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Montespertoli Luxury Holiday Homes

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    AU$919 Average
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    Travellers to Montespertoli are booking December dates now. Secure your holiday rental today, and have the perfect trip.
    32 Matching Rentals in MontespertoliView all 218 rentals
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    Studio, 35 Bathrooms, Sleeps 120 Quick View
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    13 Bedrooms, 12 Bathrooms, Sleeps 26 Quick View
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    Poggio Rosemary - luxury farmhouse1 / 27
    (5)Excellent
    8 Bedrooms, 5 Bathrooms, Sleeps 8 Quick View
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    13 Bedrooms, 13 Bathrooms, Sleeps 38 Quick View
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    Amenities & Details
    • Children's Pool
    • Cable/satellite TV
    • Wi-Fi
    • Secure Parking
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Villa La Cappella is nestled into a park of Ancient cypressus with a panoramic view over the Chianti countryside.Our villa will serve as your home in Tuscany for large groups from 20 up to 40 people. Our staff will ensure that every request will be handled with care. Villa La Cappellla is one of...
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    50025, Montespertoli, Province of Florence
    Condo/Apartment - 13 Bedrooms, 13 Bathrooms, Sleeps 38
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    6 Bedrooms, 6 Bathrooms, Sleeps 14 Quick View
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    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Villa Chianti is a wonderful villa for rent in the famouse chianti region in northern Tuscany close to florence, this Tuscan Villa can host up to 12+2 people, swimmingpool.
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    50025, Montespertoli, Province of Florence
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 14
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    Villa Tuscany rental with private pool, a/c, wifi1 / 45
    (12)Excellent
    6 Bedrooms, 7 Bathrooms, Sleeps 14 Quick View
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    • Grill
    • Mountain Views
    • Washer
    • DVD Player
    • Cable/satellite TV
    • Wi-Fi
    • Air Conditioning
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 22 August 2018
    We stayed at this beautiful villa for 4 weeks and could of stayed longer. All of the friends and family who joined us, including 5 grandchildren ages 2-7, had a wonderful time...
    Reviewed 27 June 2018
    Once again we had a great stay at Yves' place. We've now rented it four times over the last 10 years and each time it just seems to get better. The house is wonderful, each...
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    About this property
    VILLA FOR RENT BY OWNER with private pool, air conditioning and wifi, available all the year for weekly rental from Saturday 5 pm to Saturday 10 am - sleeps up to 14 persons Villa Tuscany is an authentic old stone Tuscan property totally restored. The house sits on a wonderful 10-acre/4 hectare...
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    50025, Montespertoli, Province of Florence
    Holiday Rental House - 6 Bedrooms, 7 Bathrooms, Sleeps 14
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    PODERE LE RONDINI1 / 38
    (4)Excellent
    13 Bedrooms, 14 Bathrooms, Sleeps 29 Quick View
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    • Grill
    • Balcony
    • Patio
    • Secure Parking
    • Private Outdoor Pool (Unheated)
    • Central Heating
    • Washer
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 15 April 2017
    I have never written a review for any place, yet this place was TOO good not to give it a review. Where to start....We stayed in a one bedroom villa with a huge bathroom...
    Reviewed 5 October 2015
    My daughter and son-in-law chose this Villa in Tuscany for their wedding based on all positive reviews. This was by far the most perfect location for their wedding. Nicola...
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    About this property
    Our ancient master-house called COLONICA villa, has been recently restored originating a villa made of 9 bedrooms (of which 5 double-bedrooms and 4 rooms that can be used as triple-, twin- or double-bedrooms), 10 bathrooms (each one with shower, bidet, wc, basin; one is suitable for handicapped...
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    50025, Montespertoli, Province of Florence
    Holiday Rental House - 13 Bedrooms, 14 Bathrooms, Sleeps 29
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    4 Bedrooms, 9 Bathrooms, Sleeps 9 Quick View
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    • Housekeeping Included
    • Wi-Fi
    • Washer
    • DVD Player
    • Air Conditioning
    • Mountain Views
    • Cable/satellite TV
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Poggio Rosemary is a luxurious Tuscan traditional villa that offers its guests exclusive holiday with the comfort and tranquility of the Tuscan hills. Poggio Rosemary is a beautiful building from the beginning of 1600, completely renovated, with architecture typical of the Tuscan countryside...
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    50025, Montespertoli, Province of Florence
    Holiday Rental House - 4 Bedrooms, 9 Bathrooms, Sleeps 9
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    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    • Washer
    • Internet Access
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Owner's description: VILLAthis property - FIANO Villathis property is a wonderfully renovated farmhouse with an 11th Century tower as central structure. The villa is located just between Florence and Siena overlooking the Tuscan hills. This beautiful, spacious farmhouse is set in a wonderful...
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    50052, Lucardo, Montespertoli
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    Studio, 4 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Wi-Fi
    • Cable/satellite TV
    • Central Heating
    • Washer
    • Private Outdoor Pool (Unheated)
    • Grill
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Take in views of the rolling hills of Tuscany from a charming farmhouse located on an olive oil estate. Situated between Florence and Siena, the property features a lovely garden, swimming pool and several alfresco dining areas, making it a great spot to soak up the beauty of the Italian...
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    50025, Montespertoli, Province of Florence
    Holiday Rental House - 4 Bathrooms, Sleeps 8
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    5 Bedrooms, 5 Bathrooms, Sleeps 9 Quick View
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    • Air Conditioning
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Owner's description: VILLAthis property - SAN GIMIGNANO Between Florence and Siena, this villa is an elegant Tuscan farmhouse set in a beautiful garden with swimming pool and stunning views over the surrounded hills. It is located in the hearth of Tuscany's Chianti region with views over the olive...
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    50025, Montespertoli, Province of Florence
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 9
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    Villa Leonardo1 / 33
    (5)Excellent
    6 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    • Terrace
    • Washer
    • Patio
    • Balcony
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 23 June 2016
    The villa is very nice and the view is fabulous. It is difficult to find and although they recommend a high clearance vehicle one of our party did not have one and they managed...
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    About this property
    A renovated farmhouse nestled on a private estate, Villa Leonardo charms with cozy interiors and lush garden. The 12 acre grounds provide peace, quiet and spectacular views of the countryside near Montespertoli, in the heart of Chianti, but Florence is just 30 minutes away. Take a break from it all...
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    50020, Lucardo, Montespertoli
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 12
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    6 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    Amenities & Details
    • Wi-Fi
    • Patio
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Set in the very heart of Tuscany, and resting in the middle of its own 12-acre estate is the charming Villa Leonardo, Chianti, Tuscany. It is located in the Chianti region, and surrounded by idyllic scenery comprised of vineyards, lavender fields, rows of cypresses and the famous Tuscan hills. The...
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    50025, Lucardo, Montespertoli
    Holiday Rental House - 6 Bedrooms, 6 Bathrooms, Sleeps 12
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    3 Bedrooms, 4 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Grill
    • Internet Access
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Owner's description: Description: A house with wonderful views 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. this property takes its name from...
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    50052, Lucardo, Montespertoli
    Holiday Rental House - 3 Bedrooms, 4 Bathrooms, Sleeps 6
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Grill
    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Owner's description: Description: Stunning views from the private terrace this property is a very large section of a stately 18th century villa. It comprises the entire Piano Nobile (elegant upper floor) of this ancient villa with tower dating back to around the year 1000. (See picture below:...
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    50052, Lucardo, Montespertoli
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    5 Bedrooms, 6 Bathrooms, Sleeps 10 Quick View
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    • Grill
    • DVD Player
    • Internet Access
    • Central Heating
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Owner's description: 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...
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    50052, Lucardo, Montespertoli
    Holiday Rental House - 5 Bedrooms, 6 Bathrooms, Sleeps 10
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    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Washer
    • Internet Access
    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Owner's description: Villathis property is an elegant two-story independent house surrounded by the greenery. It sleeps eight people. From Villathis property you will enjoy a spectacular view of the Tuscan hills and of the greenery. Villathis property is 200 square meters (2150 square feet). It...
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    50052, Lucardo, Montespertoli
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 8
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    Studio, 4 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Washer
    • Cable/satellite TV
    • Wi-Fi
    • Shared Outdoor Pool (Unheated)
    • Central Heating
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Ideal for a family, this charming farmhouse is one of 5 properties (a large villa and 4 apartments) for rent on a beautiful Tuscan estate. The farmhouse is next to another farmhouse with 4 units for rent, but has its own private outdoor area for dining and relaxation. Casa Gilda and the 4...
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    Location Information
    50052, Lucardo, Montespertoli
    Holiday Rental House - 4 Bathrooms, Sleeps 8
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    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Washer
    • Grill
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Owner's description: Pool will be open on: 27 Apr 2018 22:00:00 \r\nPool will be close on: 14 Sep 2018 22:00:00 \r\nMid-week linen change included. WI-FI. This a prestigious country house from middle of the 16th century, once the property of a noble florentine family. The furnishings consist of...
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    Location Information
    50025, Montespertoli, Province of Florence
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 10
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    Villa Casa di Monte with 100% Private Swimming-pool in Chianti: catered on req.1 / 34
    (4)Excellent
    6 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Porch
    • Washer
    • Central Heating
    • Patio
    • Private Outdoor Pool (Unheated)
    • Grill
    • Balcony
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 August 2016
    Perfect in every way! We hired both villas for 4 couples with three children under five and it was perfect. Plenty of room, a wonderful pool, lovely gardens, set amongst olive...
    Reviewed 7 September 2015
    We just returned with our extended family of 10 and had a wonderful experience. The villa was beautiful and provided plenty of space for all of us. We were able to go to...
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    About this property
    Our VILLA CASA DI MONTE is a country-villa that dates back to the beginning of the XIX Century and that has been recently restored preserving the original structure of the house. The whole villa consists of 2 units, but we only rent the VILLA all together to a single group at a time, as in fact as...
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    50025, Montespertoli, Province of Florence
    Holiday Rental House - 6 Bedrooms, 4 Bathrooms, Sleeps 12
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    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    • DVD Player
    • Grill
    • Hot Tub
    • Cable/satellite TV
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    External Description: The villa is very private thanks to a driveway with independent access from the main road, and stands in a wonderful position at the top of a hill with a breathtaking view of the valley and surrounding hills. The house is 450 square meters built with stones, is set on 2 floors...
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    50052, Lucardo, Montespertoli
    Holiday Rental House - 5 Bedrooms, 4 Bathrooms, Sleeps 10
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    Detached Tuscan villa with private garden1 / 27
    (31)Very good
    7 Bedrooms, 4 Bathrooms, Sleeps 13 Quick View
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    • Private Outdoor Pool (Unheated)
    • Central Heating
    • Washer
    • Grill
    • Balcony
    • Patio
    • Parking
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 20 May 2016
    Absolutely beautiful location with stunning views of the countryside. Convenient location in the Tuscany countryside that is still close to public transit to take you to...
    Reviewed 24 April 2016
    Value for money apartment compared with many over priced alternatives. Only 45 minutes from Pisa and Florence airports. Well positioned for exploring northern and central...
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    About this property
    A lovely, comfortable house [200m2] situated in a wonderful hilltop position,reached only by a private road and surrounded by the hills and valleys of the Florentine countryside. The house is divided into three apartments of various sizes located on two levels that can accommodate from 2 to 8...
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    Location Information
    50025, Montespertoli, Province of Florence
    Holiday Rental House - 7 Bedrooms, 4 Bathrooms, Sleeps 13
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    Villa I Leoni Between Florence Sienna and Pisa  - 1 km to village -  Aircond.1 / 35
    (1)Excellent
    10 Bedrooms, 9 Bathrooms, Sleeps 21 Quick View
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    • Air Conditioning
    • Mountain Views
    • Washer
    • Grill
    • Wi-Fi
    • Private Outdoor Pool (Unheated)
    • Parking
    • Cable/satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 27 August 2018
    We hired Villa 1 Leoni for a month and had friends and family with us during that time. Sergio, the owner was a wonderful host providing local knowledge about the area. It is in...
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    About this property
    Villa I Leoni With panoramic views and hues of the ever-changing Tuscan Hills of Montespertoli and sitting overlooking the ancient Castle of Montegufoni, Villa I Leoni is a charming and authentic old manor house. Located ten minutes by car from the town of Montespertoli it is especially suited for...
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    Location Information
    50025, Montespertoli, Province of Florence
    Holiday Rental House - 10 Bedrooms, 9 Bathrooms, Sleeps 21
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    4 Bedrooms, 4 Bathrooms, Sleeps 9 Quick View
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    • Patio
    • Private Garden
    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    • Secure Parking
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The COTTAGE, fully independent and free on the 4 sides, consists of two units: - the FIRST UNIT is made of 2 double bedrooms (of which one may be changed with 2 twin beds; one may be changed in a triple on request), 2 bathrooms (each one with shower, bidet, wc, basin), a large livingroom with a...
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    50025, Montespertoli, Province of Florence
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 9
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    5 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    • Washer
    • Housekeeping Included
    • Patio
    • Air Conditioning
    • Balcony
    • Secure Parking
    • Mountain Views
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    50025, Montespertoli, Province of Florence
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 14
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    3 Bedrooms, 1 Bathroom, Sleeps 12 Quick View
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    • Parking
    • Cable/satellite TV
    • Private Garden
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    Pet friendly
    Kid friendly
    Smoking allowed
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    50025, Montespertoli, Province of Florence
    Holiday Rental House - 3 Bedrooms, 1 Bathroom, Sleeps 12
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    5 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    • Grill
    • Mountain Views
    • Parking
    • Private Garden
    • Central Heating
    • Wi-Fi
    • Hot Tub
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    Location Information
    50025, Montespertoli, Province of Florence
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 12
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    Farmhouse in the Florence's hills ' La Capanna'1 / 15
    (2)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    • Balcony
    • Parking
    • Air Conditioning
    • Grill
    • Wi-Fi
    • Cable/satellite TV
    • Washer
    • Housekeeping Included
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 8 September 2016
    I don't even know where to begin. I visited this villa last week with my husband. We met up with my friend and her husband for a 3 day stay here, as my husband and I were...
    Reviewed 5 September 2016
    I can't believe there are no TA reviews (although if you want to look for more, they have a lot on listings on other sites- all positive!). My husband and I stayed here with...
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    Location Information
    50025, Montespertoli, Province of Florence
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 7
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Internet Access
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Owner's description: this property is a characteristic and welcoming two-story independent house surrounded by the greenery. It sleeps six people. From this property you will enjoy a spectacular view of the Tuscan hills and of the greenery. this property is 200 square meters (2150 square feet). It...
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    Location Information
    50052, Lucardo, Montespertoli
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    5 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Parking
    • Cable/satellite TV
    • Balcony
    • DVD Player
    • Washer
    • Internet Access
    • Private Outdoor Pool (Unheated)
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The villa is situated in a small and charming village called Renai, 3 km from Castelfiorentino, surrounded by vineyards and olive groves. In the small village of Castelfiorentino you will find: railway station, supermarket, banks, post office, pharmacies, hospital, all kind of shops, gyms and...
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    Location Information
    50051, Montespertoli, Province of Florence
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 10
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Internet Access
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Owner's description: Main Description : Very beautiful country house 'Il Casolarino', semi-detached, from the 19th century, renovated, surrounded by meadows, fields and vineyards. 8 km from the centre of Certaldo, 38 km from the centre of Firenze, 16 km from the centre of San Gimignano, in a...
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    Location Information
    50052, Lucardo, Montespertoli
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    4 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
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    • Central Heating
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    If you have ever had a hankering to stay in a historic Castle in Tuscany amidst vineyards and Chianti towns, this fits the bill. Owned by a Florentine family, this castle estate is well located for day trips throughout the region. There is a restaurant onsite open six days a week and a lovely...
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    Location Information
    50025, Montespertoli, Province of Florence
    Condo/Apartment - 4 Bedrooms, 3 Bathrooms, Sleeps 9
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