Villas in San Gimignano and Apartments - Holiday Lettings - Holiday Rentals San Gimignano

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San Gimignano

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5,837 Holiday homes

(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

from £132 / night

£878 - £2,018 / week

Book View

Responds fast!
avg. 1 hour 12 minutes

from £132 / night

(14) Excellent 

Certificate of Excellence

25

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

Certificate of Excellence

from £85 / night

£569 - £992 / week

Book View

Responds fast!
avg. 2 hours 35 minutes

from £85 / night

19

San Gimignano holiday farmhouse rental

Province of Siena / San Gimignano

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets

from £73 / night

£513 - £740 / week

Enquire View

from £73 / night

(48) Excellent 

19

Holiday 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
“A wonderful holiday home” Stayed at Azzurra in June and had the most wonderful holiday. We were a group of 3 couples, the home was spotlessly clean, very well furnished and the views, well.. they are just amazing, better than the photos show!! The o
…see more

from £162 / night

£845 - £1,338 / week

Book View

Responds fast!
avg. 2 hours 39 minutes

from £162 / night

(50) Excellent 

Certificate of Excellence

25

Holiday 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 km
  • Swimming pool
  • Child friendly
“Perfection in rural Tuscany” From the outset we knew that this place would be special. From reviewing the property on TripAdvisor, looking at the pictures, reading other travellers reviews right through to the wonderful prompt and attentive service r
…see more

Certificate of Excellence

from £90 / night

£625 - £900 / week

Book View

from £90 / night

10

Holiday finca with shared pool in San Gimignano

Province of Siena / San Gimignano

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Swimming pool
  • Child friendly

from £78 / night

£475 / week

Book View

from £78 / night

19

San Gimignano holiday farmhouse rental

Province of Siena / San Gimignano

1 5 Min stay varies

  • 1 bedroom
  • Sleeps 5
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets

from £73 / night

£513 - £740 / week

Enquire View

from £73 / night

(2) Very Good 

28

Holiday apartment with shared pool in Ulignano

San Gimignano / Ulignano

2 6 Min stay varies

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

from £105 / night

£609 - £957 / week

Book View

Responds fast!
avg. 3 hours 48 minutes

from £105 / night

(5) Excellent 

28

Holiday 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 km
  • Swimming pool
  • Child friendly

from £49 / night

£340 - £1,000 / week

Book View

Responds fast!
avg. 2 hours 33 minutes

from £49 / night

(12) Excellent 

27

San Gimignano holiday farmhouse rental

Province of Siena / San Gimignano

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Nearest beach 70 km
  • Swimming pool
  • Child friendly

from £126 / night

£740 - £1,026 / week

Book View

Responds fast!
avg. 2 hours 8 minutes

from £126 / night

8

Holiday private room in San Gimignano

Province of Siena / San Gimignano

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Suitable for children age 5+

from £70 / night

£487 / week

Book View

from £70 / night

15

Holiday apartment in San Gimignano

Province of Siena / San Gimignano

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Child friendly
  • Car not necessary
  • Air conditioning

from £83 / night

£579 / week

Book View

from £83 / night

(25) Excellent 

Certificate of Excellence

43

Castel San Gimignano holiday apartment rental

San Gimignano / Castel San Gimignano

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 55 km
  • Swimming pool
  • Child friendly
“Brilliant location, fantastic views and the warmest of welcomes.” We have just returned from Casa Verbena having had a fabulous time. The accommodation is very spacious and exceptionally clean and well equipped. The pictures of the apartment do not il
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Certificate of Excellence

from £87 / night

£479 - £653 / week

Book View

Responds fast!
avg. 1 hour 10 minutes

from £87 / night

(7) Excellent 

28

Holiday 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 km
  • Swimming pool
  • Child friendly

from £49 / night

£340 - £1,000 / week

Book View

Responds fast!
avg. 2 hours 33 minutes

from £49 / night

(2) Excellent 

18

San Gimignano holiday farmhouse rental

Province of Siena / San Gimignano

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

from £59 / night

£722 / week

Book View

from £59 / night

17

Holiday apartment in San Gimignano

Province of Siena / San Gimignano

1 6 3 nights min

  • 1 bedroom
  • Sleeps 6
  • 3 nights min
  • Child friendly

from £131 / night

£913 / week

Book View

from £131 / night

21

San Gimignano holiday farmhouse rental

Province of Siena / San Gimignano

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly

from £87 / night

£609 / week

Book View

from £87 / night

(16) Excellent 

Certificate of Excellence

42

Holiday apartment rental

Province of Siena / San Gimignano

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Nearest beach 70 km
  • Child friendly
  • Air conditioning

Certificate of Excellence

from £86 / night

£609 / week

Book View

Responds fast!
avg. 19 minutes

from £86 / night

34

San Gimignano holiday apartment rental

Province of Siena / San Gimignano

1 4 Min stay varies

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

from £57 / night

£366 - £668 / week

Book View

from £57 / night

(1) Excellent 

80

Farmhouse rental in Castel San Gimignano with shared pool, golf nearby

San Gimignano / Castel San Gimignano

3 7 3 nights min

  • 3 bedrooms
  • Sleeps 7
  • 3 nights min
  • Nearest beach 70 km
  • Swimming pool
  • Child friendly

from £157 / night

£1,044 - £2,000 / week

Book View

from £157 / night

(35) Excellent 

Certificate of Excellence

32

Castel San Gimignano holiday apartment rental

San Gimignano / Castel San Gimignano

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 55 km
  • Swimming pool
  • Child friendly
“Fabulous holiday and accommodation” We stayed at this apartment in June this year. The apartment was really well fitted out and spotlessly clean, the oven looked like it had never been used !! The facilities were great and the location is lovely, it i
…see more

Certificate of Excellence

from £87 / night

£479 - £653 / week

Book View

Responds fast!
avg. 46 minutes

from £87 / night

9

Holiday home in San Gimignano

Province of Siena / San Gimignano

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Child friendly
  • Pet friendly
  • Private garden

from £87 / night

£380 / week

Book View

from £87 / night

(1) Excellent 

99

Holiday villa with shared 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
  • Air conditioning

from £110 / night

£693 - £1,035 / week

Book View

from £110 / night

(20) 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 £522 / night

£3,044 - £8,000 / week

Enquire View

from £522 / night

(2) Excellent 

20

Ulignano holiday apartment rental

San Gimignano / Ulignano

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Private garden

from £77 / night

£536 / week

Book View

from £77 / night

(3) Average 

35

Villa accommodation in San Gimignano with swimming pool

Province of Siena / San Gimignano

7 10 Min stay varies

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

from £226 / night

£1,583 - £2,253 / week

Book View

from £226 / night

(22) Excellent 

Certificate of Excellence

26

Holiday cottage in San Gimignano

Province of Siena / San Gimignano

2 5 6 nights min

  • 2 bedrooms
  • Sleeps 5
  • 6 nights min
  • Nearest beach 75 km
  • Child friendly
  • Pet friendly

Certificate of Excellence

from £53 / night

£366 / week

Book View

Responds fast!
avg. 35 minutes

from £53 / night

(6) Excellent 

44

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

from £209 / night

£2,009 / week

Book View

Responds fast!
avg. 1 hour 30 minutes

from £209 / night

(6) Very Good 

Certificate of Excellence

21

Holiday townhouse rental

Province of Siena / San Gimignano

2 5 Min stay varies

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

Certificate of Excellence

from £109 / night

£566 - £870 / week

Book View

from £109 / night

26

Holiday apartment in San Gimignano

Province of Siena / San Gimignano

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Child friendly
  • Pet friendly

from £87 / night

£475 / week

Book View

from £87 / night

(1) Excellent 

20

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 £70 / night

£479 - £913 / week

Book View

Responds fast!
avg. 2 hours 35 minutes

from £70 / night

(2) Excellent 

25

San Gimignano holiday apartment rental

Province of Siena / San Gimignano

1 6 2 nights min

  • 1 bedroom
  • Sleeps 6
  • 2 nights min
  • Child friendly
  • Air conditioning
  • Pet friendly

from £87 / night

£609 - £696 / week

Book View

from £87 / night

26

Holiday apartment accommodation

San Gimignano / Castel San Gimignano

2 5 4 nights min

  • 2 bedrooms
  • Sleeps 5
  • 4 nights min
  • Child friendly
  • Ask about pets

from £61 / night

£392 - £540 / week

Book View

from £61 / night

(19) Excellent 

19

Apartment rental in San Gimignano

Province of Siena / San Gimignano

1 3 3 nights min

  • 1 bedroom
  • Sleeps 3
  • 3 nights min
  • Nearest beach 72 km
  • Child friendly
  • Private garden
“An all round fantastic experience...we have great memories...” My partner and I stayed here for a week in July, and count ourselves lucky to have discovered this place. About 8kms from San Gimignano (an easy jaunt in a car, the latter being vital)
…see more

from £54 / night

£313 - £387 / week

Book View

from £54 / night

19

Apartment rental in San Gimignano with shared pool

Province of Siena / San Gimignano

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Nearest beach 80 km
  • Swimming pool
  • Child friendly

from £87 / night

£696 - £1,018 / week

Book View

from £87 / night

(19) Very Good 

Certificate of Excellence

17

Holiday apartment with shared pool in San Gimignano

Province of Siena / San Gimignano

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Beach / lakeside relaxation
  • Nearest beach 55 km
  • Swimming pool
“Beautiful apartment in stunning Tuscan landscape” If you want a base in Tuscany that seems in the middle of nowhere, but is less than an hour from all of the famous Tuscan towns/villages, and a lovely apartment that is in the middle of stunning countr
…see more

Certificate of Excellence

from £85 / night

£595 / week

Book View

Responds fast!
avg. 2 hours 46 minutes

from £85 / night

(12) Excellent 

17

Holiday farmhouse in San Gimignano

Province of Siena / San Gimignano

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Nearest beach 90 km
  • Swimming pool
  • Child friendly

from £64 / night

£792 / week

Book View

from £64 / night

(1) Excellent 

23

Holiday farmhouse with shared pool in San Gimignano

Province of Siena / San Gimignano

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Nearest beach 70 km
  • Swimming pool
  • Child friendly

from £105 / night

£653 - £800 / week

Book View

Responds fast!
avg. 2 hours 8 minutes

from £105 / night

(16) Very Good 

32

Holiday farmhouse with shared pool in San Gimignano

Province of Siena / San Gimignano

2 5 1 night min

  • 2 bedrooms
  • Sleeps 5
  • 1 night min
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly
“Excellent value Tuscan villa in a lovely setting” We stayed in the Agrifolo apartment at Le Fontanelle in May 2015. I was visited with my partner and my parents as we treated them to a Tuscan trip to start the summer. The villa was lovely - simple
…see more

from £100 / night

£700 / week

Book View

Responds fast!
avg. 3 hours 44 minutes

from £100 / night

(1) Excellent 

21

San Gimignano holiday apartment rental

Province of Siena / San Gimignano

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly

from £97 / night

£676 / week

Book View

Responds fast!
avg. 2 hours 21 minutes

from £97 / night

Top Destination reviews

VILLA DEL GRILLO
Incredible hosts, cottage, and surroundings

Giovanni and Silvia were fantastic hosts. Everything in the cottage was spotless and just like the pictures. The surrounding countryside is gorgeous. The cottage is close enough to Certaldo for easy shopping and access. You can see San Gimignano from the field above the cottage. The gravel country road on which the house is located makes a wonderful walk. One of us took sick while we were there: our hosts were able to arrange for doctors to make house calls, they picked up medicine for us, and went FAR and above any reasonable expectation to care for us. We felt like part of the family. We really, really, really cannot say enough good things about how well we were looked after.see more
Garden House
Tranquil apartment but in the town

We had a fantastic stay at Casa Giardino. very peaceful but convenient for the Town centre and shopping restaurants etc. Very friendly and warm welcome from Mario and Cristina.. We had everything we needed at the apartment fantastic garden with Tommy the tortoise to greet us every morning! And we much appreciated the air con in the bedroom. w e thoroughly enjoyed every bit of our stay. We would certainly return and would recommend it to all friends and family. Thank you again Mario,Donella and Cristina.see more
Restored stone built villa near San Gimignano
Brilliant weeks holiday

We have had a great family holiday, two couples enjoying your fabulous house and views. Such a lot to see and do in the area, particularly enjoyed San Gimignano and Volterra, although sitting on your terrace takes a lot to beat. Your location is excellent as are your facilities. We also enjoyed the Vespa Museum in Pontedera, fascinating and free, combined with a visit to the beautiful town of Lari, a great day out. We will definitely return one day.see more
Casa Gelsomino, ground floor, 2 bedrooms, private garden and shared pool
Great apartment. Fantastic Tuscan hospitality.

My wife and I chose Casa Gelsomino because we were travelling with our 18-month old daughter and wanted to be in a location with amenities within walking distance. The hamlet of Castel San Gimignano itself is a sleepy one but offers a great little convenience store (run by twin sisters) just across the road from the apartment, a nice bar (opposite) and a lovely restaurant offering a variety of Tuscan/Italian cuisine. As for the apartment, located on the ground floor (we were able to park our car directly outside the front door) with a spacious lounge diner and a compact but well-equipped kitchen neatly tucked away behind double sliding doors. Beyond that, a utility room with a washing machine, a decent family bathroom (shower cubicle but no bathtub) and two bedrooms; one with a king size bed the other with a day bed that converts into two singles or a double. We used this room for our daughter and Carlo (owner) provided a travel cot and bedding as well as a highchair. Free wifi was provided also offering speeds of around 12Mbps download and around 1 Mbps upload. Not bad considering it's in such a rural setting. By far the biggest positive for us was the outdoor space. Beautifully manicured lawns and flowerbeds leading down to the private pool and then the olive groves and cherry orchards beyond, all expertly and meticulously tended to by Carlo's mother Anna and father Renzo. It has to be said at this point that these lovely people were so warm and friendly and couldn't do enough to make our stay as comfortable and relaxing as possible. Anna even went as far as picking fresh herbs for me to use in my ragu and Renzo picked a load of cherries for us also. Whilst the pool was spotlessly clean (maintained by Carlo daily) it isn't heated, and whilst it was bearable for us adults, it was a little too cold for our daughter despite the ambient temperature being in the mid-30's centigrade. Plenty of sun loungers and the views across the valley are spectacular, particularly at sundown enjoying a glass or two of Chianti. All in all, we had a most enjoyable week here whilst exploring the surrounding areas including Siena, San Gimignano and Volterra to name a few. A car is recommended if staying for longer than a few days. One recommendation I would make, is for a welcome pack to be offered (even at a small charge) including basic sundries like salt, pepper, sugar, olive oil, milk etc. as the last thing you want to do after a long journey is then thinking about going to the supermarket, especially with a toddler :-) In summary, the apartment was great but the hospitality was superb! Tantissimi grazie Carlo, Emanuela, Anna e Renzo!see more
Stunning farmhouse apartment located between Tuscan cities of San Gimignano and Volterra, shared pool, private garden, sleeps 6
Stunning accommodation in a fabulous location

Amazing apartment with everything you could need for a reaching haven after a busy day of sight seeing. The views are like paintings and the gardens are beautiful. Mary- Ann is a fabulous host, we had an amazing holiday. … see more
Podere Lo Spadino
Absolutely wonderful and picturesque!

We rented this beautiful house with two other couples for two weeks and absolutely loved our stay. Barbara and her family are gracious and kind hosts, always going our of their way to make our stay comfortable and enjoyable. The view of San Gimignano from the property is breathtaking. The pool is great for cooling off on a hot day! My wife and I hope to go back next year with our two children and grand kids!see more