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Results: 253 Rentals

  • Villa Lucia - Tuscan villa with private pool
    From $592 per night (USD)

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    Villa Lucia - Tuscan villa with private pool

    Bedrooms:
    5
    Bathrooms:
    6
    Sleeps:
    14

    VILLA LUCIA - AREZZO AREA Villa Lucia is located close to the town of Castiglion Fiorentino, just 1km outside of it, re ...

    From $592 per night (USD)

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    Details
  • Fratta Ciclamini, Cortona, Italy
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    Expedia

    Fratta Ciclamini, Cortona, Italy

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    A stunning ground-floor apartment in “Leopoldina”, a traditional Casa Colonica in the heart of the gorgeous Tuscan count ...

    Click For Pricing

    Expedia

    Details
  • Fratta Ginestre, Cortona, Italy
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    Fratta Ginestre, Cortona, Italy

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    6

    “Leopoldina”, is a traditional Casa Colonica in the heart of the gorgeous Tuscan countryside. It has been sensitively co ...

    Click For Pricing

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    Details
  • Tuscan Castle View Grand Villa
    From $402 per night (USD)

    Expedia

    Tuscan Castle View Grand Villa

    Bedrooms:
    5
    Bathrooms:
    4
    Sleeps:
    11

    This rather enormous villa is at the brink of the medieval castle of Montecchio Vespoli. With its vintage decor and bein ...

    From $402 per night (USD)

    Expedia

    Details
  • Villa in Fattoria with 9 bedrooms sleeps 18
    From $791 per night (USD)

    VRBO

    Villa in Fattoria with 9 bedrooms sleeps 18

    Bedrooms:
    9
    Bathrooms:
    10
    Sleeps:
    18

    Unforgettable holidays at Villa Michele. This wonderful villa has two swimming pool, one with hydromassage, and a sauna. ...

    From $791 per night (USD)

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    Details
  • Awesome home in Castiglion Fiorentino
    From $102 per night (USD)

    Expedia

    Awesome home in Castiglion Fiorentino

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    Charming and inviting holiday home with access to the pool. Spend a wonderful holiday as a couple or small family in ...

    From $102 per night (USD)

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    Details
  • Amazing home in Castiglion Fiorentino
    From $108 per night (USD)

    VRBO

    Amazing home in Castiglion Fiorentino

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    3

    Charming and inviting holiday home with access to the pool. Spend a wonderful holiday as a couple or small family in ...

    From $108 per night (USD)

    VRBO

    Details
  • Villa in Cortona with Pool and Valley Views
    From $229 per night (USD)

    Expedia

    Villa in Cortona with Pool and Valley Views

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

    In the hills just outside the Etruscan gem of Cortona, this beautiful home offers a perfect blend of rustic charm and co ...

    From $229 per night (USD)

    Expedia

    Details
  • Lilac apartment
    From $943 per night (USD)

    VRBO

    Lilac apartment

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    <p>Located in Castiglion Fiorentino, this 2-bedroom, 1-bathroom vacation home lets you experience it all. Fans of nature ...

    From $943 per night (USD)

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    Details
  • Stunning  villa for 4 people with A/C, WIFI, TV and balcony
    From $153 per night (USD)

    Expedia

    Stunning villa for 4 people with A/C, WIFI, TV and balcony

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    4

    Property Summary You are considering Casa Volpe, a beautiful, comfortable 2-family detached house in Castiglion Fiorenti ...

    From $153 per night (USD)

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    Details
  • Beautiful private villa for 3 people with WIFI, private pool, TV, terrace and pets allowed
    From $91 per night (USD)

    VRBO

    Beautiful private villa for 3 people with WIFI, private pool, TV, terrace and pets allowed

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    3

    Property Summary The "Nido del Sorbino" cottage offers a tranquil vacation rental nestled in the heart of Tuscany, situa ...

    From $91 per night (USD)

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    Details
  • Wonderful private villa for 6 people with WIFI, private pool, TV, terrace and pets allowed
    From $173 per night (USD)

    Expedia

    Wonderful private villa for 6 people with WIFI, private pool, TV, terrace and pets allowed

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Property Summary "Il Sorbino" is a charming rustic cottage located in Castiglion Fiorentino, Italy. Offering a tranquil ...

    From $173 per night (USD)

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    Details
  • The window on the tower apartment new castiglion fiorentino
    From $122 per night (USD)

    VRBO

    The window on the tower apartment new castiglion fiorentino

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    <p>Located in Castiglion Fiorentino, this welcoming apartment lets you experience it all. Archaeological Museum and Vasa ...

    From $122 per night (USD)

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    Details
  • Fulvia House, Rural Tuscany - CIN: IT051012C2QNJXHNQX
    From $160 per night (USD)

    Expedia

    Fulvia House, Rural Tuscany - CIN: IT051012C2QNJXHNQX

    Bedrooms:
    1
    Bathrooms:
    2
    Sleeps:
    4

    <p>Located in Castiglion Fiorentino, this welcoming apartment lets you experience it all. With convenient onsite parking ...

    From $160 per night (USD)

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    Details
  • Il Sogno Di Pietro by Interhome
    From $368 per night (USD)

    VRBO

    Il Sogno Di Pietro by Interhome

    Bedrooms:
    5
    Bathrooms:
    7
    Sleeps:
    11

    Beautiful, comfortable villa "Il Sogno Di Pietro", surrounded by trees and fields. Property composed of main house and o ...

    From $368 per night (USD)

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    Details
  • 4 Bedroom Tuscan Country Villa with Infinity pool & stunning views near Cortona
    From $621 per night (USD)

    Expedia

    4 Bedroom Tuscan Country Villa with Infinity pool & stunning views near Cortona

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    10

    Casa Sophia di Brolio is a stylish four bedroom family-friendly villa with a fabulous infinity pool, lovely views and ea ...

    From $621 per night (USD)

    Expedia

    Details
  • Stunning home in Castiglion Fiorentino
    From $75 per night (USD)

    VRBO

    Stunning home in Castiglion Fiorentino

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    7

    Enjoy your family holiday in this beautiful and large holiday home with pool. In this beautiful holiday home, you wil ...

    From $75 per night (USD)

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    Details
  • Charming Cottage in the Heart of Tuscany
    From $424 per night (USD)

    Expedia

    Charming Cottage in the Heart of Tuscany

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    Charming Cottage in the Heart of Tuscany Tucked away among the gentle, sun-drenched hills of the Tuscan countryside, th ...

    From $424 per night (USD)

    Expedia

    Details
  • Wonderful villa with private pool near Arezzo
    From $1867 per night (USD)

    VRBO

    Wonderful villa with private pool near Arezzo

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    10

    <p>Nestled in Foiano della Chiana, this 4-bedroom, 2.5-bathroom villa brings it all within your reach. Fans of nature an ...

    From $1867 per night (USD)

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    Details
  • Awesome home in Castiglion Fiorentino
    From $254 per night (USD)

    Expedia

    Awesome home in Castiglion Fiorentino

    Bedrooms:
    4
    Bathrooms:
    4
    Sleeps:
    11

    Enjoy your holiday in this colourful and family-friendly holiday home with swimming pool. Welcome to this large and i ...

    From $254 per night (USD)

    Expedia

    Details
  • Villa la Ghiandaia Comfortable holiday residence
    From $1824 per night (USD)

    VRBO

    Villa la Ghiandaia Comfortable holiday residence

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    6

    Splendid villa with infinity pool and garden, located in the countryside of Castiglion Fiorentino, near Cortona. Layout: ...

    From $1824 per night (USD)

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    Details
  • Villa Rinaldo Comfortable holiday residence
    From $1467 per night (USD)

    Expedia

    Villa Rinaldo Comfortable holiday residence

    Bedrooms:
    1
    Bathrooms:
    5
    Sleeps:
    10

    Stunning villa with private pool and dependance, located in the open countryside, halfway between Arezzo and Cortona. La ...

    From $1467 per night (USD)

    Expedia

    Details
  • Santa Lucia by Interhome
    From $153 per night (USD)

    VRBO

    Santa Lucia by Interhome

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    7

    Cottage "Santa Lucia", semi-detached. 2.5 km from the centre of Castiglion Fiorentino, 20 km from the centre of Arezzo, ...

    From $153 per night (USD)

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  • Cottage Contadina by Interhome
    From $81 per night (USD)

    Expedia

    Cottage Contadina by Interhome

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

    "rustico" cottage "Cottage Contadina", 800 m a.s.l.. 6 km from the centre of Cortona, in a secluded position, 30 km from ...

    From $81 per night (USD)

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    Details
  • La Felcaia by Interhome
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    Expedia

    La Felcaia by Interhome

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    House "La Felcaia", 600 m a.s.l.. 2.5 km from the centre of Castiglion Fiorentino, 10 km from the centre of Cortona, 35 ...

    Click For Pricing

    Expedia

    Details
  • Nido del Sorbino by Interhome
    From $79 per night (USD)

    Expedia

    Nido del Sorbino by Interhome

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    3

    "rustico" cottage "Nido del Sorbino", 460 m a.s.l.. 4 km from the centre of Castiglion Fiorentino, 15 km from the centre ...

    From $79 per night (USD)

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    Details
  • Il Sorbino by Interhome
    From $135 per night (USD)

    VRBO

    Il Sorbino by Interhome

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    6

    "rustico" cottage "Il Sorbino", 470 m a.s.l., surrounded by trees. 4 km from the centre of Castiglion Fiorentino, 15 km ...

    From $135 per night (USD)

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    Details
  • Stunning private villa for 11 guests with WIFI, A/C, private pool, TV and patio
    From $424 per night (USD)

    Expedia

    Stunning private villa for 11 guests with WIFI, A/C, private pool, TV and patio

    Bedrooms:
    5
    Bathrooms:
    7
    Sleeps:
    11

    Property Summary Il Sogno Di Pietro is a beautiful and comfortable villa surrounded by trees and fields in Castiglion Fi ...

    From $424 per night (USD)

    Expedia

    Details
  • Nice home in Castiglion Fiorentino
    From $384 per night (USD)

    VRBO

    Nice home in Castiglion Fiorentino

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    9

    Look forward to a wonderful stay in this beautiful holiday home. Enjoy your next holiday in Italy in this holiday hom ...

    From $384 per night (USD)

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    Details
  • Villa in Cegliolo with 7 bedrooms sleeps 14
    From $452 per night (USD)

    Expedia

    Villa in Cegliolo with 7 bedrooms sleeps 14

    Bedrooms:
    5
    Bathrooms:
    7
    Sleeps:
    14

    Villa San Pietro is a beautiful property located in the immediate vicinity of the town of Cortona, whose view of the gen ...

    From $452 per night (USD)

    Expedia

    Details
  • Casale la Madonnina In Castiglion Fiorentino, Tuscany
    From $537 per night (USD)

    VRBO

    Casale la Madonnina In Castiglion Fiorentino, Tuscany

    Bedrooms:
    3
    Bathrooms:
    5
    Sleeps:
    10

    Property for exclusive use Farmhouse with exclusive swimming pool, consisting of 2 apartments and an annex, which can ac ...

    From $537 per night (USD)

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    Details
  • Villa Michelangelo
    From $1225 per night (USD)

    VRBO

    Villa Michelangelo

    Bedrooms:
    10
    Bathrooms:
    9
    Sleeps:
    18

    The villa has 9 bedrooms and has capacity for 18 people. The villa is 800 m². Surrounded by flourishing olive groves and ...

    From $1225 per night (USD)

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    Details
  • Typical villa located in the rolling hills of Valdichiana, 3 km from the town of Castiglion Fiorenti
    From $261 per night (USD)

    VRBO

    Typical villa located in the rolling hills of Valdichiana, 3 km from the town of Castiglion Fiorenti

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Set on the gentle hills of the Tuscan countryside, just 3 km from the charming town of Castiglion Fiorentino, Il Pasqual ...

    From $261 per night (USD)

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    Details
  • Country house with private pool (you have a German contact person)
    From $383 per night (USD)

    VRBO

    Country house with private pool (you have a German contact person)

    Bedrooms:
    2
    Bathrooms:
    4
    Sleeps:
    9

    <p>Located in Castiglion Fiorentino, this welcoming vacation home brings it all within your reach. With the property's c ...

    From $383 per night (USD)

    VRBO

    Details
  • Villa Pasqualina Comfortable holiday residence
    From $1032 per night (USD)

    VRBO

    Villa Pasqualina Comfortable holiday residence

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    6

    Splendid villa with private garden, pool and ping-pong table, located among the rolling hills of Valdichiana area, just ...

    From $1032 per night (USD)

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    Details
  • Villa Castiglioni Comfortable holiday residence
    From $766 per night (USD)

    Expedia

    Villa Castiglioni Comfortable holiday residence

    Bedrooms:
    1
    Bathrooms:
    3
    Sleeps:
    6

    Fantastic villa with private garden and pool, located in the countryside of Castiglion Fiorentino, near Cortona. Layout: ...

    From $766 per night (USD)

    Expedia

    Details
  • VILLA DE' MICHELANGIOLI
    From $3011 per night (USD)

    VRBO

    VILLA DE' MICHELANGIOLI

    Bedrooms:
    9
    Bathrooms:
    9
    Sleeps:
    21

    [🌟 A TUSCAN PARADISE AWAITS YOU 🌟] Welcome to Villa de' Michelangioli, a luxurious retreat perched on a hilltop in th ...

    From $3011 per night (USD)

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    Details
  • Michelangioli by Interhome
    From $1379 per night (USD)

    Expedia

    Michelangioli by Interhome

    Bedrooms:
    10
    Bathrooms:
    9
    Sleeps:
    18

    Large, cosy, comfortable villa "Michelangioli", surrounded by fields. 9 km from the centre of Castiglion Fiorentino, 27 ...

    From $1379 per night (USD)

    Expedia

    Details
  • Vacation Home VILLAGE POGGIO ROSSO in the heart of Tuscany!!!
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    VRBO

    Vacation Home VILLAGE POGGIO ROSSO in the heart of Tuscany!!!

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    4

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

    Click For Pricing

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    Details
  • Villa Rivaflora: A splendid three-story villa situated in a quiet location, a few minutes from the town center, with Free WI-FI.
    From $563 per night (USD)

    Expedia

    Villa Rivaflora: A splendid three-story villa situated in a quiet location, a few minutes from the town center, with Free WI-FI.

    Bedrooms:
    5
    Bathrooms:
    4
    Sleeps:
    10

    Villa Rivaflora is a splendid three-story villa situated in a quiet location, a few minutes from the town center. It sle ...

    From $563 per night (USD)

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    Details
  • Casale Burcinella
    From $359 per night (USD)

    VRBO

    Casale Burcinella

    Bedrooms:
    2
    Bathrooms:
    3
    Sleeps:
    6

    Immerse yourself in the heart of Tuscany at this beautifully restored 200-year-old traditional farmhouse. Casale Burcine ...

    From $359 per night (USD)

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    Details
  • Villa in Tuscany with Pool and Valley Views
    From $485 per night (USD)

    Expedia

    Villa in Tuscany with Pool and Valley Views

    Bedrooms:
    5
    Bathrooms:
    4
    Sleeps:
    8

    Located near Castiglion Fiorentino, this villa has 4 bedrooms and accommodates 8 people. This luxurious villa has a swim ...

    From $485 per night (USD)

    Expedia

    Details
  • Vacation home for 18 guests with 100m² in Castiglion Fiorentino (271664)
    From $1327 per night (USD)

    VRBO

    Vacation home for 18 guests with 100m² in Castiglion Fiorentino (271664)

    Bedrooms:
    6
    Bathrooms:
    7
    Sleeps:
    18

    <p>Located in Castiglion Fiorentino, this welcoming vacation home brings it all within your reach. Val di Chiana is an e ...

    From $1327 per night (USD)

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    Details
  • Vacation home for 11 guests with 300m² in Castiglion Fiorentino (273266)
    From $802 per night (USD)

    VRBO

    Vacation home for 11 guests with 300m² in Castiglion Fiorentino (273266)

    Bedrooms:
    4
    Bathrooms:
    6
    Sleeps:
    11

    <p>Located in Castiglion Fiorentino, this welcoming vacation home lets you experience it all. With convenient onsite par ...

    From $802 per night (USD)

    VRBO

    Details
  • Vacation home for 14 guests with 300m² in Cortona (273281)
    From $553 per night (USD)

    VRBO

    Vacation home for 14 guests with 300m² in Cortona (273281)

    Bedrooms:
    5
    Bathrooms:
    7
    Sleeps:
    14

    <p>Located in Cortona, this welcoming vacation home brings it all within your reach. Jump into your car and make short w ...

    From $553 per night (USD)

    VRBO

    Details
  • Vacation home for 17 guests with 300m² in Castiglion Fiorentino (272096)
    From $728 per night (USD)

    VRBO

    Vacation home for 17 guests with 300m² in Castiglion Fiorentino (272096)

    Bedrooms:
    6
    Bathrooms:
    8
    Sleeps:
    17

    <p>Located in Castiglion Fiorentino, this welcoming vacation home lets you experience it all. Jump into your car and mak ...

    From $728 per night (USD)

    VRBO

    Details
  • Slope 15, small apartment in Castiglion Fiorentino
    From $133 per night (USD)

    VRBO

    Slope 15, small apartment in Castiglion Fiorentino

    Bedrooms:
    1
    Bathrooms:
    1
    Sleeps:
    2

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

    From $133 per night (USD)

    VRBO

    Details
  • Villa Pieve di Chio
    From $342 per night (USD)

    VRBO

    Villa Pieve di Chio

    Bedrooms:
    3
    Bathrooms:
    4
    Sleeps:
    8

    <p>Located in Castiglion Fiorentino, this welcoming villa lets you experience it all. Jump into your car and make short ...

    From $342 per night (USD)

    VRBO

    Details
  • Debora's House, apartment in residence with shared pool
    From $155 per night (USD)

    VRBO

    Debora's House, apartment in residence with shared pool

    Bedrooms:
    2
    Bathrooms:
    2
    Sleeps:
    5

    <p>A short distance from cycling, horse riding, and more, this smoke-free vacation home lets you experience it all. With ...

    From $155 per night (USD)

    VRBO

    Details
  • Beautiful farmhouse nestled in the Valdichiana where modern Tuscany was born
    From $375 per night (USD)

    Expedia

    Beautiful farmhouse nestled in the Valdichiana where modern Tuscany was born

    Bedrooms:
    4
    Bathrooms:
    3
    Sleeps:
    8

    <p>Located in Castiglion Fiorentino, this welcoming vacation home lets you experience it all. Jump into your car and mak ...

    From $375 per night (USD)

    Expedia

    Details
  • Villa Manciano nestled in the Tuscan countryside
    From $985 per night (USD)

    VRBO

    Villa Manciano nestled in the Tuscan countryside

    Bedrooms:
    4
    Bathrooms:
    6
    Sleeps:
    14

    The villa consists of two independent apartments, available for stays and rentals of at least two nights. The first apa ...

    From $985 per night (USD)

    VRBO

    Details
  • Campo Grande In Castiglion Fiorentino, Tuscany
    From $597 per night (USD)

    VRBO

    Campo Grande In Castiglion Fiorentino, Tuscany

    Bedrooms:
    5
    Bathrooms:
    5
    Sleeps:
    10

    Property for exclusive use Exclusive farmhouse with 3 apartments, exclusive swimming pool, able to accommodate 10 people ...

    From $597 per night (USD)

    VRBO

    Details
  • Agriturismo Borgo Santa Lucia, Villa Mimosa
    From $370 per night (USD)

    VRBO

    Agriturismo Borgo Santa Lucia, Villa Mimosa

    Bedrooms:
    3
    Bathrooms:
    3
    Sleeps:
    9

    Rental basis: Entire house or apartment Number of bedrooms: 3; Number of other rooms with beds: 0 Number of bathrooms: 3 ...

    From $370 per night (USD)

    VRBO

    Details