Apartments and villas with a garden in Gaiole in Chianti | Holiday Lettings UK

Close

View larger map

Also consider

Europe Holidays
430742 properties
Italy Holidays
102096 properties
Tuscany Holidays
25507 properties
Coastal Cottages
222 properties
Apartments Sardinia
478 properties
Apartments Tuscany
3181 properties
Apartments Lake Garda Area
103 properties
Apartments Lake Como Area
494 properties
Apartments Sicily
634 properties
Lecchi
8 properties

Gaiole in Chianti

No dates Enter dates for accurate prices -

Adults, Children

Enter dates for more accurate prices

Payment Protection
To book this holiday home you need to pay through the Holiday Lettings website. We can’t protect your payment if you don’t pay through us. Learn more

90 Holiday homes

Filters applied: Garden (91)

Travellers going to Gaiole in Chianti are booking June dates now. Secure your holiday home today and have the perfect trip.

(15) Excellent 

22

Holiday apartment with shared pool in Gaiole in Chianti

Province of Siena / Gaiole in Chianti

1 4 4 nights min

  • 1 bedroom
  • Sleeps 4
  • 4 nights min
  • Nearest beach 80 km
  • Swimming pool
  • Child friendly
“Charming accommodations and beautiful surroundings!” My husband and I stayed for four nights in this wonderful and clean apartment in the heart of Chianti. Phil was extremely responsive and helpful throughout the booking process and our stay even goin  …see more

from £100 / night

£560 - £760 / week

Enquire View

from £100 / night

(32) 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
“A Little Corner of Heaven” This was our fourth visit to Gaiole in Chianti and our third stay in this apartment. The apartment is modern, well furnished and equipped and spotlessly clean. The garden is beautiful and a real bonus. It is a wonderful  …see more

from £60 / night

£420 - £665 / week

Book View

from £60 / night

(6) Very Good 

43

Gaiole in Chianti 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
Recently renovated, is located in a scenic hillside location in a picturesque village nestled in the heart of Chianti, strategic point to reach in a short time two beautiful cities such as Siena and Florence. Moreover, you can go trekking in the beautiful trails and na  …see more

from £47 / night

£272 - £609 / week

Book View

from £47 / night

(13) Excellent 

23

Holiday apartment with shared pool in Gaiole in Chianti

Province of Siena / Gaiole in Chianti

3 8 4 nights min

  • 3 bedrooms
  • Sleeps 8
  • 4 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
“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  …see more

from £175 / night

£1100 - £1600 / week

Enquire View

from £175 / night

(12) Excellent 

69

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
“Perfect holiday location” Our family group of 8 adults spent 5 nights at Villa LisiDor - a perfect location for both relaxing & a great base for exploring the local region. The roads in Chianti can be narrow & windy but worth the drive to villages lik  …see more

from £412 / night

£2883 - £4435 / week

Book View

from £412 / night

(2) Excellent 

18

Province of Siena / Gaiole in Chianti

2 2 7 nights min

  • 2 bedrooms
  • Sleeps 2
  • 7 nights min
  • Swimming pool
  • Suitable for children age 5+
  • Pet friendly

 …see more

from £79 / night

£548 / week

Book View

from £79 / night

18

Province of Siena / Gaiole in Chianti

3 5 Min stay varies

  • 3 bedrooms
  • Sleeps 5
  • Min stay varies
  • Child friendly
  • Pet friendly
  • Private garden

 …see more

from £48 / night

£314 - £374 / week

Book View

from £48 / night

18

Holiday apartment with shared pool in Gaiole in Chianti

Province of Siena / Gaiole in Chianti

1 3 2 nights min

  • 1 bedroom
  • Sleeps 3
  • 2 nights min
  • Nearest beach 120 km
  • Swimming pool
  • Air conditioning
appartamento, 2 - 3 persone, 2 vano/vani, 1 camera/e da letto, 1 bagno/bagni, ca. 44 m², 1 piano/piani, alloggio al piano terra. Accesso all'alloggio indipendente.TerrenoPorzione privata del terreno, giardino, lastre.Parcheggio: 1 x posto macchina in g  …see more

from £69 / night

£348 / week

Book View

from £69 / night

(6) Excellent 

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
“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 (an  …see more

from £65 / night

£400 - £800 / week

Book View

from £65 / night

(1) Excellent 

24

Holiday apartment with shared pool in Gaiole in Chianti

Province of Siena / Gaiole in Chianti

4 10 4 nights min

  • 4 bedrooms
  • Sleeps 10
  • 4 nights min
  • Nearest beach 80 km
  • Swimming pool
  • Child friendly
“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 to  …see more

from £300 / night

£1500 - £2000 / week

Enquire View

from £300 / night

(1) Average 

10

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
  • Air conditioning
The natural extension of the existing village of Gaiole in Chianti. The 'village-inside-the village' concept that is unique of its kind. The village concept that becomes an integral part of Gaiole in Chianti. Details and the architecture are carefully planned.  …see more

from £87 / night

£392 / week

Book View

from £87 / 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
Ideal location for couples and families, set within walking distance of Gaiole in Chianti with the typical Tuscan lifestyle at your doorstep. Perfect place to unwind and come back to after a cycle, a walk, or discovering the artistic and historic cities of Tuscany.<b  …see more

from £45 / night

£314 - £344 / week

Enquire View

from £45 / night

(1) Excellent 

4

Province of Siena / Gaiole in Chianti

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Child friendly
  • Ask about pets
  • Private garden

 …see more

from £67 / night

£463 / week

Book View

from £67 / night

44

Province of Siena / Gaiole in Chianti

3 7 7 nights min

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

 …see more

from £116 / night

£809 - £1205 / week

Book View

from £116 / night

45

Holiday home in Gaiole in Chianti

Province of Siena / Gaiole in Chianti

6 13 3 nights min

  • 6 bedrooms
  • Sleeps 13
  • 3 nights min
  • Child friendly
  • Pet friendly
  • Private garden
Nestled in the lush nature of the Chianti region, this charming manor built in the early 1900s lovingly embraces and preserves the romance of bygone times. It is an ideal place for relaxing in the surrounding nature while enjoying the area’s superb foods and wines  …see more

from £287 / night

£1809 - £2787 / week

Book View

from £287 / night

7

Province of Siena / Gaiole in Chianti

2 6 3 nights min

  • 2 bedrooms
  • Sleeps 6
  • 3 nights min
  • Child friendly
  • Private garden

 …see more

from £87 / night

£548 / week

Book View

from £87 / night

(12) Very Good 

28

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

Province of Siena / Gaiole in Chianti

3 7 7 nights min

  • 3 bedrooms
  • Sleeps 7
  • 7 nights min
  • Nearest beach 110 km
  • Swimming pool
  • Child friendly
“Toscany at its best at Radda in Chianti property Villa PetrAlexa” The property itself is wonderfully placed between woods and a vinery in the picturesque Chianti area near Radda. The hospitality we have experienced was outstanding in the mean that you  …see more

from £179 / night

£1253 - £2087 / week

Book View

from £179 / 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
Fontecaresino, located in the hills of Chianti, in the heart of Tuscany, with ready access to the culinary, cultural and artistic heritage of this region, is only 4 km from Gaiole in Chianti, 35 km from Siena, 45 km from Arezzo and 55 km from Florence. Our close proximi  …see more

from £168 / night

£1392 - £2440 / week

Book View

from £168 / night

27

Villa rental in Gaiole in Chianti with shared pool

Province of Siena / Gaiole in Chianti

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Nearest beach 70 km
  • Swimming pool
  • Child friendly
The Chianti As You Always Dreamed It. A charming Medieval borgo in the heart of Chianti Classico, 15 km far from Siena. Relax and discovery hour incredible landes.<br />The charme of an ancient Medieval borgo in the heart of Chianti Classico  …see more

from £131 / night

£822 - £983 / week

Book View

from £131 / night

(4) Excellent 

17

Province of Siena / Gaiole in Chianti

2 6 1 night min

  • 2 bedrooms
  • Sleeps 6
  • 1 night min
  • Swimming pool
  • Child friendly
  • Pet friendly

 …see more

from £105 / night

£522 / week

Book View

from £105 / night

(1) Excellent 

12

Holiday farmhouse rental

Province of Siena / Gaiole in Chianti

5 16 Min stay varies

  • 5 bedrooms
  • Sleeps 16
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets
This is a traditional 5 bedroom villa situated between the towns of Gaiole in Chianti and Radda in Chianti. Accommodating up to 18 guests in total as additional apartments are available within the grounds, it's an ideal base for a stay with family or friends. The w  …see more

from £435 / night

£3044 - £4696 / week

Book View

from £435 / night

(1) Excellent 

22

Province of Siena / Gaiole in Chianti

6 14 7 nights min

  • 6 bedrooms
  • Sleeps 14
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly

 …see more

from £249 / night

£1740 - £2783 / week

Book View

from £249 / night

(3) Very Good 

24

Holiday villa with shared pool in Gaiole in Chianti

Province of Siena / Gaiole in Chianti

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Nearest beach 107 km
  • Swimming pool
  • Child friendly
Located within walking distance of the village of Gaiole in Chianti, the villa offers the perfect setting to explore the Chianti Classico region, enjoy the breathtaking views of the vineyards and olive groves, and experience the charming Tuscan lifestyle.<br />Bea  …see more

from £85 / night

£592 - £677 / week

Enquire View

from £85 / night

4

Province of Siena / Gaiole in Chianti

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Child friendly
  • Ask about pets
  • Private garden

 …see more

from £67 / night

£463 / week

Book View

from £67 / night

(1) Excellent 

22

Holiday farmhouse in Gaiole in Chianti

Gaiole in Chianti / Montegrossi

5 10 5 nights min

  • 5 bedrooms
  • Sleeps 10
  • 5 nights min
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly
Le Diacce, an enchanting 18th century old farmhouse, belonging to Podere Ciona, 40 hectares of vineyards and woodland, enjoys a unique view on the surrounding hills covered with vineyards, olive groves and woods with Siena in the far distance.  …see more

from £131 / night

£3479 / week

Book View

from £131 / night

(1) Excellent 

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
The house is located in the heart of the Chianti Classico, inside the town of Gaiole in Chianti (all kinds of shops). The apartment is on the ground floor and is part of a building where the owners reside.Outside a portion of an equipped courtyard is available for t  …see more

from £35 / night

£305 / week

Book View

from £35 / night

(2) Excellent 

45

Province of Siena / Gaiole in Chianti

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 75 km
  • Swimming pool
  • Child friendly

 …see more

from £199 / night

£1392 - £1914 / week

Book View

from £199 / night

(1) Very Good 

16

Gaiole in Chianti holiday home rental

Province of Siena / Gaiole in Chianti

2 5 1 night min

  • 2 bedrooms
  • Sleeps 5
  • 1 night min
  • Swimming pool
  • Air conditioning
  • Private garden
The natural extension of the existing village of Gaiole in Chianti. The 'village-inside-the village' concept that is unique of its kind. The village concept that becomes an integral part of Gaiole in Chianti. Details and the architecture are carefully planned.  …see more

from £87 / night

£435 / week

Book View

from £87 / night

48

Province of Siena / Gaiole in Chianti

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly

 …see more

from £91 / night

£635 / week

Book View

from £91 / night

22

Holiday home with shared pool in Gaiole in Chianti

Province of Siena / Gaiole in Chianti

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Private garden
Homelidays "Casa Guia " is immersed in the most idyllic Chiantishire: surrounded by vineyards producing world-class red wine, overlooking the rolling hills of Tuscany and is located in the village of San Vincenti, with its stone houses and clay roof tiles. The  …see more

from £109 / night

£761 / week

Book View

from £109 / night

20

Province of Siena / Gaiole in Chianti

3 5 7 nights min

  • 3 bedrooms
  • Sleeps 5
  • 7 nights min
  • Swimming pool
  • Suitable for children age 5+
  • Ask about pets

 …see more

from £81 / night

£566 / week

Book View

from £81 / 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
Fontecaresino, located in the hills of Chianti, in the heart of Tuscany, with ready access to the culinary, cultural and artistic heritage of this region, is only 4 km from Gaiole in Chianti 10 km from Radda in Chianti, 35 km from Siena, 45 km from Arezzo and 55 km from  …see more

from £121 / night

£848 - £1518 / week

Book View

from £121 / night

4

Province of Siena / Gaiole in Chianti

1 4 1 night min

  • 1 bedroom
  • Sleeps 4
  • 1 night min
  • Child friendly
  • Ask about pets
  • Private garden

 …see more

from £133 / night

£926 / week

Book View

from £133 / night

11

Province of Siena / Gaiole in Chianti

3 5 1 night min

  • 3 bedrooms
  • Sleeps 5
  • 1 night min
  • Swimming pool
  • Child friendly
  • Ask about pets

 …see more

from £192 / night

£1174 / week

Book View

from £192 / 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
Adjacent apartment with terra-cotta floors and furnished with a double Chianti iron bed (subsequently with a madonna picture above), a large armadio and an en suite bathroom. Through French doors the room leads to a 55 square meter terrace with an antique iron sofa, a f  …see more

from £96 / night

£522 / week

Book View

from £96 / 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
Casa Lecchi is a spacious two bedroom apartment facing on to the main piazza of Montefiorile which is a small hamlet of 14 villas situated in a quiet position in the heart of the Chianti Classico wine producing area. The hamlet is on a hillside and the houses enjoy st  …see more

from £74 / night

£514 - £974 / week

Enquire View

from £74 / night

19

Gaiole in Chianti / Lecchi

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Swimming pool
  • Suitable for children age 5+
  • Ask about pets

 …see more

from £63 / night

£444 / week

Book View

from £63 / night

19

Province of Siena / Gaiole in Chianti

2 5 2 nights min

  • 2 bedrooms
  • Sleeps 5
  • 2 nights min
  • Suitable for children age 5+
  • Air conditioning
  • Ask about pets

 …see more

from £366 / night

£1305 / week

Book View

from £366 / night

33

Gaiole in Chianti holiday home rental

Province of Siena / Gaiole in Chianti

13 25 3 nights min

  • 13 bedrooms
  • Sleeps 25
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Private garden
The Borgo San Vincenti is a Homelidays in Tuscany; is a beautiful stone house in a prestigious estate of 500 acres of forest in the hills above Gaiole in Chianti, a short distance from Siena. The large farmhouse has been restored by the owners. They used their experienc  …see more

from £544 / night

£3805 / week

Book View

from £544 / night

23

Home letting in Gaiole in Chianti with shared pool

Province of Siena / Gaiole in Chianti

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Nearest beach 100 km
  • Swimming pool
  • Child friendly
The house, composed of 5 delightful apartments, has as it's main objective the idea of offering guests the opportunity to enjoy the calm, the beauty and all the pleasures our region has to offer.Our apartments have been renovated with respect for tradition.  …see more

from £79 / night

£494 - £713 / week

Book View

from £79 / night