50 Best San Gimignano Villas on Holiday Lettings - Apartments

Close

View larger map

Also consider

Larniano
30 properties
Castel San Gimignano
27 properties
Pancole
24 properties
Ulignano
18 properties
Casaglia
9 properties

San Gimignano

No dates Enter dates for accurate prices -

Adults, Children

Enter dates for more accurate prices

Payment Protection
To book this vacation rental you need to pay through the Holiday Lettings website. We can’t protect your payment if you don’t pay through us. Learn more

465 Vacation rentals

Travelers going to San Gimignano are booking May dates now. Secure your vacation rental today and have the perfect trip.

(42) Excellent 

19

Vacation apartment with shared pool in San Gimignano

Province of Siena / San Gimignano

3 6 4 nights min

  • 3 bedrooms
  • Sleeps 6
  • 4 nights min
  • Swimming pool
  • Air conditioning
  • Private garden
Azzurra is an apartment in Poderra Torrichi, a gated community of three farm buildings, which is located between the medieval cities of San Gimignano and Volterra. Podera Torrichi is newly renovated and has retained the charm of the traditional Tuscan farm buildings, wi  …see more

from $240 / night

$1300 - $1900 / week

Book View

from $240 / night

(1) Very Good 

23

San Gimignano / Ulignano

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly

 …see more

from $128 / night

$742 - $1166 / week

Book View

from $128 / night

(3) Excellent 

28

Vacation apartment with shared pool in San Gimignano

Province of Siena / San Gimignano

2 7 7 nights min

  • 2 bedrooms
  • Sleeps 7
  • 7 nights min
  • Nearest beach 60 mi
  • Swimming pool
  • Child friendly
This unique, rustic and romantic self catering apartment has sleeping capacity for up to 7 (5+2) people in total. The apartment is next to Granaio nr 7 (advert nr 277234 ) and is a part of a small complex. It's perfektly located in West Chianti only 20 minutes from  …see more

from $44 / night

$308 - $1049 / week

Book View

from $44 / night

Featured properties

(5) Excellent 

21

Vacation villa with swimming pool in Casaglia

San Gimignano / Casaglia

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 75 mi
  • Swimming pool
  • Child friendly
The villa was an ancient historical structure going back to before the year 1200, originally the chapel "Santa Maria Church", near the burg of Casaglia. Over the centuries, the chapel was deconsecrated to become, first a watchtower, and then a place where the  …see more

from $159 / night

$1060 - $2437 / week

Book View

from $159 / night

13

Vacation cottage in San Gimignano

Province of Siena / San Gimignano

1 4 4 nights min

  • 1 bedroom
  • Sleeps 4
  • 4 nights min
  • Child friendly
  • Pet friendly
  • Private garden
Surrounded by idyllic countryside, this pretty holiday home contains flat-screen TV, free Wi-Fi and a barbeque. Parking is available onsite as is gas central heating. Decorated in modern-style using and bright terracotta floors, the airy home contains 1 double bedroom.  …see more

from $50 / night

$349 / week

Book View

from $50 / night

(12) Excellent 

70

Vacation villa with swimming pool in San Gimignano

Province of Siena / San Gimignano

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
  • Nearest beach 71 mi
  • Swimming pool
  • Child friendly
This superb villa, obtained from the careful restoration of an old brick kiln of 1737, is situated in a unique position on a hill opposite the towers of San Gimignano. The villa has been lovingly restored with materials of the highest quality and finished after long and  …see more

from $636 / night

$3708 - $8793 / week

Inquire View

from $636 / night

(3) Excellent 

28

Vacation apartment with shared pool in San Gimignano

Province of Siena / San Gimignano

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Nearest beach 60 mi
  • Swimming pool
  • Child friendly
This unique, rustic and romantic self catering apartment has sleeping capacity for up to 6 people (4+2) in total. The apartment is next to Granaio nr 6 (nr 277512) and is a part of a small complex. It's perfektly located in West Chianti only 20 minutes from San Gim  …see more

from $43 / night

$297 - $1017 / week

Book View

from $43 / night

100

Villa accommodation in San Gimignano with swimming pool

Province of Siena / San Gimignano

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 90 mi
  • Swimming pool
  • Child friendly
ExteriorsLocation in San Gimignano can only mean one thing: endless options to explore natural sceneries and traditional, ancient villas and cities. Siena, Florence, Pisa, Volterra and even the Chianti Classico and its vineyards are less than 30km away from the property  …see more

from $159 / night

$1060 - $2437 / week

Inquire View

from $159 / night

(46) Excellent 

25

Vacation home with shared pool in San Gimignano

Province of Siena / San Gimignano

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Nearest beach 55 mi
  • Swimming pool
  • Child friendly
Podere Torricchi is a small collection of beautifully renovated 16th Century farm buildings converted into houses and apartments. Set on a hill the entire site has stunning views of the rolling Tuscan countryside. I'l Granario' is a house set on two floors, ta  …see more

from $113 / night

$782 - $1125 / week

Book View

from $113 / night

(1) Excellent 

100

Vacation villa with swimming pool in San Gimignano

Province of Siena / San Gimignano

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
  • Nearest beach 90 mi
  • Swimming pool
  • Child friendly
Exterior:Perched on top on a hill, in the heart of Chianti countryside, Villa Magda boasts what must be one of the most enviable views of Tuscany: rolling Chianti hills decked with vines and olives, crowned by the incredible profile of San Gimignano's towers (locat  …see more

from $901 / night

$5721 - $8263 / week

Inquire View

from $901 / night

(11) Very Good 

32

Vacation farmhouse with shared pool in San Gimignano

Province of Siena / San Gimignano

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Nearest beach 100 mi
  • Swimming pool
  • Child friendly
Nestled in a centuries-old complex of farm-house buildings, just 10 minutes drive from the medieval "skyscraper" fortress town of San Gimignano...Le Fontanelle is the perfect place to soak in Tuscany's sunshine, culture, food and fun.An easy drive fro  …see more

from $75 / night

$562 - $1002 / week

Book View

from $75 / night

17

Vacation apartment in Castel San Gimignano

San Gimignano / Castel San Gimignano

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Nearest beach 60 mi
  • Child friendly
The apartment (max 4 people) located on a beautiful hill overlooking San Gimignano, is situated in Castel San Gimignano at 375 m above sea level. The village of 400 inhabitants, offers a restaurant, a grocery store and tranquility. From there you can quickly reach the  …see more

from $48 / night

$318 / week

Book View

from $48 / night

(5) Excellent 

24

San Gimignano Vacation apartment rental

Province of Siena / San Gimignano

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Private garden
Podere Torricchi is in a typical tuscan landscape characterised by hills with olive trees and mediterrenean bush. Podere Torricchi is a group of converted farm buildings. The apartment has been newly restored in a traditional Tuscan style.Gambassi Terme and San  …see more

from $75 / night

$520 - $1219 / week

Book View

from $75 / night

(9) Excellent 

42

Province of Siena / San Gimignano

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Nearest beach 70 mi
  • Child friendly
  • Private garden

 …see more

from $93 / night

$646 - $964 / week

Book View

from $93 / night

(4) Excellent 

28

Vacation farmhouse with shared pool in San Gimignano

Province of Siena / San Gimignano

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Nearest beach 80 mi
  • Swimming pool
  • Child friendly
'Podere Collinella' has been re-built to a high standard, retaining the charm of a Tuscan farmhouse.The walls are of the old stone, chestnut beams support the ceiling, and positioned on a slight hill has wonderful views of the surrounding countryside. Podere C  …see more

from $85 / night

$583 - $731 / week

Book View

from $85 / night

(1) Excellent 

10

Province of Siena / San Gimignano

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Child friendly
  • Pet friendly

 …see more

from $69 / night

$482 / week

Book View

from $69 / night

(21) Excellent 

43

Castel San Gimignano Vacation apartment rental

San Gimignano / Castel San Gimignano

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 55 mi
  • Swimming pool
  • Child friendly
The apartment is placed in the hamlet of Castel San Gimignano, very near to the best famous cities as Siena, Firenze, San Gimignano, Volterra and the sea is reachable in less than an hour by car. You can also start from here for a relaxing walk or ride through the olive  …see more

from $106 / night

$583 - $901 / week

Book View

from $106 / night

(21) Excellent 

60

San Gimignano / Pancole

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Nearest beach 90 mi
  • Child friendly
  • Air conditioning

 …see more

from $53 / night

$318 - $514 / week

Book View

from $53 / night

(1) Excellent 

20

Farmhouse rental in San Gimignano with swimming pool

Province of Siena / San Gimignano

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Nearest beach 45 mi
  • Swimming pool
  • Child friendly
Podere Le Monache set on a hillside dominates one of the most picturesque and spectacular landscapes in Tuscany. With distant views over hills, out to sea towards Livorno and Pisa. Originally a convent wrapped in history Le Monache has a magical and spiritual atmosphere  …see more

from $62 / night

$424 - $954 / week

Book View

from $62 / night

(15) Very Good 

16

Vacation apartment with shared pool in San Gimignano

Province of Siena / San Gimignano

2 4 5 nights min

  • 2 bedrooms
  • Sleeps 4
  • 5 nights min
  • Beach/lakeside relaxation
  • Nearest beach 55 mi
  • Swimming pool
Casa Florio' is a 2 bedroom apartment (upstairs apartment) incorporated into an ancient farm comprising 12 beautifully renovated stone buildings . Designed in traditional Tuscan country style with chestnut beamed ceilings and terraccota tiled floors. It is light a  …see more

from $103 / night

$718 / week

Book View

from $103 / night

(9) Excellent 

18

Vacation farmhouse with swimming pool in San Gimignano

Province of Siena / San Gimignano

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 45 mi
  • Swimming pool
  • Child friendly
Podere Le Monache set on a hillside dominates one of the most picturesque and spectacular landscapes in Tuscany. With distant views over hills, out to sea towards Livorno and Pisa. Originally a convent wrapped in history Le Monache has a magical and spiritual atmosphere  …see more

from $96 / night

$647 - $1272 / week

Book View

from $96 / night

(14) Excellent 

24

San Gimignano Vacation villa rental

Province of Siena / San Gimignano

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Nearest beach 85 mi
  • Swimming pool
  • Child friendly
Charming stone-built house located in a peaceful and panoramic position on the green, rolling hills near San Gimignano. The villa is the result of a recent renovation which has transformed this ancient barn into a beautiful and comfortable detached villa, ideal for spe  …see more

from $85 / night

$583 - $1907 / week

Inquire View

from $85 / night

(2) Very Good 

17

Vacation farmhouse rental

Province of Siena / San Gimignano

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 45 mi
  • Swimming pool
  • Child friendly
Podere Le Monache set on a hillside dominates one of the most picturesque and spectacular landscapes in Tuscany. With distant views over hills, out to sea towards Livorno and Pisa. Originally a convent wrapped in history Le Monache has a magical and spiritual atmosphere  …see more

from $71 / night

$472 - $1113 / week

Book View

from $71 / night

(5) Very Good 

21

Province of Siena / San Gimignano

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Nearest beach 77 mi
  • Swimming pool
  • Child friendly

 …see more

from $133 / night

$774 - $1176 / week

Book View

from $133 / night

27

San Gimignano / Castel San Gimignano

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly

 …see more

from $64 / night

$445 / week

Book View

from $64 / night

(6) Excellent 

27

Apartment rental in San Gimignano

Province of Siena / San Gimignano

2 5 3 nights min

  • 2 bedrooms
  • Sleeps 5
  • 3 nights min
  • Child friendly
  • Ask about pets
Holiday in San Gimignano ... a journey into the heart of Tuscany.Dear Guests, we are the sisters Stefania and Margherita and we are the owners of Appartamento Margherita. We decided to rent the apartment where we were born about 15 years ago, when we underst  …see more

from $106 / night

$636 / week

Book View

from $106 / night

(5) Excellent 

46

Vacation farmhouse rental

San Gimignano / Montauto

2 5 3 nights min

  • 2 bedrooms
  • Sleeps 5
  • 3 nights min
  • Nearest beach 80 mi
  • Swimming pool
  • Child friendly
The 200 sqm villa is a typical stone barn in an early '900 style, characterized by the tranquility of the Tuscan countryside of San Gimignano in which it is immersed.It can be accessed via a large private and completely fenced garden of 2,000 sqm.The ho  …see more

from $258 / night

$1801 / week

Book View

from $258 / night

(33) Excellent 

32

Castel San Gimignano Vacation apartment rental

San Gimignano / Castel San Gimignano

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 55 mi
  • Swimming pool
  • Child friendly
The apartment is located in the hamlet of Castel San Gimignano, very near to the best famous cities as Siena, Firenze, San Gimignano, Volterra and the sea is reachable in less than an hour by car. You can also start from here for a relaxing walk or ride through the oliv  …see more

from $106 / night

$583 - $901 / week

Book View

from $106 / night

(14) Excellent 

17

Vacation apartment in San Gimignano

Province of Siena / San Gimignano

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Nearest beach 65 mi
  • Child friendly
  • Air conditioning
Apartment "Il Duca" (2-6 beds)Bright three-roomed apartment (85 mq). With its twelve windows it offers a beautiful panoramic view of the surrounding Chianti countryside, the nearby gardens, the ancient buildings and the legendary Torre del Diavolo. It is f  …see more

from $109 / night

$763 / week

Book View

from $109 / night

7

San Gimignano Vacation b&b rental

Province of Siena / San Gimignano

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets
Conveniently placed between world famous hilltop towns of San Gimignano Florence and Siena. We offer 360° views from the top of a hill surrounded by vines and olive trees. Abundant buffet breakfast and home cooked evening meals are avaialble for our guests, relax b  …see more

from $101 / night

$636 - $890 / week

Book View

from $101 / night

(1) Excellent 

99

Province of Siena / San Gimignano

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from $133 / night

$816 - $1219 / week

Book View

from $133 / night

(9) Excellent 

16

Vacation farmhouse in San Gimignano

Province of Siena / San Gimignano

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 90 mi
  • Swimming pool
  • Child friendly
House with two apartments near San Gimignano in TuscanyHoliday Apartment offers 2 flats inside an old barn that were recently restructured.Both the apartments can accommodate up to 4 people and are composed of a bedroom with bathroom, a small bedroom and a dinin  …see more

from $78 / night

$530 - $964 / week

Book View

from $78 / night

(1) Excellent 

30

Province of Siena / San Gimignano

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Private garden

 …see more

from $85 / night

$551 - $1044 / week

Book View

from $85 / night

(1) Very Good 

20

Province of Siena / San Gimignano

3 6 2 nights min

  • 3 bedrooms
  • Sleeps 6
  • 2 nights min
  • Child friendly
  • Ask about pets

 …see more

from $245 / night

$1287 / week

Book View

from $245 / night

34

Province of Siena / San Gimignano

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Nearest beach 60 mi
  • Swimming pool
  • Child friendly

 …see more

from $75 / night

$445 - $859 / week

Book View

from $75 / night

100

San Gimignano Vacation apartment rental

Province of Siena / San Gimignano

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Nearest beach 90 mi
  • Swimming pool
  • Child friendly
4 paxThese country apartments in Tuscany range from 60 to 100 sq-m. They are situated on the ground or first floor and afford stunning picture postcard views of the landscape. They feature dining room with a fully fitted kitchen area, a double bedroom and a twin bedroom  …see more

from $149 / night

$954 - $1600 / week

Inquire View

from $149 / night

(4) Excellent 

14

Castel San Gimignano Vacation apartment rental

San Gimignano / Castel San Gimignano

3 5 Min stay varies

  • 3 bedrooms
  • Sleeps 5
  • Min stay varies
  • Nearest beach 55 mi
  • Child friendly
  • Ask about pets
C asa Titta is our third apartment ,completely new ,really comfortable, placed on the first floor with three bedrooms for 5 people and a large open space living . A new kitchen equipped with dishwasher , fridge/freezer, microwave and electrical hoven. The bathroom has  …see more

from $106 / night

$583 - $901 / week

Book View

from $106 / night

(6) Excellent 

23

Vacation villa with swimming pool in San Gimignano

Province of Siena / San Gimignano

4 9 Min stay varies

  • 4 bedrooms
  • Sleeps 9
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets
The villa, on two floors, is just 5 km from the historic center of San Gimignano, in a secluded location is surrounded by large well kept garden and green, with lawn, where you can spend time and relax. The garden also features a gazebo with garden furniture, barbecue.  …see more

from $371 / night

$1642 - $2649 / week

Inquire View

from $371 / night

100

Vacation apartment in San Gimignano

Province of Siena / San Gimignano

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Nearest beach 90 mi
  • Swimming pool
  • Child friendly
2 paxThese country apartments in Tuscany ranging from 45 to 60 sq-m are called after the purpose they were used for long ago. They are situated on the ground or first floor and feature each a large dining room with fully fitted kitchen area. Only one of them features a  …see more

from $128 / night

$731 - $1118 / week

Inquire View

from $128 / night

(20) Excellent 

49

Vacation cottage in San Gimignano

Province of Siena / San Gimignano

2 5 6 nights min

  • 2 bedrooms
  • Sleeps 5
  • 6 nights min
  • Nearest beach 75 mi
  • Child friendly
  • Pet friendly
Surrounded by idyllic countryside, this pretty holiday home contains flat-screen TV, free Wi-Fi and a barbeque. Parking is available onsite as is gas central heating. Decorated in a typical country-style using rustic furniture and bright terracotta floors, the airy hom  …see more

from $64 / night

$445 / week

Book View

from $64 / night