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  • Villa Montepulciano by MMega
    From $708 per night (USD)

    VRBO

    Villa Montepulciano by MMega

    Bedrooms:
    7
    Bathrooms:
    7
    Sleeps:
    16

    External Description Villa Montepulciano is located in a panoramic position on the rolling hills of the Val d\'Orcia, ...

    From $708 per night (USD)

    VRBO

    Details
  • Delizioso Appartamento Ampio Terrazzo e Giardino Attrezzato a 2 Passi da Terme
    From $74 per night (USD)

    VRBO

    Delizioso Appartamento Ampio Terrazzo e Giardino Attrezzato a 2 Passi da Terme

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    <p>Located in Chianciano Terme, this welcoming apartment brings it all within your reach. There's convenient onsite park ...

    From $74 per night (USD)

    VRBO

    Details
  • Studio 'La Casina Mag' with Wi-Fi
    From $211 per night (USD)

    VRBO

    Studio 'La Casina Mag' with Wi-Fi

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Characteristic studio located in the historic center of Pienza, adjacent to Piazza Pio II, ideal for weekends and couple ...

    From $211 per night (USD)

    VRBO

    Details
  • Wonderful private villa for 10 guests with WIFI, private pool, TV, patio, panoramic view and par...
    From $389 per night (USD)

    Expedia

    Wonderful private villa for 10 guests with WIFI, private pool, TV, patio, panoramic view and par...

    Bedrooms:
    4
    Bathrooms:
    5
    Sleeps:
    10

    Villa Il Troscione is located 7 km (4 mi) from San Casciano Dei Bagni, Italy and only 33 km (20 mi) from Montepulciano i ...

    From $389 per night (USD)

    Expedia

    Details
  • Apartment in villa with garden, Tuscany
    From $118 per night (USD)

    VRBO

    Apartment in villa with garden, Tuscany

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    5

    The very large and bright apartment (120m), is located on the second floor of a semi-detached house with garden in the r ...

    From $118 per night (USD)

    VRBO

    Details
  • Casa Sily by Rentbeat
    From $96 per night (USD)

    Expedia

    Casa Sily by Rentbeat

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    Casa Sily is a cozy and colorful apartment located on the first floor of a condominium building in the picturesque Piazz ...

    From $96 per night (USD)

    Expedia

    Details
  • Villa Podere del Papa by MMega
    From $1533 per night (USD)

    VRBO

    Villa Podere del Papa by MMega

    Bedrooms:
    8
    Bathrooms:
    9
    Sleeps:
    18

    External Description Villa Podere del Papa is located in the heart of the Val d\'Orcia, within the Lucciola Bella Nat ...

    From $1533 per night (USD)

    VRBO

    Details
  • L'Olivazzo Apartment
    From $178 per night (USD)

    Expedia

    L'Olivazzo Apartment

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    6

    Apartment L'Olivazzo is your retreat in the beating heart of Chiusi, a charming town in Tuscany. This spacious 170-squar ...

    From $178 per night (USD)

    Expedia

    Details
  • Apartment with A/C, private pool, WIFI, TV, veranda, pets allowed, parking, close to Montepulciano
    From $3283 per night (USD)

    VRBO

    Apartment with A/C, private pool, WIFI, TV, veranda, pets allowed, parking, close to Montepulciano

    Bedrooms:
    18
    Bathrooms:
    18
    Sleeps:
    35

    Holiday rental Borgo Dolciano is a nice stone building (600 sq m) that includes air conditioning, WiFi internet and pri ...

    From $3283 per night (USD)

    VRBO

    Details
  • AMORE RENTALS - Villa Olimpia with Pool, Garden, Ideal for Weddings
    From $2104 per night (USD)

    Expedia

    AMORE RENTALS - Villa Olimpia with Pool, Garden, Ideal for Weddings

    Bedrooms:
    8
    Bathrooms:
    8
    Sleeps:
    19

    This sumptuously designed and decorated Tuscan country house, set in a prime hilltop location in the Val d’Orcia, is an ...

    From $2104 per night (USD)

    Expedia

    Details
  • AMORE RENTALS - Villa Viola with Pool, Garden, Ideal for Weddings
    From $2003 per night (USD)

    VRBO

    AMORE RENTALS - Villa Viola with Pool, Garden, Ideal for Weddings

    Bedrooms:
    7
    Bathrooms:
    7
    Sleeps:
    14

    Exquisitely furnished historic Tuscan villa with pool, gym and jacuzzi, with sprawling gardens and heavenly views over a ...

    From $2003 per night (USD)

    VRBO

    Details
  • AMORE RENTALS - Villa Valle with Pool, Garden, Ideal for Weddings
    From $2183 per night (USD)

    Expedia

    AMORE RENTALS - Villa Valle with Pool, Garden, Ideal for Weddings

    Bedrooms:
    9
    Bathrooms:
    9
    Sleeps:
    18

    Enjoy views over the rolling hills of the Val d’Orcia in Tuscany from this sensitively restored large group villa with h ...

    From $2183 per night (USD)

    Expedia

    Details
  • Bimba Apartment in Tuscany [Quiet Location, Free Parking and Wi-Fi]
    From $109 per night (USD)

    VRBO

    Bimba Apartment in Tuscany [Quiet Location, Free Parking and Wi-Fi]

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    <p>Located in Sinalunga, this welcoming apartment lets you experience it all. Val di Chiana is just a short walk away, s ...

    From $109 per night (USD)

    VRBO

    Details
  • Villa in Sarteano with 6 bedrooms sleeps 12
    From $2280 per night (USD)

    Expedia

    Villa in Sarteano with 6 bedrooms sleeps 12

    Bedrooms:
    5
    Bathrooms:
    6
    Sleeps:
    12

    Villa Averdina: A Tuscan Luxury Retreat Between Comfort and Authenticity Discover the timeless charm of Tuscany at Vill ...

    From $2280 per night (USD)

    Expedia

    Details
  • Podere San Lorenzo 12, Emma Villas
    From $619 per night (USD)

    VRBO

    Podere San Lorenzo 12, Emma Villas

    Bedrooms:
    4
    Bathrooms:
    6
    Sleeps:
    12

    This rate includes: -Utilities: Electricity, water, gas for cooking purposes, weekly linenElectricity, water, gas for co ...

    From $619 per night (USD)

    VRBO

    Details
  • Villa Viola with Pool and Garden, Ideal for Weddings
    From $1708 per night (USD)

    Expedia

    Villa Viola with Pool and Garden, Ideal for Weddings

    Bedrooms:
    7
    Bathrooms:
    7
    Sleeps:
    14

    Exquisitely furnished historic Tuscan villa with pool, gym and jacuzzi, with sprawling gardens and heavenly views over a ...

    From $1708 per night (USD)

    Expedia

    Details
  • Casale del Conte - Three Bedroom Villa, Sleeps 6
    From $195 per night (USD)

    VRBO

    Casale del Conte - Three Bedroom Villa, Sleeps 6

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Overview Casale del Conte is located in Siena, Tuscany. This detached vacation rental property offers Free Wi-Fi a ...

    From $195 per night (USD)

    VRBO

    Details
  • Villa Rigomagno By MMega
    From $1428 per night (USD)

    Expedia

    Villa Rigomagno By MMega

    Bedrooms:
    5
    Bathrooms:
    7
    Sleeps:
    15

    External Description Villa Rigomagno is an ancient Tuscan farmhouse of the 18th century, located in the heart of Vald ...

    From $1428 per night (USD)

    Expedia

    Details
  • Villa in Sinalunga with 6 bedrooms sleeps 16
    From $800 per night (USD)

    VRBO

    Villa in Sinalunga with 6 bedrooms sleeps 16

    Bedrooms:
    7
    Bathrooms:
    6
    Sleeps:
    16

    Villa Le Pozze is an authentic villa surrounded by no less than 32 hectares of woods, olive groves and vineyards, barbec ...

    From $800 per night (USD)

    VRBO

    Details
  • Apartment 'Le Terme' with Private Terrace, Balcony and Wi-Fi
    From $123 per night (USD)

    Expedia

    Apartment 'Le Terme' with Private Terrace, Balcony and Wi-Fi

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Located in Chianciano Terme, the holiday apartment Le Terme has everything you need for a comfortable holiday. The 80 m² ...

    From $123 per night (USD)

    Expedia

    Details
  • Apartment Sarteano
    From $122 per night (USD)

    VRBO

    Apartment Sarteano

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    <p>Nestled in Sarteano, this 1-bedroom, 1-bathroom apartment brings it all within your reach. Fans of nature and the out ...

    From $122 per night (USD)

    VRBO

    Details
  • Marelli House
    From $241 per night (USD)

    Expedia

    Marelli House

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    <p>Located in Trequanda, this welcoming vacation home brings it all within your reach. Enjoy a short 5-minute walk to Va ...

    From $241 per night (USD)

    Expedia

    Details
  • Apartment 'La Capacciola - Ulivo' with Shared Pool, Private Terrace and Wi-Fi
    Click For Pricing

    VRBO

    Apartment 'La Capacciola - Ulivo' with Shared Pool, Private Terrace and Wi-Fi

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    The holiday apartment La Capacciola - Ulivo in Sinalunga is the perfect accommodation for a stress-free holiday with you ...

    Click For Pricing

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    Details
  • Apartment 'La Capacciola -  Girasole' with Shared Pool, Private Terrace and Wi-Fi
    Click For Pricing

    Expedia

    Apartment 'La Capacciola - Girasole' with Shared Pool, Private Terrace and Wi-Fi

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    Located in Sinalunga, the holiday apartment La Capacciola - Girasole has everything you need for a relaxing holiday. The ...

    Click For Pricing

    Expedia

    Details
  • Stefania Townhouse Luxury 2 Bedrooms Apartment
    From $255 per night (USD)

    VRBO

    Stefania Townhouse Luxury 2 Bedrooms Apartment

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Luxury two bedrooms apartment , located in a private small private palace in the historic center of MOntepulciano. Co ...

    From $255 per night (USD)

    VRBO

    Details
  • Pet friendly apartment
    From $75 per night (USD)

    Expedia

    Pet friendly apartment

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Enjoy a relaxing break in this charming holiday apartment with panoramic views. Welcome to this lovingly decorated ho ...

    From $75 per night (USD)

    Expedia

    Details
  • Sweet Dreams: Free WiFi  & Netflix Premium
    From $121 per night (USD)

    VRBO

    Sweet Dreams: Free WiFi & Netflix Premium

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    5

    Cozy Apartment in Chianciano Terme: Perfect for Families and Groups Discover the comfort and tranquility of this apartm ...

    From $121 per night (USD)

    VRBO

    Details
  • Villa in Montepulciano with 7 bedrooms sleeps 14
    From $901 per night (USD)

    Expedia

    Villa in Montepulciano with 7 bedrooms sleeps 14

    Bedrooms:
    7
    Bathrooms:
    7
    Sleeps:
    14

    Villa San Biagio is a lovely stone building with air conditioning, WiFi internet and private pool. The property can acco ...

    From $901 per night (USD)

    Expedia

    Details
  • Welcome to Casa Oliveto, a corner of history and comfort in the heart of Tuscany.
    From $247 per night (USD)

    VRBO

    Welcome to Casa Oliveto, a corner of history and comfort in the heart of Tuscany.

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    6

    <p>Located in Trequanda, this welcoming vacation home brings it all within your reach. Enjoy a short 5-minute walk to Va ...

    From $247 per night (USD)

    VRBO

    Details
  • Rooftops Over the Valley
    From $175 per night (USD)

    Expedia

    Rooftops Over the Valley

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    “I Tetti sulla Valle” is a delightful one-bedroom apartment in the heart of Montepulciano (Siena), just 100 meters from ...

    From $175 per night (USD)

    Expedia

    Details
  • Villa Montepulciano Comfortable holiday residence
    From $2392 per night (USD)

    VRBO

    Villa Montepulciano Comfortable holiday residence

    Bedrooms:
    4
    Bathrooms:
    7
    Sleeps:
    16

    Magnificent villa with dependance, garden and pool, located in a panoramic position in the Montepulciano countryside (Va ...

    From $2392 per night (USD)

    VRBO

    Details
  • Villa Fattorina Grande: A spacious and welcoming age-old estate surrounded by the greenery, with Free WI-FI.
    From $1047 per night (USD)

    Expedia

    Villa Fattorina Grande: A spacious and welcoming age-old estate surrounded by the greenery, with Free WI-FI.

    Bedrooms:
    11
    Bathrooms:
    12
    Sleeps:
    24

    Villa Fattorina Grande is a spacious and welcoming age-old estate surrounded by the greenery. It sleeps 24 people. From ...

    From $1047 per night (USD)

    Expedia

    Details
  • tolles Apartment in einer Residence in der Toskana
    From $355 per night (USD)

    VRBO

    tolles Apartment in einer Residence in der Toskana

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    A Tranquil Retreat in the Heart of Tuscany Surrounded by the rolling vineyards of Valiano di Montepulciano, this WiFi-eq ...

    From $355 per night (USD)

    VRBO

    Details
  • tolles Apartment in einer Residence in der Toskana
    From $302 per night (USD)

    Expedia

    tolles Apartment in einer Residence in der Toskana

    Bedrooms:
    2
    Bathrooms:
    1
    Sleeps:
    4

    A Charming Tuscan Getaway Surrounded by the rolling vineyards of Valiano di Montepulciano, this WiFi-equipped apartment ...

    From $302 per night (USD)

    Expedia

    Details
  • tolles Apartment in einer Residence in der Toskana
    From $260 per night (USD)

    VRBO

    tolles Apartment in einer Residence in der Toskana

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    This peaceful apartment in Valiano di Montepulciano offers a relaxing countryside retreat for up to four guests. Thought ...

    From $260 per night (USD)

    VRBO

    Details
  • Apartment 'La Casina In Via Fiorita' with Wi-Fi and Air Conditioning
    From $137 per night (USD)

    Expedia

    Apartment 'La Casina In Via Fiorita' with Wi-Fi and Air Conditioning

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Located in Montepulciano, the holiday apartment La Casina In Via Fiorita has everything you need for a comfortable holid ...

    From $137 per night (USD)

    Expedia

    Details
  • Holiday Home 'Beb Pulcino Nero Scrofiano' with Wi-Fi
    From $319 per night (USD)

    VRBO

    Holiday Home 'Beb Pulcino Nero Scrofiano' with Wi-Fi

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    5

    The holiday home Beb Pulcino Nero Scrofiano is located in Scrofiano and is perfect for an unforgettable holiday with you ...

    From $319 per night (USD)

    VRBO

    Details
  • Tuscany Hills - Your home in Tuscany
    From $247 per night (USD)

    Expedia

    Tuscany Hills - Your home in Tuscany

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    <p>Located in Torrita di Siena, this welcoming vacation home brings it all within your reach. Val di Chiana is just a sh ...

    From $247 per night (USD)

    Expedia

    Details
  • Room 'Papavero' with Mountain View, Shared Pool and Wi-Fi
    From $141 per night (USD)

    VRBO

    Room 'Papavero' with Mountain View, Shared Pool and Wi-Fi

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Overlooking the mountain, the Room Papavero in Chianciano Terme impresses guests with its fantastic views. The 16 m² pro ...

    From $141 per night (USD)

    VRBO

    Details
  • Room 'Giaggiolo' with Mountain View, Shared Pool and Wi-Fi
    From $146 per night (USD)

    Expedia

    Room 'Giaggiolo' with Mountain View, Shared Pool and Wi-Fi

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Overlooking the mountain, the Room Giaggiolo in Chianciano Terme impresses guests with its fantastic views. The 16 m² pr ...

    From $146 per night (USD)

    Expedia

    Details
  • Apartment 'L'uscio' with Mountain View, Shared Pool and Wi-Fi
    From $145 per night (USD)

    VRBO

    Apartment 'L'uscio' with Mountain View, Shared Pool and Wi-Fi

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    With a view of the mountain, the holiday apartment L'uscio in Chianciano Terme is perfect for a relaxing holiday. The 90 ...

    From $145 per night (USD)

    VRBO

    Details
  • Room 'Girasole' with Mountain View, Shared Pool and Wi-Fi
    From $146 per night (USD)

    Expedia

    Room 'Girasole' with Mountain View, Shared Pool and Wi-Fi

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    3

    The Room Girasole, which is situated in Chianciano Terme, overlooks the nearby mountain. The 16 m² property consists of ...

    From $146 per night (USD)

    Expedia

    Details
  • Apartment 'Granaio' with Mountain View, Shared Pool and Wi-Fi
    From $186 per night (USD)

    VRBO

    Apartment 'Granaio' with Mountain View, Shared Pool and Wi-Fi

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    8

    With a view of the mountain, the holiday apartment Il granaio in Chianciano Terme is perfect for a relaxing holiday. The ...

    From $186 per night (USD)

    VRBO

    Details
  • Room 'Acacia' with Mountain View, Shared Pool and Wi-Fi
    From $141 per night (USD)

    Expedia

    Room 'Acacia' with Mountain View, Shared Pool and Wi-Fi

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    The Room Acacia is located in Chianciano Terme and overlooks the mountain. The 16 m² property consists of 1 bedroom and ...

    From $141 per night (USD)

    Expedia

    Details
  • Apartment 'La Loggia' with Mountain View, Shared Pool and Wi-Fi
    From $153 per night (USD)

    VRBO

    Apartment 'La Loggia' with Mountain View, Shared Pool and Wi-Fi

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    5

    In Chianciano Terme, the holiday apartment La loggia offers an excellent view of the mountain. The 80 m² property consis ...

    From $153 per night (USD)

    VRBO

    Details
  • Lovely holiday home in Val d’Orcia, with pool and large garden, near Pienza
    From $298 per night (USD)

    Expedia

    Lovely holiday home in Val d’Orcia, with pool and large garden, near Pienza

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    10

    This lovely holiday home in Val d’Orcia in the Middle Ages was probably a resting place for pilgrims travelling on the V ...

    From $298 per night (USD)

    Expedia

    Details
  • Villa Pianoia – Elegance and Historic Charm for Groups and Special Events
    From $1830 per night (USD)

    VRBO

    Villa Pianoia – Elegance and Historic Charm for Groups and Special Events

    Bedrooms:
    8
    Bathrooms:
    7
    Sleeps:
    16

    Nestled in the heart of Tuscany, Villa Pianoia is a historic residence surrounded by lush greenery, located between Mont ...

    From $1830 per night (USD)

    VRBO

    Details
  • [Cetona - Val D'Orcia] Typical Tuscany Residence
    From $109 per night (USD)

    Expedia

    [Cetona - Val D'Orcia] Typical Tuscany Residence

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    5

    In the heart of the historic center of Cetona, one of the most charming villages in Italy, lies this typical Tuscan dwel ...

    From $109 per night (USD)

    Expedia

    Details
  • Holiday home with garden
    From $271 per night (USD)

    VRBO

    Holiday home with garden

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    The detached holiday home built in 1500, was renovated in 2015 and is furnished in a luxury and typical country style. T ...

    From $271 per night (USD)

    VRBO

    Details
  •  Welcoming, cosy, family-friendly Cottage in olive fields and garden with pool
    From $182 per night (USD)

    Expedia

    Welcoming, cosy, family-friendly Cottage in olive fields and garden with pool

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    A charming private cottage on 2 floors with a private terrasse and dining area in the gardens of our renovated Covent fr ...

    From $182 per night (USD)

    Expedia

    Details
  • Farmhouse in the Tuscan countryside, swimming pool. Hot springs, art cities, Etruscan archaeology
    From $287 per night (USD)

    VRBO

    Farmhouse in the Tuscan countryside, swimming pool. Hot springs, art cities, Etruscan archaeology

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    <p>Located in a rural area, this 2-bedroom, 2-bathroom vacation home lets you experience it all in Chianciano Terme. Fan ...

    From $287 per night (USD)

    VRBO

    Details
  • TUSCANY TO LOVE
    From $115 per night (USD)

    Expedia

    TUSCANY TO LOVE

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    <p>Located in Cetona, this welcoming vacation home lets you experience it all. Thanks to the convenient onsite parking, ...

    From $115 per night (USD)

    Expedia

    Details
  • Awesome home in Pienza
    From $325 per night (USD)

    VRBO

    Awesome home in Pienza

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    8

    Treat yourself to a dream holiday in this enchanting holiday home with a large pool in an idyllic rural setting. This ...

    From $325 per night (USD)

    VRBO

    Details
  • Villa Bravio: A characteristic and welcoming two-story villa made of stone, with Free WI-FI.
    From $1776 per night (USD)

    Expedia

    Villa Bravio: A characteristic and welcoming two-story villa made of stone, with Free WI-FI.

    Bedrooms:
    6
    Bathrooms:
    6
    Sleeps:
    12

    Villa Bravio is a characteristic and welcoming two-story villa made of stone. It sleeps 12 people. From Villa Bravio you ...

    From $1776 per night (USD)

    Expedia

    Details
  • Farmhouse Borgo Sette Tigli - apt 5
    From $303 per night (USD)

    VRBO

    Farmhouse Borgo Sette Tigli - apt 5

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    <p>Located in Montepulciano, this welcoming vacation home lets you experience it all. Val di Chiana is just a short walk ...

    From $303 per night (USD)

    VRBO

    Details
  • Farmhouse Borgo Sette Tigli - apt 4
    From $298 per night (USD)

    Expedia

    Farmhouse Borgo Sette Tigli - apt 4

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Farm stay in Montepulciano Along with concierge services, this smoke-free farm stay has laundry facilities and a garden. ...

    From $298 per night (USD)

    Expedia

    Details
  • Apartment 'Comfort Alle Terme' with Balcony and Wi-Fi
    From $337 per night (USD)

    VRBO

    Apartment 'Comfort Alle Terme' with Balcony and Wi-Fi

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Located in Chianciano Terme, this 110 m² apartment can accommodate up to 5 people and features 2 bedrooms, a living room ...

    From $337 per night (USD)

    VRBO

    Details
  • Poggio del Raglio: Relax&Nature
    From $209 per night (USD)

    Expedia

    Poggio del Raglio: Relax&Nature

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    5

    <p>Located in Trequanda, this welcoming vacation home brings it all within your reach. Thanks to the convenient onsite p ...

    From $209 per night (USD)

    Expedia

    Details
  • Apartment 'La Torre' with Balcony, Wi-Fi and Air Conditioning
    From $120 per night (USD)

    VRBO

    Apartment 'La Torre' with Balcony, Wi-Fi and Air Conditioning

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    Located in Torrita di Siena, Tuscany, La Torre is a 75 sqm apartment that accommodates up to 4 guests. You will find 1 b ...

    From $120 per night (USD)

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    Details
  • Boutique Apartment Family
    From $137 per night (USD)

    Expedia

    Boutique Apartment Family

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    7

    Elegant in shades of Terracotta Red and Mustard Yellow, newly renovated apartment on the first floor of 80 m2, has Tri ...

    From $137 per night (USD)

    Expedia

    Details
  • Boutique Apartment Natura
    From $126 per night (USD)

    VRBO

    Boutique Apartment Natura

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    5

    Elegant in shades of Sage Green and Brilliant, newly renovated apartment on the first floor of 60 square meters, has Tr ...

    From $126 per night (USD)

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    Details
  • Premium Apartment - Helichrysum
    From $395 per night (USD)

    Expedia

    Premium Apartment - Helichrysum

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Featuring a private entrance, this air-conditioned apartment comprises 1 living room, 2 separate bedrooms and 2 bathroom ...

    From $395 per night (USD)

    Expedia

    Details
  • NEM Tiny House by Pleiades Home
    From $135 per night (USD)

    VRBO

    NEM Tiny House by Pleiades Home

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    NEM Tiny House – Your wellness retreat in the heart of Tuscany Just 200 meters from the renowned Terme di Chianciano, ...

    From $135 per night (USD)

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    Details
  • TERRACQUA--an oasis of peace in the Tuscan hills
    From $836 per night (USD)

    Expedia

    TERRACQUA--an oasis of peace in the Tuscan hills

    Bedrooms:
    8
    Bathrooms:
    8
    Sleeps:
    18

    Bed & breakfast in Chiusi with a hot tub A hot tub and laundry facilities are available at this smoke-free bed & breakfa ...

    From $836 per night (USD)

    Expedia

    Details
  • Apartment 'Villa Rosa' with Mountain View and Balcony
    From $132 per night (USD)

    VRBO

    Apartment 'Villa Rosa' with Mountain View and Balcony

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    The holiday apartment Podere Villa Rosa, which is situated in Torrita di Siena, overlooks the nearby mountain. The 90 m² ...

    From $132 per night (USD)

    VRBO

    Details
  • Breathtaking sunsets from a peaceful farmhouse with swimming pool in Val d'Orcia
    From $1037 per night (USD)

    Expedia

    Breathtaking sunsets from a peaceful farmhouse with swimming pool in Val d'Orcia

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    9

    I Prati is a typical old Sienese farmhouse located in southern Tuscany, overlooking the Val d'Orcia valley near the medi ...

    From $1037 per night (USD)

    Expedia

    Details
  • AUNT MARISA
    From $156 per night (USD)

    VRBO

    AUNT MARISA

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    <p>Nestled in Montepulciano, this 2-bedroom, 1-bathroom apartment brings it all within your reach. Fans of nature and th ...

    From $156 per night (USD)

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    Details
  • Homerez - Enchanting House in Trequanda + Pool
    From $453 per night (USD)

    VRBO

    Homerez - Enchanting House in Trequanda + Pool

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    5

    Welcome to our charming holiday home in Trequanda, perfect for a relaxing getaway with family or friends. Here, you can ...

    From $453 per night (USD)

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    Details
  • Homerez - Charming House in Trequanda with Shared Pool
    From $196 per night (USD)

    VRBO

    Homerez - Charming House in Trequanda with Shared Pool

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    3

    Experience charm and comfort in this idyllic 50 m² holiday home for up to 3 guests. - Shared pool open from June 1st ...

    From $196 per night (USD)

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  • Homerez - Apartment in Trequanda with pool
    From $218 per night (USD)

    VRBO

    Homerez - Apartment in Trequanda with pool

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Discover a charming holiday rental with fantastic views of the garden and mountains. Perfect for couples, this studio of ...

    From $218 per night (USD)

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    Details
  • Sweet Nest -House in Montepulciano
    From $172 per night (USD)

    VRBO

    Sweet Nest -House in Montepulciano

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    <p>Nestled in Montepulciano, this 2-bedroom, 1-bathroom vacation home brings it all within your reach. Fans of nature an ...

    From $172 per night (USD)

    VRBO

    Details
  • Holiday apartment Abbadia for 1 - 2 persons with 1 bedroom - Holiday apartment
    From $188 per night (USD)

    VRBO

    Holiday apartment Abbadia for 1 - 2 persons with 1 bedroom - Holiday apartment

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    ED Refnr. 3189869 The Elefantino flat is our smallest apartment. It owes its name to the elephant in the original coat ...

    From $188 per night (USD)

    VRBO

    Details
  • Samsara Apartment, elegant apartment in the historic center.
    From $156 per night (USD)

    VRBO

    Samsara Apartment, elegant apartment in the historic center.

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    5

    <p>Located in Pienza, this welcoming apartment lets you experience it all. You're conveniently located within a 5-minute ...

    From $156 per night (USD)

    VRBO

    Details
  • Bright apartment with large terrace - perfect for families or groups
    From $197 per night (USD)

    Expedia

    Bright apartment with large terrace - perfect for families or groups

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    <p>A short distance from cycling, fishing, and more, this pet-friendly apartment lets you experience it all. Val di Chia ...

    From $197 per night (USD)

    Expedia

    Details
  • Apartment 'Piccolo Rustico' with Mountain View, Wi-Fi and Air Conditioning
    From $115 per night (USD)

    VRBO

    Apartment 'Piccolo Rustico' with Mountain View, Wi-Fi and Air Conditioning

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    3

    The holiday apartment Piccolo Rustico is located in Scrofiano and offers a wonderful view of the mountains. The 50 m² pr ...

    From $115 per night (USD)

    VRBO

    Details
  • Terrace over poetry
    From $122 per night (USD)

    Expedia

    Terrace over poetry

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    <p>Located in Sarteano, this 1-bedroom, 1-bathroom vacation home lets you experience it all. Fans of nature and the outd ...

    From $122 per night (USD)

    Expedia

    Details
  • Le rondini by Interhome
    From $92 per night (USD)

    VRBO

    Le rondini by Interhome

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    3

    Montepulciano: Modern, comfortable 2-family house "Le rondini". 2 apartments in the property. In the district of Cervogn ...

    From $92 per night (USD)

    VRBO

    Details
  • Il Cipressino - your cozy apartment in Montepulciano with parking and garden.
    From $213 per night (USD)

    VRBO

    Il Cipressino - your cozy apartment in Montepulciano with parking and garden.

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    <p>Close to horse riding, winery tours, and more, this smoke-free vacation home brings it all within reach. There's conv ...

    From $213 per night (USD)

    VRBO

    Details
  • Your Perfect Getaway: Relaxation, Nature and Authenticity for Couples - Families
    From $783 per night (USD)

    VRBO

    Your Perfect Getaway: Relaxation, Nature and Authenticity for Couples - Families

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    10

    Our structure offers different rooms, ideal for couples, families or small groups of friends The spaces are dedicated an ...

    From $783 per night (USD)

    VRBO

    Details
  • Casale Poggio al Vento 8 In Sinalunga, Tuscany
    From $348 per night (USD)

    VRBO

    Casale Poggio al Vento 8 In Sinalunga, Tuscany

    Bedrooms:
    5
    Bathrooms:
    5
    Sleeps:
    8

    Property for exclusive use Splendid stone estate comfortably hosting up to 8 persons with 3 double bedrooms, 2 singles a ...

    From $348 per night (USD)

    VRBO

    Details
  • Villa Icario by Fantasia Villas
    From $2587 per night (USD)

    VRBO

    Villa Icario by Fantasia Villas

    Bedrooms:
    6
    Bathrooms:
    5
    Sleeps:
    10

    A hidden gem nestled in the heart of our estate, where the charm of the Tuscan countryside meets the timeless beauty of ...

    From $2587 per night (USD)

    VRBO

    Details
  • Poggio Bravo by Miani Group
    From $2623 per night (USD)

    VRBO

    Poggio Bravo by Miani Group

    Bedrooms:
    5
    Bathrooms:
    5
    Sleeps:
    10

    <p>Located in Montepulciano, this welcoming vacation home brings it all within your reach. Val di Chiana is just a short ...

    From $2623 per night (USD)

    VRBO

    Details
  • CASAMORE Rentals, Tuscany Villa
    From $1897 per night (USD)

    VRBO

    CASAMORE Rentals, Tuscany Villa

    Bedrooms:
    6
    Bathrooms:
    6
    Sleeps:
    14

    <p>Located in San Casciano dei Bagni, this welcoming villa brings it all within your reach. Val di Chiana is just a shor ...

    From $1897 per night (USD)

    VRBO

    Details
  • Villa Fonte Siena promoted by WeekHomes.com
    From $956 per night (USD)

    VRBO

    Villa Fonte Siena promoted by WeekHomes.com

    Bedrooms:
    6
    Bathrooms:
    6
    Sleeps:
    12

    The villa in Monticchiello has 6 bedrooms and has capacity for 12 people. Villa Fonte Siena is located in Monticchiello ...

    From $956 per night (USD)

    VRBO

    Details
  • Podere Le Crete by Miani Group
    From $1158 per night (USD)

    VRBO

    Podere Le Crete by Miani Group

    Bedrooms:
    7
    Bathrooms:
    6
    Sleeps:
    14

    <p>Located in Trequanda, this welcoming villa brings it all within your reach. Thanks to the convenient onsite parking, ...

    From $1158 per night (USD)

    VRBO

    Details
  • Farmhouse with saltwater pool overlooking Montepuciano Tuscany
    From $370 per night (USD)

    VRBO

    Farmhouse with saltwater pool overlooking Montepuciano Tuscany

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    3

    <p>Nestled in Montepulciano, this 1-bedroom, 1-bathroom vacation home brings it all within your reach. Fans of nature an ...

    From $370 per night (USD)

    VRBO

    Details
  • Podere Dal Monte by Miani Group
    From $1684 per night (USD)

    VRBO

    Podere Dal Monte by Miani Group

    Bedrooms:
    7
    Bathrooms:
    7
    Sleeps:
    14

    <p>Located in Montepulciano, this welcoming villa lets you experience it all. Val di Chiana is just steps away and Terme ...

    From $1684 per night (USD)

    VRBO

    Details
  • House Parisina small apartment just outside the town center
    From $77 per night (USD)

    VRBO

    House Parisina small apartment just outside the town center

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    <p>Located in Chianciano Terme, this 1-bedroom, 1-bathroom apartment lets you experience it all. Fans of nature and the ...

    From $77 per night (USD)

    VRBO

    Details
  • Holiday apartment Abbadia for 1 - 6 persons with 1 bedroom - Detached holiday house
    From $321 per night (USD)

    VRBO

    Holiday apartment Abbadia for 1 - 6 persons with 1 bedroom - Detached holiday house

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    6

    ED Refnr. 3189863 Our largest flat has a spacious living/dining room with kitchenette, a double bedroom on one gallery, ...

    From $321 per night (USD)

    VRBO

    Details
  • Holiday house Abbadia for 1 - 2 persons with 1 bedroom - Holiday apartment in one or multi-family ho
    From $242 per night (USD)

    VRBO

    Holiday house Abbadia for 1 - 2 persons with 1 bedroom - Holiday apartment in one or multi-family ho

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    ED Refnr. 3189866 The Vigneto flat is located on one level on the ground floor of the villa and is also suitable for a ...

    From $242 per night (USD)

    VRBO

    Details
  • Case Vacanze I Chiari
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    VRBO

    Case Vacanze I Chiari

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    <p>While you're here, you can enjoy all the comforts of home and more, including a refrigerator and a dishwasher, as wel ...

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    Details
  • Country House with Swimming Pool
    From $171 per night (USD)

    VRBO

    Country House with Swimming Pool

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    <p>Located in Chiusi, this welcoming vacation home brings it all within your reach. Val di Chiana is just a short walk a ...

    From $171 per night (USD)

    VRBO

    Details
  • Agriturismo Mori Vetrica-San Casciano dei Bagni
    From $929 per night (USD)

    VRBO

    Agriturismo Mori Vetrica-San Casciano dei Bagni

    Bedrooms:
    6
    Bathrooms:
    6
    Sleeps:
    12

    Farm stay in San Casciano dei Bagni with a hot tub This smoke-free farm stay features a hot tub, laundry facilities, and ...

    From $929 per night (USD)

    VRBO

    Details
  • Tuscan Palace - Buratti Apartment
    From $755 per night (USD)

    Expedia

    Tuscan Palace - Buratti Apartment

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    10

    This stunning Renaissance apartment, located in Palazzo Buratti, has undergone a full restoration and offers an unforget ...

    From $755 per night (USD)

    Expedia

    Details
  • Tuscan Palace - Venturi apartment
    From $199 per night (USD)

    VRBO

    Tuscan Palace - Venturi apartment

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    The 17th-century apartment in Palazzo Venturi is a charming and luxurious place to stay in the historic district of Mont ...

    From $199 per night (USD)

    VRBO

    Details
  • A MAGICAL HOLIDAY IN TUSCANY
    From $616 per night (USD)

    Expedia

    A MAGICAL HOLIDAY IN TUSCANY

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    10

    <p>Just a short distance from winery tours, this smoke-free vacation home lets you experience it all. Val di Chiana and ...

    From $616 per night (USD)

    Expedia

    Details
  • Luxury Apartment in Siena Resort
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    VRBO

    Luxury Apartment in Siena Resort

    Bedrooms:
    17
    Bathrooms:
    17
    Sleeps:
    34

    <p>While you're here, you can enjoy all the comforts of home and more, including a seasonal outdoor pool and a full-size ...

    Click For Pricing

    VRBO

    Details
  • Casa M Honeymoon Suite
    From $348 per night (USD)

    Expedia

    Casa M Honeymoon Suite

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Fascinating boutique hotel located in the heart of Tuscany, more precisely in Chianciano Terme, with 9 rooms of differen ...

    From $348 per night (USD)

    Expedia

    Details
  • [15 min from Montepulciano] Villa Chiara
    From $474 per night (USD)

    VRBO

    [15 min from Montepulciano] Villa Chiara

    Bedrooms:
    0
    Bathrooms:
    0
    Sleeps:
    0

    <p>Located in Torrita di Siena, this welcoming apartment lets you experience it all. Val di Chiana is just a quick walk ...

    From $474 per night (USD)

    VRBO

    Details
  • Nice apartment in a quiet area a stone's throw from the historic center
    From $99 per night (USD)

    VRBO

    Nice apartment in a quiet area a stone's throw from the historic center

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    <p>Close to cycling, fishing, and more, this pet-friendly apartment brings it all within reach. There's convenient onsit ...

    From $99 per night (USD)

    VRBO

    Details