San Gimignano apartment or villa with a private pool area | Holiday Lettings

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San Gimignano

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83 Holiday homes

Filters applied: Private pool (83)

Travellers going to San Gimignano are booking May dates now. Secure your holiday home today and have the perfect trip.

(5) Excellent 

21

Holiday villa with swimming pool in Casaglia

San Gimignano / Casaglia

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 75 km
  • Swimming pool
  • Child friendly
“An awesome villa in the Tuscan hills” A wonderfully restored church with plenty of character. Privacy with trees and hedges. Fab and accessible pool. Well equipped kitchen. An amazing welcome pack. We cycled from here to San Gimignano and to Monterigg  …see more

from £132 / night

£878 - £2018 / week

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from £132 / night

(9) Excellent 

18

Holiday 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 km
  • Swimming pool
  • Child friendly
“peaceful paradise” This villa met all our expectations. The view from the bedrooms and the terrace were spectacular. Location in small village was perfect. Villa had special arragements for food delivery from local restaurants. Vila was spotless an  …see more

from £86 / night

£574 - £1087 / week

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from £86 / night

(5) Excellent 

46

Holiday farmhouse rental

San Gimignano / Montauto

2 5 3 nights min

  • 2 bedrooms
  • Sleeps 5
  • 3 nights min
  • Nearest beach 80 km
  • Swimming pool
  • Child friendly
A typical stone barn immersed in the Tuscan countryside of San Gimignano. A large garden overlooks the hills and surrounding countryside. Up to 7 people in a both modern and rustic atmosphere.  …see more

from £214 / night

£1492 / week

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from £214 / night

Featured properties

(2) Very Good 

17

Holiday farmhouse rental

Province of Siena / San Gimignano

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 45 km
  • Swimming pool
  • Child friendly
Self catering Farmhouse and 4 luxury apartments in rural Tuscany with swimming pool spectacular views ,nearby golf, walking, trekking, fishing, biking. San Gimignano, and Certaldo, 20 minutes drive, Florence one hour .  …see more

from £65 / night

£435 - £965 / week

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from £65 / night

(2) Very Good 

29

San Gimignano holiday apartment rental

Province of Siena / San Gimignano

3 7 3 nights min

  • 3 bedrooms
  • Sleeps 7
  • 3 nights min
  • Nearest beach 80 km
  • Swimming pool
  • Child friendly
.This charming accommodation lies in the countryside enjoying the most marvellous views of the undulating landscape and the towers of the city of San Gimignano only 3km away. It is a lovely location for enjoying country walks and relaxing<br />The pool and the gar  …see more

from £176 / night

£1229 - £1843 / week

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from £176 / night

(4) Very Good 

33

Holiday apartment with swimming pool in San Gimignano

Province of Siena / San Gimignano

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Private garden
Just 1800 mt from the historical centre of San Gimignano, along the Francigena road, you will find a place where you can spend beautiful Tuscany holidays. The apartment is located in the countryside of the medieval town, in the centre of Tuscany. The house is surround  …see more

from £47 / night

£351 - £746 / week

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from £47 / night

(1) Excellent 

20

Holiday villa with swimming pool in San Gimignano

Province of Siena / San Gimignano

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Nearest beach 75 km
  • Swimming pool
  • Child friendly
Offers a unique view of the surrounding valley typical of the Sienese hills (olives and grapes) and is located a short distance (3 km) from the town of San Gimignano famous for its medieval towers.  …see more

from £163 / night

£1141 - £1799 / week

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from £163 / night

(14) Excellent 

24

Holiday villa in San Gimignano

Province of Siena / San Gimignano

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Nearest beach 70 km
  • Swimming pool
  • Child friendly
“If only we could live here!” We spent the 1st 2 weeks of June here with 7 of us in total, 6 adults 1 child. The property is fantastic, it has all the facilities you want with huge rooms. We didn't realise that 2 of the rooms were adjoining which was a  …see more

from £176 / night

£1579 - £2808 / week

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from £176 / night

(14) Excellent 

24

San Gimignano holiday villa rental

Province of Siena / San Gimignano

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Nearest beach 85 km
  • Swimming pool
  • Child friendly
“Beautiful!” Four of us stayed here in October 2012, the house is beautiful and immaculately maintained as are the gardens. Unfortunately the weather wasn't on our side so we didn't spend as much time in the garden as we'd have liked but you could spe  …see more

from £71 / night

£483 - £1579 / week

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from £71 / night

(4) Excellent 

24

Villa rental in San Gimignano with swimming pool

Province of Siena / San Gimignano

6 17 7 nights min

  • 6 bedrooms
  • Sleeps 17
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets
Self-catering Tuscany villa just 4 kms from San Gimignano. Private pool and garden for al fresco dining. Perfect centre for taking day trips to the cities and towns of Tuscany.  …see more

from £157 / night

£1097 - £2886 / week

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from £157 / night

(9) Excellent 

20

San Gimignano holiday villa rental

Province of Siena / San Gimignano

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Ask about pets
  • Private garden
Naturally cool stone villa for 11 persons with large private pool & gardens in San Gimignano area. Divided into two apartments for 6 and 5 people.  …see more

from £188 / night

£1141 - £2106 / week

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from £188 / night

(1) Very Good 

24

San Gimignano holiday cottage rental

Province of Siena / San Gimignano

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 80 km
  • Swimming pool
  • Child friendly
Self-catering Tuscany cottage with stunning views over the Chianti hills, half way (35 km) between Florence and Siena.  …see more

from £88 / night

£615 - £1711 / week

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from £88 / 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 km
  • Swimming pool
  • Child friendly
Self catering Farmhouse with 4 luxury apartments in rural Tuscany with swimming pool spectacular views ,nearby golf, walking, trekking, fishing, biking. San Gimignano, and Certaldo, 20 minutes drive, Florence, Siena and Pisa one hour from the house.  …see more

from £58 / night

£386 - £834 / week

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from £58 / night

13

Province of Siena / San Gimignano

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from £176 / night

£1009 - £2895 / week

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from £176 / night

100

Holiday villa with swimming pool in San Gimignano

Province of Siena / San Gimignano

3 5 7 nights min

  • 3 bedrooms
  • Sleeps 5
  • 7 nights min
  • Swimming pool
  • Child friendly
This property is a lovely house set in Tuscany Italy. It has 3 bedrooms and 1 bathroom, and it is perfect for those who are looking for a charming holiday. This property features: a swimming Pool .  …see more

from £110 / night

£768 - £1535 / week

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from £110 / night

100

Larniano holiday villa rental

San Gimignano / Larniano

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Set in Tuscany Italy, this vacation villa is the perfect place for your holidays. The villa features: a swimming Pool, air Conditioning, an internet Connection, a pet friendly space .  …see more

from £342 / night

£1974 - £3290 / week

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from £342 / night

(6) Excellent 

23

Holiday 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
“What a wonderful place in Italy” We stayed now the second time in Podere Lo Spadino, we are a Group with 8 peoples, and everything in this house is amazing. The whole house, the garden, the pool and of course Barbara with her Family, they are helpful  …see more

from £308 / night

£1360 - £2193 / week

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from £308 / night

(1) Excellent 

100

Holiday 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 km
  • Swimming pool
  • Child friendly
Villa Magda is a luxurious villa in San Gimignano, and is perfect for a large group of family or friends that appreciate tranquility, privacy, and beautiful natural surroundings.  …see more

from £740 / night

£4696 - £6783 / week

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from £740 / night

(1) Excellent 

17

Province of Siena / San Gimignano

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Nearest beach 109 km
  • Swimming pool
  • Child friendly

 …see more

from £97 / night

£658 / week

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from £97 / night

(1) Excellent 

19

Holiday farmhouse in San Gimignano

Province of Siena / San Gimignano

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 45 km
  • Swimming pool
  • Child friendly
“Very good appartment, with great views” We stayed in Podere Le Monache 4 for one week in August. It was more then we expected from the pictures and the description. The appartment was very clean and spacious, with two large bedrooms and enough furnitu  …see more

from £71 / night

£483 - £1009 / week

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from £71 / night

(1) Very Good 

35

Province of Siena / San Gimignano

7 10 Min stay varies

  • 7 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly

 …see more

from £255 / night

£1667 - £2369 / week

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from £255 / night

19

Holiday apartment rental

San Gimignano / Casaglia

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly
Located on the first floor of the main villa, Viola is a large apartment comprised of one double bedroom (with king size bed and a bed for a child), a bathroom (with shower stall), kitchen and dining room / living room.  …see more

from £93 / night

£605 - £876 / week

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from £93 / night

(12) Excellent 

70

Holiday 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 km
  • Swimming pool
  • Child friendly
“Wonderful vacation villa!” Our family had a wonderful vacation. Gabrielle and Lucia are so nice and the best hosts. They are always available for anything you might need and willing to provide help in getting to local places. The villa is absolutely  …see more

from £527 / night

£3071 - £7281 / week

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from £527 / night

20

San Gimignano / Ulignano

4 9 7 nights min

  • 4 bedrooms
  • Sleeps 9
  • 7 nights min
  • Nearest beach 90 km
  • Swimming pool
  • Suitable for children age 5+

 …see more

from £370 / night

£2588 / week

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from £370 / night

20

Holiday apartment in Casaglia

San Gimignano / Casaglia

3 2 Min stay varies

  • 3 bedrooms
  • Sleeps 2
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Located in the annex, Glicine is our largest apartment and probably the most private as it is detached from the main villa.It has one double bedroom (with king size bed), single bedroom for 2 child, one bathroom (with shower stall ), kitchen/living room<br />Baby  …see more

from £145 / night

£868 - £1207 / week

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from £145 / night

7

Holiday apartment rental

San Gimignano / Casaglia

2 3 Min stay varies

  • 2 bedrooms
  • Sleeps 3
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly
Mimosa is a very nice and cozy apartment on the ground floor of the main villa, with a private entrance.<br />Enfant bed  …see more

from £91 / night

£563 - £834 / week

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from £91 / night

19

Holiday apartment with swimming pool, golf nearby in Larniano

San Gimignano / Larniano

10 22 3 nights min

  • 10 bedrooms
  • Sleeps 22
  • 3 nights min
  • Nearest beach 70 km
  • Swimming pool
  • Child friendly
The whole property Sassi Bianchi is ideal for large groups, because there are four farmhouses, eachfamily live in its farmhouse and you can be together for dinner or to another at Lilium farmhouseAlso swimming pool, tennis court, booling green is only for you  …see more

from £562 / night

£3948 - £6316 / week

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from £562 / night

22

Holiday tower with swimming pool in San Gimignano

Province of Siena / San Gimignano

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Swimming pool
  • Ask about pets
  • Private garden
Stunning medieval tower near San Gimignano for holiday rentals  …see more

from £126 / night

£878 - £2150 / week

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from £126 / night

(1) Very Good 

16

Holiday villa with swimming pool, golf nearby in Larniano

San Gimignano / Larniano

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Not far from Siena, for 5 minutes along the road from San Gimignano goes towards Gambassi, we find the gates of Villa Panorama.It is an old building of more than 5 centuries and tastefully decorated and with quality furniture and style typical of the villas in Tuscany  …see more

from £220 / night

£1536 - £2193 / week

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from £220 / 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 km
  • Swimming pool
  • Child friendly
Set in the heart of the Tuscan countryside, offering full privacy and a warm atmosphere in its interiors, this lovely villa is ready to welcome guests. It is fitted with modern comforts, and it sleeps up to six people.  …see more

from £131 / night

£870 - £2000 / week

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from £131 / night

19

Holiday apartment in Casaglia

San Gimignano / Casaglia

2 2 Min stay varies

  • 2 bedrooms
  • Sleeps 2
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Located in the elegantly renovated barn, Iris is particularly spacious and filled with natural light.<br />Baby bed on request is free  …see more

from £131 / night

£844 - £1159 / week

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from £131 / night

100

Holiday villa with swimming pool in San Gimignano

Province of Siena / San Gimignano

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
This property is a lovely villa set in Tuscany Italy. It has 2 bedrooms and 2 bathrooms, and it is perfect for those who are looking for a unique experience. This property features: a swimming Pool, air Conditioning .  …see more

from £171 / night

£1000 - £1668 / week

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from £171 / night

100

Villa rental in San Gimignano with swimming pool

Province of Siena / San Gimignano

7 14 7 nights min

  • 7 bedrooms
  • Sleeps 14
  • 7 nights min
  • Nearest beach 120 km
  • Swimming pool
  • Child friendly
This Tuscan villa can host up to 14 guests in 7 double bedrooms. It has a fully equipped kitchen with its own dining area, formal dining room, 2 living rooms, 6 bathrooms and an outdoor swimming pool.  …see more

from £460 / night

£3218 - £4174 / week

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from £460 / night

25

Holiday farmhouse rental

Province of Siena / San Gimignano

8 22 Min stay varies

  • 8 bedrooms
  • Sleeps 22
  • Min stay varies
  • Nearest beach 45 km
  • Swimming pool
  • Child friendly
Perfect location self - catering accommodation for a group holiday in the historical and cultural heart of Tuscany. Conveniently situated in a small village with restaurants, mini market and cafe/bar all at our door step.Beautiful setting for a memorable occasion.  …see more

from £255 / night

£1711 - £3729 / week

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from £255 / night

24

San Gimignano / Larniano

7 17 7 nights min

  • 7 bedrooms
  • Sleeps 17
  • 7 nights min
  • Swimming pool
  • Private garden

 …see more

from £615 / night

£4299 / week

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from £615 / night

24

Farmhouse rental in San Gimignano with swimming pool

Province of Siena / San Gimignano

3 5 7 nights min

  • 3 bedrooms
  • Sleeps 5
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets
Villa in San Gimignano with 3 bedrooms sleeps 5  …see more

from £110 / night

£768 - £1535 / week

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from £110 / night

(19) Excellent 

24

Holiday villa with swimming pool in San Gimignano

Province of Siena / San Gimignano

4 9 Min stay varies

  • 4 bedrooms
  • Sleeps 9
  • Min stay varies
  • Nearest beach 70 km
  • Swimming pool
  • Child friendly
“Fabulous house with stunning view and great location, 20 minute walk to the town.” We visited villa La Porticciola on the outskirts of San Gimignano in May with a group of friends and had a fantastic time. Everything was perfect, the house had everyt  …see more

from £176 / night

£1404 - £2544 / week

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from £176 / night

20

Holiday farmhouse rental

Province of Siena / San Gimignano

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Swimming pool
  • Ask about pets
Villa in Santa Lucia with 4 bedrooms sleeps 8  …see more

from £324 / night

£2264 - £3500 / week

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from £324 / night

22

Holiday farmhouse with swimming pool in San Gimignano

Province of Siena / San Gimignano

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets
Villa in San Gimignano with 2 bedrooms sleeps 5  …see more

from £171 / night

£1000 - £1668 / week

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from £171 / night

17

Holiday apartment with swimming pool in Casaglia

San Gimignano / Casaglia

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly
A very private and quiet apartment, located on the ground floor of the main villa, and sharing the entrance with two other apartments.It is comprised of a bedroom with king size bed with direct outdoor access, bathroom with shower stall and kitchen / living room.<br  …see more

from £91 / night

£563 - £834 / week

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from £91 / night