List your home
Apply filters
£ to

Price

£10 - 500+

Price per night

£ to per night

Location

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

Location

Gaiole in Chianti

  • Show all locations
  • Lecchi (16)
  • Montefienali (2)
  • Montegrossi (13)
  • San Sano (1)

more +

less -

Bedrooms

Show all

  • Show all
  • Studio
  • 1 Bedroom
  • 2 Bedrooms
  • 3 Bedrooms
  • 4 Bedrooms
  • 5 Bedrooms
  • 6 Bedrooms
  • 7 Bedrooms
  • 8 Bedrooms
  • 9 Bedrooms
  • 10 Bedrooms
  • 11 Bedrooms
  • 12 Bedrooms
  • 13 Bedrooms
  • 14 Bedrooms
  • 15+ Bedrooms

more +

less -

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
32 of 129 Results

Sort by: Default

  • Default
  • Price low to high
  • Price high to low
  • Reviews

from £347 / night

£2429 - £3500 / week

View

(1) Excellent 5/5 

1 / 13

Holiday farmhouse rental

Province of Siena / Gaiole in Chianti

Farmhouse / 5 Bedrooms / sleeps 18

  • Great for children of all ages
  • Car essential
  • No pets allowed

Excellent 5/5 

Add to shortlist

from £347 / night

£2429 - £3500 / week

View

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 wonderful gardens and exceptionally large private swimming pool will mean it's hard to drag yourself away to see the sights of Tuscany. However, for those that do want to enjoy some sightseeing during their stay, the property is perfectly placed for exploring the best that this region has to offer.  …see more

from £65 / night

£450 - £800 / week

View

(5) Excellent 5/5 

1 / 20

Apartment accommodation in Gaiole in Chianti with shared pool

Province of Siena / Gaiole in Chianti

Apartment / 2 Bedrooms / sleeps 6

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning

Excellent 5/5 

Add to shortlist

from £65 / night

£450 - £800 / week

View

With beautiful views over the village, this ground floor, comfortable apartment is the perfect spot! Modern facilities including a Swimming pool a gym, and table tennis. The apartment has 2 bedrooms, a well equipped kitchen, a dining terrace, and underground parking. The multinational users are generally quiet and friendly, respectful of the natural ambience of the Borgo.  …see more

from £75 / night

£525 - £850 / week

View

(4) Very Good 4.5/5 

1 / 23

Holiday apartment with shared pool in Gaiole in Chianti

Province of Siena / Gaiole in Chianti

Apartment / 2 Bedrooms / sleeps 6

  • Nearest beach 0 km
  • Swimming pool
  • Great for children of all ages
  • Car advised

Very Good 4.5/5 

Add to shortlist

from £75 / night

£525 - £850 / week

View

Apartment with spectacular views in the heart of the Chianti Region in Tuscany. A €150 deposit for air con payable on arrival usage will be calculated and refund given.€1.50 p/n local tax  …see more

Featured properties

from £42 / night

£288 - £1008 / week

View

(3) Excellent 5/5 

1 / 13

Holiday villa with swimming pool in Gaiole in Chianti

Province of Siena / Gaiole in Chianti

Villa / 2 Bedrooms / sleeps 4

  • Swimming pool
  • Suitable for children over 5
  • Car essential
  • No pets allowed

Excellent 5/5 

Add to shortlist

from £42 / night

£288 - £1008 / week

View

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. Fontecaresino 2 when rented without Fontecaresino 1 does not have access to the swimming pool.  …see more

from £114 / night

£792 - £1655 / week

View

(1) Very Good 4/5 

1 / 17

Villa rental in Gaiole in Chianti with swimming pool

Province of Siena / Gaiole in Chianti

Villa / 4 Bedrooms / sleeps 8

  • Swimming pool
  • Suitable for children over 5
  • Car essential
  • Some pets are welcome - please contact the owner

Very Good 4/5 

Add to shortlist

from £114 / night

£792 - £1655 / week

View

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, and 55 km from Florence. EXCLUSIVE USE of the Swimming Pool! The swimming pool is available from April 1 to October 15, it may varies depending on weather conditions.  …see more

from £124 / night

£864 - £2662 / week

View

(1) Excellent 5/5 

1 / 16

Villa rental in Gaiole in Chianti with swimming pool

Province of Siena / Gaiole in Chianti

Villa / 6 Bedrooms / sleeps 12

  • Swimming pool
  • Suitable for children over 5
  • Car essential
  • Some pets are welcome - please contact the owner

Excellent 5/5 

Add to shortlist

from £124 / night

£864 - £2662 / week

View

2 Villas in the heart of Chianti with the exclusive use of a swimming pool! Beautiful, isolated property with breathtaking views of the hills of Tuscany. The villas are located close by to Gaiole in Chianti and all the cultural and artistic activities of the region.  …see more

from £62 / night

£432 / week

View

(1) Excellent 5/5 

1 / 10

Holiday villa rental

Province of Siena / Gaiole in Chianti

Villa / 2 Bedrooms / sleeps 6

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

Excellent 5/5 

Add to shortlist

from £62 / night

£432 / week

View

Una vacanza all'insegna del riposo con l'alternativa di poter viaggiare e visitare i luoghi che furono di Dante, dei Medici e di quanti hanno sete di cultura. Gaiole in Chianti cittadina divenuta famosa per "L'EROICA" si trova al centro della Toscana.  …see more

from £87 / night

£605 - £719 / week

View

(2) Very Good 4.5/5 

1 / 25

Holiday apartment with shared pool in Gaiole in Chianti

Gaiole in Chianti / Lecchi

Apartment / 3 Bedrooms / sleeps 6

  • Nearest beach 108 km
  • Swimming pool
  • Great for children of all ages
  • Car essential

Very Good 4.5/5 

Add to shortlist

from £87 / night

£605 - £719 / week

View

L'appartamento " Brunello " è l'ideale per un unico nucleo familiare con bambini Max.6 px. L'Appartamento è composto da tre camere che sono disposte in sequenza e perciò comunicanti e di passo una dopo l'altra. L'appartamento ha un bagno con vasca, lavabo, bidet, wc -DINNER PARTY CON PRIVATE CHEF E LEZIONI DI CUCINA -WINE TASTING EXPERIENCE -BREAKFAST, LUNCH E DINNER  …see more

from £42 / night

£288 / week

View

(2) Very Good 4.5/5 

1 / 11

Montegrossi holiday home rental

Gaiole in Chianti / Montegrossi

House / 2 Bedrooms / sleeps 5

  • Great for children of all ages
  • Car advised
  • No pets allowed
  • Private garden

Very Good 4.5/5 

Add to shortlist

from £42 / night

£288 / week

View

Located in an excellent position to visit the typical villages of the Chianti Classico and Chianti Fiorentino Chainti ... Paved road to the village Montegrossi  …see more

from £90 / night

£630 - £770 / week

View

(30) Excellent 5/5 

1 / 24

Gaiole in Chianti holiday apartment accommodation

Province of Siena / Gaiole in Chianti

Apartment / 1 Bedroom / sleeps 2

  • Swimming pool
  • Not suitable for children
  • Car advised
  • Air conditioning

Excellent 5/5 

Add to shortlist

from £90 / night

£630 - £770 / week

View

Ideal for couples seeking relaxation "Home from Home". Everything you need in walking distance to the village, private garden with views over the village, covered decking & pergola perfect for "al fresco" dining, patio heater, BBQ, sun loungers. Read our Guest Reviews There are five restaurants within walking distance and numerous more a short drive away. FREE WI-FI  …see more

from £114 / night

£794 - £1590 / week

View

1 / 39

Gaiole in Chianti holiday apartment rental

Province of Siena / Gaiole in Chianti

Apartment / 7 Bedrooms / sleeps 16

  • Swimming pool
  • Great for children of all ages
  • Car not necessary
  • Pets welcome

Add to shortlist

from £114 / night

£794 - £1590 / week

View

"Il Gufo n°1", 9-room apartment 180 m2 on 2 levels on 1st floor: living/dining room with open-hearth fireplace. Small living room with 1 double sofabed (160 cm), satellite TV. 1 double bedroom. Kitchenette (4 hot plates, dishwasher, microwave). Shower/WC. Upper floor: 2  …see more

from £347 / night

£2425 - £3180 / week

View

1 / 12

Holiday villa with swimming pool in Montefienali

Gaiole in Chianti / Montefienali

Villa / 7 Bedrooms / sleeps 18

  • Swimming pool
  • Great for children of all ages
  • Some pets are welcome - please contact the owner
  • Private garden

Add to shortlist

from £347 / night

£2425 - £3180 / week

View

The Village was completely restored for everyone loves take a refuge in a uncontaminated place that is the kingdom of silence and serenity. Come to Villa degli Albizi to stay the calm of a panorama out of the time. Montefienali, 53010 Gaiole in Chianti (SI)  …see more

from £309 / night

£2159 - £3094 / week

View

1 / 24

Holiday castle accommodation

Gaiole in Chianti / Lecchi

Castle / 6 Bedrooms / sleeps 16

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • Some pets are welcome - please contact the owner

Add to shortlist

from £309 / night

£2159 - £3094 / week

View

Castle, tuscany, italy, swimmingpool, bed and breakfast, gaiole in chianti, events, wedding, private castle, private villa, Yoga, wine  …see more

from £47 / night

£324 - £533 / week

View

1 / 10

Gaiole in Chianti holiday apartment rental

Province of Siena / Gaiole in Chianti

Apartment / 3 Bedrooms / sleeps 5

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • Pets welcome

Add to shortlist

from £47 / night

£324 - £533 / week

View

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. Availabil  …see more

from £83 / night

£576 - £1655 / week

View

1 / 18

Villa rental in Lecchi with swimming pool

Gaiole in Chianti / Lecchi

Villa / 4 Bedrooms / sleeps 8

  • Swimming pool
  • Suitable for children over 5
  • Car essential
  • Some pets are welcome - please contact the owner

Add to shortlist

from £83 / night

£576 - £1655 / week

View

Tuscany. Heart of Chiant.iExclusive use of private swimming pool. The Villa accommodates up to 8/9 people. Beautiful views of the country side. Only a few other farmhouses are visible in the distance. Outdoor dining area. Fontecaresino, located in the hills of Chianti, in the heart of Tuscany. Breathtaking views.  …see more

from £52 / night

£358 - £508 / week

View

1 / 27

Holiday apartment with shared pool in Gaiole in Chianti

Province of Siena / Gaiole in Chianti

Apartment / 1 Bedroom / sleeps 2

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • Some pets are welcome - please contact the owner

Add to shortlist

from £52 / night

£358 - £508 / week

View

The apartment Gaiole 15, is a wonderful apartment in the heart of Chianti. This structure, located in the beautiful Borgo di Gaiole, can comfortably host up to 3 person.  …see more

from £215 / night

£1500 - £2800 / week

View

1 / 24

Farmhouse rental in Gaiole in Chianti with swimming pool

Province of Siena / Gaiole in Chianti

Farmhouse / 6 Bedrooms / sleeps 12

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Some pets are welcome - please contact the owner

Add to shortlist

from £215 / night

£1500 - £2800 / week

View

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

from £56 / night

£386 - £857 / week

View

1 / 18

Gaiole in Chianti holiday apartment rental

Province of Siena / Gaiole in Chianti

Apartment / 3 Bedrooms / sleeps 6

  • Swimming pool
  • Great for children of all ages
  • Car not necessary
  • Pets welcome

Add to shortlist

from £56 / night

£386 - £857 / week

View

"San Giovese n°4", 4-room apartment 105 m2, on the upper ground floor: living room with satellite TV. 1 room with 1 bed and 1 double bed. 1 double bedroom. 1 room with 1 bed. Kitchen (4 hot plates, dishwasher) with open-hearth fireplace and dining table. Shower/WC, show  …see more

from £47 / night

£329 - £768 / week

View

1 / 22

Holiday apartment with shared pool in Gaiole in Chianti

Province of Siena / Gaiole in Chianti

Apartment / 2 Bedrooms / sleeps 6

  • Swimming pool
  • Great for children of all ages
  • Car not necessary
  • Pets welcome

Add to shortlist

from £47 / night

£329 - £768 / week

View

"La Farfalla n°5", 3-room apartment 75 m2 on 2 levels, on the ground floor: living/dining room with 1 double sofabed (160 cm), satellite TV. Kitchenette (4 hot plates). Sep. WC. Upper floor: 1 double bedroom. 1 room, 2 beds. Shower/bidet/WC. Small patio. Terrace furnitu  …see more

from £67 / night

£468 / week

View

1 / 24

Gaiole in Chianti holiday apartment rental

Gaiole in Chianti / Lecchi

Apartment / 2 Bedrooms / sleeps 5

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Pets welcome

Add to shortlist

from £67 / night

£468 / week

View

This lovely 11th century castle for holiday rental in the Chianti Classico area is a tiny, medieval hamlet located at 10 km from Gaiole in Chianti.  …see more

from £45 / night

£313 - £626 / week

View

1 / 16

Gaiole in Chianti holiday apartment rental

Province of Siena / Gaiole in Chianti

Apartment / 2 Bedrooms / sleeps 6

  • Swimming pool
  • Great for children of all ages
  • Car not necessary
  • Pets welcome

Add to shortlist

from £45 / night

£313 - £626 / week

View

"Malvasia n°6", 3-room apartment 60 m2, on the lower ground floor: living/dining room with 1 double sofabed and satellite TV. 1 double bedroom. 1 room with 1 x 2 bunk beds. Kitchenette. Shower/bidet/WC. Maximum 1 pet/ dog allowed. Included: Power costs, Gas, Laundry (i  …see more

from £62 / night

£432 / week

View

1 / 13

Holiday b&b rental

Gaiole in Chianti / Lecchi

B&B / 1 Bedroom / sleeps 2

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • No pets allowed

Add to shortlist

Not on the map

from £62 / night

£432 / week

View

Borgo in genuine Chianti town. Scenery perfect for hiking and biking. Proximity to Siena and Florence alongside other cultural and historical Chianti villages. Excellent local dining and wine tasting. Property provides easy access to spacious terrace and pool area.  …see more

from £39 / night

£270 - £554 / week

View

1 / 44

Holiday apartment with shared pool in Gaiole in Chianti

Province of Siena / Gaiole in Chianti

Apartment / 1 Bedroom / sleeps 4

  • Swimming pool
  • Great for children of all ages
  • Car not necessary
  • Pets welcome

Add to shortlist

from £39 / night

£270 - £554 / week

View

"Pulcino n°3", 2-room apartment 32 m2, on the ground floor: living/dining room with 1 double sofabed (160 cm), satellite TV. 1 small double bedroom. Kitchenette. Shower/WC. Small patio. Maximum 1 pet/ dog allowed. Included: Power costs, Gas, Highchair, Laundry (initial  …see more

from £34 / night

£237 - £532 / week

View

1 / 24

Holiday home rental

Province of Siena / Gaiole in Chianti

House / 1 Bedroom / sleeps 2

  • Swimming pool
  • Great for children of all ages
  • Car not necessary
  • No pets allowed

Add to shortlist

from £34 / night

£237 - £532 / week

View

"Cerbiatto n°5A", 2-room apartment 35 m2 on 2 levels, on the ground floor: living/dining room with satellite TV. Kitchenette (4 hot plates). On the lower ground floor: 1 double bedroom. Shower/bidet/WC. Small patio. Terrace furniture. Please note: The showwer has not sh  …see more

from £36 / night

£247 - £475 / week

View

1 / 14

Gaiole in Chianti holiday apartment rental

Province of Siena / Gaiole in Chianti

Apartment / 1 Bedroom / sleeps 3

  • Swimming pool
  • Great for children of all ages
  • Car not necessary
  • Pets welcome

Add to shortlist

from £36 / night

£247 - £475 / week

View

"Trebbiano n°5", 2-room apartment 40 m2, on the lower ground floor: living/dining room with satellite TV. 1 double bedroom with 1 bed and 1 double bed. Kitchenette. Shower/WC. Maximum 1 pet/ dog allowed. Included: Power costs, Gas, Laundry (initial supply of bed linen  …see more

from £44 / night

£307 - £595 / week

View

1 / 36

Holiday apartment with shared pool in Gaiole in Chianti

Province of Siena / Gaiole in Chianti

Apartment / 2 Bedrooms / sleeps 4

  • Swimming pool
  • Great for children of all ages
  • Car not necessary
  • Pets welcome

Add to shortlist

from £44 / night

£307 - £595 / week

View

"Il Pettirosso n°7", 2-room apartment 55 m2 on 2 levels, on the ground floor: kitchen (4 hot plates) with dining table and satellite TV. Upper floor: 1 double bedroom. 1 room, 2 beds. Shower/bidet/WC. Small patio. Terrace furniture. Maximum 1 pet/ dog allowed. Included  …see more

from £47 / night

£329 - £674 / week

View

1 / 21

Holiday apartment with shared pool in Gaiole in Chianti

Province of Siena / Gaiole in Chianti

Apartment / 2 Bedrooms / sleeps 6

  • Swimming pool
  • Great for children of all ages
  • Car not necessary
  • Pets welcome

Add to shortlist

from £47 / night

£329 - £674 / week

View

"Coccinella n°6", 3-room apartment 50 m2, on the upper ground floor: living/dining room with 1 double sofabed (160 cm), satellite TV. 1 double bedroom. 1 room with 2 beds. Kitchenette (4 hot plates). Shower/bidet/WC. Small patio. Terrace furniture. Maximum 1 pet/ dog al  …see more

from £44 / night

£302 - £585 / week

View

1 / 87

Home rental in Gaiole in Chianti with shared pool

Province of Siena / Gaiole in Chianti

House / 2 Bedrooms / sleeps 6

  • Swimming pool
  • Great for children of all ages
  • Car not necessary
  • Pets welcome

Add to shortlist

from £44 / night

£302 - £585 / week

View

3-room terraced house 56 m2, on the upper floor. Renovated, comfortable furnishings: living/dining room with panoramic window with 1 double sofabed, dining table and satellite TV (flat screen). 1 double bedroom. 1 small double bedroom. Kitchenette (4 hot plates, dishwas  …see more

from £58 / night

£401 - £475 / week

View

1 / 91

Holiday apartment in Gaiole in Chianti

Province of Siena / Gaiole in Chianti

Apartment / 2 Bedrooms / sleeps 4

  • Great for children of all ages
  • Car not necessary
  • No pets allowed
  • Private garden

Add to shortlist

from £58 / night

£401 - £475 / week

View

"Casa Selvolini", 4-room apartment 80 m2 on 1st floor, comfortable furnishings: open living/dining room with open-hearth fireplace, digital TV and air conditioning. Exit to the terrace. 1 double bedroom. 1 room with 2 beds. Small lounge. Kitchenette (4 hot plates, oven,  …see more

from £30 / night

£208 - £417 / week

View

1 / 15

Gaiole in Chianti holiday apartment rental

Province of Siena / Gaiole in Chianti

Apartment / 1 Bedroom / sleeps 2

  • Swimming pool
  • Great for children of all ages
  • Car not necessary
  • Pets welcome

Add to shortlist

from £30 / night

£208 - £417 / week

View

"Prugnolino n°7", 1-room apartment 25 m2, on the ground floor: 1 double bedroom with satellite TV. Kitchen (2 hot plates) with dining table. Shower/WC. Maximum 1 pet/ dog allowed. Private outdoor area, 6 m2, furnished with 2 loungers and sunbed. Included: Power costs,  …see more

from £52 / night

£358 - £508 / week

View

1 / 28

Holiday apartment in Gaiole in Chianti

Province of Siena / Gaiole in Chianti

Apartment / 1 Bedroom / sleeps 2

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • Some pets are welcome - please contact the owner

Add to shortlist

from £52 / night

£358 - £508 / week

View

The apartment Gaiole 13, is a wonderful apartment in the heart of Chianti. This structure, located in the beautiful Borgo di Gaiole, can comfortably host up to 3 person.  …see more

from £42 / night

£288 - £360 / week

View

1 / 18

Holiday apartment with shared pool in Gaiole in Chianti

Province of Siena / Gaiole in Chianti

Apartment / 1 Bedroom / sleeps 3

  • Nearest beach 120 km
  • Swimming pool
  • Not suitable for children
  • Car advised

Add to shortlist

from £42 / night

£288 - £360 / week

View

La naturale estensione del paese di Gaiole in Chianti. Il concetto del “villaggio - nel - villaggio” unico nel suo genere. Il concetto del borgo che diventa parte integrante del villaggio. Una cura maniacale dell' architettura e dei materiali. Disponibilità di appartame  …see more
first

Also consider

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