We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.
We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Vacation Rentals in Montefiridolfi, Italy

Map
Satellite
Map updates are paused. Zoom in to see updated info.
Reset zoom
Updating Map...
Your filters are still active.
There are no pins in your viewport. Try moving the map or changing your filters.
dd/mm/yyyy dd/mm/yyyy
    There are no pins in your viewport. Try moving the map or changing your filters.
    • {providername} {price}
    {providername} {price}
      {listitems}
    {sold_out_text}
    We can't find prices for this accommodation
    From {rate_price} {rate_periodicity}
    List your property
    Payment Protection
    Use a credit card to book with our Peace of Mind Protection.Learn more
    Find a rental
    Price range
    ($279 Average)
    $0per night $2,000+
    Bedrooms
    Any
    Amenities
    Select
    Payment
    Select
    Go to map view
    More filters
    loading...
    From
    $71
    / Night
    Payment Protection
    View Details
    2 Bedrooms, 2 Bathrooms, Sleeps 6
    Overview Make Enquiry
    Overview
    From
    $136
    / Night
    Payment Protection
    View Details
    2 Bedrooms, 2 Bathrooms, Sleeps 4
    Overview Make Enquiry
    Overview
    From
    $111
    / Night
    Payment Protection
    View Details
    1 / 17
    5 of 5 stars (3) Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6
    Overview Reviews (3) Make Enquiry
    Overview Reviews (3)
    From
    $177
    / Night
    Payment Protection
    View Details
    2 Bedrooms, 8 Bathrooms, Sleeps 4
    Overview Make Enquiry
    Overview
    Location Information
    50026, Montefiridolfi, San Casciano in Val di Pesa
    From
    $10,189
    / Week
    View Details
    1 / 48
    5 of 5 stars (2) Excellent
    5 Bedrooms, 6 Bathrooms, Sleeps 10
    Overview Reviews (2) Make Enquiry
    Overview Reviews (2)
    Amenities & Details
    • Refrigerator
    • DVD Player
    • Dryer
    • Grill
    • Stereo System
    • Washer
    • Shared Outdoor Pool...
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    Surrounded by vineyards and olive groves, Casale Classico is perfect for five couples or an extended family, and the location couldn't be better. Located in the heart of Tuscany's Chianti Classico region and set on an idyllic hillside just 15 minutes from Florence (18 km) and less than an hour from... View all property information
    Make Enquiry
    Location Information
    Montefiridolfi, San Casciano in Val di Pesa
    From
    $1,580
    / Week
    View Details
    1 / 53
    5 of 5 stars (1) Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6
    Overview Reviews (1) Make Enquiry
    Overview Reviews (1)
    Amenities & Details
    • Shared Garden
    • Internet Access
    • Stereo System
    • Parking
    • Satellite TV
    • Shared Outdoor Pool...
    • Refrigerator
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    This is the perfect starting point to explore Tuscany. Located in the heart of Chianti, Borgo in Rosa is just 20 minutes from Florence, 50 minutes from Siena, one hour from Lucca, and all of the beautiful hill towns of Chianti are within easy reach. The location couldn't be better. The closest... View all property information
    Make Enquiry
    Location Information
    Montefiridolfi, San Casciano in Val di Pesa
    From
    $222
    / Night
    Payment Protection
    View Details
    5 Bedrooms, 4 Bathrooms, Sleeps 10
    Overview Make Enquiry
    Overview
    Amenities & Details
    • Dishwasher
    • Grill
    • TV
    • Private Outdoor...
    • Washer
    • Fireplace
    • Parking
    • Private Garden
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • Smoking allowed
    • Elder access
    • x
    About this property
    6-room house 200 m2 on 2 levels, on the ground floor. Comfortable and cosy furnishings: entrance hall with 1 sofabed, dining table, satellite TV and hi-fi system. Exit to the garden. Living/dining room with open-hearth fireplace. 1 room with 1 double bed. Exit to the swimming pool. Kitchen (5 hot... View all property information
    Make Enquiry
    Location Information
    50024, Montefiridolfi, San Casciano in Val di Pesa
    From
    $1,580
    / Week
    View Details
    1 / 57
    5 of 5 stars (1) Excellent
    3 Bedrooms, 7 Bathrooms, Sleeps 6
    Overview Reviews (1) Make Enquiry
    Overview Reviews (1)
    Amenities & Details
    • Shared Outdoor Pool...
    • Stereo System
    • Shared Garden
    • Satellite TV
    • Internet Access
    • Refrigerator
    • Parking
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    This is the perfect starting point to explore Tuscany. Located in the heart of Chianti, Borgo in Rosa is just 20 minutes from Florence, 50 minutes from Siena, one hour from Lucca, and all of the beautiful hill towns of Chianti are within easy reach. The location couldn't be better. The closest... View all property information
    Make Enquiry
    Location Information
    Montefiridolfi, San Casciano in Val di Pesa
    From
    $1,580
    / Week
    View Details
    1 / 51
    1 Bedroom, 1 Bathroom, Sleeps 2
    Overview Make Enquiry
    Overview
    Amenities & Details
    • Parking
    • Satellite TV
    • Refrigerator
    • Stereo System
    • Shared Garden
    • Internet Access
    • Shared Outdoor Pool...
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    This is the perfect starting point to explore Tuscany. Located in the heart of Chianti, Borgo in Rosa is just 20 minutes from Florence, 50 minutes from Siena, one hour from Lucca, and all of the beautiful hill towns of Chianti are within easy reach. The location couldn't be better. The closest... View all property information
    Make Enquiry
    Location Information
    Montefiridolfi, San Casciano in Val di Pesa
    From
    $1,580
    / Week
    View Details
    1 / 54
    2 Bedrooms, 2 Bathrooms, Sleeps 4
    Overview Make Enquiry
    Overview
    Amenities & Details
    • Satellite TV
    • Stereo System
    • Shared Garden
    • Internet Access
    • Refrigerator
    • Shared Outdoor Pool...
    • Parking
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    This is the perfect starting point to explore Tuscany. Located in the heart of Chianti, Borgo in Rosa is just 20 minutes from Florence, 50 minutes from Siena, one hour from Lucca, and all of the beautiful hill towns of Chianti are within easy reach. The location couldn't be better. The closest... View all property information
    Make Enquiry
    Location Information
    Montefiridolfi, San Casciano in Val di Pesa
    List your property for free!
    List your holiday rental where TripAdvisor travellers can find it.
    Add a Listing
    From
    $1,580
    / Week
    View Details
    1 / 60
    2 Bedrooms, 14 Bathrooms, Sleeps 4
    Overview Make Enquiry
    Overview
    Amenities & Details
    • Stereo System
    • Refrigerator
    • Internet Access
    • Parking
    • Satellite TV
    • Shared Garden
    • Shared Outdoor Pool...
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    This is the perfect starting point to explore Tuscany. Located in the heart of Chianti, Borgo in Rosa is just 20 minutes from Florence, 50 minutes from Siena, one hour from Lucca, and all of the beautiful hill towns of Chianti are within easy reach. The location couldn't be better. The closest... View all property information
    Make Enquiry
    Location Information
    Montefiridolfi, San Casciano in Val di Pesa
    From
    $2,240
    / Week
    View Details
    1 / 24
    2 Bedrooms, 2 Bathrooms, Sleeps 4
    Overview Make Enquiry
    Overview
    Amenities & Details
    • Dishwasher
    • Grill
    • Satellite TV
    • Ping Pong Table
    • Safe
    • Internet Access
    • Private Outdoor...
    • Balcony
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • Smoking allowed
    • Elder access
    • x
    About this property
    In the heart of Chianti, halfway between Florence and Siena The farmhouse I Greppi Di Silli located 300 mt above sea level. rises and looks out over a green valley, surrounded on all sides by cultivated hills covered in olive groves and vineyards. Alongside the borgo, in the middle of the olive... View all property information
    Make Enquiry
    Location Information
    50024, Montefiridolfi, San Casciano in Val di Pesa
    From
    $5,918
    / Week
    View Details
    1 / 70
    5 of 5 stars (1) Excellent
    4 Bedrooms, 4 Bathrooms, Sleeps 11
    Overview Reviews (1) Make Enquiry
    Overview Reviews (1)
    Amenities & Details
    • Private Outdoor...
    • Washer
    • Dishwasher
    • Hairdryer
    • Cooker
    • Central Heating
    • TV
    • Gym
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    With traditional furnishings, a private swimming pool, and a fantastic location just south of Florence, this Tuscan villa for rent is right out of your Italian fantasies! This is not a bare hotel; this is a home, a Tuscany villa near Florence filled with character and elegance. From this vacation... View all property information
    Make Enquiry
    Location Information
    50020, Montefiridolfi, San Casciano in Val di Pesa
    From
    $2,496
    / Week
    View Details
    1 / 11
    3 Bedrooms, 2 Bathrooms, Sleeps 6
    Overview Make Enquiry
    Overview
    Amenities & Details
    • Microwave
    • TV
    • Dishwasher
    • Shared Outdoor Pool...
    • Safe
    • Grill
    • Cooker
    • Hairdryer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    This location is for those who have always wanted to stay in the midst of a famous wine estate in the Chianti Classico. The farmhouse, on a hill overlooking the main complex, houses the 7 Rosso apartments with a shared pool. Down the hill there is a trattoria, reception office, another pool and a... View all property information
    Make Enquiry
    Location Information
    50020, Montefiridolfi, San Casciano in Val di Pesa
    From
    $1,997
    / Week
    View Details
    1 / 10
    1 Bedroom, 2 Bathrooms, Sleeps 4
    Overview Make Enquiry
    Overview
    Amenities & Details
    • Dishwasher
    • Grill
    • Shared Outdoor Pool...
    • Cooker
    • Hairdryer
    • TV
    • Safe
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    This location is for those who have always wanted to stay in the midst of a famous wine estate in the Chianti Classico. The farmhouse, on a hill overlooking the main complex, houses the 7 Rosso apartments with a shared pool. Down the hill there is a trattoria, reception office, another pool and a... View all property information
    Make Enquiry
    Location Information
    50020, Montefiridolfi, San Casciano in Val di Pesa
    From
    $370
    / Night
    View Details
    1 / 11
    3 Bedrooms, 2 Bathrooms, Sleeps 5
    Overview Make Enquiry
    Overview
    Amenities & Details
    • TV
    • Cooker
    • Dishwasher
    • Safe
    • Hairdryer
    • Shared Outdoor Pool...
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    This location is for those who have always wanted to stay in the midst of a famous wine estate in the Chianti Classico. The farmhouse, on a hill overlooking the main complex, houses the 7 Rosso apartments with a shared pool. Down the hill there is a trattoria, reception office, another pool and a... View all property information
    Make Enquiry
    Location Information
    50020, Montefiridolfi, San Casciano in Val di Pesa
    From
    $2,958
    / Week
    View Details
    1 / 21
    3 Bedrooms, 2 Bathrooms, Sleeps 6
    Overview Make Enquiry
    Overview
    Amenities & Details
    • Cooker
    • Highchair
    • Dishwasher
    • Internet Access
    • Air Conditioning
    • TV
    • Shared Outdoor Pool...
    • Safe
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    This location is for those who have always wanted to stay in the midst of a famous wine estate in the Chianti Classico. Vineyards, a trattoria, pool, tennis court, and reception are all there for your enjoyment. The borgo, though rural, is conveniently located between Florence and Siena. This... View all property information
    Make Enquiry
    Location Information
    50020, Montefiridolfi, San Casciano in Val di Pesa
    From
    $96
    / Night
    Payment Protection
    View Details
    2 Bedrooms, 1 Bathroom, Sleeps 5
    Overview Make Enquiry
    Overview
    Location Information
    50020, Montefiridolfi, San Casciano in Val di Pesa