List your home
Apply filters
£ to

Holiday homes 182

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 (28)
  • Montefienali (2)
  • Montegrossi (23)
  • 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
182 Results   |  

Excellent 5/5 

26 Photos

Gaiole in Chianti / Lecchi

Apartment / 3 Bedrooms / sleeps 6

Excellent 5/5 

4 Nights min stay

Add to shortlist

from £89 / night

£621 - £745 / week

View

Key info:

  • Nearest beach 108 km
  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Some pets are welcome - please contact the owner
  • Private garden
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  …see more


10 Oct 2014

5/5

"Great place to stay to visit Tuscany and the charming Chianti Classico area"

We had a wonderfull stay at Bacchino in Chianti. Anna and Andrea made us feel at home and were very kind and welcoming hosts. Poggio San Polo is a quiet location in the middle of the stunning Chianti … More


6 Jul 2014

4/5

"Quiet location with great outdoor living area by the pool"

We received a warm welcome by the owners and shared stories over a complimentary local Chianti wine.

The unit is situated in a 500 year old villa and although refurbished, still has authentic f… More

See all reviews Continue

100 Photos

Province of Siena / Gaiole in Chianti

Apartment / 2 Bedrooms / sleeps 6

Short stays welcome

Add to shortlist

from £41 / night

£287 - £680 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car not necessary
  • Pets welcome
  • Private garden
"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 a  …see more

100 Photos

Province of Siena / Gaiole in Chianti

House / 1 Bedroom / sleeps 2

Short stays welcome

Add to shortlist

from £31 / night

£215 - £483 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car not necessary
  • No pets allowed
  • Private garden
"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 s  …see more

Featured properties

23 Photos

Gaiole in Chianti / Lecchi

Apartment / 2 Bedrooms / sleeps 5

3 Nights min stay

Add to shortlist

from £71 / night

£496 / week

View

Key info:

  • Swimming pool
  • Suitable for children over 5
  • Car essential
  • Pets welcome
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

24 Photos

Gaiole in Chianti / Lecchi

Apartment / 2 Bedrooms / sleeps 5

3 Nights min stay

Add to shortlist

from £66 / night

£461 / week

View

Key info:

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

4 Photos

Gaiole in Chianti / Montegrossi

Apartment / 2 Bedrooms / sleeps 6

2 Nights min stay

Add to shortlist

from £49 / night

£340 - £898 / week

View

Key info:

  • Swimming pool
  • Not suitable for children
  • Pets welcome

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

4 Photos

Gaiole in Chianti / Montegrossi

Townhouse / 1 Bedroom / sleeps 2

2 Nights min stay

Add to shortlist

from £35 / night

£244 - £558 / 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.  …see more

25 Photos

Province of Siena / Gaiole in Chianti

Apartment / 3 Bedrooms / sleeps 5

4 Nights min stay

Add to shortlist

from £85 / night

£590 - £708 / week

View

Key info:

  • Nearest beach 108 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Some pets are welcome - please contact the owner
  • Private garden
L'appartamento " RICASOLI " è l'ideale per un unico nucleo familiare con bambini Max.5 px. L'Appartamento è composto da due camere. L'appartamento dispone di un bagno con doccia, lavabo, wc, bidet -DINNER PARTY CON PRIVATE CHEF E LEZIONI DI CUCINA -WINE TASTING EXPERI  …see more

18 Photos

Gaiole in Chianti / Lecchi

Villa / 4 Bedrooms / sleeps 8

3 Nights min stay

Add to shortlist

from £142 / night

£993 - £1632 / week

View

Key info:

  • Swimming pool
  • Suitable for children over 5
  • Car essential
  • Some pets are welcome - please contact the owner
  • Private garden
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,  …see more

Excellent 5/5 

24 Photos

Province of Siena / Gaiole in Chianti

Apartment / 1 Bedroom / sleeps 2

Excellent 5/5 

4 Nights min stay

Add to shortlist

from £90 / night

£630 - £770 / week

View

Key info:

  • Swimming pool
  • Not suitable for children
  • Car advised
  • Air conditioning
  • No pets allowed
  • Private garden
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 T  …see more


31 Jul 2012

5/5

"Comfort, beauty, views and quietness"

The apartment is furnitured and equipped to high standard, well kept and clean. Perfectly situated in the "borgo" with an amazing garden with views, shadow and sun and access both from the k… More


1 Jun 2012

5/5

"Great Tuscany Escape"

The apartment was exactly as described. It had everything that one could need, fully equipped kitchen, dishwasher, pool, laundry and gym. The apartment is beautifuly appointed and was very comfortabl… More


10 May 2012

5/5

"Fantastic Apartment and Great Service"

My sister & I stayed at the apartment for a long weeknd and had a fabulous time. The apartment is spotlessly clean with everything you need and more. John and Tracy supplied plenty of information, map… More

See all reviews Continue

Excellent 5/5 

20 Photos

Province of Siena / Gaiole in Chianti

Apartment / 2 Bedrooms / sleeps 6

Excellent 5/5 

2 Nights min stay

Add to shortlist

from £72 / night

£500 - £800 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
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.  …see more


29 May 2014

5/5

"Great place!"

We stayed there 5 nights. The apartment is located in a quiet area within a walking distance from the center of the town.The apartment is clean, comfortable and very well equipped. The owner is helpf… More


14 Sep 2013

5/5

"Wonderful place to stay in the heart of the Chianti region"

We are a family of four, with two children aged 11 and 13, and stayed at Unit H3 of Borgo di Gaiole for a week in August 2013.

This place was terrific! The apartment had everything we needed… More


7 Dec 2012

5/5

"perfection"

Cannot fault this place, quiet, clean, everything worked and did what it says in the brochure.The situation is stunning, set on a steep hill overlooking a beautiful small town, but well removed from i… More

See all reviews Continue

Excellent 5/5 

16 Photos

Province of Siena / Gaiole in Chianti

Villa / 6 Bedrooms / sleeps 12

Excellent 5/5 

3 Nights min stay

Add to shortlist

from £213 / night

£1490 - £2341 / week

View

Key info:

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


18 Jun 2014

5/5

"charming, romantic, unforgettable"

This is a wonderful villa for spending some days enjoying the real Italian life. Children enjoyed the pool, we relaxed and had grest food and wine. A neat garden surrounds the property where you can … More

See all reviews Continue

Very Good 4/5 

17 Photos

Province of Siena / Gaiole in Chianti

Villa / 4 Bedrooms / sleeps 8

Very Good 4/5 

3 Nights min stay

Add to shortlist

from £142 / night

£993 - £1632 / week

View

Key info:

  • Swimming pool
  • Suitable for children over 5
  • Car essential
  • Some pets are welcome - please contact the owner
  • 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, 35 km from Siena, and 55 km from Florence. EXCLUSIVE USE of the Swimming Pool!  …see more


17 Jun 2014

4/5

"really something special"

We stayed Fontecaresino 1 over the Easter holiday period and were very impressed. A real gem hidden in the hills. The surrounding gardens where beautiful and well kept. While it was a bit too cold to … More

See all reviews Continue

18 Photos

Province of Siena / Gaiole in Chianti

Apartment / 2 Bedrooms / sleeps 2

Short stays welcome

Add to shortlist

from £63 / night

£440 - £469 / 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

Excellent 5/5 

13 Photos

Province of Siena / Gaiole in Chianti

Farmhouse / 5 Bedrooms / sleeps 18

Excellent 5/5 

7 Nights min stay

Add to shortlist

from £345 / night

£2412 - £3476 / week

View

Key info:

  • Great for children of all ages
  • Car essential
  • No pets allowed
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 wonder  …see more


29 Dec 2014

5/5

"Spacious, beautiful, and so relaxing that I felt spoiled!"

I spent a week at Il Mulinaccio with friends this summer, and my only regret is that I spent too much time exploring the region and not enough just relaxing at the villa. Everything was impeccable and… More

I am so pleased you enjoyed your stay. We hope to welcome you back in the future!

See all reviews Continue

20 Photos

Province of Siena / Gaiole in Chianti

House / 3 Bedrooms / sleeps 5

4 Nights min stay

Add to shortlist

from £73 / night

£511 - £635 / 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 airp  …see more

13 Photos

Gaiole in Chianti / Lecchi

B&B / 1 Bedroom / sleeps 2

1 night min stay

Add to shortlist

from £61 / night

£426 / week

View

Key info:

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

24 Photos

Gaiole in Chianti / Lecchi

Castle / 6 Bedrooms / sleeps 16

5 Nights min stay

Add to shortlist

from £345 / night

£2412 - £3667 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • Some pets are welcome - please contact the owner
  • Private garden
Castle, tuscany, italy, swimmingpool, bed and breakfast, gaiole in chianti, events, wedding, private castle, private villa, Yoga, wine  …see more

27 Photos

Province of Siena / Gaiole in Chianti

Villa / 2 Bedrooms / sleeps 5

5 Nights min stay

Add to shortlist

from £56 / night

£391 - £781 / 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

23 Photos

Province of Siena / Gaiole in Chianti

House / 1 Bedroom / sleeps 3

5 Nights min stay

Add to shortlist

from £41 / night

£284 - £568 / 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

21 Photos

Province of Siena / Gaiole in Chianti

Villa / 2 Bedrooms / sleeps 4

1 night min stay

Add to shortlist

from £139 / night

£972 / 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

20 Photos

Province of Siena / Gaiole in Chianti

Villa / 1 Bedroom / sleeps 2

5 Nights min stay

Add to shortlist

from £120 / night

£837 / 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

27 Photos

Province of Siena / Gaiole in Chianti

Apartment / 1 Bedroom / sleeps 2

1 night min stay

Add to shortlist

from £51 / night

£353 - £500 / week

View

Key info:

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

28 Photos

Province of Siena / Gaiole in Chianti

Apartment / 1 Bedroom / sleeps 2

1 night min stay

Add to shortlist

from £51 / night

£353 - £500 / week

View

Key info:

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

15 Photos

Province of Siena / Gaiole in Chianti

Villa / 6 Bedrooms / sleeps 12

1 night min stay

Add to shortlist

from £152 / night

£1064 - £1632 / 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

Excellent 5/5 

17 Photos

Province of Siena / Gaiole in Chianti

Villa / 2 Bedrooms / sleeps 6

Excellent 5/5 

1 night min stay

Add to shortlist

from £61 / night

£426 / week

View

Key info:

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


4 Dec 2014

5/5

"sentirsi a casa propria"

Un ottimo contatto con i proprietari Donatella e Santo che stanno prendendo quattro per noi; Una posizione molto buona che permette per la spesa quotidiana al villaggio e quindi condividere il ritmo d… More

See all reviews Continue

20 Photos

Gaiole in Chianti / Montefienali

House / 3 Bedrooms / sleeps 6

3 Nights min stay

Add to shortlist

from £32 / night

£222 - £401 / week

View

Key info:

  • Great for children of all ages
  • Pets welcome
  • Private garden
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.Nice thermal SPA and fashion outlet in the vicinity.  …see more

12 Photos

Gaiole in Chianti / Montefienali

Villa / 7 Bedrooms / sleeps 18

7 Nights min stay

Add to shortlist

from £342 / night

£2391 - £3135 / week

View

Key info:

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

Very Good 4.5/5 

11 Photos

Gaiole in Chianti / Montegrossi

House / 2 Bedrooms / sleeps 5

Very Good 4.5/5 

Min stay varies

Add to shortlist

from £41 / night

£284 / week

View

Key info:

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


20 Aug 2013

5/5

"Small Sleepy Tuscan Village"

Il Poggetto is a steal at the price you pay. Situated in the middle of Tuscany, on a small hilltop within a very small village, you are away from the main tourist areas and the only visitor in town.More


30 Sep 2014

4/5

"Qualita' prezzo ottimo!!"

Carino economico logisticamente ottimo per visitare il chianti e siena ottimo per il giro delle tre citta firenze siena arezzo.… More

See all reviews Continue

17 Photos

Province of Siena / Gaiole in Chianti

Apartment / 2 Bedrooms / sleeps 4

6 Nights min stay

Add to shortlist

from £71 / night

£497 - £561 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • Pets welcome
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. l  …see more

15 Photos

Province of Siena / Gaiole in Chianti

Apartment / 2 Bedrooms / sleeps 5

7 Nights min stay

Add to shortlist

from £51 / night

£355 - £568 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Pets welcome
  • Private garden
Appartamento con 4/5 posti letto, giardino privato, piscin Situata in un antico tranquillo borgo rurale del XV secolo, in mezzo a vigneti su una collina a ca. 500 m di altitudine. Il borgo è stato completamente ristrutturato, in un parco condominiale con olivi.  …see more

48 Photos

Province of Siena / Gaiole in Chianti

Apartment / 2 Bedrooms / sleeps 4

7 Nights min stay

Add to shortlist

from £74 / night

£518 - £696 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • No pets allowed
  • Private garden
2 camere da letto, 1 bagno, grande cucina-soggiorno, loggia e giardino privato Tassa di soggiorno: € 1.50/persona per i primi 7 notti, esclusi bambini sotto 14 anni.  …see more

10 Photos

Province of Siena / Gaiole in Chianti

Apartment / 3 Bedrooms / sleeps 5

1 night min stay

Add to shortlist

from £46 / night

£320 - £525 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • Pets welcome
  • 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. Availabil  …see more

16 Photos

Province of Siena / Gaiole in Chianti

Condo / 3 Bedrooms / sleeps 5

1 night min stay

Add to shortlist

from £36 / night

£249 - £426 / 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

21 Photos

Gaiole in Chianti / Lecchi

Townhouse / 1 Bedroom / sleeps 5

1 night min stay

Add to shortlist

from £51 / night

£355 - £504 / week

View

Key info:

  • Great for children of all ages
  • No pets allowed
5 posti letto, WiFi, TV, Barbecue, Cucina completa  …see more

19 Photos

Province of Siena / Gaiole in Chianti

Apartment / 1 Bedroom / sleeps 4

7 Nights min stay

Add to shortlist

from £55 / night

£384 - £540 / 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

18 Photos

Province of Siena / Gaiole in Chianti

Villa / 6 Bedrooms / sleeps 14

Short stays welcome

Add to shortlist

from £254 / night

£1774 - £2270 / 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  …see more

24 Photos

Province of Siena / Gaiole in Chianti

Farmhouse / 6 Bedrooms / sleeps 12

3 Nights min stay

Add to shortlist

from £258 / night

£1800 - £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

12 Photos

Province of Siena / Gaiole in Chianti

House / 2 Bedrooms / sleeps 4

2 Nights min stay

Add to shortlist

from £61 / night

£426 - £603 / 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

45 Photos

Province of Siena / Gaiole in Chianti

Villa / 5 Bedrooms / sleeps 10

7 Nights min stay

Add to shortlist

from £558 / night

£3901 - £4610 / 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

11 Photos

Province of Siena / Gaiole in Chianti

House / 2 Bedrooms / sleeps 6

1 night min stay

Add to shortlist

from £56 / night

£391 - £532 / 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 c  …see more

11 Photos

Province of Siena / Gaiole in Chianti

Apartment / 3 Bedrooms / sleeps 5

1 night min stay

Add to shortlist

from £137 / night

£958 - £1135 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Some pets are welcome - please contact the owner
Wine resort con piscina nel cuore del Chianti. Organizziamo corsi di cucina, visite e degustazioni.  …see more

13 Photos

Province of Siena / Gaiole in Chianti

Apartment / 2 Bedrooms / sleeps 4

3 Nights min stay

Add to shortlist

from £56 / night

£391 / 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

19 Photos

Province of Siena / Gaiole in Chianti

Villa / 2 Bedrooms / sleeps 5

2 Nights min stay

Add to shortlist

from £152 / night

£1064 / 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 Breakf  …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.  …see more


12 Jul 2014

5/5

"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 going … More


21 Jun 2014

5/5

"A little piece of heaven on earth..."

Casacorvo Minore -- what a perfect place to call home for six days! Phil was terrific to deal with right from our first enquiry. (And we had the added pleasure of meeting him at the tail end of our va… More


16 May 2013

5/5

"Perfect - that is all"

We have just got back from a 5 day stay at Casa Minore and are keen to share our experience with everyone.

The weather was fantastic throughout but that only added to what was a wonderful stay.… More

See all reviews Continue

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 / 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. Ma  …see more


10 Nov 2014

5/5

"Great townhouse in Gaiole in Chianti"

Casacorvo Maggiore provides great accommodation for a group or family. The townhouse is well equipped and provides a lovely view over the town and the surrounding countryside. Our group stayed here wh… More


3 Feb 2014

5/5

"Beautifully appointed and well located"

Set within easy reach of many vineyards, beautiful Siena and only 50 minutes from Florence, my friends and I found the house to be perfectly equipped and finished to a high standard (even has an espre… More


12 Sep 2013

5/5

"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… More

See all reviews Continue

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


6 Jul 2013

5/5

"A delight"

The villa is set within a delightful vineyard, with magnificent views over surrounding countryside and hills in all directions. The villa itself is fantastic - well equipped, luxuriously decorated, br… More

See all reviews Continue

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 £192 / night

£1341 - £2944 / 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


19 Aug 2013

4/5

"Privacy and Relaxation in a Scenic Area"

We spent 2 weeks at this wonderful historic home with friends. The house was spacious for 8 people with separate areas to relax if desired. The building has been restored with great care and has all… More

See all reviews Continue

Very Good 4.5/5 

23 Photos

Province of Siena / Gaiole in Chianti

Apartment / 2 Bedrooms / sleeps 6

Very Good 4.5/5 

Short stays welcome

Add to shortlist

from £108 / night

£750 - £850 / week

View

Key info:

  • Nearest beach 0 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
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


27 Jul 2014

5/5

"Great family break"

Stay for a week and had a great time. Apartment was ideal for the pool, handy for our children to nip in and out. 2 nice size bedrooms, galley kitchen and a good size lounge/dining room was great for … More


23 Aug 2013

5/5

"Absolutely idyllic"

Stayed at this charming apartment mid July with my wife and three small children. The apartment was ideally situated right beside the sun terrace and the swimming pool which was so convenient, not onl… More


24 Apr 2013

5/5

"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 vineya… More

See all reviews Continue

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

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