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

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5,890 Holiday homes

(55) 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
“Great Tuscan getaway” Azzurra is part of a relatively new apartment complex, consisting a number of apartments. Half of them are owned by Italians who are there mostly for the weekends. Azzurra is by far the best located apartment, with sun all day as well as amazing views over the Tuscan countryside. The apartment is very tastefully decorated and well equipped. Unfortunatley both TV and wifi did not work when we were there (wifi should be fixed by now). The amazing sunsets and a large enough (shared,unheated) pool as well as the lovely gardens made it a place where we really felt relaxed. We had the pool mostly for ourselves. A car was essential in order to gain access to the place and its surroundings. Access was via a 2 km dirt road which is about half an hour from both San Gimignano and Volterra. The remote location contributed to the countryside feeling and charm which we liked. We stayed with our one year old baby, which was fine. As there is limited space for children to run around we would not recommend it for children from 2-5. One thing to keep in mind is that there is only a portable airco unit in the apartment, which can cool just one bedroom at the same time. Even in July it tends to cool down at night, so we found it bearable even without airco. The booking process was smooth and owner Mary Ann made sure everything was according to expectations, also checking with us just after arrival. When we arrived we did not see anyone at check in which after a long drive was not ideal as finding the apartment and the safe with the key was not entirely clear from the instructions provided. This part of the process could be made more "user friendly".

from £175 / night

£913 - £1,445 / week

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Responds fast!
avg. 2 hours 1 minutes

from £175 / night

(19) Very Good 

Certificate of Excellence

19

San Gimignano holiday villa accommodation

Province of Siena / San Gimignano

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Nearest beach 30 km
  • Swimming pool
  • Child friendly

Certificate of Excellence

from £79 / night

£550 - £950 / week

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Responds fast!
avg. 3 hours 57 minutes

from £79 / night

(51) Excellent 

Certificate of Excellence

25

Holiday home with shared pool in San Gimignano

Province of Siena / San Gimignano

2 4 5 nights min

  • 2 bedrooms
  • sleeps 4
  • 5 nights min
  • Nearest beach 55 km
  • Swimming pool
  • Child friendly
“Wonderful accommodations in the spectacular Tuscan countryside.” Had a wonderful time at I'l Granario! The owner provided extremely accurate driving directions from Pisa Airport, as well as many helpful hints about things to do in the area. He was most responsive with the many questions I had prior to departure. The accommodations were practically new and the maid service was efficient and on time. The surrounding countryside was stunningly beautiful and quiet.

Certificate of Excellence

from £90 / night

£625 - £735 / week

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from £90 / night

(30) Excellent 

Certificate of Excellence

127

Cottage rental in Pancole

San Gimignano / Pancole

1 3 min stay varies

  • 1 bedroom
  • sleeps 3
  • min stay varies
  • Nearest beach 90 km
  • Child friendly
  • Air conditioning

Certificate of Excellence

from £45 / night

£298 - £329 / week

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Responds fast!
avg. 38 minutes

from £45 / 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 £63 / night

£400 / week

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from £63 / night

(3) Very Good 

28

Holiday apartment with shared pool in Ulignano

San Gimignano / Ulignano

2 6 2 nights min

  • 2 bedrooms
  • sleeps 6
  • 2 nights min
  • Swimming pool
  • Child friendly

from £107 / night

£622 / week

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from £107 / night

(25) Excellent 

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

from £54 / night

£374 / week

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Responds fast!
avg. 55 minutes

from £54 / night

(2) 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

from £71 / night

£489 - £1,022 / week

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from £71 / night

(2) Excellent 

99

Holiday villa with shared pool in San Gimignano

Province of Siena / San Gimignano

1 4 3 nights min

  • 1 bedroom
  • sleeps 4
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

from £111 / night

£702 - £756 / week

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from £111 / night

(20) Very Good 

17

Holiday apartment with shared pool in San Gimignano

Province of Siena / San Gimignano

2 4 3 nights min

  • 2 bedrooms
  • sleeps 4
  • 3 nights min
  • Beach / lakeside relaxation
  • Nearest beach 55 km
  • Swimming pool
“Perfect. The peace and tranquility of the place seeps into your bones” This apartment is lovely. The location is unbelievable - don't be put off by the drive from the main road - it's worth it when you arrive. The views of the Tuscan countryside from every angle are breathtaking.

from £85 / night

£595 / week

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Responds fast!
avg. 1 hour 48 minutes

from £85 / night

(2) Very Good 

10

San Gimignano holiday apartment rental

Province of Siena / San Gimignano

2 4 1 night min

  • 2 bedrooms
  • sleeps 4
  • 1 night min
  • Nearest beach 75 km
  • Child friendly
  • Pet friendly

from £58 / night

£405 / week

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Responds fast!
avg. 3 hours 19 minutes

from £58 / night

(26) 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

from £178 / night

£1,599 - £3,019 / week

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Responds fast!
avg. 3 hours 57 minutes

from £178 / night

(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 £134 / night

£889 - £2,133 / week

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Responds fast!
avg. 1 hour 6 minutes

from £134 / night

43

San Gimignano holiday b&b accommodation

Province of Siena / San Gimignano

1 2 1 night min

  • 1 bedroom
  • sleeps 2
  • 1 night min
  • Child friendly
  • Pet friendly
  • Private garden

from £49 / night

£342 / week

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from £49 / night

(6) Very Good 

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

from £112 / night

£579 - £748 / week

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from £112 / night

(2) Very Good 

29

San Gimignano holiday apartment rental

Province of Siena / San Gimignano

3 7 min stay varies

  • 3 bedrooms
  • sleeps 7
  • min stay varies
  • Nearest beach 80 km
  • Swimming pool
  • Child friendly

from £147 / night

£978 - £1,955 / week

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from £147 / night

(2) Excellent 

80

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

San Gimignano / Castel San Gimignano

3 7 min stay varies

  • 3 bedrooms
  • sleeps 7
  • min stay varies
  • Nearest beach 70 km
  • Swimming pool
  • Child friendly

from £160 / night

£1,067 - £2,044 / week

Book View

from £160 / night

(14) Excellent 

Certificate of Excellence

14

Castel San Gimignano holiday apartment rental

San Gimignano / Castel San Gimignano

3 5 3 nights min

  • 3 bedrooms
  • sleeps 5
  • 3 nights min
  • Nearest beach 55 km
  • Child friendly
  • Ask about pets

Certificate of Excellence

from £89 / night

£356 - £667 / week

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Responds fast!
avg. 1 hour 20 minutes

from £89 / night

59

Holiday villa in San Gimignano

Province of Siena / San Gimignano

3 8 4 nights min

  • 3 bedrooms
  • sleeps 8
  • 4 nights min
  • Nearest beach 90 km
  • Child friendly
  • Car not necessary

from £187 / night

£1,307 / week

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from £187 / 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 £85 / night

£591 / week

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from £85 / night

(37) Excellent 

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

from £89 / night

£356 - £401 / week

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Responds fast!
avg. 1 hour 20 minutes

from £89 / night

(23) 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

from £56 / night

£320 / week

Book View

from £56 / night

(21) Very Good 

Certificate of Excellence

32

Holiday farmhouse with shared pool in San Gimignano

Province of Siena / San Gimignano

2 5 2 nights min

  • 2 bedrooms
  • sleeps 5
  • 2 nights min
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly

Certificate of Excellence

from £103 / night

£716 / week

Book View

Responds fast!
avg. 3 hours 47 minutes

from £103 / night

(1) Very Good 

39

Farmhouse rental in Castel San Gimignano with shared pool

San Gimignano / Castel San Gimignano

3 7 min stay varies

  • 3 bedrooms
  • sleeps 7
  • min stay varies
  • Nearest beach 70 km
  • Swimming pool
  • Child friendly

from £147 / night

£978 - £1,955 / week

Book View

from £147 / night

(4) Excellent 

16

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

from £65 / night

£440 - £978 / week

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from £65 / night

(1) Very Good 

9

Holiday apartment rental

San Gimignano / Larniano

1 4 7 nights min

  • 1 bedroom
  • sleeps 4
  • 7 nights min
  • Child friendly

from £83 / night

£578 / week

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from £83 / night

(1) Very Good 

57

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

San Gimignano / Castel San Gimignano

3 7 min stay varies

  • 3 bedrooms
  • sleeps 7
  • min stay varies
  • Nearest beach 80 km
  • Swimming pool
  • Child friendly

from £147 / night

£978 - £1,955 / week

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from £147 / night

18

Ulignano holiday finca rental

San Gimignano / Ulignano

2 4 5 nights min

  • 2 bedrooms
  • sleeps 4
  • 5 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

from £116 / night

£791 / week

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from £116 / night

(6) Very Good 

23

Apartment rental in San Gimignano

Province of Siena / San Gimignano

2 5 3 nights min

  • 2 bedrooms
  • sleeps 5
  • 3 nights min
  • Nearest beach 72 km
  • Child friendly
  • Private garden

from £103 / night

£578 / week

Book View

from £103 / night

(8) Very Good 

28

Holiday farmhouse with shared pool in San Gimignano

Province of Siena / San Gimignano

1 2 4 nights min

  • 1 bedroom
  • sleeps 2
  • 4 nights min
  • Nearest beach 80 km
  • Swimming pool
  • Child friendly

from £80 / night

£560 / week

Book View

from £80 / night

(4) Very Good 

20

Holiday apartment rental

Province of Siena / San Gimignano

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Child friendly
  • Ask about pets

from £170 / night

£892 - £1,470 / week

Book View

from £170 / 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 £98 / night

£684 / week

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Responds fast!
avg. 2 hours 10 minutes

from £98 / night

(4) Excellent 

7

San Gimignano holiday apartment rental

Province of Siena / San Gimignano

2 4 1 night min

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

from £54 / night

£374 / week

Book View

Responds fast!
avg. 3 hours 19 minutes

from £54 / night

(6) Very Good 

8

Condo rental in San Gimignano

Province of Siena / San Gimignano

2 5 1 night min

  • 2 bedrooms
  • sleeps 5
  • 1 night min
  • Nearest beach 80 km
  • Car not necessary

from £116 / night

£809 / week

Book View

Responds fast!
avg. 1 hour 24 minutes

from £116 / night

(1) Excellent 

7

San Gimignano holiday b&b rental

Province of Siena / San Gimignano

1 2 2 nights min

  • 1 bedroom
  • sleeps 2
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets

from £116 / night

£746 / week

Book View

from £116 / night

(13) Excellent 

Certificate of Excellence

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

Certificate of Excellence

from £65 / night

£455 / week

Book View

Responds fast!
avg. 3 hours 47 minutes

from £65 / night

8

Holiday apartment with shared pool in San Gimignano

Province of Siena / San Gimignano

1 5 2 nights min

  • 1 bedroom
  • sleeps 5
  • 2 nights min
  • Beach / lakeside relaxation
  • Nearest beach 80 km
  • Swimming pool

from £125 / night

£845 / week

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from £125 / night

17

San Gimignano holiday b&b rental

Province of Siena / San Gimignano

1 2 5 nights min

  • 1 bedroom
  • sleeps 2
  • 5 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

from £81 / night

£526 / week

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from £81 / night

(17) Excellent 

32

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

from £356 / night

£1,689 - £3,289 / week

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Responds fast!
avg. 3 hours 57 minutes

from £356 / night

(7) Very Good 

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 £214 / night

£1,825 / week

Book View

Responds fast!
avg. 1 hour 25 minutes

from £214 / night

Top Destination reviews

Bright and Spacious Apartment in the heart of town
Wonderful apartment in San Gimignano

We had a wonderful and great time in San Gimignano. Stefania is really a very dedicated, courteous and friendly host! The apartment and its furniture was very, very clean, what was more than comfortable (we have already seen other things in Rome…). The site of the apartment was really quiet, the balcony convenient in the evening for having diner outside. We don’t have one thing to criticize and recommend this apartment without any exceptions! Thank you, Stefania, for everything and also for the fine bottle of wine which we got on the first day of our arrival!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
VILLA DEL GRILLO
Loved it!

I am so happy I came and stayed here. I loved every moment. The entire family is wonderful and made me feel at home. Each one is so helpful and genuinely kind. It's a lovely setting on a farm and I enjoyed hearing the rooster and chickens, smelling the good air, meditating, writing and sleeping like a baby. The wifi is good, which was important for my work and the cottage is a classic Tuscany style with adorable touches inside. Really, it was perfect! I loved it so much that I will be back for sure. Thank you Giovanni and Sylvia!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
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