We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.
We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Vacation rentals in Gaiole in Chianti, Italy

Payment Protection
Use a credit card to book with our Peace of Mind Protection.Learn more
Find a rental
Price per night
Min
to
Max
Bedrooms
Any
Amenities
Select
More filters
Find more rentals you can book on TripAdvisor!   We're showing you properties you can book on TripAdvisor first.
All 129 Rentals in Gaiole in Chianti
loading...
Sort by
From
$165
Per Night
1 / 24
Payment Protection
3 Bedrooms, 1 Bathroom, Sleeps 6
Booking
Details Reviews (2) Make Enquiry
From
$129
Per Night
1 / 33
Payment Protection
2 Bedrooms, 1 Bathroom, Sleeps 5
Bookings
Details Reviews (1) Make Enquiry
From
$164
Per Night
1 / 24
Payment Protection
1 Bedroom, 1 Bathroom, Sleeps 2
Details Reviews (29) Make Enquiry
From
$128
Per Night
1 / 13
Payment Protection
2 Bedrooms, 2 Bathrooms, Sleeps 4
Booking
Details Reviews (3) Make Enquiry
5 of 5 stars Reviewed 23 April 2014
The villa is beautiful, the room we stayed in was spacious, comfortable, stylish, very clean and had everything we needed. The fantastic view over make a perfect surrounding for...
5 of 5 stars Reviewed 21 April 2014
I've spent, with my family, few days last October in this charmy country house located in the heart of chiantishire ... The house is surrounded by a wonderful landscape made by...
See all reviews
From
$72
Per Night
1 / 20
Payment Protection
2 Bedrooms, 1 Bathroom, Sleeps 6
Bookings
Details Reviews (5) Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dryer
  • Gym
  • Internet Access
  • Ping Pong Table
  • Satellite TV
  • Shared Outdoor Pool...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
About this property
A fabulous place to relax, this apartment is at the edge of the Borgo furthest from the road. Designed in a traditional style incorporating a range of modern comforts and facilities, the apartment is the best of both worlds. Stone tiled floors with chestnut beams overhead give a smart but homely... View all property information
Make Enquiry
5 of 5 stars Reviewed 29 May 2014
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...
4 of 5 stars Reviewed 26 March 2014
Sadly only 2 nights here in this beautiful quiet village. Accommodation was great, large rooms, well equipped and clean. Nothing to complain about at all. Would love to return.
See all reviews
From
$2,425
Per Week
1 / 23
5 Bedrooms, 3 Bathrooms, Sleeps 10
Details Reviews (2) Make Enquiry
Amenities & Details
  • Balcony
  • Dishwasher
  • Dryer
  • Fireplace
  • Grill
  • Internet Access
  • Private Outdoor...
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
About this property
The property is in a great location only five minutes away from Gaiole with all the amenities a large town has to offer. The property is surrounded by a lovely mature garden with an attractive private pool which is set in a secluded area of the garden partly screened by mature hedging and trees... View all property information
Make Enquiry
5 of 5 stars Reviewed 4 June 2012
Fantastic holiday. Villa was perfect with plenty of social areas. Villa contained everything you could have hoped for, i.e. in the utility room and kitchens. Walking distance to...
5 of 5 stars Reviewed 4 November 2011
Sue who owns the property and lives next door was a perfect host and very laid back, just like us, we were there for a 40th Birthday celebration and couldnt have wished for a...
See all reviews
From
$286
Per Night
1 / 17
Payment Protection
4 Bedrooms, 3 Bathrooms, Sleeps 8
Bookings
Details Reviews (1) Make Enquiry
4 of 5 stars Reviewed 17 June 2014
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...
See all reviews
From
$458
Per Night
1 / 16
Payment Protection
6 Bedrooms, 5 Bathrooms, Sleeps 12
Details Reviews (1) Make Enquiry
5 of 5 stars Reviewed 18 June 2014
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...
See all reviews
From
$172
Per Night
1 / 24
3 Bedrooms, 3 Bathrooms, Sleeps 6
Details Make Enquiry
Amenities & Details
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Internet Access
  • Satellite TV
  • Shared Outdoor Pool...
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • Wheelchair access
  • Elder access
  • x
  • x
About this property
Typical Chianti estate with a fully renovated barn to rent, and two other accommodations, with pool, olive trees, typical Chianti scenery between Gaiole in Chianti and Radda in Chianti. The Chianti Classico area is rich in wineries and wine producing properties, and wordly known for its wine... View all property information
Make Enquiry
From
$172
Per Night
1 / 5
Payment Protection
2 Bedrooms, 4 Bathrooms, Sleeps 6
Details Reviews (1) Make Enquiry
5 of 5 stars Reviewed 4 December 2014
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...
See all reviews
Get the List
From
$186
Per Night
1 / 54
Payment Protection
2 Bedrooms, 1 Bathroom, Sleeps 4
Details Make Enquiry
Amenities & Details
  • Balcony
  • Dishwasher
  • Fireplace
  • Grill
  • Internet Access
  • Mountain Views
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
In the very heart of the charming Tuscan countryside, among the smooth hills of Sienese Chianti and the fragrance of its green vineyards, you will find the Podere Lucignano Secondo Agriturismo, a mansion built in 1898, now elegantly restored and turned into an exclusive relais. The Podere... View all property information
Make Enquiry
From
$129
Per Night
1 / 11
Payment Protection
2 Bedrooms, 1 Bathroom, Sleeps 4
Details Make Enquiry
Amenities & Details
  • Children's Pool
  • Garden
  • Internet Access
  • Mountain Views
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • Wheelchair access
  • Elder access
  • ?
About this property
The Gaiole area, with its woods, vinyards and olivegroves, can be discovered on foot, on horseback, by bike or any other means of transport you prefer. The tourist information office in Gaiole will supply you with detailed route descriptions and maps, wich will guide you along well signposted... View all property information
Make Enquiry
From
$100
Per Night
1 / 21
Payment Protection
1 Bedroom, 1 Bathroom, Sleeps 2
Details Make Enquiry
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • ?
  • Wheelchair access
  • Elder access
  • ?
About this property
On the highest point of a hill set among the mosaic of the vineyards, typical of the Chianti Classico area, in the heart of a medieval village, you'll find the Pieve Marsina. The house, composed of 5 delightful apartments, has as it's main objective the idea of offering guests the opportunity to... View all property information
Make Enquiry
From
$99
Per Night
1 / 12
Payment Protection
2 Bedrooms, 1 Bathroom, Sleeps 4
Details Make Enquiry
Amenities & Details
  • Balcony
  • Garden
  • Pool
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
Please note these Check-in Day Requirements for this property: May 09 - May 11 : Saturday check-in required, Monday check-out required.; May 17 - May 18 : Monday check-out required.; May 24 - May 25 : Monday check-out required.; May 31 - Jun 01 : Monday check-out required.; Jun 07 - Jun 08 : Monday... View all property information
Make Enquiry
From
$737
Per Week
1 / 24
2 Bedrooms, 1 Bathroom, Sleeps 6
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Dishwasher
  • Gym
  • Internet Access
  • Ping Pong Table
  • Satellite TV
  • Shared Outdoor Pool...
  • Wi-Fi
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • x
About this property
This beautiful and tastefully furnished 2 bedroom apartment is located in the spectacular Borgo di Gaiole, a popular hamlet just a short walk from the centre of the renown Gaiole in Chianti, right in the heart of the Chianti region, and only 20 minutes away from the wonderful Siena The apartment is... View all property information
Make Enquiry
From
$1,717
Per Night
1 / 21
Payment Protection
7 Bedrooms, 7 Bathrooms, Sleeps 14
Details Make Enquiry
Amenities & Details
  • Balcony
  • Dishwasher
  • Fireplace
  • Garden
  • Grill
  • Internet Access
  • Mountain Views
  • Private Outdoor...
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • ?
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
Charming Villa in Chianti with private pool, tennis court, concierge service, wi-fi and garden with stunning view on Tuscan hills. The villa can be rented up to 14 guest (Main Villa); in alternative up to 22 guest ( Main Villa plus apartment); For weddings, events and bigger groups up to 34... View all property information
Make Enquiry
From
$127
Per Night
1 / 9
Payment Protection
2 Bedrooms, 1 Bathroom, Sleeps 6
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dryer
  • Gym
  • Internet Access
  • Mountain Views
  • Shared Outdoor Pool...
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
About this property
The traditional Tuscan style cool stone walls, terracotta floors and dark chestnut beams give a pleasant, relaxed atmosphere to the interior of the apartment which also has air conditioning/central heating and double glazing. The kitchen is well-equipped with full-sized oven and hob, microwave,... View all property information
Make Enquiry
From
$4,865
Per Week
1 / 12
Payment Protection
5 Bedrooms, 5 Bathrooms, Sleeps 18
Details Make Enquiry
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
About this property
On entering the property, guests will find a welcoming living area, furnished with sofas around a traditional, focal fireplace. The kitchen is adjacent to this room. The kitchen is a typical Tuscan kitchen, well-equipped with plenty of pots and pans for those that enjoy cooking. A central table is... View all property information
Make Enquiry
From
$146
Per Night
1 / 24
Payment Protection
2 Bedrooms, 1 Bathroom, Sleeps 5
Details Make Enquiry
Amenities & Details
  • Balcony
  • Fireplace
  • Grill
  • Internet Access
  • Satellite TV
  • Shared Outdoor Pool...
  • Washer
  • Wi-Fi
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
About this property
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. Built around the year 1000 by the noble family of Guidi, today it is an esteemed wine estate with self catering holiday apartments, where visitors can... View all property information
Make Enquiry
From
$432
Per Night
1 / 17
4 Bedrooms, 3 Bathrooms, Sleeps 8
Details Make Enquiry
Amenities & Details
  • Fireplace
  • Grill
  • Internet Access
  • Private Outdoor...
  • Wi-Fi
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
About this property
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. This has produced a light and airy property with comfortable internal furnishings and beautiful outdoor spaces.... View all property information
Make Enquiry
From
$165
Per Night
1 / 24
Payment Protection
3 Bedrooms, 1 Bathroom, Sleeps 5
Booking
Details Make Enquiry
Amenities & Details
  • Shared Outdoor Pool...
  • Wi-Fi
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
  • x
About this property
' IL BACCHINO IN CHIANTI ' è una antica casa colonica rustica nel cuore della Toscana. Questo caratteristico casale in pietra del 1500, accuratamente ristrutturato, affonda le sue radici intorno all'XI secolo d.c.: le fondamenta murarie e le cantine della struttura risalgono a tale periodo... View all property information
Make Enquiry
From
$100
Per Night
1 / 15
Payment Protection
1 Bedroom, 1 Bathroom, Sleeps 3
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Shared Outdoor Pool...
  • Wi-Fi
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
  • x
About this property
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.Terreno Porzione privata del terreno, giardino, lastre. Parcheggio: 1 x posto macchina in garage sotterraneo. Accesso alla casa tramite... View all property information
Make Enquiry
From
$243
Per Night
1 / 20
Payment Protection
1 Bedroom, 2 Bathrooms, Sleeps 2
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Grill
  • Wi-Fi
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
  • x
About this property
Luxury 1Bedroom unit in the heart of Chianti,surrounded by Vineyards. Master bedroom with kingsize bed, writing desk and chair and exceptional bath. The lounge is comfortably furnished with two leather sofas and chairs, and has a flat screen TV with DVD and video player at one end. Private... View all property information
Make Enquiry
From
$653
Per Night
1 / 24
Payment Protection
6 Bedrooms, 5 Bathrooms, Sleeps 12
Details Make Enquiry
Amenities & Details
  • Dishwasher
  • Fireplace
  • Grill
  • Gym
  • Internet Access
  • Ping Pong Table
  • Private Outdoor...
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • Wheelchair access
  • Elder access
  • x
About this property
Podere Scopeto is a former Chianti hill farm on the west-facing slopes of the Montagni di Chianti. The present owners bought it some 15 years ago and restored the farmhouse and a separate self-contained studio for family holidays. It has kept its family feel and charm. The main house sleeps 10... View all property information
Make Enquiry
From
$4,865
Per Night
1 / 12
5 Bedrooms, 5 Bathrooms, Sleeps 18
Details Make Enquiry
Amenities & Details
  • Balcony
  • Dishwasher
  • Grill
  • Internet Access
  • Private Outdoor...
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
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... View all property information
Make Enquiry
From
$4,292
Per Week
1 / 24
Payment Protection
6 Bedrooms, 7 Bathrooms, Sleeps 14
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Fireplace
  • Grill
  • Internet Access
  • Private Outdoor...
  • Satellite TV
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • Wheelchair access
  • Elder access
  • x
About this property
A dive into an ancient culture in the heart of Tuscany, the Chianti Classico. Il Castello Medievale is situated in a medieval hamlet, constructed of white stone, built around 1000AD, surrounded by forests and olive groves, immersed in a magical atmosphere of tranquility. The Relais has five... View all property information
Make Enquiry
From
$105
Per Night
1 / 11
Payment Protection
2 Bedrooms, 2 Bathrooms, Sleeps 6
Details Make Enquiry
Amenities & Details
  • Balcony
  • Garden
  • Pool
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
Please note these Check-in Day Requirements for this property: May 09 - May 11 : Saturday check-in required, Monday check-out required.; May 17 - May 18 : Monday check-out required.; May 24 - May 25 : Monday check-out required.; May 31 - Jun 01 : Monday check-out required.; Jun 07 - Jun 08 : Monday... View all property information
Make Enquiry
From
$122
Per Night
1 / 9
Payment Protection
3 Bedrooms, 2 Bathrooms, Sleeps 6
Details Make Enquiry
Amenities & Details
  • Balcony
  • Dishwasher
  • Fireplace
  • Grill
  • Pool
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
Please note these Check-in Day Requirements for this property: May 30 - Jun 01 : Saturday check-in required, Monday check-out required.; Jun 07 - Jun 08 : Monday check-out required.; Jun 14 - Jun 15 : Monday check-out required.; Jun 21 - Jun 22 : Monday check-out required.; Jun 28 - Jun 29 : Monday... View all property information
Make Enquiry
From
$105
Per Night
1 / 13
Payment Protection
2 Bedrooms, 2 Bathrooms, Sleeps 6
Details Make Enquiry
Amenities & Details
  • Balcony
  • Garden
  • Pool
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
Please note these Check-in Day Requirements for this property: May 09 - May 11 : Saturday check-in required, Monday check-out required.; May 17 - May 18 : Monday check-out required.; May 24 - May 25 : Monday check-out required.; May 31 - Jun 01 : Monday check-out required.; Jun 07 - Jun 08 : Monday... View all property information
Make Enquiry
From
$1,654
Per Week
1 / 23
2 Bedrooms, 3 Bathrooms, Sleeps 7
Details Reviews (4) Make Enquiry
Amenities & Details
  • Dishwasher
  • Grill
  • Private Pool
  • Safe
  • Satellite TV
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • ?
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
In the heart of the Chianti Classico is where you'll find this house and it's location is not only to be appreciated because it's a short drive to town, but because it's set high on a hill with magnificent views outside of the surrounding vineyards and olive groves. This is definitely a place to... View all property information
Make Enquiry
From
$99
Per Night
1 / 6
Payment Protection
2 Bedrooms, 1 Bathroom, Sleeps 6
Details Make Enquiry
Amenities & Details
  • Balcony
  • Grill
  • Pool
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
Please note these Check-in Day Requirements for this property: May 30 - Jun 01 : Saturday check-in required, Monday check-out required.; Jun 07 - Jun 08 : Monday check-out required.; Jun 14 - Jun 15 : Monday check-out required.; Jun 21 - Jun 22 : Monday check-out required.; Jun 28 - Jun 29 : Monday... View all property information
Make Enquiry
From
$134
Per Night
1 / 9
Payment Protection
2 Bedrooms, 2 Bathrooms, Sleeps 4
Details Make Enquiry
Amenities & Details
  • Balcony
  • Dishwasher
  • Fireplace
  • Garden
  • Grill
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
Please note these Check-in Day Requirements for this property: Apr 05 - Apr 06 : Monday check-out required.; Jun 28 - Jun 29 : Monday check-out required.; Jul 05 - Jul 06 : Monday check-out required.; Jul 12 - Jul 13 : Monday check-out required.; Jul 19 - Jul 20 : Monday check-out required.; Jul 26... View all property information
Make Enquiry
From
$105
Per Night
1 / 11
Payment Protection
2 Bedrooms, 1 Bathroom, Sleeps 6
Details Make Enquiry
Amenities & Details
  • Balcony
  • Garden
  • Pool
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
Please note these Check-in Day Requirements for this property: May 09 - May 11 : Saturday check-in required, Monday check-out required.; May 17 - May 18 : Monday check-out required.; May 24 - May 25 : Monday check-out required.; May 31 - Jun 01 : Monday check-out required.; Jun 07 - Jun 08 : Monday... View all property information
Make Enquiry
From
$81
Per Night
1 / 11
Payment Protection
1 Bedroom, 1 Bathroom, Sleeps 4
Details Make Enquiry
Amenities & Details
  • Balcony
  • Garden
  • Pool
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
Please note these Check-in Day Requirements for this property: May 09 - May 11 : Saturday check-in required, Monday check-out required.; May 17 - May 18 : Monday check-out required.; May 24 - May 25 : Monday check-out required.; May 31 - Jun 01 : Monday check-out required.; Jun 07 - Jun 08 : Monday... View all property information
Make Enquiry
From
$130
Per Night
1 / 30
2 Bedrooms, 1 Bathroom, Sleeps 4
Details Make Enquiry
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
Ancient hamlet dating back to the year 998, situated in the Chianti region and offering 5 nice apartments. In the year 1204 this hamlet used to be border-line between Florence and Siena regions. The hamlet comprises 4 houses, a small church and a small B&B; but all of the 5 apartments are in a... View all property information
Make Enquiry
From
$244
Per Night
1 / 13
Payment Protection
7 Bedrooms, 4 Bathrooms, Sleeps 16
Details Make Enquiry
Amenities & Details
  • Dishwasher
  • Fireplace
  • Garden
  • Pool
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
Please note these Check-in Day Requirements for this property: May 09 - May 11 : Saturday check-in required, Monday check-out required.; May 17 - May 18 : Monday check-out required.; May 24 - May 25 : Monday check-out required.; May 31 - Jun 01 : Monday check-out required.; Jun 07 - Jun 08 : Monday... View all property information
Make Enquiry
From
$76
Per Night
1 / 6
Payment Protection
1 Bedroom, 1 Bathroom, Sleeps 3
Details Make Enquiry
Amenities & Details
  • Balcony
  • Grill
  • Pool
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
Please note these Check-in Day Requirements for this property: May 30 - Jun 01 : Saturday check-in required, Monday check-out required.; Jun 07 - Jun 08 : Monday check-out required.; Jun 14 - Jun 15 : Monday check-out required.; Jun 21 - Jun 22 : Monday check-out required.; Jun 28 - Jun 29 : Monday... View all property information
Make Enquiry
From
$142
Per Night
1 / 21
Payment Protection
3 Bedrooms, 3 Bathrooms, Sleeps 8
Booking
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Dryer
  • Grill
  • Gym
  • Internet Access
  • Mountain Views
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • ?
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
This beautiful and tastefully furnished 3 bedroom semi-detached villa is located in the popular hamlet of Gaiole in Chianti, near Siena in Tuscany. The ground floor consists of a spacious living room with a double sofa bed, and French doors opening on the patio and front garden, with vista on the... View all property information
Make Enquiry
From
$186
Per Night
1 / 20
Payment Protection
1 Bedroom, 1 Bathroom, Sleeps 2
Details Make Enquiry
Amenities & Details
  • Hot Tub
  • Internet Access
  • Safe
  • Shared Outdoor Pool...
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
About this property
Exclusive apartment with private garden in medieval village in the heart of the Chianti Classico area, a few kilometers from Siena. Tastefully renovated, refined and lovely garden overlooking the vineyards. View all property information
Make Enquiry
From
$1,224
Per Week
1 / 62
2 Bedrooms, 1 Bathroom, Sleeps 4
Details Make Enquiry
Amenities & Details
  • Dishwasher
  • Garden
  • Internet Access
  • Pool
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • ?
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
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. Villa Diora D is 100 square meters (1076 square feet). It features a... View all property information
Make Enquiry
From
$172
Per Night
1 / 20
Payment Protection
3 Bedrooms, 1 Bathroom, Sleeps 5
Details Make Enquiry
From
$70
Per Night
1 / 12
Payment Protection
1 Bedroom, 1 Bathroom, Sleeps 2
Details Make Enquiry
Amenities & Details
  • Balcony
  • Garden
  • Pool
  • Washer
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
Please note these Check-in Day Requirements for this property: May 09 - May 11 : Saturday check-in required, Monday check-out required.; May 17 - May 18 : Monday check-out required.; May 24 - May 25 : Monday check-out required.; May 31 - Jun 01 : Monday check-out required.; Jun 07 - Jun 08 : Monday... View all property information
Make Enquiry
From
$155
Per Night
1 / 23
Payment Protection
2 Bedrooms, 1 Bathroom, Sleeps 5
Details Make Enquiry
Amenities & Details
  • Balcony
  • Grill
  • Internet Access
  • Satellite TV
  • Shared Outdoor Pool...
  • Washer
  • Wi-Fi
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
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. Built around the year 1000 by the noble family of Guidi, today it is an esteemed wine estate with self catering holiday apartments, where visitors can... View all property information
Make Enquiry
From
$1,145
Per Week
1 / 18
Payment Protection
4 Bedrooms, 5 Bathrooms, Sleeps 8
Bookings
Details Make Enquiry
Amenities & Details
  • Dishwasher
  • Grill
  • Internet Access
  • Private Outdoor...
  • Satellite TV
  • Wi-Fi
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • x
  • ?
  • Wheelchair access
  • Elder access
  • x
  • x
About this property
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 proximity to numerous wineries,... View all property information
Make Enquiry
From
$1,717
Per Night
1 / 102
Payment Protection
7 Bedrooms, 7 Bathrooms, Sleeps 13
Details Make Enquiry
Amenities & Details
  • Dishwasher
  • Garden
  • Private Pool
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • ?
  • ?
  • ?
  • Wheelchair access
  • Elder access
  • ?
  • ?
About this property
This exclusive villa with private swimming pool and tennis court offers luxurious accommodation in Tuscany for 13 people. The apartments and farmhouse can be rented separately or combined with the villa to accommodate up to 35 guests. Additional amenities include: heating. View all property information
Make Enquiry
From
$129
Per Night
1 / 10
Payment Protection
2 Bedrooms, 1 Bathroom, Sleeps 5
Details Make Enquiry
Amenities & Details
  • Balcony
  • Fireplace
  • Hot Tub
  • Ping Pong Table
  • Shared Outdoor Pool...
  • Washer
  • Wi-Fi
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • Wheelchair access
  • Elder access
  • x
About this property
In the top of a hill set in the patchwork of vineyards that characterizes the area of Chianti Classico, in the heart of an ancient medieval village, was born a few years ago Pieve Marsina. The structure, made up of nice apartments, has as principal objective to allow our guests to enjoy the calm,... View all property information
Make Enquiry
From
$100
Per Night
1 / 24
Payment Protection
1 Bedroom, 1 Bathroom, Sleeps 3
Details Make Enquiry
Amenities & Details
  • Grill
  • Hot Tub
  • Ping Pong Table
  • Shared Outdoor Pool...
  • Washer
  • Wi-Fi
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • Wheelchair access
  • Elder access
  • x
  • x
About this property
On the highest point of a hill set among the mosaic of the vineyards, typical of the Chianti Classico area, in the heart of a medieval village, you'll find the Pieve Marsina. The house, composed of 5 delightful apartments, has as it's main objective the idea of offering guests the opportunity to... View all property information
Make Enquiry
From
$143
Per Night
1 / 11
Payment Protection
2 Bedrooms, 1 Bathroom, Sleeps 5
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Mountain Views
  • Shared Outdoor Pool...
  • Wi-Fi
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
  • x
About this property
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. Availability of apartments an... View all property information
Make Enquiry
From
$115
Per Night
1 / 14
Payment Protection
2 Bedrooms, 1 Bathroom, Sleeps 4
Booking
Details Make Enquiry
Amenities & Details
  • Air Conditioning
  • Balcony
  • Dishwasher
  • Gym
  • Shared Outdoor Pool...
  • Washer
  • Wi-Fi
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • Wheelchair access
  • Elder access
  • x
  • ?
About this property
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. Availability of apartments an... View all property information
Make Enquiry
From
$887
Per Week
1 / 21
2 Bedrooms, 2 Bathrooms, Sleeps 4
Details Reviews (2) Make Enquiry
Amenities & Details
  • Dishwasher
  • Fireplace
  • Grill
  • Internet Access
  • Satellite TV
  • Shared Outdoor Pool...
  • Washer
  • Wi-Fi
Suitability
  • Pets allowed
  • Smoking allowed
  • Suitable for children
  • x
  • x
  • Wheelchair access
  • Elder access
  • x
  • x
About this property
One of Italy's national monuments; Montefienali hamlet emerged in the middle of the 13th Century as a remote staging post on an ancient Roman road into the Chianti. After a two-year restoration project Montefienali is once more the ideal place for rest and recuperation for both body and mind and an... View all property information
Make Enquiry
4 of 5 stars Reviewed 16 January 2014
We enjoyed our time at the villa. It was very quiet as it was off season so we relaxed outside the villa and went on trips to Florence and Sienna. A car is essential to get to...
4 of 5 stars Reviewed 13 January 2012
My partner and I booked this one for a family wedding in Radda in Chianti. Other family menbers and guests booked other villas on the complex. This particular villa is secluded...
See all reviews
Go to map view
Book Online(60)
Use filters to find the best results!

Suitability

  • Wheelchair access (2)
  • Elder access (33)
  • Suitable for children (75)
  • Pet friendly (33)
  • Smoking allowed (38)

Amenities

  • All pools (96)
  • Parking (94)
  • Public pool (68)
  • Garden (65)
  • Internet (65)
  • View all amenities
List your property for free!
List your accommodation
for free on our website.
Reach millions worldwide.
Add a Listing


In partnership with
Get the List