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Montespertoli Luxury Rentals

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    Travelers to Montespertoli are booking December dates now. Secure your vacation rental today, and have the perfect trip.
    27 Matching Rentals in MontespertoliView all 180 rentals
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    5 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    4 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    Detached Tuscan villa with private garden1 / 81
    (31)Very good
    7 Bedrooms, 4 Bathrooms, Sleeps 13 Quick View
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    Amazing house in Tuscany with a fantastic indoor private pool and spa_LA ROCCA1 / 201
    (1)Excellent
    3 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Hot Tub
    • Sauna
    • Cable/satellite TV
    • Wi-Fi
    • Washer
    • Private Indoor Pool
    • Mountain Views
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Superior Apartment with3 double bedroom with ensuite bathroom, one additional bathroom at ground floor, dining room + living room, full equipped kitchen and direct access to a private garden with an amazing panoramic view where you can have relaxing time or breakfast, lunch or dinner. You also...
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    50025, Montespertoli, Province of Florence
    Condo/Apartment - 3 Bedrooms, 4 Bathrooms, Sleeps 8
    Villa Maria Luana1 / 41
    (3)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 7 Quick View
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    • Secure Parking
    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    • Private Yard
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
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    50025, Lucardo, Montespertoli
    Condo/Apartment - 3 Bedrooms, 2 Bathrooms, Sleeps 7
    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 September 7, 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 September 5, 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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    50025, Montespertoli, Province of Florence
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 7
    3 Bedrooms, 1 Bathroom, Sleeps 12 Quick View
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    • Parking
    • Cable/satellite TV
    • Private Yard
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    Pet friendly
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    Smoking allowed
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    50025, Montespertoli, Province of Florence
    Rental Home - 3 Bedrooms, 1 Bathroom, Sleeps 12
    Villa Casa di Monte with 100% Private Swimming-pool in Chianti: catering on req.1 / 61
    (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 July 31, 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 September 6, 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
    Rental Home - 6 Bedrooms, 4 Bathrooms, Sleeps 12
    PODERE LE RONDINI Villa with AIR-CONDITIONING, WIFI, CATERING; SWIM-POOL!1 / 35
    (5)Excellent
    9 Bedrooms, 10 Bathrooms, Sleeps 22 Quick View
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    • Grill
    • Balcony
    • Patio
    • Secure Parking
    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    • Washer
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed April 27, 2019
    Traveled for a family wedding held on site with over 16 guests, Nicola was always on site and very accommodating. Rooms were very neat and clean with all amenities, kitchen...
    Reviewed April 14, 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...
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    About this property
    FULLY AIR-CONDITIONED!!!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...
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    50025, Montespertoli, Province of Florence
    Rental Home - 9 Bedrooms, 10 Bathrooms, Sleeps 22
    13 Bedrooms, 13 Bathrooms, Sleeps 38 Quick View
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    • Children's Pool
    • Cable/satellite TV
    • Wi-Fi
    • Secure Parking
    • Private Yard
    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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    Poggio Rosemary - luxury farmhouse1 / 27
    (5)Excellent
    8 Bedrooms, 5 Bathrooms, Sleeps 8 Quick View
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    • Private Outdoor Pool (Unheated)
    • Housekeeping Included
    • DVD Player
    • Washer
    • Cable/satellite TV
    • Wi-Fi
    • Air Conditioning
    • Mountain Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed May 2, 2016
    This is the second time I have had the pleasure of staying at Poggio Rosemary and it was even more delightful than the first time! This year we were able to go in April rather...
    Reviewed June 10, 2015
    Our very warm and caring hosts helped make our stay an exceptionally memorable one. Thank you Egle and Claudia!!!! From the beautifully furnished spacious rooms, a kitchen...
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    About this property
    Nestled in the breathtaking Tuscan countryside, Poggio Rosemary offers splendid views of the vineyards and olive groves of the Chianti hills. The villa itself was originally a casa colonica or farmhouse, and formed part of a farmstead which has existed on this site since the 12th century. Despite...
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    50025, Montespertoli, Province of Florence
    Rental Home - 8 Bedrooms, 5 Bathrooms, Sleeps 8
    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 August 22, 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 June 27, 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
    Rental Home - 6 Bedrooms, 7 Bathrooms, Sleeps 14
    4 Bedrooms, 3 Bathrooms, Sleeps 9 Quick View
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    Amenities & Details
    • 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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    50025, Montespertoli, Province of Florence
    Condo/Apartment - 4 Bedrooms, 3 Bathrooms, Sleeps 9
    5 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    • Grill
    • Mountain Views
    • Parking
    • Private Yard
    • Central Heating
    • Wi-Fi
    • Hot Tub
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
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    Location Information
    50025, Montespertoli, Province of Florence
    Rental Home - 5 Bedrooms, 5 Bathrooms, Sleeps 12
    10 Bedrooms, 9 Bathrooms, Sleeps 20 Quick View
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    • Private Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Grill
    • Parking
    • Wi-Fi
    • Air Conditioning
    • Housekeeping Included
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    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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    50025, Montagnana Val di Pesa, Montespertoli
    Rental Home - 10 Bedrooms, 9 Bathrooms, Sleeps 20
    Studio, 35 Bathrooms, Sleeps 120 Quick View
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    Amenities & Details
    • Central Heating
    • Private Outdoor Pool (Unheated)
    • Washer
    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
    Rental Home - 35 Bathrooms, Sleeps 120
    4 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    • Parking
    • Air Conditioning
    • Cable/satellite TV
    • Children's Pool
    • Wi-Fi
    • Private Yard
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Casa Lucardo is nestled on the rolling hillsides of Montespertoli. The 300 year old south facing villa is surrounded by a private olive grove with panoramic views of Tuscany’s sun-basked countryside. The villa consists of four bedrooms, spacious living areas, a fireplace, anda pool with barbeque...
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    50025, Montespertoli, Province of Florence
    Rental Home - 4 Bedrooms, 3 Bathrooms, Sleeps 10
    4 Bedrooms, 4 Bathrooms, Sleeps 9 Quick View
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    • Washer
    • Secure Parking
    • Wi-Fi
    • Patio
    • Grill
    • Air Conditioning
    • Balcony
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The COTTAGE is FULLY AIR-CONDITIONED and it is 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,...
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    50025, Montespertoli, Province of Florence
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 9
    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Mountain Views
    • Washer
    • Patio
    • Cable/satellite TV
    • Wi-Fi
    • Private Outdoor Pool (Unheated)
    • Housekeeping Included
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautiful farmhouse right in the heart of Chianti region, half way between Florence and Siena, in a unique and panoramic position, Villa Novellina covers over 69 hectares surrounded by wine yards, olive groves and the characteristic Tuscan vegetation, owners are also producing extra virgin olive...
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    50050, Lucardo, Montespertoli
    Rental Home - 5 Bedrooms, 5 Bathrooms, Sleeps 10
    6 Bedrooms, 6 Bathrooms, Sleeps 12 Quick View
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    • 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
    Rental Home - 6 Bedrooms, 6 Bathrooms, Sleeps 12
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    4 Bedrooms, 5 Bathrooms, Sleeps 9 Quick View
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    Amenities & Details
    • Grill
    • Shared Outdoor Pool (Unheated)
    • Cable/satellite TV
    • Wi-Fi
    • DVD Player
    • Washer
    • Air Conditioning
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Ground floor: * Entry hall with beautiful mirrors and coat room * Guest bathroom * Large double living room (air-conditioned) elegantly furnished with couches and armchairs and a wood stove; large French windows overlook the garden and the two patios * Gaming table area, with backgammon, chess,...
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    50025, Montespertoli, Province of Florence
    Condo/Apartment - 4 Bedrooms, 5 Bathrooms, Sleeps 9
    6 Bedrooms, 7 Bathrooms, Sleeps 14 Quick View
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    Amenities & Details
    • Patio
    • Balcony
    • DVD Player
    • Washer
    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    • Air Conditioning
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    1 double living room with dining and sitting area, 1 kitchen, 1 office room, 6 bedrooms, 6 bathrooms, 1 guest toilet, 1 laundry area: Ground floor: * 1 living room with access to the garden, comfortable armchairs and settee next to the fireplace, piano and two dining areas (a long wooden table for...
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    50025, Montespertoli, Province of Florence
    Rental Home - 6 Bedrooms, 7 Bathrooms, Sleeps 14
    4 Bedrooms, 4 Bathrooms, Sleeps 8 Quick View
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    • Balcony
    • Washer
    • Terrace
    • Air Conditioning
    • Cable/satellite TV
    • Internet Access
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Additional amenities: Full Kitchen
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    50025, Montespertoli, Province of Florence
    Rental Home - 4 Bedrooms, 4 Bathrooms, Sleeps 8
    6 Bedrooms, 4 Bathrooms, Sleeps 11 Quick View
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    • Grill
    • Terrace
    • Washer
    • Balcony
    • Cable/satellite TV
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Additional amenities: Full Kitchen
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    Location Information
    50052, Lucardo, Montespertoli
    Rental Home - 6 Bedrooms, 4 Bathrooms, Sleeps 11
    5 Bedrooms, 5 Bathrooms, Sleeps 12 Quick View
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    • Private Outdoor Pool (Heated)
    • Cable/satellite TV
    • Private Yard
    • Wi-Fi
    • Secure Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Share of an ancient farmhouse, whose first foundations date back to the 15th century. Completely restored, is independent and surrounded by centuries-old pine and cypress trees which adorn a large adjoining partly terraced garden. It is located on the hills surrounding Montespertoli, the city of...
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    50025, Montespertoli, Province of Florence
    Rental Home - 5 Bedrooms, 5 Bathrooms, Sleeps 12
    4 Bedrooms, 5 Bathrooms, Sleeps 12 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
    Private Room - 4 Bedrooms, 5 Bathrooms, Sleeps 12
    Studio, 4 Bathrooms, Sleeps 8 Quick View
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    • 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
    Rental Home - 4 Bathrooms, Sleeps 8
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    • Exchange rate: 1 Euros = 1.12 U.S. Dollars
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