Villas in San Gimignano
San Gimignano is a hill town with 13 surviving medieval towers, and our homes spread through the countryside around it. Nearly all have a private pool, and a good share sleep eight or more. A car is essential, because the homes are spread through the hills rather than inside the town.
- Villas
- 28
- From, per week
- £463
About San Gimignano
San Gimignano once had 65 towers and 13 still stand, hence the nickname Medieval Manhattan. The tallest, the Torre Grossa, is 54 metres and dates from 1311, and the town has been a World Heritage Site since 1990. The homes are scattered around the town over several kilometres, so one may be a short drive from the walls while another sits further out in the hills; check the position of the one you like. Nearly all have a private pool, and gardens are common. The hills produce Vernaccia di San Gimignano, a white wine produced only in these hills, and the Vernaccia di San Gimignano Wine Experience at La Rocca has a tasting table. Evenings usually mean a drive back out of town, so settle who is driving. In winter, check opening times first.
Is San Gimignano right for you?
- Best for
- Groups wanting pool stays in wine hills near a medieval town
- Not for you if
- You want to walk to restaurants from your door, because the homes are spread around the countryside.
Near San Gimignano
Monteriggioni
Village about 30 km south of San Gimignano, within reach for a half day by car.
Castelvecchio Nature Reserve
Nature reserve a few miles from the town, for countryside away from the towers.
Certaldo
Walled hill town with a funicular and Boccaccio's birthplace, easy to reach from San Gimignano.
Gambassi Terme
Village roughly a three-hour walk from the centre of San Gimignano, much quicker by car.
Getting to San Gimignano
Pisa airport is about an hour and ten minutes by road and Florence airport about an hour. Public transport is slow: from Pisa it takes nearly three hours by train to Empoli, train to Poggibonsi and bus 130. Almost every guest hires a car.
When to go to San Gimignano
Staying in the hills rather than inside the walls lets you choose your own hours in town, which helps on the busiest summer days. A private pool earns its keep in the warm months. Outside summer, check opening times for the wine tastings at La Rocca and for restaurants in the hills before planning a day around them.
Villas in San Gimignano
3-star property
3-star property
3-star property
4-star property
Vineyard View
San Gimignano, Tuscany Chianti, Italy
10
4
0
Air ConBBQDishwasher+10 more
from£550
per night
5-star property
2-Bedroom Home, San Gimignano
San Gimignano, Tuscany Chianti, Italy
5
2
0
ParkingDishwasherFireplace+9 more
from£151
per night
3-star property
3-star property
Le Sodole - Papavero e Pervinca
San Gimignano, Tuscany Chianti, Italy
8
4
0
BBQGardenParking+8 more
10-Bedroom Home, San Gimignano
San Gimignano, Tuscany Chianti, Italy
17
10
0
BBQParkingDishwasher+12 more
4-star property
3-star property
Rustico Cavernoso
San Gimignano, Tuscany Chianti, Italy
8
3
0
BBQDishwasherGarden+9 more
from£142
per night
3-star property
Le Sodole - Petunia
San Gimignano, Tuscany Chianti, Italy
8
4
0
BBQDishwasherFireplace+10 more
3-star property
3-star property
Il Fienile di Leo
San Gimignano, Tuscany Chianti, Italy
4
1
0
Air ConBBQDishwasher+10 more
from£73
per night
4-star property
Casa Alfredo
San Gimignano, Tuscany Chianti, Italy
6
3
0
Air ConDishwasherFireplace+11 more
from£137
per night
3-star property
Casa Tibesa
San Gimignano, Tuscany Chianti, Italy
4
2
0
DishwasherFireplaceMicrowave+9 more
from£155
per night
5-star property
4-star property
Podere San Michele
San Gimignano, Tuscany Chianti, Italy
10
5
0
BBQDishwasherFireplace+12 more
3-star property
3-star property
3-star property
3-star property
Fattoria di Fugnano
San Gimignano, Tuscany Chianti, Italy
2
1
0
BBQGardenParking+6 more
from£66
per night
3-star property
Fattoria di Fugnano
San Gimignano, Tuscany Chianti, Italy
4
2
0
BBQGardenParking+6 more
from£95
per night
2-star property
5-star property
Le Fonti di Santa Lucia
San Gimignano, Tuscany Chianti, Italy
10
5
0
Air ConBBQParking+11 more
from£393
per nightSan Gimignano villa holidays: questions answered
How many towers does San Gimignano have?
Thirteen medieval towers survive out of an original 65. The tallest is the Torre Grossa at 54 metres, built in 1311.
Can you get to San Gimignano without a car?
Only slowly. There is no direct public transport from Pisa airport: the route is train to Empoli, train to Poggibonsi, then bus 130, which takes close to three hours.
What is Vernaccia di San Gimignano?
A white wine produced solely in the hills around the town. You can taste it at the Vernaccia di San Gimignano Wine Experience at La Rocca, which also covers local produce.
San Gimignano or Certaldo for a villa stay?
San Gimignano suits those who want the towers and a World Heritage centre; Certaldo is smaller, with a funicular and Boccaccio's house. Both are a short drive apart, so one base can cover each.
Are the villas near the centre of San Gimignano?
Some are, but they are spread around the countryside over several kilometres, so check the distance for the particular home. Expect to drive for most trips into town.
Nearby towns to San Gimignano
Written by the TrustedVillas team. Last reviewed October 2026.
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