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

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Gaiole in Chianti

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5,951 Holiday homes

(7) Very Good 

43

Montefienali holiday home accommodation

Gaiole in Chianti / Montefienali

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly

from £48 / night

£278 - £668 / week

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Responds fast!
avg. 1 hour 32 minutes

from £48 / night

(16) Excellent 

22

Holiday apartment with shared pool in Gaiole in Chianti

Province of Siena / Gaiole in Chianti

1 4 min stay varies

  • 1 bedroom
  • sleeps 4
  • min stay varies
  • Nearest beach 80 km
  • Swimming pool
  • Child friendly
“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 £110 / night

£560 - £760 / week

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from £110 / night

18

Gaiole in Chianti holiday condo rental

Province of Siena / Gaiole in Chianti

3 5 1 night min

  • 3 bedrooms
  • sleeps 5
  • 1 night min
  • Child friendly
  • Pet friendly
  • Private garden

from £49 / night

£321 / week

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from £49 / night

(4) Excellent 

28

Gaiole in Chianti holiday barn let

Province of Siena / Gaiole in Chianti

2 4 2 nights min

  • 2 bedrooms
  • sleeps 4
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly

from £98 / night

£624 / week

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from £98 / night

(13) Excellent 

24

Holiday apartment with shared pool in Gaiole in Chianti

Province of Siena / Gaiole in Chianti

3 8 min stay varies

  • 3 bedrooms
  • sleeps 8
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“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 £175 / night

£1,100 - £1,600 / week

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from £175 / night

23

Holiday home with shared pool in Gaiole in Chianti

Province of Siena / Gaiole in Chianti

3 7 7 nights min

  • 3 bedrooms
  • sleeps 7
  • 7 nights min
  • Swimming pool
  • Child friendly

from £245 / night

£1,603 - £1,728 / week

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from £245 / night

(6) Very Good 

23

Holiday apartment with shared pool in Gaiole in Chianti

Province of Siena / Gaiole in Chianti

2 6 7 nights min

  • 2 bedrooms
  • sleeps 6
  • 7 nights min
  • Nearest beach 0 km
  • Swimming pool
  • Child friendly

from £150 / night

£600 / week

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Responds fast!
avg. 3 hours 27 minutes

from £150 / night

18

Villa rental in Gaiole in Chianti with swimming pool

Province of Siena / Gaiole in Chianti

4 9 min stay varies

  • 4 bedrooms
  • sleeps 9
  • min stay varies
  • Swimming pool
  • Suitable for children age 5+
  • Ask about pets

from £147 / night

£1,029 / week

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from £147 / night

(7) Very Good 

20

Apartment accommodation in Gaiole in Chianti with shared pool

Province of Siena / Gaiole in Chianti

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

from £70 / night

£500 - £700 / week

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from £70 / night

(39) Excellent 

24

Gaiole in Chianti holiday apartment accommodation

Province of Siena / Gaiole in Chianti

1 2 min stay varies

  • 1 bedroom
  • sleeps 2
  • min stay varies
  • Swimming pool
  • Air conditioning
  • Private garden
“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 £90 / night

£630 / week

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Responds fast!
avg. 1 hour 49 minutes

from £90 / night

15

Gaiole in Chianti holiday farmhouse rental

Province of Siena / Gaiole in Chianti

9 22 1 night min

  • 9 bedrooms
  • sleeps 22
  • 1 night min
  • Child friendly
  • Private garden

from £68 / night

£446 / week

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from £68 / night

(2) Average 

23

Lecchi holiday apartment rental

Gaiole in Chianti / Lecchi

2 5 3 nights min

  • 2 bedrooms
  • sleeps 5
  • 3 nights min
  • Swimming pool
  • Suitable for children age 5+
  • Pet friendly

from £89 / night

£508 - £650 / week

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Responds fast!
avg. 2 hours 15 minutes

from £89 / night

(2) Very Good 

13

Holiday apartment with swimming pool in Gaiole in Chianti

Province of Siena / Gaiole in Chianti

2 4 1 night min

  • 2 bedrooms
  • sleeps 4
  • 1 night min
  • Swimming pool
  • Child friendly
  • Air conditioning

from £45 / night

£312 - £561 / week

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from £45 / night

(4) Excellent 

17

Holiday villa rental

Province of Siena / Gaiole in Chianti

2 6 1 night min

  • 2 bedrooms
  • sleeps 6
  • 1 night min
  • Nearest beach 110 km
  • Swimming pool
  • Child friendly

from £107 / night

£532 / week

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Responds fast!
avg. 1 hour 53 minutes

from £107 / night

(2) Excellent 

45

Holiday farmhouse with swimming pool in Gaiole in Chianti

Province of Siena / Gaiole in Chianti

3 7 min stay varies

  • 3 bedrooms
  • sleeps 7
  • min stay varies
  • Nearest beach 75 km
  • Swimming pool
  • Child friendly

from £191 / night

£1,536 - £2,048 / week

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from £191 / night

24

Holiday apartment in Gaiole in Chianti

Province of Siena / Gaiole in Chianti

2 5 7 nights min

  • 2 bedrooms
  • sleeps 5
  • 7 nights min
  • Nearest beach 107 km
  • Swimming pool
  • Child friendly

from £53 / night

£365 - £783 / week

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from £53 / night

21

Holiday apartment with shared pool in Gaiole in Chianti

Province of Siena / Gaiole in Chianti

2 5 3 nights min

  • 2 bedrooms
  • sleeps 5
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly

from £112 / night

£713 - £793 / week

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Responds fast!
avg. 2 hours 15 minutes

from £112 / night

24

Holiday apartment with shared pool in Gaiole in Chianti

Province of Siena / Gaiole in Chianti

2 4 7 nights min

  • 2 bedrooms
  • sleeps 4
  • 7 nights min
  • Nearest beach 125 km
  • Swimming pool
  • Child friendly

from £143 / night

£998 / week

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from £143 / night

100

Gaiole in Chianti holiday villa rental

Province of Siena / Gaiole in Chianti

4 8 7 nights min

  • 4 bedrooms
  • sleeps 8
  • 7 nights min
  • Nearest beach 130 km
  • Swimming pool
  • Child friendly

from £407 / night

£2,850 - £4,186 / week

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from £407 / night

(12) Excellent 

70

Holiday villa with swimming pool, tennis court in Gaiole in Chianti

Province of Siena / Gaiole in Chianti

4 10 7 nights min

  • 4 bedrooms
  • sleeps 10
  • 7 nights min
  • Nearest beach 110 km
  • Swimming pool
  • Child friendly
“Excellent, spacious accommodation with a fantastic pool and view.” Very good, clear communication with the owner. Spacious, clean property Wonderful pool About 2 miles from villa to nearest village with bar, restaurant and small store Character property with high ceilings and lots of room Keeps cool indoors

from £464 / night

£1,283 - £4,996 / week

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from £464 / night

6

Gaiole in Chianti holiday farmhouse rental

Province of Siena / Gaiole in Chianti

2 2 3 nights min

  • 2 bedrooms
  • sleeps 2
  • 3 nights min
  • Nearest beach 127 km
  • Child friendly
  • Pet friendly

from £76 / night

£508 - £544 / week

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from £76 / night

(1) Average 

25

Lecchi holiday apartment rental

Gaiole in Chianti / Lecchi

2 5 3 nights min

  • 2 bedrooms
  • sleeps 5
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly

from £98 / night

£561 - £713 / week

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Responds fast!
avg. 2 hours 15 minutes

from £98 / night

(1) Excellent 

20

Gaiole in Chianti holiday apartment rental

Province of Siena / Gaiole in Chianti

1 3 7 nights min

  • 1 bedroom
  • sleeps 3
  • 7 nights min
  • Nearest beach 105 km
  • Swimming pool
  • Child friendly

from £50 / night

£348 - £656 / week

Enquire View

from £50 / night

22

Holiday apartment with shared pool in Gaiole in Chianti

Province of Siena / Gaiole in Chianti

1 3 7 nights min

  • 1 bedroom
  • sleeps 3
  • 7 nights min
  • Nearest beach 107 km
  • Swimming pool
  • Child friendly

from £50 / night

£348 - £379 / week

Enquire View

from £50 / night

(6) Excellent 

26

Holiday apartment with shared pool in Gaiole in Chianti

Province of Siena / Gaiole in Chianti

2 6 7 nights min

  • 2 bedrooms
  • sleeps 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

from £88 / night

£615 - £975 / week

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Responds fast!
avg. 1 hour 36 minutes

from £88 / night

23

Holiday apartment with shared pool in Gaiole in Chianti

Province of Siena / Gaiole in Chianti

2 5 3 nights min

  • 2 bedrooms
  • sleeps 5
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly

from £112 / night

£713 - £793 / week

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Responds fast!
avg. 2 hours 15 minutes

from £112 / night

22

Holiday apartment with shared pool in Gaiole in Chianti

Province of Siena / Gaiole in Chianti

1 4 7 nights min

  • 1 bedroom
  • sleeps 4
  • 7 nights min
  • Nearest beach 105 km
  • Swimming pool
  • Child friendly

from £50 / night

£348 - £731 / week

Enquire View

from £50 / night

24

Holiday apartment with shared pool in Gaiole in Chianti

Province of Siena / Gaiole in Chianti

2 6 7 nights min

  • 2 bedrooms
  • sleeps 6
  • 7 nights min
  • Nearest beach 105 km
  • Swimming pool
  • Suitable for children age 5+

from £63 / night

£437 - £905 / week

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from £63 / night

(13) Excellent 

4

Holiday villa with indoor pool, golf nearby in Montefienali

Gaiole in Chianti / Montefienali

7 16 7 nights min

  • 7 bedrooms
  • sleeps 16
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

from £1,479 / night

£10,348 / week

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Responds fast!
avg. 2 hours 43 minutes

from £1,479 / night

(14) Very Good 

37

Holiday villa with swimming pool, tennis court in Gaiole in Chianti

Province of Siena / Gaiole in Chianti

2 6 7 nights min

  • 2 bedrooms
  • sleeps 6
  • 7 nights min
  • Nearest beach 110 km
  • Swimming pool
  • Child friendly

from £184 / night

£1,283 - £2,138 / week

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from £184 / night

(1) Very Good 

15

Gaiole in Chianti holiday home rental

Province of Siena / Gaiole in Chianti

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Child friendly

from £67 / night

£428 - £577 / week

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from £67 / night

24

Holiday apartment with shared pool in Gaiole in Chianti

Province of Siena / Gaiole in Chianti

1 3 7 nights min

  • 1 bedroom
  • sleeps 3
  • 7 nights min
  • Nearest beach 105 km
  • Swimming pool
  • Child friendly

from £50 / night

£346 - £653 / week

Enquire View

from £50 / night

11

Gaiole in Chianti holiday apartment rental

Province of Siena / Gaiole in Chianti

3 5 1 night min

  • 3 bedrooms
  • sleeps 5
  • 1 night min
  • Swimming pool
  • Child friendly
  • Pet friendly

from £196 / night

£1,203 / week

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from £196 / night

21

Holiday apartment with shared pool in Gaiole in Chianti

Province of Siena / Gaiole in Chianti

1 3 7 nights min

  • 1 bedroom
  • sleeps 3
  • 7 nights min
  • Nearest beach 107 km
  • Swimming pool
  • Child friendly

from £50 / night

£346 - £377 / week

Enquire View

from £50 / night

(3) Average 

12

Holiday apartment with shared pool in Gaiole in Chianti

Province of Siena / Gaiole in Chianti

1 2 7 nights min

  • 1 bedroom
  • sleeps 2
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly

from £75 / night

£526 / week

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from £75 / night

19

Holiday cottage with shared pool in Lecchi

Gaiole in Chianti / Lecchi

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Swimming pool
  • Suitable for children age 5+
  • Ask about pets

from £85 / night

£597 - £926 / week

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from £85 / night

7

Holiday apartment in Gaiole in Chianti

Province of Siena / Gaiole in Chianti

2 6 3 nights min

  • 2 bedrooms
  • sleeps 6
  • 3 nights min
  • Child friendly
  • Pet friendly
  • Private garden

from £121 / night

£824 - £846 / week

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from £121 / night

38

Holiday home in Gaiole in Chianti

Province of Siena / Gaiole in Chianti

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Child friendly
  • Private garden

from £124 / night

£867 / week

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from £124 / night

(1) Excellent 

24

Holiday apartment with shared pool in Gaiole in Chianti

Province of Siena / Gaiole in Chianti

4 10 min stay varies

  • 4 bedrooms
  • sleeps 10
  • min stay varies
  • Nearest beach 80 km
  • Swimming pool
  • Child friendly

from £300 / night

£1,500 - £2,000 / week

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from £300 / night

44

Holiday home with shared pool in Gaiole in Chianti

Province of Siena / Gaiole in Chianti

3 7 7 nights min

  • 3 bedrooms
  • sleeps 7
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Private garden

from £100 / night

£695 - £1,229 / week

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from £100 / night

Top Destination reviews

LUXURY APARTMENT WITH PRIVATE GARDEN & VIEWS
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
Casacorvo Minore *2018 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
Experience the "Chiantishire" at LisiDor - September is at 25% OFF!
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
Cottage with pool for 2 couples - Interesting promotions for late Summer weeks..
Villa PetrAlexa - excellent leisure facility

This years stay was even better than our stay last year. Despite the fact we arrived late at night due to repeated traffic jams on the motorway because of terrible weather conditions, everything was perfectly prepared. The house was heated up and food and beverage was available (from the region of course). Everything was clean and tidy. We had great fun during hiking and cycling and enjoyed ourselves in one of the best places in Tuscany. We again had a great time and our next stay is already booked.see more
Villa Podere Earthly
Perfect, beautifil little place in tuscany

A beautiful place full of happines, were you can stay The time you want for a very very good price ,there's a beautiful view, is very relaxing and you can enjoy The animals and nature … see 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