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.

Holiday Rentals in Gaiole in Chianti

Map
Satellite
Map updates are paused. Zoom in to see updated info.
Reset zoom
Updating Map...
Your filters are still active.
Check In Check Out
    There are no pins in your viewport. Try moving the map or changing your filters.
    • {providername} {price}
    {providername} {price}
      {listitems}
    {sold_out_text}
    We can't find prices for this accommodation
    From {rate_price} {rate_periodicity}
    View Map
    Location
    Any Distance
    from
    Price
    per night
    €205 Average
    |||
    |||
    €0€1,000+
    Suitability
    Suitability
    More filters
    Travellers to Gaiole in Chianti are booking September dates now. Secure your holiday rental today, and have the perfect trip.
    All 198 Rentals in Gaiole in Chianti
    Sort by:
    Default
    Experience the 'Chiantishire' at LisiDor - September is at 25% OFF!1 / 70
    (12)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Cottage with pool for 2 couples - Interesting promotions for late Summer weeks..1 / 72
    (14)Very good
    2 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    LUXURY APARTMENT WITH PRIVATE GARDEN & VIEWS1 / 24
    (39)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Casa Felice is a 2 bedroom apartment in village of Gaiole, sleeps 6, shared pool1 / 20
    (7)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Patio
    • Washer
    • DVD Player
    • Mountain Views
    • Air Conditioning
    • Cable/satellite TV
    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 24 July 2017
    We had a lovely holiday in Micks apartment in Borgo Gaiole. The Borgo is a wonderful complex, built in ancient style. It has a nice atmosphere to it. The surroundings in chianti...
    Reviewed 8 August 2015
    This apartment is great for a family of 4. We had a wonderful stay in Gaiole. The village is 5 min by walk and the pool was really appreciate by the children. Garage spot (small...
    See all reviews
    About this property
    Casa Felice is 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...
    View all property information
    Location Information
    53013, Gaiole in Chianti, Province of Siena
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 6
    Make Enquiry
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Patio
    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    • Parking
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Gaiole Suites is a compound of terraced houses just renewed, situated 500m away from Gaiole in Chianti center. They are placed in a quiet and silent zone, surrounded by the green Tuscany hills, not familiar with rush hour since the traffic is very little. At guests’ disposal, there is one swimming...
    View all property information
    Location Information
    53013, Gaiole in Chianti, Province of Siena
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
    Make Enquiry
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Shared Outdoor Pool (Unheated)
    • Patio
    • Parking
    • Wi-Fi
    • Cable/satellite TV
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Gaiole Suites is a compound of terraced houses just renewed, situated 500m away from Gaiole in Chianti center. They are placed in a quiet and silent zone, surrounded by the green Tuscany hills, not familiar with rush hour since the traffic is very little. At guests’ disposal, there is one swimming...
    View all property information
    Location Information
    53013, Gaiole in Chianti, Province of Siena
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
    Make Enquiry
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Parking
    • Patio
    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Gaiole Suites is a compound of terraced houses just renewed, situated 500m away from Gaiole in Chianti center. They are placed in a quiet and silent zone, surrounded by the green Tuscany hills, not familiar with rush hour since the traffic is very little. At guests’ disposal, there is one swimming...
    View all property information
    Location Information
    53013, Gaiole in Chianti, Province of Siena
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
    Make Enquiry
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Parking
    • Cable/satellite TV
    • Wi-Fi
    • Patio
    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Gaiole Suites is a compound of terraced houses just renewed, situated 500m away from Gaiole in Chianti center. They are placed in a quiet and silent zone, surrounded by the green Tuscany hills, not familiar with rush hour since the traffic is very little. At guests’ disposal, there is one swimming...
    View all property information
    Location Information
    53013, Gaiole in Chianti, Province of Siena
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
    Make Enquiry
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Patio
    • Terrace
    • Wi-Fi
    • Air Conditioning
    • Parking
    • Cable/satellite TV
    • Shared Outdoor Pool (Unheated)
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Gaiole Suites is a compound of terraced houses just renewed, situated 500m away from Gaiole in Chianti center. They are placed in a quiet and silent zone, surrounded by the green Tuscany hills, not familiar with rush hour since the traffic is very little. At guests’ disposal, there is one swimming...
    View all property information
    Location Information
    53013, Gaiole in Chianti, Province of Siena
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
    Make Enquiry
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Patio
    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    • Parking
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Gaiole Suites is a compound of terraced houses just renewed, situated 500m away from Gaiole in Chianti center. They are placed in a quiet and silent zone, surrounded by the green Tuscany hills, not familiar with rush hour since the traffic is very little. At guests’ disposal, there is one swimming...
    View all property information
    Location Information
    53013, Gaiole in Chianti, Province of Siena
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
    Make Enquiry
    Save time - get the best Gaiole in Chianti rentals sent straight to your email!
    Get the List
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Patio
    • Air Conditioning
    • Parking
    • Terrace
    • Shared Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Gaiole Suites is a compound of terraced houses just renewed, situated 500m away from Gaiole in Chianti center. They are placed in a quiet and silent zone, surrounded by the green Tuscany hills, not familiar with rush hour since the traffic is very little. At guests’ disposal, there is one swimming...
    View all property information
    Location Information
    53013, Gaiole in Chianti, Province of Siena
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
    Make Enquiry
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Wi-Fi
    • Patio
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Gaiole Suites is a compound of terraced houses just renewed, situated 500m away from Gaiole in Chianti center. They are placed in a quiet and silent zone, surrounded by the green Tuscany hills, not familiar with rush hour since the traffic is very little. At guests’ disposal, there is one swimming...
    View all property information
    Location Information
    53013, Gaiole in Chianti, Province of Siena
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
    Make Enquiry
    UNA VACANZA DA SOGNO1 / 14
    (2)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Central Heating
    • Wi-Fi
    • Private Garden
    • Parking
    • DVD Player
    • Grill
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    View all property information
    Location Information
    53013, Gaiole in Chianti, Province of Siena
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 8
    Make Enquiry
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Central Heating
    • Shared Outdoor Pool (Unheated)
    • DVD Player
    • Washer
    • Cable/satellite TV
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Borgo di Gaiole is located in the heart of Chianti Senese, a known area all over the world for its excellent gourmet products. The apartments are inside the ancient but recently restructured Borgo, which enjoys a magnificent view on the surrounding hills. At guests' disposal, for relaxing and...
    View all property information
    Location Information
    53013, Gaiole in Chianti, Province of Siena
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
    Make Enquiry
    Hilltop Poolside 2 Bedroom Villa in Chianti1 / 27
    (2)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Hot Tub
    • Internet Access
    • Outdoor Dining Area
    • Central Heating
    • Cable/satellite TV
    • Washer
    • Parking
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 30 August 2015
    We spent 15 days at la Pieve Marsina. The host Gabriele, the old-stone house on a hilltop, the swimming pool, and the countryside (we were surrounded by Chianti vineyard) were...
    Reviewed 1 August 2014
    With my husband and 2 daughters we had a great vacation in Tuscany.The oldest is 17 and the youngest is 13 year old. We had a split level appartement with authentic...
    See all reviews
    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
    Location Information
    53013, Gaiole in Chianti, Province of Siena
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 5
    Make Enquiry
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Parking
    • Cable/satellite TV
    • Air Conditioning
    • Terrace
    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    • Patio
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Gaiole Suites is a compound of terraced houses just renewed, situated 500m away from Gaiole in Chianti center. They are placed in a quiet and silent zone, surrounded by the green Tuscany hills, not familiar with rush hour since the traffic is very little. At guests’ disposal, there is one swimming...
    View all property information
    Location Information
    53013, Gaiole in Chianti, Province of Siena
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
    Make Enquiry
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
    • DVD Player
    • Cable/satellite TV
    • Balcony
    • Central Heating
    • Parking
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Borgo di Gaiole is located in the heart of Chianti Senese, a known area all over the world for its excellent gourmet products. The apartments are inside the ancient but recently restructured Borgo, which enjoys a magnificent view on the surrounding hills. At guests' disposal, for relaxing and...
    View all property information
    Location Information
    53013, Gaiole in Chianti, Province of Siena
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Make Enquiry
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Private Outdoor Pool (Unheated)
    • Washer
    • Grill
    • Balcony
    • Terrace
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This cozy and nice Villa is a restored hay barn that lays on the hillside 300 meters walk (or 2 km drive) from the exquisite village of Lecchi in the middle of Chianti. The Villa is on two levels that are joined by external stairs. The ground floor entrance is from the lower terrace and enters the...
    View all property information
    Location Information
    53013, Gaiole in Chianti, Province of Siena
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    Torre di Cancelli - luxury villa in Chianti!1 / 30
    (1)Excellent
    7 Bedrooms, 4 Bathrooms, Sleeps 14 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Washer
    • Private Outdoor Pool (Unheated)
    • Private Garden
    • Cable/satellite TV
    • Parking
    • Patio
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 23 July 2016
    This Gorgeous villa exceeded all my expectations for a perfect family summer vacation in Italy. The home is a perfect marriage of ancient charm and modern conveniences. The...
    See all reviews
    About this property
    This is a unique and historic wine country villa set in the heart of one of the most famous wine countries in the world, Chianti. The Tower was built in 1085, making it nearly 1000 years young. The interior has been completely remodeled and outfitted with all of the modern amenities. Contemporary...
    View all property information
    Location Information
    53013, Gaiole in Chianti, Province of Siena
    Holiday Rental House - 7 Bedrooms, 4 Bathrooms, Sleeps 14
    Make Enquiry
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Cable/satellite TV
    • Wi-Fi
    • DVD Player
    • Parking
    • Shared Outdoor Pool (Unheated)
    • Central Heating
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Borgo di Gaiole is located in the heart of Chianti Senese, a known area all over the world for its excellent gourmet products. The apartments are inside the ancient but recently restructured Borgo, which enjoys a magnificent view on the surrounding hills. At guests' disposal, for relaxing and...
    View all property information
    Location Information
    53013, Gaiole in Chianti, Province of Siena
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
    Make Enquiry
    List your property for free!
    List your holiday rental where TripAdvisor travellers can find it.
    Add a Listing
    Chianti house, Florence, Jacuzzi, Tuscany up to 6p1 / 42
    (7)Very good
    3 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Private Outdoor Pool (Heated)
    • Grill
    • Wi-Fi
    • Parking
    • Outdoor Dining Area
    • Central Heating
    • Mountain Views
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 20 August 2017
    A great place to stay. Very central in the Chianti region and very quiet and a little isolated which suited us very well indeed
    Reviewed 5 September 2016
    Our stay at the Villa was as expected. The location is isolated which we were looking for and most definitely in a beautiful and tranquil setting. Both Marcello and Sarah were...
    See all reviews
    About this property
    Recently renovated, is located in a scenic hillside location in a picturesque village nestled in the heart of Chianti, strategic point to reach in a short time two beautiful cities such as Siena and Florence. Moreover, you can go trekking in the beautiful trails and nature walks on foot or by...
    View all property information
    Location Information
    53013, Gaiole in Chianti, Province of Siena
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 6
    Make Enquiry
    6 Bedrooms, 5 Bathrooms, Sleeps 13 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Central Heating
    • Parking
    • Private Garden
    • Patio
    • Grill
    • Wi-Fi
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Nestled in the lush nature of the Chianti region, this charming manor built in the early 1900s lovingly embraces and preserves the romance of bygone times. It is an ideal place for relaxing in the surrounding nature while enjoying the area’s superb foods and wines. The house comprises about 800...
    View all property information
    Location Information
    53013, Gaiole in Chianti, Province of Siena
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 13
    Make Enquiry
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    • Balcony
    • Washer
    • Cable/satellite TV
    • Patio
    • Grill
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Large and comfortable apartment of 80 sqm for 5 people, located in the building near the swimming pool, at 200 meters from the restaurant and the reception. It is on the ground floor and consists of a living room with stone fireplace, a single sofa bed, Sat TV, a dining area and a kitchen corner...
    View all property information
    Location Information
    53013, Gaiole in Chianti, Province of Siena
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 5
    Make Enquiry
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Cable/satellite TV
    • Shared Outdoor Pool (Unheated)
    • Washer
    • Patio
    • Grill
    • Wi-Fi
    • Balcony
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Large and comfortable apartment of 80 sqm for 5 people, located in the building near the swimming pool, at 200 meters from the restaurant and the reception. It is on the ground floor and consists of a living room with stone fireplace, a single sofa bed, Sat TV, a dining area and a kitchen corner...
    View all property information
    Location Information
    53013, Gaiole in Chianti, Province of Siena
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 5
    Make Enquiry
    Villa Podere Terrena1 / 44
    (2)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Private Outdoor Pool (Unheated)
    • DVD Player
    • Mountain Views
    • Washer
    • Wi-Fi
    • Grill
    • Cable/satellite TV
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 17 March 2016
    A dream farmhouse , with olive trees and and beautiful countryside , surrounded by cozy villages in the Chianti region , just and over what we have imagined .. and...
    See all reviews
    About this property
    THE BUILDING. The building is located in a mountainous area of the classic chianti and is built entirely with local stones. It is surrounded by an olive grove from which high quality oil is obtained. The mountainous landscape with its views full of green is an invitation to relax. The whole house...
    View all property information
    Location Information
    53013, Gaiole in Chianti, Province of Siena
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 7
    Make Enquiry
    LA VACANZA NEL CUORE DEL CHIANTI1 / 17
    (4)Excellent
    2 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Parking
    • Children's Pool
    • Grill
    • Mountain Views
    • Wi-Fi
    • Central Heating
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    View all property information
    Location Information
    53013, Gaiole in Chianti, Province of Siena
    Holiday Rental House - 2 Bedrooms, 4 Bathrooms, Sleeps 6
    Make Enquiry
    castello in Chianti  conte1 / 23
    (2)Average
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Balcony
    • Cable/satellite TV
    • Washer
    • Shared Outdoor Pool (Unheated)
    • Parking
    • Grill
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 September 2017
    Wonderful old building with beautiful views over the surrounding countryside. Pool was a 5 minute walk from our apartment - nothing our kids couldn't handle, and they had a...
    Reviewed 9 November 2015
    One of the reasons we chose the place was because although remote, it had a restaurant so, with a small child, this would make things more convenient. When arrived unfortunately...
    See all reviews
    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
    Location Information
    53013, Gaiole in Chianti, Province of Siena
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
    Make Enquiry
    Le Diacce1 / 17
    (1)Excellent
    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Grill
    • Central Heating
    • Wi-Fi
    • Cable/satellite TV
    • Shared Outdoor Pool (Unheated)
    • DVD Player
    • Balcony
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 22 July 2016
    We stayed at Le Diacce for a week with our adult sons and their partners. This was an absolutely idyllic stay! Franca is the best hostess ever! She makes you feel so welcome...
    See all reviews
    About this property
    Le Diacce villa, benefits of a total privacy and enjoys splendid sunsets and a beautiful pool. The living room and kitchen open onto spacious terraces fully equipped for outdoor dining and surrounded by lawns, gardens and ancient trees. Ideal for families or a group of friends with plenty to see...
    View all property information
    Location Information
    53013, Gaiole in Chianti, Province of Siena
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
    Make Enquiry
    Bio Agriturismo Reggioli - Stanza dell'Ortolano1 / 4
    (1)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Private Garden
    • Wi-Fi
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    View all property information
    Location Information
    53013, Gaiole in Chianti, Province of Siena
    Private Room - 1 Bedroom, 1 Bathroom, Sleeps 2
    Make Enquiry
    Exclusive and reserved in Chianti - Quercia1 / 26
    (1)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    • Shared Garden
    • Secure Parking
    • Hot Tub
    • Outdoor Dining Area
    • Shared Outdoor Pool (Unheated)
    • Internet Access
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 29 August 2017
    Loved this quiet and authentic apartment, we had everything we needed, the location was a bit remote but directions to get there clear. Beautiful outdoor area, the highlight...
    See all reviews
    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
    Location Information
    53013, Gaiole in Chianti, Province of Siena
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
    Make Enquiry
    San Sano hamlet in the Heart of the Chianti, the Best choice in Tuscany !1 / 21
    (2)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • DVD Player
    • Balcony
    • Cable/satellite TV
    • Shared Outdoor Pool (Unheated)
    • Grill
    • Parking
    • Washer
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 18 February 2017
    If you are looking for a beautiful, relaxing vacation Casa del Vignaiolo is the perfect place to stay. In addition, owner Chuck is a wealth of knowledge & gave us numerous...
    See all reviews
    About this property
    Upon your arrival in San Sano, a quiet, medieval hamlet, surrounded by vineyards and olive groves, the drive into the small village seems very familiar as you approach. That's because it was the setting for the movie, 'Stealing Beauty' with Liv Taylor. This familiar feeling will stay with you...
    View all property information
    Location Information
    53013, Gaiole in Chianti, Province of Siena
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 5
    Make Enquiry
    Casacorvo Minore *2018 Late Summer Discounts*:  *Exclusive EV Point Included*1 / 22
    (18)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Cable/satellite TV
    • Air Conditioning
    • DVD Player
    • Patio
    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    • Washer
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 5 days ago
    Beautiful apartment with swimming pool in Gaiole Di Chianti.We had a great time A short distance to montevarchi were we took the train to Florence and then to Venice which we...
    Reviewed 1 week ago
    Just what we needed. A comfortable apartment for 2 with outdoor terrace.The complex is modern but built in Tuscan style. Walking distance albeit up and down a steep hill to...
    See all reviews
    About this property
    Set in the Chianti Hills just 30 mins from Siena is Borgo di Gaiole, situated on the edge of Gaiole in Chianti, one of the historic 'Chianti League' townships. The Borgo comprises the best of old and new. Built in traditional Tuscan architectural style with solid stone walls, chestnut beams and...
    View all property information
    Location Information
    53013 SI, Gaiole in Chianti, Province of Siena
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
    Make Enquiry
    Casa Ciaccheri1 / 13
    (2)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Cable/satellite TV
    • Wi-Fi
    • Private Outdoor Pool (Unheated)
    • Parking
    • Air Conditioning
    • Washer
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The house is located in the heart of the Chianti Classico, inside the town of Gaiole in Chianti (all kinds of shops). The apartment is on the ground floor and is part of a building where the owners reside. Outside a portion of an equipped courtyard is available for the exclusive use of the guests...
    View all property information
    Location Information
    53013, Gaiole in Chianti, Province of Siena
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
    Make Enquiry
    4 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Shared Outdoor Pool (Unheated)
    • Washer
    • Parking
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The charm of the ancient Eremo nel Chianti will capture your soul all the while you stay there and it will cling to your memories. In the heart of the Chianti, surrounded by woodlands and vineyards, this ancient construction has opened its doors to tourists who wish to have a rare and unique...
    View all property information
    Location Information
    53013, Gaiole in Chianti, Province of Siena
    Condo/Apartment - 4 Bedrooms, 3 Bathrooms, Sleeps 7
    Make Enquiry
    Fienile con vista sui vigneti1 / 28
    (3)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Parking
    • Private Outdoor Pool (Heated)
    • Private Garden
    • Mountain Views
    • Washer
    • Cable/satellite TV
    • Hot Tub
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 13 March 2018
    We spent a wonderful long weekend in Gaiole, hung out by the fireplace, went for long walks and to pretty little Siena. We had amazing Italian food, friendly neighbors and at...
    See all reviews
    About this property
    View all property information
    Location Information
    53013, Gaiole in Chianti, Province of Siena
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Make Enquiry
    Casacorvo Maggiore: *2018 Easter Discounts: Exclusive EV Point Included*1 / 23
    (14)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Washer
    • DVD Player
    • Patio
    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    • Wi-Fi
    • Cable/satellite TV
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 week ago
    We stayed in Casacorvo Maggiore for ten days at the end of July and found it to be the ideal base for relaxing and enjoying the beautiful weather and scenery and also for...
    Reviewed 2 September 2016
    It's exactly as it says on the tin. The property is very well equipped, clean and comfortable. Home from home comforts such as quality mattresses and bedding made it...
    See all reviews
    About this property
    A spacious well furnished three double bedroom, two bathroom apartment with an eight seating dining room and large lounge, just a few minutes stroll from the restaurants, cafes and wide range of services provided by Gaiole village. Outside, enjoy a game of boules in the tiered garden, or swing in...
    View all property information
    Location Information
    53013 SI, Gaiole in Chianti, Province of Siena
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 8
    Make Enquiry
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Terrace
    • Shared Outdoor Pool (Unheated)
    • Balcony
    • Secure Parking
    • Wi-Fi
    • Patio
    • Washer
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    View all property information
    Location Information
    53013, Gaiole in Chianti, Province of Siena
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 7
    Make Enquiry
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Owner's description:This property is a welcoming apartment that is part of a villa in the characteristic style of the Tuscan countryside. It sleeps six people. It is approximately 160 square meters (1720 square feet). It features a shared swimming pool, a private patio, a shared garden, air...
    View all property information
    Location Information
    53013, Gaiole in Chianti, Province of Siena
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Parking
    • Private Garden
    • Grill
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    View all property information
    Location Information
    53013, Gaiole in Chianti, Province of Siena
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Make Enquiry
    castello in Chianti ginestra1 / 25
    (1)Average
    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
    other travellers have booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Wi-Fi
    • Balcony
    • Shared Outdoor Pool (Unheated)
    • Washer
    • Grill
    • Parking
    • Cable/satellite TV
    • Central Heating
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 30 May 2016
    The location is gorgeous, high up in the mountains with fantastic views.The bedrooms were very large and there was plenty of storage space. The beds were large and...
    See all reviews
    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
    Location Information
    53013, Gaiole in Chianti, Province of Siena
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 5
    Make Enquiry
    4 Bedrooms, 4 Bathrooms, Sleeps 2 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Air Conditioning
    • Wi-Fi
    • Private Outdoor Pool (Unheated)
    • Hot Tub
    • Parking
    • Cable/satellite TV
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    EXTERNAL DESCRIPTION Il Bindaccio is an elegant property part of a historic castle (called Castello di Cacchiano), located near Gaiole in Chianti, in the heart of the Chianti area. The castle, founded in the tenth century by the aristocratic Ricasoli family, has become a modern farm producing wine...
    View all property information
    Location Information
    53013, Gaiole in Chianti, Province of Siena
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 2
    Make Enquiry
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Internet Access
    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Owner's description:This property is a characteristic two-story apartment that is part of a villa surrounded by vineyards and olive groves. It sleeps six people. It is approximately 130 square meters (1400 square feet). It features a shared swimming pool, a private patio, a shared garden, air...
    View all property information
    Location Information
    53013, Gaiole in Chianti, Province of Siena
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
    Make Enquiry
    3 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Shared Outdoor Pool (Unheated)
    • Central Heating
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The charm of the ancient Eremo nel Chianti will capture your soul all the while you stay there and it will cling to your memories. In the heart of the Chianti, surrounded by woodlands and vineyards, this ancient construction has opened its doors to tourists who wish to have a rare and unique...
    View all property information
    Location Information
    53013, Gaiole in Chianti, Province of Siena
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 5
    Make Enquiry
    TOSCANAFERIEN - PODERE L'AQUILA - OSKAR SIGRIST1 / 12
    (3)Average
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Shared Outdoor Pool (Unheated)
    • Balcony
    • Parking
    • Wi-Fi
    • Central Heating
    • Terrace
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    View all property information
    Location Information
    53013, Gaiole in Chianti, Province of Siena
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
    Make Enquiry
    Cavalcanti1 / 13
    (6)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Terrace
    • Housekeeping Included
    • Balcony
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 11 June 2015
    Cavalcanti was very nicely appointed. Two real master suites with en-suite baths and one double room with twin beds and en-suite bath at the opposite end of the house. The...
    See all reviews
    About this property
    Tucked between the villages of Gaiole and Radda in Chianti in the heart of Tuscany, Cavalcanti offers the privacy of a villa and the amenities of a larger estate. As part of the restored hamlet of Castello di San Donato in Perano, the three-bedroom property is surrounded by vineyards, a...
    View all property information
    Location Information
    53013, Gaiole in Chianti, Province of Siena
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
    Make Enquiry
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Internet Access
    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Owner's description:This property is a graceful apartment that is part of a villa surrounded by meadows and by green hills. It sleeps two people. It is approximately 65 square meters (700 square feet). It features a shared swimming pool, a private patio, a shared garden, air conditioning (please...
    View all property information
    Location Information
    53013, Gaiole in Chianti, Province of Siena
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
    Make Enquiry
    6 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
    other traveller has booked this property
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Private Outdoor Pool (Unheated)
    • Washer
    • Wi-Fi
    • Air Conditioning
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    EXTERNAL DESCRIPTION Villa Gaiole is a beautiful villa located near Gaiole in Chianti, in the heart of Chianti area. The property is accessed through a short tree-lined path, along which you can admire a wonderful panorama of the surrounding countryside. The villa boasts a large private garden...
    View all property information
    Location Information
    53013, Gaiole in Chianti, Province of Siena
    Holiday Rental House - 6 Bedrooms, 5 Bathrooms, Sleeps 12
    Make Enquiry
    1 Bedroom, 4 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Balcony
    • Washer
    • Wi-Fi
    • Terrace
    • DVD Player
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Savor a quintessential Tuscan holiday at Villa Rietine. This charming vacation rental has everything you’d want in an Italian country retreat, from historic architecture and modern amenities to a private garden. It’s even close to the village of Gaiole, the heart of Chianti and the perfect base...
    View all property information
    Location Information
    53013, Gaiole in Chianti, Province of Siena
    Holiday Rental House - 1 Bedroom, 4 Bathrooms, Sleeps 8
    Make Enquiry
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Amenities & Details
    • Cable/satellite TV
    • Hot Tub
    • Sauna
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Owner's description:Villa is situated at the very heart of Chianti Classico, about 5 km from Gaiole in Chianti, a medieval village famous for L’Eroica vintage cycling race. The villa sits nestled amongst the vines of an organic winery producing high quality wines and olive oil.This is a traditional...
    View all property information
    Location Information
    53013, Gaiole in Chianti, Province of Siena
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
    Make Enquiry
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
    Check in Check out
    Show Prices
    Payment Protection
    Amenities & Details
    • Private Indoor Pool
    • Wi-Fi
    • Washer
    • Air Conditioning
    • Parking
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Typical converted barn, 200 sq. m., for up to 8 people with 4 double bedrooms each with its own bathroom. Large garden, furnished terrace with pergola and private swimming pool, which can be covered and heated on request, connected internally with the house. The property maintains traditional...
    View all property information
    Location Information
    53013, Gaiole in Chianti, Province of Siena
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
    Make Enquiry
    1
    List your property
    Owner log in