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Villas in Gaiole in Chianti and Apartments – Holiday Lettings - Holiday Rentals Gaiole in Chianti

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48 Holiday homes

Holiday b&b rental

Lecchi b&b

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £108 / night

£585 / week

1 / 16

Holiday villa rental

Gaiole in Chianti villa

  • 2 bedrooms
  • 4 bathrooms
  • sleeps 6

from £215 / night

£1,502 / week

1 / 40

Holiday home with swimming pool in Gaiole in Chianti

Gaiole in Chianti house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 5

from £167 / night

£1,953 / week

1 / 42

Gaiole in Chianti holiday home rental

Gaiole in Chianti house

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 8

from £1,021 / night

£6,232 / week

1 / 31

Gaiole in Chianti holiday home rental

Gaiole in Chianti house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 2

from £108 / night

£751 / week

1 / 20

Holiday apartment in Nusenna

Nusenna apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from £176 / night

£1,229 / week

1 / 27

Holiday apartment with shared pool in Nusenna

Nusenna apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

from £156 / night

£1,092 / week

1 / 29

Rietine holiday apartment rental

Rietine apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from £450 / night

£2,743 / week

1 / 23

Apartment rental in Rietine with shared pool

Rietine apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from £450 / night

£2,743 / week

1 / 21

Holiday apartment with shared pool in Rietine

Rietine apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from £536 / night

£3,271 / week

1 / 29

Holiday home with swimming pool in Gaiole in Chianti

Gaiole in Chianti house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

from £781 / night

£4,875 - £6,828 / week

1 / 42

Gaiole in Chianti holiday apartment rental

Gaiole in Chianti apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 5

from £215 / night

£1,318 / week

1 / 11

Gaiole in Chianti holiday apartment rental

Gaiole in Chianti apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 3

from £198 / night

£1,366 - £2,185 / week

1 / 30

Gaiole in Chianti holiday apartment rental

Gaiole in Chianti apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 5

from £333 / night

£2,124 - £3,414 / week

1 / 35

Gaiole in Chianti holiday villa rental

Gaiole in Chianti villa

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 8

from £506 / night

£3,537 / week

1 / 32

Gaiole in Chianti holiday apartment rental

Gaiole in Chianti apartment

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 6

from £333 / night

£2,124 - £3,414 / week

1 / 38

Holiday guest house in Montefienali

Montefienali guest house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

from £66 / night

£454 / week

1 / 21

Holiday apartment with shared pool in Gaiole in Chianti

Gaiole in Chianti apartment

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 7

from £307 / night

£1,974 - £4,097 / week

1 / 32

Gaiole in Chianti holiday villa rental

Gaiole in Chianti villa

  • 6 bedrooms
  • 4 bathrooms
  • sleeps 12

from £603 / night

£4,220 / week

1 / 49

Holiday manor house with swimming pool in Barbischio

Barbischio manor house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

from £130 / night

£908 / week

1 / 22

Holiday villa in Nusenna

Nusenna villa

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from £234 / night

£1,638 / week

1 / 20

Castagnoli holiday villa rental

Castagnoli villa

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 12

from £1,216 / night

£8,510 - £10,520 / week

1 / 30

Gaiole in Chianti holiday villa rental

Gaiole in Chianti villa

  • 10 bedrooms
  • 7 bathrooms
  • sleeps 20

from £1,226 / night

£8,579 / week

1 / 42

Gaiole in Chianti holiday villa rental

Gaiole in Chianti villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

from £250 / night

£1,584 - £2,793 / week

1 / 36

Holiday apartment with shared pool in Gaiole in Chianti

Gaiole in Chianti apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £83 / night

£576 / week

1 / 12

Gaiole in Chianti holiday apartment accommodation

Gaiole in Chianti apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

“Fantastic stay in a beautiful setting” Have just returned from a week stay in Gaiole in Chianti following l'eroica and everything you hear and read about the region is true - it really is idyllic and a perfect place to relax, visit local villages, cycle or walk around. Siena, which is equally stunning, is also barely 30 minutes away. The apartment is perfectly located with stunning views overlooking the village - it was great to sit out in the private garden in the morning and at sunset and just relax. However this wasn't at the expense of being away from the centre of the village and the amenities - it was not even a 5 minute walk to the deli, butcher etc. (and only 3 minutes to the local takeaway pizza - I timed it!). The apartment itself is very well appointed with seemingly everything thought of - there were even umbrellas that we could use when there was rain one morning. The 'borgo' also has a swimming pool and gym as well as plenty of parking nearby. From the initial booking, John and Tracy made everything very easy and the service was simple and hassle free. - we'd definitely go again!

from £92 / night

£642 / week

1 / 24

Apartment accommodation in Gaiole in Chianti with shared pool

Gaiole in Chianti apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

from £86 / night

£573 / week

1 / 20

Gaiole in Chianti holiday apartment rental

Gaiole in Chianti apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from £137 / night

£956 / week

1 / 31

Gaiole in Chianti holiday villa rental

Gaiole in Chianti villa

  • 7 bedrooms
  • 6 bathrooms
  • sleeps 14

from £614 / night

£3,319 - £5,524 / week

1 / 46

Holiday villa in Gaiole in Chianti

Gaiole in Chianti villa

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

from £606 / night

£4,240 / week

1 / 48

Holiday apartment with swimming pool in Gaiole in Chianti

Gaiole in Chianti apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from £117 / night

£488 / week

1 / 13

Nusenna holiday villa rental

Nusenna villa

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

from £546 / night

£3,822 / week

1 / 38

Nusenna holiday villa rental

Nusenna villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from £351 / night

£2,457 / week

1 / 29

Holiday home in Gaiole in Chianti

Gaiole in Chianti house

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 8

from £558 / night

£3,900 / week

1 / 7

Holiday villa in Gaiole in Chianti

Gaiole in Chianti villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 7

from £536 / night

£3,414 - £4,643 / week

1 / 36

Holiday townhouse in Gaiole in Chianti

Gaiole in Chianti townhouse

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 4

from £195 / night

£1,365 / week

1 / 4

Holiday villa in Gaiole in Chianti

Gaiole in Chianti villa

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

from £460 / night

£3,218 / week

1 / 62

Holiday villa with shared pool in Gaiole in Chianti

Gaiole in Chianti villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

from £147 / night

£1,024 / week

1 / 48

Villa rental in Gaiole in Chianti with swimming pool

Gaiole in Chianti villa

  • 7 bedrooms
  • 4 bathrooms
  • sleeps 14

from £605 / night

£4,232 / week

1 / 30

Holiday home with shared pool in Gaiole in Chianti

Gaiole in Chianti house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

from £147 / night

£951 / week

1 / 21

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Top Destination reviews

LUXURY APARTMENT WITH PRIVATE GARDEN & VIEWS IDEAL FOR COUPLES
Peaceful Retreat

We stayed here for 3 weeks and found this location very central to the entire Chianti region. Heaps to do and see, great accommodation, the unit was extremely well appointed and the pool was a "God-send" especially when temperatures exceeded 45 deg C. Mosquitoes made their unwelcome presence known, their numbers may however diminish as the family of frogs in the garden increases over time. Underground parking was great too helping the car to stay cool. We really appreciated the extent of information available in the compendium which included clear instructuctions on how best to get to various places such as Siena and Firenze. We have to also endorse John's favourite restaurant, Ristorante Il Celliere a Castagnoli. Superb doesn't begin to describe our experience there!!! The locals of Gaiole In Chianti made us feel welcome, especially "Papa" at Tutte Birra. Thanks to John and Tracy for your hospitality.see more
Casa Felice is a 2 bedroom apartment in village of Gaiole, sleeps 6, shared pool
Great Location in heart of Tuscany

We had a lovely stay in Case Felice. Well equipped apartment with fantastic views. The Borgo complex was perfect, we enjoyed a swim most days. The village is about 5 mins walk away with plenty of restaurants and a local co-op. We visited Florence (park on outskirts and got the tram in), Siena (our favourite), Pisa, Monteriggioni, San Gimignano (gets very busy, go early or later in afternoon), Radda and Panzano (recommend MacDarios for an excellent burger!)see more
Private secluded retreat in the Chianti hills between Siena and Florence
A hidden gem.

We stayed at Villa LisiDor at the end of May with family. We made the trip to Tuscany by train to Florence from the UK and hired a car from there. We arrived during an unseasonably chilly spell and in torrential rain after a very long journey. Stopping at the Co-op in Radda in Chianti to collect supplies it was a relief to arrive at the villa and chill out. We were met by a charming old gent and despite his lack of English and our lack of Italian we were able to get by with sign language to get some wood for the fire. The main room in the villa is like a baronial hall with a huge inglenook fireplace and long banqueting table. The kitchen is well equipped and the bedrooms are simply furnished and comfortable. A favourite room was the small studio that catches the morning sun. It was too chilly for the pool but we enjoyed a few evenings watching the sun setting over the vineyards. There is an outside kitchen area with dining table and pizza oven which in warmer weather we'd definitely have used. The villa is in a very rural setting but just a short drive to Radda or other local towns and villages. We enjoyed after dinner walks along the track through the vineyards. Very quiet and peaceful if you're looking to get away from it all.see more
Barn overlooking the vineyards
Great stay!

We had an absolutely fantastic stay at this beautiful barn in the Tuscan hills. The views are lovely and if you want somewhere a bit more out of the way this is perfect. We were greeted at the property by Edoardo even though we were late arriving - there was some food for us to use which was brilliant. Edoardo was around if you needed him but otherwise left you to enjoy the holiday! Lying in the hot tub in the evenings- perfect! Many thanks, we would like to revisit this lovely part of Italy! Stevesee more
A HOLIDAY IN THE HEART OF CHIANTI
Authentic unspoiled Italian charm!

My family and I stayed at this beautiful property and had a relaxed and wonderful holiday. Gaiole in Chianti is a small village totally unspoilt by tourism and the location of this property is ideal if you hire a car and travel to all the surroundings various attractions. It is a home from home with everything you could possibly want in a holiday home. The pool is big enough for swimming and both Donatella and her husband were warm, friendly and very helpful. I would highly recommend this property as it is also very secure with entry gates into the property. Tuscany is stunning and a joy to explore the area from this location.see more

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