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Vacation Rentals in Certaldo, Italy

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    Travelers to Certaldo are booking December dates now. Secure your vacation rental today, and have the perfect trip.
    1 / 15
    5 of 5 stars (4) Excellent
    3 Bedrooms, 4 Bathrooms, Sleeps 8 | Quick View
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    1 / 11
    4.5 of 5 stars (5) Very good
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    1 / 13
    5 Bedrooms, 3 Bathrooms, Sleeps 12 | Quick View
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    1 / 16
    2 of 5 stars (1) Poor
    3 Bedrooms, 2 Bathrooms, Sleeps 7 | Quick View
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    50052, Certaldo, Province of Florence
    1 / 18
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    50055, Certaldo, Province of Florence
    1 / 13
    5 of 5 stars (18) Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    A rustic 1st floor apartment in a villa set amongst vineyards and olive groves in one of the most beautiful corners of the Chianti region. Use of shared garden and pool and allocated outside eating area.<BR><BR>Located halfway between Florence and Siena, not only it provides an ideal base for... View all property information
    Location Information
    50052, Certaldo, Province of Florence
    5 of 5 stars Reviewed July 21, 2016
    This apartment was a perfect home base for two adults and two teenagers visiting Tuscany. It's very clean and comfortable, and has all of the amenities needed to make it feel...
    5 of 5 stars Reviewed November 2, 2015
    We had a brilliant time in Tuscany and loved the apartment. The views are marvellous and it is so peaceful there and you supplied us with everything that we needed. Thank you so...
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    1 / 30
    4.5 of 5 stars (19) Very good
    4 Bedrooms, 3 Bathrooms, Sleeps 10 | Quick View
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    About this property
    L'Antica Cisterna is an authentic traditional Tuscan farmhouse in San Donnino, Certaldo, and has been tastefully converted into a residential villa for holiday lets. The accommodation comprises four bedrooms (including two triples), three bathrooms, a kitchen, large dining room and living room.... View all property information
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    50052, Certaldo, Province of Florence
    5 of 5 stars Reviewed May 22, 2016
    Just finished up an amazing stay at Charley and Anne's farmhouse in Tuscany and I can't say enough about how great this place is! Charley and Anne were both amazing hosts, the...
    5 of 5 stars Reviewed March 9, 2016
    This was an opportunity to get together with family from 3 different countries. The house itself had character, its thick walls betraying its age. Nice views from the outside...
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    1 / 21
    5 of 5 stars (2) Excellent
    Private Room, 2 Bathrooms, Sleeps 5 | Quick View
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    • ?
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    • x
    About this property
    Mirtillo is a luxury apartment on the first floor of a classic 18th century Tuscan manor house in an old park amongst vineyards and olive groves. It is located in the heart of Tuscany, midway between Florence and Siena in the most characteristic Chianti landscape. The rooms are spacious and... View all property information
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    50052, Certaldo, Province of Florence
    1 / 104
    4.5 of 5 stars (3) Very good
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • Central Heating
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    50052, Certaldo, Province of Florence
    5 of 5 stars Reviewed October 30, 2015
    We stay in three residences in Certaldo, and this was the best of the three. Conveniently located near the main piazza , the train station and Certaldo Alto and it was also close...
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    1 / 88
    5 of 5 stars (7) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    50052, Certaldo, Province of Florence
    5 of 5 stars Reviewed April 24, 2016
    What a charming place to stay! You are living in the town where Boccaccio may have been born but he definitely died here. You can visit his house which is now a museum. My wife...
    5 of 5 stars Reviewed September 22, 2015
    A great location to visit all Tuscany has to offer. The apartment is a joy to stay in. Veronica is so pleasant to deal with. She went above and beyond when my partner was...
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    1 / 25
    5 of 5 stars (3) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    Location Information
    50052, Certaldo, Province of Florence
    5 of 5 stars Reviewed July 13, 2016
    This one bedroom apartment with a beautiful garden is clean and very comfortable with all that is required for a fine stay. Our host Isa was so good to us, welcoming us with...
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    1 / 21
    5 of 5 stars (2) Excellent
    3 Bedrooms, 4 Bathrooms, Sleeps 6 | Quick View
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    About this property
    The apartment has two entrances and a large courtyard where you can park your car. Certaldo High is a medieval village still intact, is ideal for a holiday of peace, art and history. <BR><BR>Here you can visit the house, the tower and the church with the tomb of Giovanni Boccaccio and the Palace... View all property information
    Location Information
    50052, Certaldo, Province of Florence
    5 of 5 stars Reviewed October 9, 2015
    I travelled with my wife and sister in law and this appartment with two bedrooms with double bed and two bathrooms suited perfect. The appartment is spacious and the old Palazzo...
    5 of 5 stars Reviewed April 19, 2015
    We, a family of five, have just returned home after the most wonderful week in Tuscany. Certaldo Alto stole our hearts. It is a beautiful, unspoilt medieval town steeped in...
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    1 / 25
    3.5 of 5 stars (3) Average
    3 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    About this property
    Apartment in original Tuscan farmhouse located in the Chianti area near Certaldo. Close to Florence and Siena and surrounded by vineyards. The apartment is composed of two double bedrooms, one bedroom with twin beds, one bathroom and a livingroom. Apartment located in an original Tuscan farmhouse,... View all property information
    Location Information
    50022, Certaldo, Province of Florence
    4 of 5 stars Reviewed October 15, 2014
    We stayed here in August 2014 as 3 couples and thoroughly enjoyed our stay. The villa is recently renovated and yet still of an authentic style, with many of the building's...
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    1 / 20
    5 of 5 stars (5) Excellent
    6 Bedrooms, 4 Bathrooms, Sleeps 14 | Quick View
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    50052, Certaldo, Province of Florence
    5 of 5 stars Reviewed July 26, 2015
    Rented accommodation for family to discover Tuscany and the villa is ideally situated to do this, with Pisa Florence and Siena all within an hours drive. The rooms within the...
    5 of 5 stars Reviewed May 31, 2014
    This villa is outstanding. It offers everything you could possibly want. Its location in the Tuscan Hills is beautiful, the villa itself is full of Italian charm and the grounds...
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    1 / 72
    9 Bedrooms, 7 Bathrooms, Sleeps 24 | Quick View
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    About this property
    All'interno di una tenuta di 200 ha. di boschi, campi, vigneti e oliveti si trova l'antico complesso di Villa Avanella, comprendente la tradizionale villa signorile di campagna composta da due grandi appartamenti, il caratteristico Fienile e, a circa 100 mt ci sono altri n. 4 appartamenti. Tutto il... View all property information
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    50052, Certaldo, Province of Florence
    1 / 79
    5 of 5 stars (2) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Outdoor Dining Area
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    50052, Certaldo, Province of Florence
    1 / 60
    5 of 5 stars (2) Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    Casa al Cantone' apposite 12th Pretorio Palace offers guests the chance to experience the atmosphere of a medieval town in two charming independent apartment.<BR><BR>Apart. "La Terrazza" <BR>This apartment has traditional beamed ceilings and terracota floors<BR>Consists: sitting/dining room,... View all property information
    Location Information
    50052, Certaldo, Province of Florence
    5 of 5 stars Reviewed October 5, 2015
    Our stay at this nicely outfitted apartment in magical Certaldo Alto was very peaceful. The apartment is located at the top of the main via through town- stick your head out any...
    5 of 5 stars Reviewed September 3, 2013
    We had a wonderful trip in late May 2013. The apartment is not fancy, but it was exactly what we needed. Central location, good train access, and wonderful dining experiences in...
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    1 / 27
    5 of 5 stars (1) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    • Outdoor Dining Area
    • Private Yard
    • Air Conditioning
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    • Shared Yard
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    • Pet-friendly
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    • Smoking allowed
    About this property
    La casa vacanze "Poggio ai Venti" dispone di due ampi monolocali di circa 40 mq. ciascuno, con ingresso indipendente, finemente arredati in stile toscano e dotati di ogni confort e comodità. Gli appartamenti (Girasole e Papavero), dispongono di una zona pranzo composta da una graziosa ma funzionale... View all property information
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    50052, Certaldo, Province of Florence
    1 / 17
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    50052, Certaldo, Province of Florence
    1 / 31
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • Air Conditioning
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    • ?
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    • ?
    About this property
    Charming stone-built house located in a peaceful and panoramic position on the green, rolling hills near San Gimignano. The villa is the result of a recent renovation which has transformed this ancient barn into a beautiful and comfortable detached villa, ideal for spending a relaxing holiday in... View all property information
    Location Information
    53037, Certaldo, Province of Florence
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    1 / 30
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • ?
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    About this property
    Beautiful former barn situated in quiet and panoramic location on the Chianti hills. This house has been recently and carefully restored and turned into a charming country house offering welcoming, tastefully furnished interiors. Outside guests can enjoy use of a beautiful, well-groomed garden with... View all property information
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    50052, Certaldo, Province of Florence
    1 / 23
    Marcialla
    7 Bedrooms, 7 Bathrooms, Sleeps 13 | Quick View
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    About this property
    Distance to Horse riding 4kmDistance to Golf course 20KmFacilitiesChildren friendlyPet allowedPets AllowedAir conditioningHair dryerDryerIroning boardPortable barbecueWeekly linen changeKitchenOutdoor showerIronSmall electric ovenGas ovenFridgeBlenderGazeboPrivate gardenInternet... View all property information
    Location Information
    50028, Marcialla, Certaldo
    1 / 30
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • ?
    • ?
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    • ?
    About this property
    Beautiful former barn situated in quiet and panoramic location on the Chianti hills. This house has been recently and carefully restored and turned into a charming country house offering welcoming, tastefully furnished interiors. Outside guests can enjoy use of a beautiful, well-groomed garden with... View all property information
    Location Information
    Certaldo, Province of Florence
    1 / 30
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Shared Outdoor Pool...
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    • ?
    • ?
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    • ?
    About this property
    Beautiful former barn situated in quiet and panoramic location on the Chianti hills. This house has been recently and carefully restored and turned into a charming country house offering welcoming, tastefully furnished interiors. Outside guests can enjoy use of a beautiful, well-groomed garden with... View all property information
    Location Information
    Certaldo, Province of Florence
    1 / 31
    3 Bedrooms, 1 Bathroom, Sleeps 8 | Quick View
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    About this property
    The property is a beautiful detached villa converted from a lovely, old hay store situated in the Chianti hills half way (35 km) between Florence and Siena. In the well kept garden there is an inviting swimming pool (8 x 5 m) available from May to October opening onto a magnificent panorama over... View all property information
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    53037, Certaldo, Province of Florence
    1 / 80
    4 of 5 stars (1) Very good
    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    50052, Certaldo, Province of Florence
    1 / 100
    5 of 5 stars (1) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Satellite TV
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    50052, Certaldo, Province of Florence
    1 / 97
    4 of 5 stars (1) Very good
    2 Bedrooms, 1 Bathroom, Sleeps 8 | Quick View
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    • Wi-Fi
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    50052, Certaldo, Province of Florence
    1 / 59
    1 Bedroom, Sleeps 2 | Quick View
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    • x
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    About this property
    Casale Elsa is a perfect starting point to explore Tuscany: situated in the heart of Chianti, the major attractions of the region can easily be reached. It is only a 15 minutes' drive to the jewel of San Gimignano, and within an hour you can reach both Florence and Siena. Closer are some... View all property information
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    Certaldo, Province of Florence
    1 / 16
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    This villa near San Gimignano offers a pristine swimming pool, covered terraces and three bedrooms, two bathrooms, a kitchen, dining room and sitting room. This villa near San Gimignano offers a pristine swimming pool, covered terraces and three bedrooms, two bathrooms, a kitchen, dining room and... View all property information
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    53037, Certaldo, Province of Florence
    1 / 61
    1 Bedroom, Sleeps 2 | Quick View
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    • x
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    About this property
    Casale Elsa is a perfect starting point to explore Tuscany: situated in the heart of Chianti, the major attractions of the region can easily be reached. It is only a 15 minutes' drive to the jewel of San Gimignano, and within an hour you can reach both Florence and Siena. Closer are some... View all property information
    Location Information
    Certaldo, Province of Florence
    1 / 15
    5 of 5 stars (1) Excellent
    Private Room, 4 Bathrooms, Sleeps 9 | Quick View
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    About this property
    Our Locanda has been open to guests since 1987, is an epoch home dating back to approximately the XIV century. The interior has been restructured with extreme care and the furnishings, fabrics and various objects carefully chosen after a lengthy and scrupulous historical research. Everithing... View all property information
    Location Information
    50052, Certaldo, Province of Florence
    5 of 5 stars Reviewed June 2, 2016
    We loved Locando Linando II - a comfortable, quiet and unique place to stay in an incredibly picturesque Medieval Tuscan hill town. Our stay was a delight, helped enormously by...
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    1 / 20
    4.5 of 5 stars (9) Very good
    8 Bedrooms, 7 Bathrooms, Sleeps 15 | Quick View
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    About this property
    Immerse yourself in the Victorian-era atmosphere of this Tuscany villa rental, an excellent choice for a family holiday, full of period furniture and elegant decor. Surrounded by olive trees, rolling hills, and the vineyards of Tuscany, you will be at your leisure to cool off in the private pool,... View all property information
    Location Information
    50052, Certaldo, Province of Florence
    4 of 5 stars Reviewed July 22, 2016
    Very beautiful old Tuscany villa. Very nice pool with a view to die for. 8 bedrooms only 6 with aircon. One Tv not working. Free internet , working in a part of the...
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    1 / 6
    5 of 5 stars (2) Excellent
    19 Bedrooms, 19 Bathrooms, Sleeps 40 | Quick View
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    Location Information
    50052, Certaldo, Province of Florence
    5 of 5 stars Reviewed September 8, 2015
    We just got home from visiting Castello di S. Maria Novella with a group of 18. We had never visited before but the couple who organized the trip has been there 3 previous times...
    5 of 5 stars Reviewed June 12, 2014
    What an unforgettable experience. From our arrival at the castle to our departure our experience was unbelievable. The people at the castle (Fernando, Martha and the chef...
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    1 / 26
    5 of 5 stars (1) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    About this property
    Charming and welcoming apartment located in the medieval village of Certaldo Alto, in the heart of Tuscany, a few kilometers from Florence, Siena, Pisa, San Gimignano and Volterra.<BR>The apartment, on the ground floor with private entrance, has a kitchen / living room with sofa bed, two double... View all property information
    Location Information
    50052, Certaldo, Province of Florence
    5 of 5 stars Reviewed December 31, 2015
    Loved this medieval apartment. Gracious hostess who provides all modern conveniences, advice and unexpected extras. We stayed here for 10 nights, including over christmas day. Was...
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    1 / 30
    2 Bedrooms, 1 Bathroom, Sleeps 5 | Quick View
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    50052, Certaldo, Province of Florence
    1 / 13
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    50052, Certaldo, Province of Florence
    1 / 73
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Wi-Fi
    • Hot Tub
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    • x
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    About this property
    Beautiful former barn situated in quiet and panoramic location on the Chianti hills. This house has been recently and carefully restored and turned into a charming country house offering welcoming, tastefully furnished interiors. Outside guests can enjoy use of a beautiful, well-groomed garden with... View all property information
    Location Information
    50052, Certaldo, Province of Florence
    1 / 10
    3 Bedrooms, 5 Bathrooms, Sleeps 8 | Quick View
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    • Wi-Fi
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    • Pet-friendly
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    • ?
    • Smoking allowed
    • x
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    50052, Certaldo, Province of Florence
    1 / 31
    5 Bedrooms, 6 Bathrooms, Sleeps 10 | Quick View
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    • Terrace
    • Patio
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    • Pet-friendly
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    • Smoking allowed
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    50052, Certaldo, Province of Florence
    1 / 16
    8 Bedrooms, 8 Bathrooms, Sleeps 18 | Quick View
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    • Satellite TV
    • Private Yard
    • Private Outdoor...
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    • Balcony
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    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Staying at Farmhouse Villa Sticci, if even only for a few days, will allow you to spend valuable time indulging yourself and sharing special moments with your loved ones.<BR><BR>Enjoy the birdsong, loose yourself in the marvelous sunset and taste this wonderful land through our excellent... View all property information
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    Certaldo, Province of Florence
    1 / 21
    4 Bedrooms, 4 Bathrooms, Sleeps 9 | Quick View
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    • Private Outdoor...
    • Balcony
    • Washer
    • Air Conditioning
    • Satellite TV
    • DVD Player
    • Grill
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Il Podere is a beautiful farmhouse located halfway between Florence and Siena, in the heart of the Chianti Hills. This is one of the most popular regions in central Tuscany, and the scenery around this house is of incredible beauty. Vineyards, olive groves and fields form a paradise-like landscape,... View all property information
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    Certaldo, Province of Florence
    1 / 97
    5 of 5 stars (1) Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 8 | Quick View
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    • Wi-Fi
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    • Washer
    • Central Heating
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    • Outdoor Dining Area
    • Balcony
    • Shared Outdoor Pool...
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    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    Location Information
    50052, Certaldo, Province of Florence
    1 / 23
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Balcony
    • Shared Outdoor Pool...
    • Grill
    • Secure Parking
    • Washer
    • Satellite TV
    • Air Conditioning
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    This elegant farmstead is located in the most coveted region of central Tuscany. Strategically positioned in the middle of the Golden Triangle - Florence, Siena and Pisa - it sits on top of a hill. Capanna Olivo takes its name from the vast groves of olive trees that surround it in every direction,... View all property information
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    Certaldo, Province of Florence
    1 / 64
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Parking
    • Patio
    • Shared Yard
    • Outdoor Dining Area
    • Grill
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    Location Information
    50052, Certaldo, Province of Florence
    1 / 14
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    Amenities & Details
    • Washer
    • Private Yard
    • Terrace
    • Secure Parking
    • Balcony
    • Grill
    • Shared Outdoor Pool...
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Villa della Torre is a large, historic estate halfway between Florence and Siena (22 miles each), perched on a hilltop amidst a lush green countryside. This location is outstanding: From the garden you can enjoy stunning views of the gentle rolling hills, vineyards, olive trees leading to the... View all property information
    Location Information
    Certaldo, Province of Florence
    1 / 9
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    Amenities & Details
    • Washer
    • Shared Outdoor Pool...
    • Balcony
    • Secure Parking
    • Terrace
    • Shared Yard
    • Grill
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Villa della Torre is a large, historic estate halfway between Florence and Siena (22 miles each), perched on a hilltop amidst a lush green countryside. This location is outstanding: From the garden you can enjoy stunning views of the gentle rolling hills, vineyards, olive trees leading to the... View all property information
    Location Information
    Certaldo, Province of Florence
    1 / 12
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    Amenities & Details
    • Secure Parking
    • Terrace
    • Satellite TV
    • Shared Outdoor Pool...
    • Grill
    • Washer
    • Balcony
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    The elegant farmstead Villa Olivo is located in the most coveted region of central Tuscany. Strategically positioned in the middle of the Golden Triangle - Florence, Siena and Pisa - it sits on top of a hill looking out onto the panoramic valley to south-west. Surrounded by vast groves of olive... View all property information
    Location Information
    Certaldo, Province of Florence
    1 / 11
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    Amenities & Details
    • Washer
    • Secure Parking
    • Air Conditioning
    • Shared Outdoor Pool...
    • Grill
    • Satellite TV
    • Balcony
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    The elegant farmstead Villa Olivo is located in the most coveted region of central Tuscany. Strategically positioned in the middle of the Golden Triangle - Florence, Siena and Pisa - it sits on top of a hill looking out onto the panoramic valley to south-west. Surrounded by vast groves of olive... View all property information
    Location Information
    Certaldo, Province of Florence
    1 / 11
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
    Inquire for rates
    Amenities & Details
    • Grill
    • Balcony
    • Secure Parking
    • Air Conditioning
    • Washer
    • Satellite TV
    • Shared Outdoor Pool...
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    The elegant farmstead Villa Olivo is located in the most coveted region of central Tuscany. Strategically positioned in the middle of the Golden Triangle - Florence, Siena and Pisa - it sits on top of a hill looking out onto the panoramic valley to south-west. Surrounded by vast groves of olive... View all property information
    Location Information
    Certaldo, Province of Florence