List your home
Apply filters
£ to

Holiday homes 143

Reset search

Show results on map

Filter your search

Price per night

Price per night

£ to per night

Bedrooms

Location

  • Italy Clear
  • Tuscany Clear
  • Province of Siena Clear
  • Gaiole in Chianti Clear

Location

  • All locations
  • Lecchi (16)
  • Montefienali (2)
  • Montegrossi (26)
  • San Sano (1)

more +

less -

Also consider

Coastal Cottages
222 properties
Sardinia
478 properties
Tuscany
3,181 properties
Lake Garda Area
103 properties
Lake Como Area
494 properties
Sicily
634 properties
Lecchi
16 properties
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
143 Results   |  
4 Photos

Gaiole in Chianti / Montegrossi

Apartment / 1 Bedroom / sleeps 2

2 Nights min stay

Add to shortlist

from £36 / night

£252 - £504 / week

View

Key info:

  • Swimming pool
  • Not suitable for children
  • Pets welcome

"Prugnolino n?7", 1-room apartment 25 m2, on the ground floor: 1 double bedroom with satellite-TV. Kitchen (2 hotplates) with dining table. Shower/WC. Maximum 1 pet/ dog allowed. Private outdoor area, 6 m2, furnished with 2 loungers and sunbed.

Farm house Ensoli  …see more

4 Photos

Gaiole in Chianti / Montegrossi

Apartment / 1 Bedroom / sleeps 4

2 Nights min stay

Add to shortlist

from £47 / night

£328 - £676 / week

View

Key info:

  • Swimming pool
  • Not suitable for children
  • Pets welcome

"Pulcino n?3", 2-room apartment 32 m2, on the ground floor: living/dining room with 1 double sofa bed (160 cm), satellite-TV. 1 small double bedroom. Kitchenette. Shower/WC. Small patio. Maximum 1 pet/ dog allowed.

Localita la Massa 15 km from Gaiole in Chianti:  …see more

4 Photos

Gaiole in Chianti / Montegrossi

Townhouse / 1 Bedroom / sleeps 2

2 Nights min stay

Add to shortlist

from £40 / night

£275 - £653 / week

View

Key info:

  • Swimming pool
  • Not suitable for children
  • No pets allowed

"Cerbiatto n?5A", 2-room apartment 35 m2 on 2 levels, on the ground floor: living/dining room with satellite-TV. Kitchenette (4 hotplates). On the lower ground floor: 1 double bedroom. Shower/bidet/WC. Small patio. Terrace furniture. Please note: only 1 dog accepted. The showwer  …see more

Featured properties

4 Photos

Gaiole in Chianti / Montegrossi

Apartment / 7 Bedrooms / sleeps 16

2 Nights min stay

Add to shortlist

from £137 / night

£954 - £1954 / week

View

Key info:

  • Swimming pool
  • Not suitable for children
  • Pets welcome

"Il Gufo n?1", 9-room apartment 180 m2 on 2 levels on 1st floor: living/dining room with open fireplace. Small living room with 1 double sofa bed (160 cm), satellite-TV. 1 double bedroom. Kitchenette (4 hotplates, dishwasher, micro wave). Shower/WC. Upper floor: 2 double bedrooms  …see more

24 Photos

Province of Siena / Gaiole in Chianti

House / 1 Bedroom / sleeps 3

5 Nights min stay

Add to shortlist

from £43 / night

£295 - £589 / week

View

Key info:

  • Nearest beach 100 km
  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Pets welcome
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

20 Photos

Province of Siena / Gaiole in Chianti

Villa / 1 Bedroom / sleeps 2

5 Nights min stay

Add to shortlist

from £124 / night

£868 / week

View

Key info:

  • Not suitable for children
  • Air conditioning
  • No pets allowed
You can upgrade your stay to include 2 Vespa 125cc Scooters for a daily cost of Euro 60 per day per scooter plus IVA tax. Ask when booking about the scooters!  …see more

18 Photos

Province of Siena / Gaiole in Chianti

Apartment / 2 Bedrooms / sleeps 2

Short stays welcome

Add to shortlist

from £66 / night

£456 - £486 / week

View

Key info:

  • Swimming pool
  • Suitable for children over 5
  • Pets welcome
Siena (Km30), Monteriggioni, Colle Val d'Elsa, Firenze (Km60), San Gimigniano, Volterra, Arezzo to reache into an hour APT. 1) 4 LOCATAIRES APT. 7) 2 " APT.8) 6 " APT.4) 8 " APT.5) 6 "  …see more

11 Photos

Province of Siena / Gaiole in Chianti

House / 2 Bedrooms / sleeps 6

1 night min stay

Add to shortlist

from £58 / night

£405 - £552 / week

View

Key info:

  • Great for children of all ages
  • No pets allowed
Un posto accogliente e familiare, ideale per chi vuole scoprire la terra del buon vino tra famosi vigneti e affascinanti castelliSiamo nel cuore del paese. Due passi per raggiunbere l'edicola, il tabaccaio, il market, la farmacia etc. La biancheria da letto, bagno e cucina è inclusa nel prezzo. Extra: garage, riscaldamento, legna camino.  …see more

15 Photos

Province of Siena / Gaiole in Chianti

Villa / 6 Bedrooms / sleeps 12

1 night min stay

Add to shortlist

from £158 / night

£1103 - £1692 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Pets welcome
  • Private garden
Tranquilla Confortevole Cibo Cucina Salumi Vino Olio Piscina Palestra Panorama Chianti Castello  …see more

16 Photos

Province of Siena / Gaiole in Chianti

Condo / 3 Bedrooms / sleeps 5

1 night min stay

Add to shortlist

from £37 / night

£258 - £442 / week

View

Key info:

  • Great for children of all ages
  • Car advised
  • Some pets are welcome - please contact the owner
  • Private garden
Nel periodo invernale l'uso del riscaldamento AUTONOMO è a pagamnento euro 4,00 a metro cubo. Tassa di soggiorno dal 6 Aprile al 31 Ottobre da pagare all'arrivo, euro 1,50 a notte per persona per un massimo di sette pernottamenti esclusi i minori fino a 14 anni.  …see more

19 Photos

Province of Siena / Gaiole in Chianti

Apartment / 1 Bedroom / sleeps 4

7 Nights min stay

Add to shortlist

from £57 / night

£398 - £559 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Pets welcome
  • Private garden
This is a quiet and peaceful corner of the property idea for relaxing after sighseeing or for cooling off after the warm Tuscan day. Pool fenced - a 16x6 mtr pool open from mid-May to mid-September (weather permitting)  …see more

19 Photos

Province of Siena / Gaiole in Chianti

Villa / 2 Bedrooms / sleeps 5

2 Nights min stay

Add to shortlist

from £158 / night

£1103 / week

View

Key info:

  • Suitable for children over 5
  • Car advised
  • Air conditioning
  • Some pets are welcome - please contact the owner
  • Private garden
Experience Tuscany cooking class, Italian dining and Tuscany tours to Siena, Cortona, San Giminiano and the wine regions of Montalcino and Montepulciano, Pienza, Volterra. Villa Oliviera is a really ' A Taste of Tuscany ' in an authentic, unique, Tuscany Villa Breakfast with home made specialities is served in a charming patio in the stunning Chianti wines view.  …see more

12 Photos

Province of Siena / Gaiole in Chianti

House / 2 Bedrooms / sleeps 4

2 Nights min stay

Add to shortlist

from £64 / night

£442 - £625 / week

View

Key info:

  • Not suitable for children
  • Car essential
  • Some pets are welcome - please contact the owner
Casa colonica chiantigiana di grande charme, comoda e arredata con gusto e attenzione al dettaglio.  …see more

9 Photos

Province of Siena / Gaiole in Chianti

Villa / 2 Bedrooms / sleeps 5

5 Nights min stay

Add to shortlist

from £58 / night

£405 - £809 / week

View

Key info:

  • Nearest beach 70 km
  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Pets welcome
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. The charme of an ancient Medieval borgo in the heart of Chianti Classico  …see more

20 Photos

Province of Siena / Gaiole in Chianti

House / 3 Bedrooms / sleeps 5

4 Nights min stay

Add to shortlist

from £76 / night

£530 - £659 / week

View

Key info:

  • Swimming pool
  • Suitable for children over 5
  • Some pets are welcome - please contact the owner
maison toscane, appartement, piscine, chianti, gaiole in chianti, Sienne, visites de producters de vin, dégustations de vin, outlet shopping, siteseeing, marcher, villes d'art, repos, grand panorama, avec restaurant et bar, familiaire,chiens bien venus. Distances airport 60km gare 16km emplettes 10 km hopital 16 km  …see more

13 Photos

Province of Siena / Gaiole in Chianti

Apartment / 2 Bedrooms / sleeps 4

3 Nights min stay

Add to shortlist

from £48 / night

£331 - £405 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • Some pets are welcome - please contact the owner
  • Private garden
Chianti, famous not only for its landscape but also for the fruit which its land offers. The exquisite wine that is produced here, known as far back as the Etruscan times, has given the region prestige and worldwide fame.  …see more

24 Photos

Province of Siena / Gaiole in Chianti

Farmhouse / 6 Bedrooms / sleeps 12

2 Nights min stay

Add to shortlist

from £329 / night

£2300 - £2800 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Some pets are welcome - please contact the owner
  • Private garden
Podere Scopeto, a former hill farm on sunset-facing slopes of the Chianti in the heart of the wine-region. Main House sleeps 10 and separately available self-contained studio for 2 in its own 30 acres of woodland. 15m saltwater pool on terraces with spectacular views.  …see more

45 Photos

Province of Siena / Gaiole in Chianti

Villa / 5 Bedrooms / sleeps 10

7 Nights min stay

Add to shortlist

from £578 / night

£4045 - £4780 / week

View

Key info:

  • Nearest beach 120 km
  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Air conditioning
  • No pets allowed
  • Private garden
VILLA DEL SOLE is a lovely Tuscan villa near the popular towns of Gaiole and Radda in Chianti. This wonderful villa comprises of the main house which is spread over three floors and a separate ground floor villa which is aproximately 50 metres away.  …see more

18 Photos

Province of Siena / Gaiole in Chianti

Villa / 6 Bedrooms / sleeps 14

Short stays welcome

Add to shortlist

from £211 / night

£1471 - £2353 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Pets welcome
  • Private garden
The "Molino della Carpinese" is located in the municipality of Gaiole in Chianti. The peace and silence characterize the environment that makes it particularly suitable for a relaxing vacation that helps you to forget the stress of those who live in big cities. The Mill of Carpinese is located in the municipality of Gaiole in Chianti, Province of Siena. The peace and  …see more

100 Photos

Province of Siena / Gaiole in Chianti

House / 2 Bedrooms / sleeps 6

Short stays welcome

Add to shortlist

from £45 / night

£309 - £523 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car not necessary
  • Pets welcome
3-room terraced house 57 m2. Renovated, comfortable furnishings: living/dining room with 1 double sofabed, dining table and satellite TV (flat screen). Exit to the patio. 1 double bedroom. Exit to the garden. 1 small double bedroom. Kitchenette (4 hot plates). Shower/bi  …see more

21 Photos

Province of Siena / Gaiole in Chianti

Villa / 2 Bedrooms / sleeps 4

1 night min stay

Add to shortlist

from £144 / night

£1008 / week

View

Key info:

  • Not suitable for children
  • Air conditioning
  • No pets allowed
You can upgrade your stay to include 2 Vespa 125cc Scooters for a daily cost of Euro 60 per day per scooter plus IVA tax. Ask when booking about the scooters!  …see more

Excellent 5/5 

24 Photos

Province of Siena / Gaiole in Chianti

Villa / 5 Bedrooms / sleeps 10

Excellent 5/5 

7 Nights min stay

Add to shortlist

from £179 / night

£1247 - £2762 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
This comfortably furnished country style Tuscan villa sleeps up to ten persons. Set amongst a mature well tended garden with its own private swimming pool. The property is in a great location only five minutes away from Gaiole.  …see more

Excellent 5/5 

24 Photos

Province of Siena / Gaiole in Chianti

Villa / 6 Bedrooms / sleeps 12

Excellent 5/5 

7 Nights min stay

Add to shortlist

from £315 / night

£2203 - £4059 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • No pets allowed
  • Private garden
Private Villa with pool in Gaiole in Chianti in Tuscany sleeping up to 12 people with 5 beds 5 baths in main house and a barn conversion with a separate one bedroomed apartment in the grounds. A great property for large families or groups travelling together.  …see more

Excellent 5/5 

23 Photos

Province of Siena / Gaiole in Chianti

Apartment / 3 Bedrooms / sleeps 8

Excellent 5/5 

4 Nights min stay

Add to shortlist

from £143 / night

£1000 - £1500 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
  • Private garden
A bright roomy south facing 3 bed/2 bath apartment with panaramic views over Gaiole and the hills beyond. Enjoy al fresco dining on the terrace or doze in a wisteria shaded hammock. Relax by the pool, take a cycle ride or just stroll down to the village restuarants. Maggiore is ideally situated to enjoy the areas premier events including Siena Palio and Gaiole Eroica.  …see more

Very Good 4.5/5 

24 Photos

Province of Siena / Gaiole in Chianti

Villa / 3 Bedrooms / sleeps 8

Very Good 4.5/5 

Short stays welcome

Add to shortlist

from £75 / night

£523 - £1192 / week

View

Key info:

  • Nearest beach 107 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • Pets welcome
  • Private garden
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. Beautiful villa located within walking distance of the village of Gaiole in Chianti, near Siena, Tuscany  …see more

Excellent 5/5 

20 Photos

Province of Siena / Gaiole in Chianti

Apartment / 1 Bedroom / sleeps 3

Excellent 5/5 

7 Nights min stay

Add to shortlist

from £42 / night

£291 - £534 / week

View

Key info:

  • Nearest beach 105 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • Some pets are welcome - please contact the owner
  • Private garden
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. Gaiole is in the Chianti Classico area, ideal to taste and enjoy the best wines and olive oil in Italy.  …see more

Excellent 5/5 

19 Photos

Province of Siena / Gaiole in Chianti

Villa / 4 Bedrooms / sleeps 8

Excellent 5/5 

2 Nights min stay

Add to shortlist

from £536 / night

£3751 - £5762 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Some pets are welcome - please contact the owner
This beautiful, rustic villa is built on the side of a hill and surrounded by vineyards and woods. The villa is at the heart of an agricultural estate that produces organic wine and extra virgin olive oil. Good food, wine and relaxation await you in the heart of Tuscany  …see more

Excellent 5/5 

24 Photos

Province of Siena / Gaiole in Chianti

Apartment / 2 Bedrooms / sleeps 6

Excellent 5/5 

7 Nights min stay

Add to shortlist

from £71 / night

£497 - £732 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Air conditioning
  • Some pets are welcome - please contact the owner
A fantastic apartment, 2 bedrooms, 2 bathrooms and livingroom/kitchen. The apartment is one of the towers in beautiful Borgo Gaoile. From the livingroom/kitchen there is a wonderful view over Gaiole and the valley. The wall in the living/kitchen is a glasfoldingdoor. You can open the whole wall in the livingroom/kitchen and make an "out side room" - and what a view.  …see more

Very Good 4/5 

21 Photos

Province of Siena / Gaiole in Chianti

Villa / 2 Bedrooms / sleeps 4

Very Good 4/5 

7 Nights min stay

Add to shortlist

from £66 / night

£456 - £835 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • No pets allowed
This well positioned house has gardens to the South and East and enjoys a sunny aspect from sun rise to sun set, the house has a high quality finish in the old Tuscan style and has superb views all around of pine forest, vineyards and olive groves.  …see more

Very Good 4/5 

24 Photos

from £135 / night

£942 - £1574 / week

View

View

Holiday villa rental

Gaiole in Chianti / Lecchi

Villa / 3 Bedrooms / sleeps 8

Very Good 4/5 

7 Nights min stay

Add to shortlist

from £135 / night

£942 - £1574 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
Vignale is a small hamlet that has a total of 6 private homes. It is located on top of a Chianti hill that gives it the luxury of a stunning view all around. Within a short drive there are three of the five famous Chianti towns.  …see more

Excellent 5/5 

22 Photos

Province of Siena / Gaiole in Chianti

Apartment / 1 Bedroom / sleeps 4

Excellent 5/5 

4 Nights min stay

Add to shortlist

from £75 / night

£525 - £725 / week

View

Key info:

  • Nearest beach 80 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
  • Private garden
A spacious 1 bed apartment with garden and bbq terrace, in a picturesque setting, only a short walk to local services. Enjoy free use of cycles & gym or just relax by the pool. Launderette & internet services add home comforts and a glass of wine greets you on arrival. Minore is ideally situated to enjoy the areas premier events including Siena Palio & Gaiole Eroica.  …see more

Excellent 5/5 

20 Photos

Gaiole in Chianti / San Sano

Villa / 3 Bedrooms / sleeps 6

Excellent 5/5 

7 Nights min stay

Add to shortlist

from £174 / night

£1214 - £2023 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
La Fontanella is fantastically located in the heart of the Chianti, just on the edge of a quaint stone village filled with Tuscan character and charm. Several of the main Chianti vineyards can easily be reached for wine tastings, these include Brolio, Dievole and Meleto  …see more

Excellent 5/5 

37 Photos

Province of Siena / Gaiole in Chianti

Villa / 3 Bedrooms / sleeps 6

Excellent 5/5 

4 Nights min stay

Add to shortlist

from £74 / night

£515 - £1030 / week

View

Key info:

  • Nearest beach 0 km
  • Swimming pool
  • Great for children of all ages
  • Car essential
  • No pets allowed
  • Private garden
Chianti farmhouse, Gaiole in Chianti, pool, Barn, Gite, Demeure de charme, piscine, cités d'art, barn, la casa in chianti, Casa Forcheri Fico for 6 people Cipresso for 4/5 p Olivo for 4-6 p Cipresso+Olivo, maximum 11p  …see more

Very Good 4/5 

17 Photos

Province of Siena / Gaiole in Chianti

Villa / 6 Bedrooms / sleeps 12

Very Good 4/5 

7 Nights min stay

Add to shortlist

from £199 / night

£1390 - £3052 / week

View

Key info:

  • Nearest beach 125 km
  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Some pets are welcome - please contact the owner
  • Private garden
The building of Villa Brolio was originally an old XII century watchtower later transformed into a mill and finally restored to become a villa.  …see more

Excellent 5/5 

24 Photos

Province of Siena / Gaiole in Chianti

Apartment / 4 Bedrooms / sleeps 12

Excellent 5/5 

4 Nights min stay

Add to shortlist

from £229 / night

£1600 - £2100 / week

View

Key info:

  • Nearest beach 80 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
  • Private garden
A spacious townhouse complex on two levels well suited to sharing families in easy strolling distance of restaurants, delicatessens, bars etc; large pool, gym, free bicycle hire and plenty of private outdoor space with lovely views offers something for all the family.  …see more

20 Photos

Province of Siena / Gaiole in Chianti

Farmhouse / 3 Bedrooms / sleeps 6

3 Nights min stay

Add to shortlist

from £141 / night

£983 - £1403 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Some pets are welcome - please contact the owner
Villa / Farmhouse / Home in Gaiole In Chianti with 3 bedrooms sleeps 6  …see more

8 Photos

Province of Siena / Gaiole in Chianti

Apartment / 3 Bedrooms / sleeps 6

4 Nights min stay

Add to shortlist

from £171 / night

£1192 - £1509 / week

View

Key info:

  • Not suitable for children
  • Car not necessary
  • No pets allowed
Gaiole-Apartment Nestandnbsp;is a striking countryside apartment inandnbsp;Gaiole in Chianti, a municipality in Siena, Tuscany 'Forbes', a reputed American magazine, rates Gaiole in Chianti as "Europe's . Theandnbsp;Chianti Classico wineandnbsp;region is situated to  …see more

20 Photos

Province of Siena / Gaiole in Chianti

House / 2 Bedrooms / sleeps 4

7 Nights min stay

Add to shortlist

from £129 / night

£900 - £1040 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • No pets allowed
  • Private garden
Villa Diora D is a characteristic and welcoming independent house surrounded by vineyards and olive groves. It sleeps four people. From Villa Diora D you will enjoy an enchanting view of the Tuscan hills and of the Chianti valley  …see more

16 Photos

Province of Siena / Gaiole in Chianti

Farmhouse / 6 Bedrooms / sleeps 11

7 Nights min stay

Add to shortlist

from £544 / night

£3802 - £5589 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • No pets allowed
  • Private garden
Breathtaking views over the Chianti Classico valleys. Attractive and panoramic terrace.  …see more

24 Photos

Province of Siena / Gaiole in Chianti

Villa / 5 Bedrooms / sleeps 10

3 Nights min stay

Add to shortlist

from £794 / night

£5552 - £8824 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • No pets allowed
This exclusive and luxurious villa in Chianti affords 5 bedrooms, dining room, 2 sitting rooms, kitchen, gym, games room and a fabulous infinity swimming pool.  …see more

17 Photos

Province of Siena / Gaiole in Chianti

Farmhouse / 4 Bedrooms / sleeps 8

2 Nights min stay

Add to shortlist

from £136 / night

£949 - £2299 / week

View

Key info:

  • Swimming pool
  • Not suitable for children
  • Car advised
  • Some pets are welcome - please contact the owner
This beautiful, detached farmhouse has been carefully restored by the architect owner to the highest standards. He has maintained the original structure, while adding modern design ideas.  …see more

22 Photos

Gaiole in Chianti / Montegrossi

Farmhouse / 5 Bedrooms / sleeps 10

Min stay varies

Add to shortlist

Pricing unknown

View

Key info:

  • Nearest beach 100 km
  • Swimming pool
  • Great for children of all ages
  • Car essential
  • No pets allowed
  • Private garden
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

22 Photos

Province of Siena / Gaiole in Chianti

Apartment / 1 Bedroom / sleeps 4

7 Nights min stay

Add to shortlist

from £42 / night

£291 - £556 / week

View

Key info:

  • Nearest beach 105 km
  • Swimming pool
  • Great for children of all ages
  • Car not necessary
  • Air conditioning
  • Some pets are welcome - please contact the owner
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. Gaiole is in the Chianti Classico area, ideal to taste and enjoy the best wine and food in Italy.  …see more

12 Photos

Gaiole in Chianti / Montegrossi

Castle / 3 Bedrooms / sleeps 5

3 Nights min stay

Add to shortlist

from £191 / night

£1337 - £1560 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Some pets are welcome - please contact the owner
Castle in Badia Coltibuono with 3 bedrooms sleeps 5  …see more

24 Photos

Gaiole in Chianti / Lecchi

Farmhouse / 1 Bedroom / sleeps 2

3 Nights min stay

Add to shortlist

from £63 / night

£441 - £527 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Some pets are welcome - please contact the owner
Villa / Farmhouse / Home in Vagliagli with 1 bedrooms sleeps 2  …see more

24 Photos

Province of Siena / Gaiole in Chianti

Farmhouse / 4 Bedrooms / sleeps 8

3 Nights min stay

Add to shortlist

from £320 / night

£2239 - £3359 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Pets welcome
  • Private garden
Villa in Gaiole In Chianti with 4 bedrooms sleeps 8  …see more

12 Photos

Province of Siena / Gaiole in Chianti

Apartment / 3 Bedrooms / sleeps 6

4 Nights min stay

Add to shortlist

from £171 / night

£1192 - £1509 / week

View

Key info:

  • Not suitable for children
  • Car not necessary
  • No pets allowed
Gaiole-Apartment Ventoandnbsp;is a andnbsp;threeandnbsp;bedroom rental countryside apartment in the hamlet of Gaiole in theandnbsp;Chianti region of Siena, Tuscany. San Gimignano, a small walled hill town in the province of Siena, is famous for itsandnbsp;medieval  …see more

9 Photos

Province of Siena / Gaiole in Chianti

B&B / 1 Bedroom / sleeps 2

4 Nights min stay

Add to shortlist

from £114 / night

£795 - £953 / week

View

Key info:

  • Not suitable for children
  • Car not necessary
  • No pets allowed
Apartmentandnbsp;Barnandnbsp;is located in splendid Chianti country side on the ground floor, can comfortably accommodate andnbsp;twoandnbsp;people.andnbsp; There is aandnbsp;double bed roomandnbsp;with open fireplace,andnbsp;small kitchen, bath room with hydro  …see more

8 Photos

from £114 / night

£795 - £953 / week

View

View

Holiday b&b rental

Province of Siena / Gaiole in Chianti

B&B / 2 Bedrooms / sleeps 2

4 Nights min stay

Add to shortlist

from £114 / night

£795 - £953 / week

View

Key info:

  • Not suitable for children
  • Car not necessary
  • No pets allowed
Apartment Archesandnbsp;is ideally located inandnbsp;Chianti countryside. It is on theandnbsp;ground floor, aboutandnbsp;80 m2, can comfortably sleepandnbsp;3andnbsp;people.andnbsp; There is aandnbsp;living roomandnbsp;with open fireplace,andnbsp;dining room,  …see more

12 Photos

Gaiole in Chianti / Montegrossi

Castle / 1 Bedroom / sleeps 2

3 Nights min stay

Add to shortlist

from £131 / night

£915 - £1092 / week

View

Key info:

  • Swimming pool
  • Not suitable for children
  • Some pets are welcome - please contact the owner
Castle in Badia Coltibuono with 1 bedrooms sleeps 2  …see more

Don’t let an old browser slow down your holiday

Your browser is out of date and might not work well with our website. Download the latest version to speed up your hunt for the perfect holiday home.

Just click on the icons to get to the download page