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Certaldo Luxury Rentals

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    Travelers to Certaldo are booking December dates now. Secure your vacation rental today, and have the perfect trip.
    34 Matching Rentals in CertaldoView all 229 rentals
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    Castello di S. Maria Novella1 / 6
    (2)Excellent
    19 Bedrooms, 19 Bathrooms, Sleeps 40 Quick View
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    13 Bedrooms, 12 Bathrooms, Sleeps 26 Quick View
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    Studio, 12 Bathrooms, Sleeps 24 Quick View
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    9 Bedrooms, 12 Bathrooms, Sleeps 15 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Balcony
    • Patio
    • Wi-Fi
    • Secure Parking
    • Outdoor Dining Area
    • Terrace
    • Central Heating
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The beatiful 19th century Villa origianlly was a monastery. For five generations it has belonged to the Cascino family who restored it and started to host events like weddings, painting, theatre, tango courses and cooking classes. MINIMUM RESERVE FOR 8 PERSONS The luxuriant garden surrounding...
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    50052, Certaldo, Province of Florence
    Rental Home - 9 Bedrooms, 12 Bathrooms, Sleeps 15
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    6 Bedrooms, 10 Bathrooms, Sleeps 12 Quick View
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    • Internet Access
    • DVD Player
    • Shared Outdoor Pool (Unheated)
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    • Air Conditioning
    • Hot Tub
    • Cable/satellite TV
    • Washer
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located in the Tuscan countryside, Castello di Renai is a magnificent property just 30' away from Florence. Surrounded by a beautiful garden with a private pool (10 x 5 m), set on its own terrace, it can be reached from a flight of open stairs from the entrance courtyard, with an adjacent enclosed...
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    50051, Certaldo, Province of Florence
    Rental Home - 6 Bedrooms, 10 Bathrooms, Sleeps 12
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    6 Bedrooms, 7 Bathrooms, Sleeps 12 Quick View
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    • Private Outdoor Pool (Unheated)
    • Washer
    • Grill
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Originally the residence of a noble Tuscan family, the villas interiors are spacious and beautifully furnished with antiques and family heirlooms. On the ground floor there are two large living rooms with fireplaces, comfortable settees and armchairs, a sumptuous dining room with fireplace and...
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    50051, Certaldo, Province of Florence
    Rental Home - 6 Bedrooms, 7 Bathrooms, Sleeps 12
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    6 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    • Private Outdoor Pool (Unheated)
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    Pet friendly
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    About this property
    Atop a hill with sweeping views over its vast estate of vineyards, olive groves and farmland in the beautiful Chianti country, this grand villa with pool and chapel is the ideal setting for a special wedding or luxury holiday.
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    50051, Certaldo, Province of Florence
    Rental Home - 6 Bedrooms, 6 Bathrooms, Sleeps 12
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    5 Bedrooms, 4 Bathrooms, Sleeps 9 Quick View
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    • Air Conditioning
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    Pet friendly
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    About this property
    Owner's description: Description: In a landscape of rare beauty this property 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...
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    50052, Marcialla, Certaldo
    Rental Home - 5 Bedrooms, 4 Bathrooms, Sleeps 9
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    7 Bedrooms, 8 Bathrooms, Sleeps 13 Quick View
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    • Air Conditioning
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    Pet friendly
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    Owner's description: chateau is a lovely villa situated in the Chianti area between the provinces of Florence and Siena. The location, in the heart of Tuscany, is rich in history with many Renaissance cities and towns nearby, including Florence, Siena, San Gimignano, and Volterra. Many activities...
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    50028, Marcialla, Certaldo
    Rental Home - 7 Bedrooms, 8 Bathrooms, Sleeps 13
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    9 Bedrooms, 9 Bathrooms, Sleeps 18 Quick View
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    • Patio
    • Wi-Fi
    • Parking
    • Grill
    • Cable/satellite TV
    • Washer
    • Shared Outdoor Pool (Unheated)
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Villa il Sole is a villa in Tuscany with swimming pool, located in one of the hills that characterize the landscape, a few steps from Certaldo, an ancient town located halfway between Siena and Florence, suitable to spend holidays in Tuscany for groups. Beautiful and unique, it is perfect for give...
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    50052, Certaldo, Province of Florence
    Rental Home - 9 Bedrooms, 9 Bathrooms, Sleeps 18
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    7 Bedrooms, 7 Bathrooms, Sleeps 13 Quick View
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    • Internet Access
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    • DVD Player
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    Pet friendly
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    Smoking allowed
    About this property
    Owner's description: “this property” is an ancient Tuscan villa on the Chianti hills, surrounded by vineyards and olive trees, enjoying a wonderful view of the typical countryside. This accommodation is part of a small group of houses with a bell tower and small church. Restoration works have kept...
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    50028, Marcialla, Certaldo
    Rental Home - 7 Bedrooms, 7 Bathrooms, Sleeps 13
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    6 Bedrooms, 5 Bathrooms, Sleeps 9 Quick View
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    • Garden or Yard
    • Pool
    • Air Conditioning
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    • Balcony
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    (Minimum of one week rental required) Minimum rental one week rental Saturday to Saturday except for urban apartments. This beautiful, spacious, traditional Italian vacation villa is set in a wonderfully quiet position halfway between Florence and Siena in the heart of the Chianti district. It is...
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    50052, Certaldo, Province of Florence
    Rental Home - 6 Bedrooms, 5 Bathrooms, Sleeps 9
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Outdoor Dining Area
    • Shared Yard
    • Patio
    • Porch
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Lovely restored farm house with woodbeamed ceilings and tiled floors is situated in the garden of Villa Bacìo the main building. Although Casa Azalea shares the same big garden with other guests, the beautiful Azaleas give the opportunity for creating one's own secluded corner. The apartment is...
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    50052, Certaldo, Province of Florence
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    2 Bedrooms, 4 Bathrooms, Sleeps 4 Quick View
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    • Grill
    • Shared Outdoor Pool (Unheated)
    • Porch
    • Shared Yard
    • Outdoor Dining Area
    • Private Yard
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Located at 30 metres distance from a beautiful 19th tipycal Tuscan Villa Bacìo, this nice farm house surrounded by olive groves has been restored in the authentic Tuscan style. Downstairs there is a large living room with characteristic fire place used in the past by the old farmers, a sofa bed and...
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    50052, Certaldo, Province of Florence
    Condo/Apartment - 2 Bedrooms, 4 Bathrooms, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Shared Yard
    • Terrace
    • Shared Outdoor Pool (Unheated)
    • Outdoor Dining Area
    • Patio
    • Balcony
    • Grill
    • Porch
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Very close to The Cascinale, sharing the same big garden of the beautiful 19th century Villa Bacìo, this apartment with woodbeamed ceilings and terracotta floors is nicely furnished. It includes a living room with kitchen corner, 2 double bedrooms, 1 bathroom with shower. It comes with a baking...
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    50052, Certaldo, Province of Florence
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    • Secure Parking
    • Grill
    • Porch
    • Shared Yard
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This apartment with woodbeamed ceilings and terracotta floors is nicely furnished. It includes a living room with kitchen corner, 2 double bedrooms, 1 bathroom with shower. It comes with a baking oven under the outside porch. The apartment has independent heating. The swimming pool (16m x 6.50m)...
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    50052, Certaldo, Province of Florence
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Balcony
    • Central Heating
    • Patio
    • Outdoor Dining Area
    • Shared Yard
    • Terrace
    • Secure Parking
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This lovely restored farm house with woodbeamed ceilings and tiled floors is situated in the garden of a beautiful 19th s century Tuscan Villa the main building. Although Casa Azalea shares the same big garden with other guests, the beautiful Azaleas give the opportunity for creating one's own...
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    Location Information
    52100, Certaldo, Province of Florence
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Balcony
    • Shared Yard
    • Shared Outdoor Pool (Unheated)
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This nice farm house surrounded by olive groves has been restored in the authentic Tuscan style. Downstairs there is a large living room with characteristic fire place used in the past by the old farmers, a sofa bed and a dining-room corner. From the kitchen there is access to a paved garden. It...
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    50052, Certaldo, Province of Florence
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    VILLA AVANELLA  tuscany holiday with swimming pool1 / 72
    (2)Excellent
    9 Bedrooms, 7 Bathrooms, Sleeps 24 Quick View
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    • Housekeeping Included
    • Patio
    • Terrace
    • Balcony
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    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 weeks ago
    What a magnificent experience Francesca provided for our large group at Villa Avanella!! We were 26 family and friends who travelled from all corners of the world (Australia, NZ...
    Reviewed September 11, 2016
    We've just arrived home from Villa Avanella after the most amazing week visiting Tuscany. We hired out the bottom apartment which was ideal for our family which includes 3...
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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...
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    50052, Certaldo, Province of Florence
    Rental Home - 9 Bedrooms, 7 Bathrooms, Sleeps 24
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    7 Bedrooms, 13 Bathrooms, Sleeps 18 Quick View
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    • Shared Yard
    • Shared Outdoor Pool (Unheated)
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    • Patio
    • Wi-Fi
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    Location Information
    50021, Marcialla, Certaldo
    Private Room - 7 Bedrooms, 13 Bathrooms, Sleeps 18
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Internet Access
    • Washer
    • Cable/satellite TV
    • Shared Outdoor Pool (Unheated)
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    • Terrace
    • Balcony
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    DEAR TRAVELER, PLEASE KINDLY NOTE: The rental price includes: Wi-Fi Internet connection; parking; linens and towels; electricity. To be paid at the property:final cleaning EUR 130.00.Available for a fee, if desired:heating (when needed) EUR 19.00/day;air conditioning EUR 19.00/day;baby bed EUR...
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    50052, Certaldo, Province of Florence
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    9 Bedrooms, 6 Bathrooms, Sleeps 18 Quick View
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    • Terrace
    • Shared Yard
    • Balcony
    • Shared Outdoor Pool (Unheated)
    • Mountain Views
    • Air Conditioning
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The prestigious period house surrounded by a garden with beautiful trees sits on top of a hill on a splendid scenic site. From there you can admire groups of cypress trees, vineyards, olive groves, wheat and sunflower fields, woodlands and, in the distance, even San Gimignano's towers. Downstairs...
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    50052, Certaldo, Province of Florence
    Condo/Apartment - 9 Bedrooms, 6 Bathrooms, Sleeps 18
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    Studio, 9 Bathrooms, Sleeps 18 Quick View
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    • Central Heating
    • Grill
    • Wi-Fi
    • DVD Player
    • Washer
    • Private Outdoor Pool (Unheated)
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This Tuscany villa near Certaldo is ideal for a large group traveling together. Each of the nine double bedrooms has its own ensuite facilities, providing everyone staying at this Tuscany vacation rental with privacy and personal space when they need it. Otherwise, it's likely that everyone will be...
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    Location Information
    Certaldo, Province of Florence
    Rental Home - 9 Bathrooms, Sleeps 18
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    5 Bedrooms, 6 Bathrooms, Sleeps 10 Quick View
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    • DVD Player
    • Washer
    • Grill
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    • Central Heating
    • Wi-Fi
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Villa Casolare is located on a hilltop between Certaldo, the hometown of Boccaccio, and Montespertoli. The surrounding countryside is covered with olive groves and vineyards , offering a particularly beautiful and relaxing view. The building dates back to the 1800s and was renovated in 2014 adding...
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    50052, Certaldo, Province of Florence
    Rental Home - 5 Bedrooms, 6 Bathrooms, Sleeps 10
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    9 Bedrooms, 10 Bathrooms, Sleeps 18 Quick View
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    • Washer
    • Grill
    • Air Conditioning
    • Hot Tub
    • Internet Access
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Owner's description: Main Description : This historic villa is a typical country house located in the countryside around Florence in the Chianti area and once belonged to the Pucci family. Completely renovated in 2000, it measures 600 square metres across three storeys. The property is on two...
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    50052, Certaldo, Province of Florence
    Rental Home - 9 Bedrooms, 10 Bathrooms, Sleeps 18
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    9 Bedrooms, 10 Bathrooms, Sleeps 18 Quick View
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    • Grill
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    Pet friendly
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    Owner's description: Nine Bedroom Independent Villa Chianti Villathis property is a splendid 19th Century independent villa with private swimming pool, surrounded by gardens. The villa is in a perfect position enjoying fabulous unspoilt views of the unique rolling countryside of the famous Chianti...
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    50052, Certaldo, Province of Florence
    Rental Home - 9 Bedrooms, 10 Bathrooms, Sleeps 18
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    9 Bedrooms, 9 Bathrooms, Sleeps 18 Quick View
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    • Air Conditioning
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    Pet friendly
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    Smoking allowed
    About this property
    Owner's description: Large and exclusive, classic Tuscan-style villa on three floors over a total of 630 sq.m., sleeping 18 in 9 double bedrooms and 9 bathrooms. The villa is on a hill enjoying a wonderful view and has a large garden with the same view, air conditioning, wi-fi Internet connection...
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    50052, Certaldo, Province of Florence
    Rental Home - 9 Bedrooms, 9 Bathrooms, Sleeps 18
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    Villa Belsole1 / 48
    (1)Very good
    9 Bedrooms, 9 Bathrooms, Sleeps 18 Quick View
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    • Private Outdoor Pool (Heated)
    • Washer
    • DVD Player
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    • Grill
    • Air Conditioning
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed June 26, 2017
    Our family, 9 couples, celebrated my mother's birthday here. Absolutely wonderful stay. Negatives - needs outdoor umbrellas. Larger garbage bins when hiring to bigger groups
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    About this property
    Large and exclusive, classic Tuscan-style villa on three floors over a total of 630 sq.m., sleeping 18 in 9 double bedrooms and 9 bathrooms. The villa is on a hill enjoying a wonderful view and has a large garden with the same view, air conditioning, wi-fi Internet connection and private swimming...
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    50052, Certaldo, Province of Florence
    Rental Home - 9 Bedrooms, 9 Bathrooms, Sleeps 18
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    9 Bedrooms, 10 Bathrooms, Sleeps 19 Quick View
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    • Washer
    • Cable/satellite TV
    • Private Outdoor Pool (Heated)
    • Air Conditioning
    • Grill
    • DVD Player
    • Wi-Fi
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    If you require superior accommodation with an unmistakable touch of class, this fully refurbished, early 19th century, two-storey villa will not disappoint you. It is furnished with valuable antiques dating back to the 1700’s, complemented by elegant, Venetian-design mirrors, chandeliers and...
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    50052, Certaldo, Province of Florence
    Rental Home - 9 Bedrooms, 10 Bathrooms, Sleeps 19
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    9 Bedrooms, 10 Bathrooms, Sleeps 18 Quick View
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    • Terrace
    • Washer
    • Grill
    • Parking
    • Private Outdoor Pool (Unheated)
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Villa Pucci, originally the abode of the noble Florentine family, has been recently restored to its former splendour and is now a lovely private villa. It is surrounded by ancient cypress trees, olive groves and vineyards and below the house is a large swimming pool (18m x 4m) which enjoys a...
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    Location Information
    50052, Certaldo, Province of Florence
    Rental Home - 9 Bedrooms, 10 Bathrooms, Sleeps 18
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    9 Bedrooms, 10 Bathrooms, Sleeps 18 Quick View
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    • Private Outdoor Pool (Heated)
    • Air Conditioning
    • Wi-Fi
    • DVD Player
    • Grill
    • Patio
    • Washer
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    If you require superior accommodation with an unmistakable touch of class, this fully refurbished, early 19th century, two-storey villa will not disappoint you. It is furnished with valuable antiques dating back to the 1700’s, complemented by elegant, Venetian-design mirrors, chandeliers and...
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    Location Information
    50052, Certaldo, Province of Florence
    Rental Home - 9 Bedrooms, 10 Bathrooms, Sleeps 18
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    9 Bedrooms, 10 Bathrooms, Sleeps 18 Quick View
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    • Washer
    • Air Conditioning
    • Wi-Fi
    • Hot Tub
    • Balcony
    • Private Outdoor Pool (Heated)
    • Cable/satellite TV
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    Location Information
    50052, Certaldo, Province of Florence
    Rental Home - 9 Bedrooms, 10 Bathrooms, Sleeps 18
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    5 Bedrooms, 6 Bathrooms, Sleeps 10 Quick View
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    • Terrace
    • Washer
    • Central Heating
    • Balcony
    • Grill
    • Patio
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    Location Information
    50052, Certaldo, Province of Florence
    Rental Home - 5 Bedrooms, 6 Bathrooms, Sleeps 10
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    APARTMENT VILLA AVANELLA 1 tuscany holiday1 / 20
    (6)Excellent
    6 Bedrooms, 4 Bathrooms, Sleeps 14 Quick View
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    • Grill
    • Central Heating
    • Housekeeping Included
    • Cable/satellite TV
    • Porch
    • Washer
    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed September 6, 2017
    Stayed for 11 days but wish it could have been for longer. It was a lovely extended family holiday with plenty of room for everyone to live happily. The pool is massive for one...
    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...
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    Location Information
    50052, Certaldo, Province of Florence
    Condo/Apartment - 6 Bedrooms, 4 Bathrooms, Sleeps 14
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    • Local time: 07:59 PM (CET)
    • Exchange rate: 1 Euros = 1.14 U.S. Dollars
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