Discover a selection of 3,000 vacation rentals in San Gimignano, IT that are perfect for your trip. Whether you’re traveling with friends, family, or even pets, Vrbo vacation homes have the best amenities for hanging out with the people that matter most, including swimming pools and WiFi. Prices start at $73 per night, and houses and villas are popular options for a stay in San Gimignano. Either way, you'll find a rental for everyone's needs.
Top rated rentals — San Gimignano
Destination guide

San Gimignano: the perfect Tuscan town

If there was a model Tuscan town, the one you see on the front cover of guidebooks, it would be San Gimignano. The town, along with its pretty skyline of 13th-century towers, is perched on top of a Tuscan hill surrounded by the old city walls and sweeping cypress trees. When you come to stay in a San Gimignano vacation rental, you'll quickly realize why it was designated a UNESCO World Heritage Site. You'll feel like you've stepped back in time when you wander along the narrow streets, which open onto a sunny piazza flanked by gorgeous Medieval buildings.

Things to do

San Gimignano is bursting with cultural attractions

When you pop out of your San Gimignano vacation rental, you'll find a town which is easily explored by foot and, though small, it's bursting at the seams with things to see. You could start your day with a cappuccino and pastry in the sunny piazza, before discovering the ancient artwork inside the Palazzo Comunale. Afterwards, you'll be puffed out when you climb the Torre Grossa, but the views from the top are worth the effort. In the afternoon, grab yourself that obligatory, and delicious, Italian gelato and then dive into the rather grizzly but fascinating Medieval Torture Museum.


The rolling hills of San Gimignano await

Italy has always been about good food, good wine and good company, and Tuscany is no exception. Staying in a San Gimignano vacation rental puts you in the heart of these rolling hills. Whether you go by car or by bicycle, it's unthinkable not to drop into one of the Chianti wineries, to sample some of the country's finest reds. To learn the art of Tuscan cuisine, you should consider taking the family to one of the many cooking classes on offer, where you can learn about Italian produce and try your hand at cooking fresh pasta dishes.


Spring and fall are San Gimignano's sweet spot

While the summer months see the most glorious weather, with little rain and endlessly bright skies, it also attracts the biggest crowds, who book up the San Gimignano vacation rentals. If you don't mind a slightly cooler temperature, arguably better if you plan to hike or bike, try to nab a rental between April and May or September and October, when the summer crowds are back at home and the town feels decidedly more quiet and local. For rock-bottom prices, you could visit in winter, when you'll likely be the only foreigner in town but expect cold and rainy weather.

Natural features

San Gimignano lies close to nature

While you're staying in a San Gimignano vacation rental, it would be a shame to miss the 700-hectre Castelvecchio, a forest-covered nature reserve just a short drive away. This wild land holds your best chances of spotting wildlife in Tuscany. If you take a hike through the park, you'll likely encounter several critters including deer, red foxes and the occasional wild boar which rustles around on the forest floor, not to mention the scampering hares and porcupines. If you look up to the treetops and towards the marshes, there's more to see, including tawny owls, pheasants and beautiful herons.

How to get there

Traveling to and around San Gimignano

The nearest airport is in Florence Airport, Peretola (FLR), located 24.4 mi (39.3 km) from the city center.

What are the top vacation rentals in or near San Gimignano?

Whatever vacation experience you're seeking, you'll find a rental property in or around San Gimignano that's perfect for you. Why not try these on for size?:

  • "Farmhouse In The Heart Of The Real Chiantishire" is a hit with guests. Around 12 miles from San Gimignano, it has 2 bedrooms and lots of handy amenities, including a garden and a kitchen.
  • Alternatively, make your home away from home at "La Casina Toscana - Near Center". Located around 45 miles from the heart of San Gimignano, it has 3 bedrooms and comes with an elevator and a kitchenette.

For even more great options, use the search bar at the top of the page to find the perfect San Gimignano vacation rental for you.

What are the top-rated vacation rentals for weekend getaways in or near San Gimignano?

Your Monday to Friday will be easier to face if you've got something epic lined up for the weekend. Give yourself something fun to look forward to by arranging a stay at one of these top weekend getaways in or near San Gimignano:

  • Around 0.1 miles to the southeast of San Gimignano, "Apartment In San Gimignano With 3 Bedrooms" has everything you need for a fun weekend escape, including a kitchen and a fridge. When you're ready to explore, there are plenty of outdoor attractions to visit like Museo del Tessuto and Parco del Neto.
  • Another terrific option is "Apartment In San Gimignano With 4 Bedrooms", around 0.1 miles southeast of San Gimignano. When you're not cozying up in your rental making the most of air conditioning and coffee and tea making facilities, be sure to visit Castelvecchio Natural Reserve and Sentierelsa Trail.

Can I find studio apartments for rent in and around San Gimignano?

Generally compact, inexpensive and conveniently located, it's easy to be impressed by a studio apartment. Escape to one of these options and experience San Gimignano up close:

  • Make "Apartment In San Gimignano With 1 Bedrooms" your home for a week or more. This appealing vacation rental features amenities including WiFi and a TV.
  • Alternatively, get into vacation mode at "Bright Flat With Views Of The Duomo", which comes with conveniences such as a bicycle and WiFi.

With the moolah you save on your studio apartment, you'll be able to explore even more of San Gimignano. Cultural sights like Chianti Sculpture Park and Podesta's Palace will help you get a better feel for the character of this destination.

Can I find short term rentals in or near San Gimignano?

Short-term rentals are easy to find in and around San Gimignano. Chill out for a night or two in a condo, a resort-style apartment or a large home. Whatever sort of vacation rental you're looking for, you'll have plenty to select from with Vrbo. Here are some of our favorite options:

  • If you'd love to be near the action, "Apartment In San Gimignano With 4 Bedrooms" is calling your name. It's within reach of the center of San Gimignano and a good base to explore attractions like Monte Oliveto Maggiore Abbey and La Porta Gallery.
  • "Country House With Panoramic View Over San Gimignano Hills" is another fabulous option. Don't forget to add Museum of Sacred Art in Val d’Arbia and Museo della Mezzadria to your must-do list when you're ready to sightsee.

What are the best romantic weekend getaways in or near San Gimignano?

Nothing says "I love you" quite like a romantic weekend together. If you want to spend a couple of relaxing evenings away with your partner, we've got some romantic getaways in and around San Gimignano that will get your heart racing:

  • Put on some soft music and chill together at "Farmhouse In The Heart Of The Real Chiantishire". Around 12 miles from San Gimignano, this property has all you need for a couple's weekend away, including beauty services and winery tours.
  • Alternatively, spend your break enjoying each other's company at "Splendido Appartamento Con Giardino Privato", around 0.1 miles from San Gimignano. A fireplace and air conditioning will help set the scene for romance.

What are the best large group vacation rentals in or near San Gimignano?

Share your trip and double the fun. Whether you're organizing an action-packed getaway with your best friends or a big family get-together, there's no shortage of large group vacation rentals in and around San Gimignano:

  • A wealth of amenities including a garden and off-street parking options make "Historical Palace Buonaccorsi San Gimignano" a group favorite. This generous retreat has 4 bedrooms and sleeps up to 13 people. From the heart of San Gimignano, it's around 0.1 miles away to the northwest.
  • Nothing takes priority over being together with loved ones, and "Villa In A Panoramic Position In San Gimignano" is the ideal place to do that. Located around 1 mile to the southeast of San Gimignano, as many as 12 guests can stay in this vacation rental which has 5 bedrooms. A fireplace and a swimming pool are among the various amenities here.

What are the best houses for rent with a pool in or near San Gimignano?

Of all the conveniences a vacation rental can offer, a pool is hands down the most fun. Browse these houses for rent with a pool in or near San Gimignano and spend your time splashing about. Just remember to bring your unicorn floatie:

  • Pack your swimming gear and book a few days at "Country House With Panoramic View Over San Gimignano Hills". There are also lots of other appealing amenities here, including a balcony and a toaster.
  • Spend leisurely days swimming or just unwinding beside the water at "San Gimignano: Ancient House Renovated In The Heart Of San Gimignano". This vacation rental is another favorite and offers a microwave oven, coffee and tea making facilities and more.

San Gimignano has a humid subtropical climate, with average summertime temperatures hovering between 60 ºF and 85 ºF. But you don't have to wait until summer to visit. Check out the search bar at the top of the page and adjust the filters to find the ideal San Gimignano vacation rental and plan your escape for whatever season you like.

What are the best large family vacation rentals in or near San Gimignano?

Whether your ideal escape is up in the hills or on the beach, you'll enjoy it even more if you share it with family and friends. Check out these large family vacation rentals in or near San Gimignano and bring the entire crew along:

  • Around 0.1 miles to the southeast of San Gimignano, "Apartment In San Gimignano With 4 Bedrooms" has 4 bedrooms and can sleep up to 8 guests. It comes with a host of amenities, including coffee and tea making facilities and a fridge.
  • Another top choice is "Country House With Panoramic View Over San Gimignano Hills". This property is 0.1 miles northwest of San Gimignano and features a kitchenette, a microwave oven and more. With 5 bedrooms accommodating up to 11 people, there's no need to leave anyone off your invitation list.

If you'd like to do some sightseeing, there are lots of family-friendly attractions nearby to put on your to-do list. Palazzo Pubblico, Palazzo Piccolomini and Monteriggioni Castle are fine places to start.

What are the best large houses to rent with indoor pools in or near San Gimignano?

Nothing says "glamorous getaway" like having an indoor pool. Pack your swimwear and enjoy a dip in the privacy of one of these roomy vacation homes in or near San Gimignano:

  • With 5 bedrooms sleeping up to 10 guests, "Villa I Cipressini Tuscany Private Luxury Heated Pool Spa Gym Pienza Siena" is the perfect place to enjoy some downtime with close friends. Make use of this retreat's many amenities, such as a kitchen and a swimming pool.
  • Besides its swish indoor pool, "Private Villa With Sauna, A/c, Wifi" features a fireplace and a kitchen. It has 13 bedrooms that can accommodate up to 26 guests, so you can bring all your buddies along.

If you're after more options, use the search bar at the top of the page and adjust the filters to find the San Gimignano vacation rental that's perfect for your needs.

Can I find two-bedroom vacation rentals in or near San Gimignano?

Absolutely. From swish apartments to cute cottages, Vrbo offers a selection of great getaways. Traveling families will like these two-bedroom properties in or near San Gimignano:

  • First on the list — "Splendido Appartamento Con Giardino Privato". This two-bedroom stay provides handy amenities like a kitchen and a fireplace. You can easily visit San Gimignano's awesome attractions from this homely base.
  • Another popular option is "Zafferano Panoramic Terrace 4 Pax". With convenient amenities such as a kitchen and a fireplace, it'll be plain sailing making yourselves at home here. Pick your favorite room, unpack your suitcases and let the good times begin!