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

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5,688 Holiday homes

(6) Excellent 

29

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 £109 / night

£758 - £1,106 / week

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Responds fast!
avg. 1 hour 42 minutes

from £109 / night

(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 £55 / night

£316 / week

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Responds fast!
avg. 1 hour 42 minutes

from £55 / night

(3) 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 £112 / night

£707 / week

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from £112 / night

(8) Excellent 

20

Apartment accommodation in Gaiole in Chianti with shared pool

Province of Siena / Gaiole in Chianti

2 6 2 nights min

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

from £81 / night

£573 / week

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from £81 / 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

£344 - £375 / week

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from £50 / night

(14) Excellent 

34

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

from £180 / night

£1,200 - £1,600 / week

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from £180 / 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 £278 / night

£1,819 - £1,960 / week

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from £278 / 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 £137 / night

£939 / week

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from £137 / night

(14) Very Good 

39

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

Province of Siena / Gaiole in Chianti

2 5 7 nights min

  • 2 bedrooms
  • sleeps 5
  • 7 nights min
  • Nearest beach 110 km
  • Swimming pool
  • Child friendly

from £208 / night

£1,455 - £2,425 / week

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Responds fast!
avg. 3 hours 59 minutes

from £208 / night

(1) Excellent 

4

Holiday b&b in Gaiole in Chianti

Province of Siena / Gaiole in Chianti

1 2 1 night min

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

from £89 / night

£606 / week

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from £89 / 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 £113 / night

£788 / week

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from £113 / night

29

Gaiole in Chianti holiday home rental

Province of Siena / Gaiole in Chianti

1 2 7 nights min

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

from £79 / night

£551 / week

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from £79 / night

(18) Excellent 

33

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

from £110 / night

£560 - £775 / week

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from £110 / 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 £51 / night

£354 - £814 / week

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from £51 / night

(1) Excellent 

22

Holiday farmhouse in Montegrossi

Gaiole in Chianti / Montegrossi

5 10 5 nights min

  • 5 bedrooms
  • sleeps 10
  • 5 nights min
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly

from £152 / night

£4,041 / week

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from £152 / night

(13) Excellent 

69

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

Province of Siena / Gaiole in Chianti

4 10 min stay varies

  • 4 bedrooms
  • sleeps 10
  • min stay varies
  • Nearest beach 110 km
  • Swimming pool
  • Child friendly

from £527 / night

£3,349 - £5,667 / week

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Responds fast!
avg. 3 hours 59 minutes

from £527 / night

(4) Excellent 

21

Holiday villa rental

Province of Siena / Gaiole in Chianti

2 7 min stay varies

  • 2 bedrooms
  • sleeps 7
  • min stay varies
  • Nearest beach 110 km
  • Swimming pool
  • Child friendly

from £91 / night

£455 - £1,010 / week

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Responds fast!
avg. 33 minutes

from £91 / 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 £86 / night

£576 / week

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from £86 / night

(2) Average 

23

Lecchi holiday apartment rental

Gaiole in Chianti / Lecchi

2 5 min stay varies

  • 2 bedrooms
  • sleeps 5
  • min stay varies
  • Swimming pool
  • Suitable for children age 5+
  • Pet friendly

from £81 / night

£475 - £707 / week

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from £81 / night

17

Nusenna holiday apartment rental

Gaiole in Chianti / Nusenna

2 5 min stay varies

  • 2 bedrooms
  • sleeps 5
  • min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly

from £81 / night

£566 / week

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from £81 / 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 £106 / night

£627 - £899 / week

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from £106 / night

21

Holiday guest house in Montefienali

Gaiole in Chianti / Montefienali

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Child friendly
  • Ask about pets
  • Private garden

from £55 / night

£354 / week

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Responds fast!
avg. 1 hour 42 minutes

from £55 / 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 £41 / night

£287 - £874 / week

Enquire View

from £41 / 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 £56 / night

£364 / week

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from £56 / 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 £39 / night

£269 - £640 / week

Enquire View

from £39 / 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 £86 / night

£599 / week

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from £86 / night

23

Holiday apartment with shared pool in Gaiole in Chianti

Province of Siena / Gaiole in Chianti

2 5 min stay varies

  • 2 bedrooms
  • sleeps 5
  • min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly

from £106 / night

£627 - £899 / week

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from £106 / night

12

Nusenna holiday home rental

Gaiole in Chianti / Nusenna

1 2 1 night min

  • 1 bedroom
  • sleeps 2
  • 1 night min
  • Swimming pool
  • Child friendly
  • Pet friendly

from £87 / night

£604 / week

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from £87 / night

29

Gaiole in Chianti holiday apartment rental

Province of Siena / Gaiole in Chianti

4 8 3 nights min

  • 4 bedrooms
  • sleeps 8
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly

from £183 / night

£1,147 - £1,391 / week

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from £183 / night

23

Apartment rental in Gaiole in Chianti with shared pool

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 £52 / night

£362 - £786 / week

Enquire View

from £52 / 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 £39 / night

£269 - £652 / week

Enquire View

from £39 / night

(41) Excellent 

24

Gaiole in Chianti holiday apartment accommodation

Province of Siena / Gaiole in Chianti

1 2 4 nights min

  • 1 bedroom
  • sleeps 2
  • 4 nights min
  • Swimming pool
  • Air conditioning
  • Private garden

from £103 / night

£722 / week

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Responds fast!
avg. 1 hour 8 minutes

from £103 / night

20

Gaiole in Chianti holiday apartment rental

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 £52 / night

£362 - £786 / week

Enquire View

from £52 / night

25

Apartment rental in Gaiole in Chianti with shared pool, golf nearby

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 £52 / night

£362 - £786 / week

Enquire View

from £52 / night

16

Holiday b&b rental

Gaiole in Chianti / Lecchi

1 2 1 night min

  • 1 bedroom
  • sleeps 2
  • 1 night min
  • Nearest beach 95 km
  • Swimming pool
  • Car not necessary

from £112 / night

£606 / week

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from £112 / night

(2) Very Good 

13

Holiday apartment with swimming pool in Gaiole in Chianti

Province of Siena / Gaiole in Chianti

2 4 2 nights min

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

from £56 / night

£354 - £920 / week

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from £56 / night

13

Nusenna holiday apartment rental

Gaiole in Chianti / Nusenna

2 5 min stay varies

  • 2 bedrooms
  • sleeps 5
  • min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly

from £91 / night

£637 / week

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from £91 / 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 £91 / night

£556 - £788 / week

Book View

from £91 / night

(1) Very Good 

15

Gaiole in Chianti holiday home rental

Province of Siena / Gaiole in Chianti

2 6 2 nights min

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

from £77 / night

£488 - £658 / week

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from £77 / night

16

Holiday apartment with shared pool in Nusenna

Gaiole in Chianti / Nusenna

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly

from £71 / night

£495 / week

Book View

from £71 / 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
Casa Felice is a 2 bedroom apartment in village of Gaiole, sleeps 6, shared pool
Comfortable new apartment in a traditional style, highly recommended.

The apartment has a lovely view over the town and the hills beyond. It's an easy walk down into the town centre which has bars, restaurants and a pizza cafe, though it's uphill (and quite steep) all the way back. The region is hilly with fantastic scenery. We only stayed a short while but what we saw of the nearby towns & villages made us book a return visit to investigate more. The apartment was spotless with simple but tasteful decor. The drive from Pisa airport takes about 2 hours, but the exit off the motorway is poorly signposted, so full navigational attention is suggested.see more
Casacorvo Maggiore: *2019 Early Bird Discounts: Exclusive EV Point Included*
Perfect and plaisant location to explore Tuscany

We were 4 people staying in this very nice apartment : comfortable, clean, modern, well equipped. We loved the location. I never heard of Gaiole before, but it was a nice discovery. Quiet village, but big enough to go out for drink, lunch or dinner or buy some food. Very friendly place and very good location to visit the most important cities around : San Gimigniano, Sienna, Arezzo, Firenze. Good recommendations also in the apartment for hikes around Gaiole. Very lovely villages in this area. We had the most enjoyable time, despite the weather which was not perfect. The swimming pool has a good size also. I would love to go back.see more
Casacorvo Grande *Early Bird & Group Discounts* Exclusive EV Point Included*
Fabulous place to stay with a group of friends or family.

My Husband and I stayed here with a group of our friends for a week. It was the perfect size and location. Great for day trips to the hill towns of Tuscany or just hanging out in the cute town of Gaiole. The place was very clean, comfortable, and inviting. The pool was great but a little cold since it is not heated but we swam anyway. The owner also suggested a cooking class for us all to take which was one of the highlights of our trip. I would definitely come back again or recommend to friends.see more
Spacious Chianti apartment with pool access, terrace and outdoor dining area
Peaceful taste of Tuscany!!!!

Stayed here for a lovely, idyllic, December week. Amazing apartment with all home comforts. Loved walking through the village, stopping for pizza and fine wines :-) The views over the hills and vineyards are incredibly inspiring and a joy to wake up to! Day trip to Siena is a must! Great place to stay, will most definitely be back! Thanks!see more
Casacorvo Minore *2019 Early Bird 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 villa LisiDor - unique and strategic location
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, unique and strategic location in Chianti area
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
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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