pool in Chianti
Gorgeous Villa with Postcard Views in Historical Florence

Giovanna apartment 100m from San Gimignano

House with a breathless view in Tuscany

Casa Al Poggio & Chianti view

Tuscany house: near San Gimignano, Siena, Firenze

Casa Dante
Other great vacation rentals in San Gimignano

Apartament Tortoli San Gimignano

★ Romantic apartment & stunning view of Tuscany ★

L'Attico dei Sogni

Apartment La Roccaia

Casale Esclusivo Piscina & vista su San Gimignano

The Verde apartment-Farmhouse San Gimignano

S. Gimignano charming & traditional - Apt. Garden

Casa Iris (with jacuzzi) - Close to San Gimignano
When is the best time to visit San Gimignano?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$24,269 GYD | G$21,968 GYD | G$26,152 GYD | G$28,453 GYD | G$28,453 GYD | G$29,918 GYD | G$32,847 GYD | G$32,847 GYD | G$30,546 GYD | G$29,081 GYD | G$28,663 GYD | G$30,964 GYD |
| Avg. temp | 7°C | 8°C | 11°C | 14°C | 18°C | 23°C | 25°C | 25°C | 21°C | 16°C | 11°C | 7°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 920 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 35,670 verified reviews to help you choose

Family-friendly vacation rentals
500 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 410 rentals that welcome pets

Vacation rentals with a pool
510 properties feature pools

Rentals with dedicated workspaces
310 properties have a dedicated workspace

Wi-Fi availability
880 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!
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- Santa Maria Novella
- Cathedral of Santa Maria del Fiore
- Strozzi Palace
- Mercato Centrale
- Santa Maria Novella
- Ponte Vecchio
- Great Synagogue of Florence
- Basilica Di San Miniato A Monte
- Marina di Cecina
- Porta Elisa
- Del Chianti
- Basilica of Santa Maria Novella
- Pisa Centrale Railway Station
- Spiagge Bianche
- Eremo Di Camaldoli
- Cala Violina
- Piazza del Duomo (Pisa)
- Piazza della Signoria
- Uffizi Gallery
- Fortezza da Basso
- Parco Nazionale delle Foreste Casentinesi, Monte Falterona e Campigna
- Piazzale Michelangelo
- Piazza della Repubblica
- Parco delle Cascine
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