Villa rentals near San Gimignano

San Gimignano is so perfect; it can seem like a medieval stage set (it’s real, we promise). As a movie backdrop it has been a favourite of Franco Zeffirelli, among many other directors. Parts of “Tea with Mussolini” we’re filmed here. Guarded by a ring of fortified walls, Tuscany’s “Medieval Manhattan” is a hill-town of stone towers, rustic medieval palaces and narrow, winding lanes.

Our San Gimignano villas are scattered amid some of Tuscany’s prettiest countryside — the hills around San Gimignano. They include luxury converted stone farmhouses, distinguished villas ideal for a large gathering, and smaller properties just right for a family vacation in Tuscany. All these villas near San Gimignano have air-conditioned bedrooms — which you’ll appreciate in the hot Tuscan summer. Many have air-conditioning throughout.

Every Tuscany Now & More villa has a private swimming pool, free use of our concierge service, for pre-trip arrangements and an emergency number available 24/7 while you are in-destination. Your concierge can arrange a private chef, daily maid service, or shopping delivered to your villa, and memorable experiences like Tuscan cookery classes in your holiday rental’s kitchen.

We can arrange unforgettable experiences from your San Gimignano villa, like a Tuscan cookery class in your holiday rental kitchen or a guided cycle ride through the San Gimignano vineyards that ends up at a famous gelateria in the town square. (Why not both?)

At Tuscany Now & More we take pride in our service. For 30 years we have been matching every guest to their ideal villa in Italy. Someone from our small team visits or stays in every San Gimignano villa we list. We know the area intimately. This is why we keep our portfolio small — and probably why the world’s leading luxury travel magazine says we’re Tuscany’s best villa company.

To also read what real travellers think of our service, and the experience of staying in a Tuscany Now & More luxury villa, check out our verified reviews.

About San Gimignano

Twenty-five miles north-west of Siena, this is one of Italy’s most spectacular small towns, set amid the photogenic scenery of the central Tuscan hills. San Gimignano is famed for its standing medieval towers, the painted interior of its medieval Collegiate Church, and a fine white wine made from grapes picked on the surrounding hills: Vernaccia di San Gimignano.

An immaculately preserved Gothic centre is a magnet for visitors, certainly, but in its backstreets and frescoed churches, you can easily find a corner to yourself.

Staying nearby in a San Gimignano villa gives you the chance to see San Gimignano at its best: early in the morning and at dusk. Without the day-trippers, the place takes on an entirely different atmosphere: secretive, silent, even a little spooky. Standing alone, in Piazza della Cisterna, the town suddenly feels every one of its 800 or so years of age.

What to Do in San Gimignano

Twin central squares — Piazza della Cisterna and Piazza del Duomo — are the heart of the town.

Dominating the latter is the Collegiata (a Collegiate Church, basically a cathedral without a bishop’s seat). Its interior walls are covered in fresco, a technique used in medieval times to apply fresh paint to wet plaster.

The earliest artworks here date to medieval Tuscany. They recount narratives from the Old and New Testaments, including a lurid “Last Judgement” by Sienese painter Taddeo di Bartolo above the main door. It’s like a scene from “The Walking Dead”.

Also inside, the Chapel of Santa Fina is a Renaissance collaboration between sculptor Benedetto di Maiano and architect Giuliano da Maiano (both from Fiesole) and Florentine Renaissance painter, Domenico Ghirlandaio.

Ghirlandaio’s frescoes tell the legend of San Gimignano’s local saint, Fina. As she lies dying, flowers bloom spontaneously from a plank (her makeshift bed). On the left-hand wall, angels hover, ringing tower bells in her memory. A few San Gim sights and shops shut each March 12th, to remember their little 13th-century saint.

Nearby, the painting collection at the Museo Civico testifies to the artists who passed through San Gimignano in its heyday. The showcase is a “Maestà” (Virgin Mary surrounded by saints) painted in 1317 by Lippo Memmi.

After you have seen the art, you can climb the 54m (177-ft.) medieval Torre Grossa. Views stretch for miles over hills smothered in vines and olive groves.

Moving way along the historical timeline, San Gimignano has a growing reputation for contemporary art. The Galleria Continua is a warren-like space that often displays works by global names like Antony Gormley and Ai Weiwei

There are several excellent rural walks around San Gimignano, through the vines and olive groves that approach the town on all sides, or among the wildflowers in spring and early summer.

For more on what to see and do in San Gimignano, see our San Gimignano travel guide.

Food and Drink in San Gimignano

The longest queue in San Gimignano is not for a famous sight or museum, but for the sweet-toothed kitchen artisans at Gelateria Dondoli. This ice-cream parlour is more often known as Gelateria “di Piazza” after its location on San Gim’s prettiest square, Piazza della Cisterna.

Ice-cream flavours range from traditional to weird-and-wonderful, like “Rosemary’s Baby” (raspberry and rosemary), blackberries and lavender, or zabaione con vin santo (custard with the famous Tuscan sweet wine, Vin Santo).

Their signature flavour is crema di Santa Fina, a cream gelato with added saffron. The town has long been a centre for organic saffron farming.

San Gimignano is also the name behind Tuscany’s only dry white DOCG wine, Vernaccia di San Gimignano. This straw-coloured white dates at least to the 1200s.

Inside San Gimignano’s ruined 14th-century castle, the Vernaccia di San Gimignano Wine Experience offers tastings and displays on the wine’s history.

Almost 2,000 acres of terrain around San Gimignano are given over to olive trees. Fruits are farmed in late autumn and pressed to produce a renowned extra-virgin olive oil.

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Showing: 11 villas

Sleeping: 14 - Bedrooms: 7 - Bathrooms: 6

  • Maid included
  • Air Conditioned Bedrooms
  • Internet Connection
  • Private Pool
  • Tennis Court

Spacious hill top villa & guest house with stunning views on the edge of the Chianti ideal for large families. Eight air-con bedrooms. Private swimming pool and tennis court. The kitchen is noteworthy.

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€ 4,610
€ 7,113
$ 6,251
$ 9,644
£ 4,434
£ 6,840

Sleeping: 18 - Bedrooms: 9 - Bathrooms: 6

  • Maid included
  • Air Conditioned Bedrooms
  • Internet Connection
  • Private Pool
  • Tennis Court

Spacious hill top villa & guest house with stunning views on the edge of the Chianti ideal for large families. Eight air-con bedrooms. Private swimming pool and tennis court. The kitchen is noteworthy.

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€ 5,763
€ 8,891
$ 7,813
$ 12,055
£ 5,542
£ 8,550

Sleeping: 10 - Bedrooms: 5 - Bathrooms: 5

  • Maid included
  • Air Conditioned Bedrooms
  • Internet Connection
  • Private Pool

Luxury hill top farmhouse with large saltwater infinity pool, air conditioned bedrooms and en-suite bathrooms near San Gimignano. Modern interiors with stylish shaded seating & dining areas. Cook and cooking lessons available.

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€ 4,500
€ 8,400
$ 6,101
$ 11,389
£ 4,328
£ 8,078

Sleeping: 10 - Bedrooms: 5 - Bathrooms: 5

  • Maid included
  • Air Conditioned Bedrooms
  • Internet Connection
  • Private Pool

Luxury hill top farmhouse with large infinity-edge pool, air conditioned bedrooms and en-suite bathrooms near San Gimignano. Modern interiors with stylish shaded seating & dining areas. Cook & cooking lessons available.

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€ 6,309
€ 10,208
$ 8,554
$ 13,840
£ 6,067
£ 9,817

Sleeping: 10 - Bedrooms: 5 - Bathrooms: 5

  • Maid included
  • Air Conditioned Bedrooms
  • Internet Connection
  • Private Pool
  • Tennis Court

Luxury villa with stunning views overlooking San Gimignano with an oversized private swimming pool and full size tennis court. Air conditioned bedrooms with en suite bathrooms.  

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€ 5,531
€ 7,999
$ 7,499
$ 10,845
£ 5,319
£ 7,692

Sleeping: 10 - Bedrooms: 5 - Bathrooms: 5

  • Maid included
  • Air Conditioned Bedrooms
  • Internet Connection
  • Private Pool
  • Tennis Court

This rental option for Diaspero includes services of a professional chef for breakfast 6 days a week and dinner upon arrival. The cost of food and drinks is not included. Additional meals can be arranged as an extra.

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€ 7,159
€ 9,627
$ 9,706
$ 13,052
£ 6,884
£ 9,258

Sleeping: 10 - Bedrooms: 5 - Bathrooms: 5

  • Maid included
  • Air Conditioned Bedrooms
  • Internet Connection
  • Private Pool
  • Tennis Court

This staffed rental option for Diaspero includes an unlimited supply of DOCG Vernaccia di San Gimignano & the services of a professional chef for breakfast 6 days a week & dinner upon arrival.

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€ 7,446
€ 10,433
$ 10,096
$ 14,145
£ 7,161
£ 10,033

Sleeping: 16 - Bedrooms: 8 - Bathrooms: 9

  • Maid included
  • Fully Air-conditioned villa
  • Internet Connection
  • Private Pool
  • Tennis Court

Rural 18th-century farmhouse & guesthouse with A/C in all rooms 12km from San Gimignano. Classic Tuscan interiors with large bedrooms & en-suite bathrooms. Manicured lawns with panoramic outdoor dining & seating areas. Private pool & all-weather tennis court. Rental option with staff & cook available.

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€ 4,315
€ 7,117
$ 5,850
$ 9,650
£ 4,150
£ 6,844

Sleeping: 18 - Bedrooms: 9 - Bathrooms: 10

  • Maid included
  • Fully Air-conditioned villa
  • Internet Connection
  • Private Pool
  • Tennis Court

Rural 18th-century farmhouse & guesthouse with A/C in all rooms 12km from San Gimignano. Classic Tuscan interiors with large bedrooms & en-suite bathrooms. Manicured lawns with panoramic outdoor dining & seating areas. Private pool & all-weather tennis court. Rental option with staff & cook available.

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€ 4,439
€ 7,396
$ 6,019
$ 10,027
£ 4,269
£ 7,112

Sleeping: 20 - Bedrooms: 10 - Bathrooms: 11

  • Maid included
  • Fully Air-conditioned villa
  • Internet Connection
  • Private Pool
  • Tennis Court

Rural 18th-century farmhouse & guesthouse with A/C in all rooms 12km from San Gimignano. Classic Tuscan interiors with large bedrooms & en-suite bathrooms. Manicured lawns with panoramic outdoor dining & seating areas. Private pool & all-weather tennis court. Rental option with staff & cook available.

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€ 4,722
€ 7,866
$ 6,403
$ 10,664
£ 4,541
£ 7,564

Sleeping: 20 - Bedrooms: 10 - Bathrooms: 11

  • Maid included
  • Fully Air-conditioned villa
  • Internet Connection
  • Private Pool
  • Tennis Court

This rental option for Il Renaccio includes services of a professional chef for dinner 6 days a week. The cost of food & drinks is not included. Rental option with chef & all-inclusive wine available.

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€ 6,927
€ 10,071
$ 9,392
$ 13,654
£ 6,662
£ 9,685

Sleeping: 10 - Bedrooms: 5 - Bathrooms: 4

  • Air Conditioned Bedrooms
  • Internet Connection
  • Private Pool

Luxurious stone farmhouse & guest house with private swimming pool and air-con bedrooms. Near San Gimignano & Florence and close to a stunning 18-hole golf course. Large bedrooms & modern en suite bathrooms. Fantastic kitchen. Air-con bedrooms in the main house only. 

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€ 3,312
€ 6,575
$ 4,490
$ 8,915
£ 3,185
£ 6,323

Sleeping: 12 - Bedrooms: 6 - Bathrooms: 6

  • Air Conditioned Bedrooms
  • Internet Connection
  • Private Pool

Luxurious stone farmhouse & guest house with private swimming pool and air-con bedrooms. Near San Gimignano & Florence and close to a stunning 18-hole golf course. Large bedrooms & modern en suite bathrooms. Fantastic kitchen. Air-con bedrooms in the main house only. 

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€ 3,588
€ 7,099
$ 4,864
$ 9,625
£ 3,450
£ 6,827

Sleeping: 14 - Bedrooms: 7 - Bathrooms: 7

  • Air Conditioned Bedrooms
  • Internet Connection
  • Private Pool

Luxurious stone farmhouse & guest house with private swimming pool and air-con bedrooms. Near San Gimignano & Florence and close to a stunning 18-hole golf course. Large bedrooms & modern en suite bathrooms. Fantastic kitchen. Air-con bedrooms in the main house only. 

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€ 3,867
€ 7,619
$ 5,242
$ 10,329
£ 3,719
£ 7,327

Sleeping: 10 - Bedrooms: 5 - Bathrooms: 6

  • Air Conditioned Bedrooms
  • Internet Connection
  • Private Pool

Spacious stone farmhouse in central Tuscany with a private swimming pool and air-con bedrooms. Picturesque, natural setting high in the hills with spectacular views. Plenty of space indoors & outside, ideal for a large family or a group of friends.

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€ 3,194
€ 6,269
$ 4,331
$ 8,500
£ 3,072
£ 6,029

Sleeping: 14 - Bedrooms: 7 - Bathrooms: 7

  • Air Conditioned Bedrooms
  • Internet Connection
  • Private Pool

Spacious stone farmhouse in central Tuscany with a private swimming pool and air-con bedrooms. Picturesque, natural setting high in the hills with spectacular views. Plenty of space indoors & outside, ideal for a large family or a group of friends.

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€ 4,056
€ 7,463
$ 5,499
$ 10,119
£ 3,901
£ 7,177

Sleeping: 6 - Bedrooms: 3 - Bathrooms: 3

  • Maid included
  • Fully Air-conditioned villa
  • Air Conditioned Bedrooms
  • Internet Connection
  • Private Pool

Charming country stone farmhouse with a private pool enjoying beautiful views of the countryside near the pretty town of Montaione. Air-con. bedrooms, en-suite bathrooms & professional kitchen.

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€ 3,639
€ 4,991
$ 4,934
$ 6,767
£ 3,500
£ 4,800

Sleeping: 12 - Bedrooms: 6 - Bathrooms: 5

  • Maid included
  • Fully Air-conditioned villa
  • Air Conditioned Bedrooms
  • Internet Connection
  • Private Pool

Charming country stone farmhouse with a private pool enjoying beautiful views of the countryside near the pretty town of Montaione. Air-con. bedrooms, en-suite bathrooms & professional kitchen.

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€ 5,199
€ 7,130
$ 7,049
$ 9,667
£ 5,000
£ 6,857

Sleeping: 12 - Bedrooms: 6 - Bathrooms: 5

  • Maid included
  • Fully Air-conditioned villa
  • Air Conditioned Bedrooms
  • Internet Connection
  • Private Pool

Host your wedding or event at this charming country stone farmhouse with a private pool near the pretty town of Montaione. Fantastic managment arranges weddings up to 60 persons.

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€ 6,399
€ 8,330
$ 8,676
$ 11,294
£ 6,154
£ 8,011

Sleeping: 10 - Bedrooms: 5 - Bathrooms: 5

  • Air Conditioned Bedrooms
  • Internet Connection
  • Private Pool

Very comfortable farmhouse with a private pool near San Gimignano. Large air-conditioned bedrooms, pretty garden with lawns. Large modern kitchen. Great views of rolling hills. Big loggia.

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€ 3,668
€ 6,716
$ 4,974
$ 9,105
£ 3,528
£ 6,458

Sleeping: 6 - Bedrooms: 3 - Bathrooms: 3

  • Air Conditioned Bedrooms
  • Internet Connection
  • Private Pool
  • Heated Pool
  • Hot Tub

Very comfortable hilltop villa with a private heated pool & hot tub, part of a small hamlet near to San Gimignano. Air conditioned bedrooms, modern kitchen & bathrooms.

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€ 2,387
€ 4,971
$ 3,236
$ 6,740
£ 2,295
£ 4,781

Sleeping: 8 - Bedrooms: 4 - Bathrooms: 3

  • Air Conditioned Bedrooms
  • Internet Connection
  • Private Pool
  • Heated Pool
  • Hot Tub

Very comfortable hilltop villa with a private heated pool & hot tub, part of a small hamlet near to San Gimignano. Air conditioned bedrooms, modern kitchen & bathrooms.

Weekly prices
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€ 2,801
€ 6,214
$ 3,798
$ 8,425
£ 2,694
£ 5,976

Sleeping: 8 - Bedrooms: 4 - Bathrooms: 3

  • Air Conditioned Bedrooms
  • Internet Connection
  • Private Pool
  • Heated Pool
  • Hot Tub

Very comfortable hilltop villa with a private heated pool & hot tub and A/C bedrooms, part of a small hamlet near to San Gimignano. Six breakfast buffets, two evening meals in the restaurant of the estate and a pizza lunch in the villa are included in the price.

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€ 5,500
€ 8,000
$ 7,457
$ 10,847
£ 5,289
£ 7,693

Sleeping: 4 - Bedrooms: 2 - Bathrooms: 2

  • Air Conditioned Bedrooms
  • Internet Connection
  • Private Pool
  • Heated Pool

Modern stone farmhouse with private heated pool under 1km from Poggibonsi, between Florence & Siena. A/C bedrooms with en-suite bathrooms. Panoramic outdoor living space terraced into the hillside with additional summer kitchen & dining loggia. Rental option with all-inclusive wine available.

Weekly prices
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€ 2,661
€ 4,033
$ 3,608
$ 5,467
£ 2,560
£ 3,878

Sleeping: 6 - Bedrooms: 3 - Bathrooms: 3

  • Air Conditioned Bedrooms
  • Internet Connection
  • Private Pool
  • Heated Pool

Modern stone farmhouse with private heated pool under 1km from Poggibonsi, between Florence & Siena. A/C bedrooms with en-suite bathrooms. Panoramic outdoor living space terraced into the hillside with additional summer kitchen & dining loggia. Rental option with all-inclusive wine available.

Weekly prices
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€ 2,957
€ 4,481
$ 4,009
$ 6,075
£ 2,844
£ 4,309

Sleeping: 8 - Bedrooms: 4 - Bathrooms: 4

  • Air Conditioned Bedrooms
  • Internet Connection
  • Private Pool
  • Heated Pool

Modern stone farmhouse with private heated pool under 1km from Poggibonsi, between Florence & Siena. A/C bedrooms with en-suite bathrooms. Panoramic outdoor living space terraced into the hillside with additional summer kitchen & dining loggia. Rental option with all-inclusive wine available.

Weekly prices
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€ 3,479
€ 5,271
$ 4,717
$ 7,147
£ 3,346
£ 5,069

Why Stay near San Gimignano

Every traveller is different, so there is no such thing as the “best” villa near San Gimignano; only the best San Gimignano holiday rental for you. When you contact Tuscany Now & More, you will talk to someone who has stayed at the San Gimignano villas which interest you. It’s our golden rule — and why we stick to a focused, specialist portfolio of around 130 handpicked villas.

For a first-time visitor to Tuscany, San Gimignano is the iconic Tuscan hill-town. Its stone buildings and narrow streets have hardly changed since the Middle Ages: time seems to have stood still. The town’s most famous feature — which earned it the nickname “San Gimignano delle belle torri — are its towers. Thirteen remain, from a total of more than 70 at the peak of San Gim’s wealth in the 1300s.

Another reason to stay in the hills around San Gimignano are the daytrips on your doorstep. Florence has the largest concentration of sights, things to see and do, and places to shop in central Italy. It is the regional capital, with the Uffizi Gallery; Michelangelo’s “David”; Medici villas, palaces and tombs; Renaissance gardens; countless painted chapels and much more. It takes around an hour to reach Florence from most of our San Gimignano villas.

The Chianti hills are just to the east, and within easy reach of San Gim via some of Europe’s most scenic backroads through vineyards and olive groves. This is one of the most famous wine zones in the world. If you have an idea of “classic Tuscan scenery” in your mind, you will find it in around here. (And as an alternative to a villa near San Gimignano, you could also consider our luxury Chianti villas.)

The sights of Siena are around 45 minutes away by car, including the Campo, Palazzo Pubblico and Duomo. Like San Gimignano (though bigger), Siena is a Gothic-period town almost unchanged in appearance since medieval times. Dante could still find his way around either one, without Google Maps.

We have created detailed guides to some more of the best small-town daytrips from our San Gimignano villas. Read the following while you are researching your trip:

When to Visit San Gimignano

Spring temperatures are pleasant over most of the Tuscany region, including San Gimignano. You should expect an average daytime high of 23℃ (73℉) and lows of 11℃ (51℉) overnight by late Spring.

Summer in the hills around San Gimignano is high season. The daytime temperature rises to an average high of 30℃ (86℉), with 17℃ (62℉) overnight typical. This is the ideal season for relaxing by your private pool, especially in the heat of the day. Cultural and food festivals happen outdoors close to San Gimignano, from the Palio di Siena horserace (July and August) to August’s Watermelon Festival in Castellina in Chianti.

Both places are less than 1 hour’s drive from your San Gimignano villa.

Despite cooler temperatures, autumn and winter are still lots of fun around San Gimignano. The sun shines most days, with an average daytime high of 13℃ (55℉) and overnight lows of 4℃ (39℉). Low season means you can enjoy the town and nearby villages at your own pace — with much thinner crowds. You can easily find a table at top restaurants like Il Colombaio in Casole d’Elsa or the Osteria di Passignano in the Chianti hills.

For more month-by-month detail for travelling to Tuscany, read our guide: When is the Best Time to Visit Tuscany.

About Our Handpicked Villas near San Gimignano

If you are interested in learning more about what makes us different, you can read the Tuscany Now & More story.

Concierge service
Everyone renting a villa near San Gimignano with Tuscany Now & More gets free use of our renowned concierge service. If you want shopping stocked in your fridge on arrival, or a private chef to cook everyone dinner for a special occasion, just ask. Making your holiday lettings extra-special is all part of our service. While in Italy, our 24-hour ground staff are available by phone or WhatsApp. We can also connect you with an experienced local wedding planner service.

Checking in & out
You should check in at your San Gimignano holiday rental between 4pm and 7pm. We can accommodate different arrival times — just communicate this in advance to our office staff. It takes just over an hour to drive from Pisa Airport to San Gimignano. Rome’s main international airport is around 3 hours, 15 minutes away by car.

Upon arrival, the villa owner or caretaker will inspect the property with you and demonstrate appliances, equipment and utilities.

Check-out is 10am on the last day of your holiday rental. The villa owner or caretaker will arrive at 9am to settle any outstanding payments. If you want to depart earlier, you can let us know in advance.

Cleaning
Both the luxury villa and your private swimming pool will be cleaned prior to your arrival. Some of our holiday villas around San Gimignano have additional cleaning and pool/garden maintenance scheduled during the week. Maid service included with vacation rentals involves cleaning and tidying, but does not cover making beds, kitchen cleaning, laundry or ironing. Extra services can be organised via our dedicated travel concierge team.

Bed linen & towels
Our San Gimignano holiday rentals include bed linens, bathroom and swimming pool towels for all guests. These are provided weekly. Extra services and changes can be organised via our concierges.

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