Updating

Tell us your dates, and we will find the most accurate rates and availability for you

Updating

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

All filters

Filters

2,750 Holiday homes

Holiday b&b rental

Lecchi b&b

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £106 / night

£579 / week

1 / 16

Holiday apartment with swimming pool in Gaiole in Chianti

Gaiole in Chianti apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from £116 / night

£483 / week

1 / 13

Gaiole in Chianti holiday apartment rental

Gaiole in Chianti apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 3

from £290 / night

£1,310 / week

1 / 30

Holiday home with swimming pool in Gaiole in Chianti

Gaiole in Chianti house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 5

from £165 / night

£1,155 - £1,931 / week

1 / 42

Gaiole in Chianti holiday apartment rental

Gaiole in Chianti apartment

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 6

from £579 / night

£2,025 / week

1 / 38

Holiday apartment with shared pool in Gaiole in Chianti

Gaiole in Chianti apartment

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 7

from £579 / night

£1,890 / week

1 / 32

Gaiole in Chianti holiday home rental

Gaiole in Chianti house

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 8

from £598 / night

£3,651 - £4,867 / week

1 / 31

Holiday apartment in Nusenna

Nusenna apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from £135 / night

£945 / week

1 / 27

Home rental in Gaiole in Chianti

Gaiole in Chianti house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from £145 / night

£868 / week

1 / 19

Rietine holiday apartment rental

Rietine apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from £445 / night

£2,712 / week

1 / 23

Apartment rental in Rietine with shared pool

Rietine apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from £445 / night

£2,712 / week

1 / 21

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 £103 / night

£722 / week

1 / 24

Holiday manor house with swimming pool in Barbischio

Barbischio manor house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

from £129 / night

£898 / week

1 / 22

Gaiole in Chianti holiday home rental

Gaiole in Chianti house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 2

from £106 / night

£743 / week

1 / 20

Holiday villa in Gaiole in Chianti

Gaiole in Chianti villa

  • 5 bedrooms
  • 6 bathrooms
  • sleeps 13

“Idyllic stay in very comfortable, beautifully furnished house” Driving up to La Pratola you get a great view of the house as you climb the hill to it, but nothing could have prepared us for the amazing view back down the hill and across the valley from the infinity pool. Breathtaking. We were supplied with amazing food and service by a really sweet lady who looked after us well, whilst also discretely blending in, never making us feel self-conscious, and the maid service was excellent. Nearby Gaiole has all you could need, and is pretty, but Florence and Siena are wonderfully close by for a day trip. There are good walks and bike rides ( or runs) straight out from the house, but we just wanted to chill out by the pool or in the lovely courtyard most of the time. The Interior is very comfortably furnished to a high standard, with plenty of places for people to relax, so if you are in a big group it works well to go off and do you own thing for a while - the upstairs living room is great- huge squishy leather sofas and a big screen TV. We particularly enjoyed the pool table too. We weren't disappointed by La Pratola and would happily go back there again.

from £1,860 / night

£13,018 - £17,839 / week

1 / 71

Holiday home with swimming pool in Castagnoli

Castagnoli house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 9

from £312 / night

£2,182 - £3,554 / week

1 / 30

Gaiole in Chianti holiday apartment rental

Gaiole in Chianti apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 5

from £213 / night

£1,303 / week

1 / 11

Holiday apartment with shared pool in Gaiole in Chianti

Gaiole in Chianti apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £64 / night

£430 - £606 / week

1 / 20

Gaiole in Chianti holiday villa rental

Gaiole in Chianti villa

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 8

from £477 / night

£3,335 / week

1 / 32

Holiday apartment with shared pool in Gaiole in Chianti

Gaiole in Chianti apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £87 / night

£606 / week

1 / 22

Holiday villa rental

Gaiole in Chianti villa

  • 2 bedrooms
  • 4 bathrooms
  • sleeps 6

from £145 / night

£724 / week

1 / 32

Home rental in Castagnoli with shared pool

Castagnoli house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

from £96 / night

£674 - £2,064 / week

1 / 17

Home rental in Castagnoli with shared pool

Castagnoli house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

from £96 / night

£674 - £2,064 / week

1 / 18

Castagnoli holiday home rental

Castagnoli house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

from £96 / night

£674 - £2,064 / week

1 / 18

Holiday villa with swimming pool in Rietine

Rietine villa

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 12

from £705 / night

£4,937 / week

1 / 42

Holiday guest house in Montefienali

Montefienali guest house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

from £65 / night

£449 - £700 / week

1 / 21

Castagnoli holiday villa rental

Castagnoli villa

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 12

from £996 / night

£6,975 - £10,280 / week

1 / 30

Holiday villa with shared pool in Gaiole in Chianti

Gaiole in Chianti villa

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from £158 / night

£1,104 - £1,186 / week

1 / 33

Holiday apartment with shared pool in Gaiole in Chianti

Gaiole in Chianti apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

“Comfort and relaxation in Chianti” We enjoyed everything about Casacorvo. The view from the terrace is still in our minds weeks after we returned. Those beautiful rolling hills and the view over to Barbischio. Great pool which, in September was very quiet. We visited Siena, Florence, San Gimignano, Arezzo andthe wine festival at Greve in Chianti. Nice local wine left by Phil was much appreciated. The facilities in the Borgo were great. Gaiole is lovely and friendly and you don't have to go far to find nice meals and bars.

from £125 / night

£875 / week

1 / 52

Holiday apartment with shared pool in Gaiole in Chianti

Gaiole in Chianti apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

“We felt part of a Tuscan village” The Borgo di Gaoile in the Chianti region of Tuscany is a modern complex of apartments sympathetically set in a hillside adjacent to the town. The complex is, if not luxurious, then very well appointed with well designed and appointed flats containing varying numbers of bedrooms - ours had three (we were with friends). There was a swimming pool, which my wife liked, and I did a few workouts at the small but adequately equipped gym. The walk into town was about 5 - 10 minutes, where there were local shops, bars and restaurants; my wife and I felt very much part of the local culture and certainly the town's people were very friendly and hospitable. I won't go on any more, but just to say we found it a good location to explore the beautiful Tuscan region and taste the regional wine and food. Ciao!

from £200 / night

£1,400 / week

1 / 43

Gaiole in Chianti holiday home rental

Gaiole in Chianti house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £61 / night

£426 / week

1 / 11

Gaiole in Chianti holiday home rental

Gaiole in Chianti house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

from £75 / night

£520 / week

1 / 12

Gaiole in Chianti holiday home rental

Gaiole in Chianti house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

from £75 / night

£520 / week

1 / 12

Gaiole in Chianti holiday home rental

Gaiole in Chianti house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

from £75 / night

£520 / week

1 / 12

Holiday home in Gaiole in Chianti

Gaiole in Chianti house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

from £75 / night

£520 / week

1 / 15

Holiday home in Gaiole in Chianti

Gaiole in Chianti house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

from £75 / night

£520 / week

1 / 12

Holiday home rental

Gaiole in Chianti house

  • 5 bedrooms
  • 2 bathrooms
  • sleeps 10

from £203 / night

£1,418 / week

1 / 37

Gaiole in Chianti holiday villa rental

Gaiole in Chianti villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

from £234 / night

£1,482 - £2,760 / week

1 / 36

Holiday apartment with shared pool in Gaiole in Chianti

Gaiole in Chianti apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from £82 / night

£569 / week

1 / 12

Holiday villa in Nusenna

Nusenna villa

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from £181 / night

£1,263 / week

1 / 20

×

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
Casacorvo Minore *20% late Summer Discounts *Exclusive EV Point Included*
Very comfortable home away from home

Casacorvo Minore is a very comfortable apartment well located in the heart of Chianti. It has great views from its veranda which fostered perfect starts for each day as we had breakfast sitting in the morning sun. A glass or two in the afternoon was also most pleasant. It helped that the weather was great throughout our stay in Gaiole.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

Also consider