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Italy Vacation Rentals - 37 Properties

Welcome to Italy! Ancient Roman architecture, impossible beauty, and the best food ever! Experience Italy’s cultural diversity -- from trendy Turin, to romantic Venice, to historic Rome, to the island Sicily. No matter where you wind up, RedAwning has many gorgeous vacation homes, villas, apartments and condos in Italy, all ready to rent with a simple, hotel-style reservation process.

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  1. Sleeps 19, $2437 to $2887/night

    City : San Casciano Val di Pesa
    Bedrooms : 10
    Bathrooms : 9
    Pool Pets OK

    Villa Lorenzo is all you could ask for in an historic villa for a...

  2. Sleeps 8, ~$2376/night

    City : Torrita di Siena
    Bedrooms : 4
    Bathrooms : 4
    Pool Hot Tub

    The Tuscany Dream Compound is immersed in the Tuscan countryside...

  3. Sleeps 10, $1118 to $1754/night

    City : Porto Ercole
    Bedrooms : 5
    Bathrooms : 3.5
    Pool

    If you are debating between a visit to Italy's historic cities and...

  4. Sleeps 2, ~$771/night

    City : Torrita di Siena (SI)
    Bedroom : 1
    Bathroom : 1
    Pool Hot Tub

    The Tuscany Dream Compound is immersed in the Tuscan countryside...

  5. Sleeps 8, ~$705/night

    City : Elba
    Bedrooms : 4
    Bathrooms : 4
    Pets OK

    Just off the Tuscan Coast is the beautiful Island of Elba. Your...

  6. Sleeps 2, ~$696/night

    City : Torrita di Siena (SI)
    Bedroom : 1
    Bathroom : 1
    Pool Hot Tub

    The Tuscany Dream Compound is immersed in the Tuscan countryside...

  7. Sleeps 6, ~$662/night

    City : Rome
    Bedrooms : 3
    Bathrooms : 3

    Savour a Roman interlude in an elegant, tastefully restored, and...

  8. Sleeps 5, ~$653/night

    City : Rome
    Bedrooms : 3
    Bathrooms : 2

    Coming to Rome? Don't miss a stay in this splendid duplex apartment...

  9. Sleeps 2, ~$630/night

    City : Torrita di Siena (SI)
    Bedroom : 1
    Bathroom : 1
    Pool Hot Tub

    The Tuscany Dream Compound is immersed in the Tuscan countryside...

  10. Sleeps 2, ~$630/night

    City : Torrita di Siena (SI)
    Bedroom : 1
    Bathroom : 1
    Pool Hot Tub

    The Tuscany Dream Compound is immersed in the Tuscan countryside...

  11. Sleeps 6, $580 to $666/night

    City : Rome
    Bedrooms : 3
    Bathrooms : 3

    Savour a Roman interlude in a seventeenth century Historical Palazzo...

  12. Sleeps 9, ~$540/night

    City : Sabaudia
    Bedrooms : 4
    Bathrooms : 4

    Sabaudia is one of the most chic of Italian beach resorts and is...

  13. Sleeps 4, $462 to $521/night

    City : Rome
    Bedrooms : 2
    Bathrooms : 2

    In a prime location in Rome’s Historic Center, near the Colosseum...

  14. Sleeps 5, $426 to $465/night

    City : Sermoneta
    Bedrooms : 2
    Bathrooms : 2
    Pool

    Come to one of the most perfect medieval towns in Italy and enjoy...

  15. Sleeps 7, $328 to $389/night

    City : Calvi di Umbria
    Bedrooms : 3
    Bathrooms : 2
    Pets OK

    In the Medieval hill town of Calvi di Umbria, this stone village...

  16. Sleeps 8, $318 to $636/night

    City : Naples
    Bedrooms : 4
    Bathrooms : 2
    Pool

    Absolutely Gorgeous 4 bedroom home located in a serene community in...

  17. Sleeps 5, ~$310/night

    City : Rome
    Bedrooms : 2
    Bathrooms : 2

    This up-scale second-floor apartment is located in the best part of...

  18. Sleeps 4, $310 to $422/night

    City : Rome
    Bedrooms : 2
    Bathroom : 1

    Hip designer furnishings and clean lines are a bright surprise...

  19. Sleeps 4, $296 to $342/night

    City : Rome
    Bedroom : 1
    Bathroom : 1

    Vacation in Rome as though you lived there. "Mio Giardino Romano",...

  20. Sleeps 4, $287 to $508/night

    City : Siena
    Bedrooms : 2
    Bathroom : 1

    Black and White Reigns is this Stylish Siena Apartment of...

  21. Sleeps 3, $281 to $375/night

    City : Cortona
    Bedroom : 1
    Bathroom : 1

    Cortona Concerto is the perfect Tuscan getaway for a couple or small...

  22. Sleeps 4, $258 to $637/night

    City : Naples
    Bedrooms : 2
    Bathrooms : 3
    Pool

    This waterfront gem rests on Johnson's Bay and looks directly into...

  23. Sleeps 3, $258 to $348/night

    City : Rome
    Bedroom : 1
    Bathroom : 1

    Savour a Roman interlude in a 17th century Historic Palazzo...

  24. Sleeps 6, ~$206/night

    City : Naples
    Bedrooms : 3
    Bathrooms : 2
    Pool Pets OK

    Discover the convenience and value of Lely Resort. Amenities include...

  25. Sleeps 6, ~$206/night

    City : Naples
    Bedrooms : 3
    Bathrooms : 2
    Pool

    Golf Course CommunityTee off in your own backyard! This home has it...

  26. Sleeps 10, $206 to $551/night

    City : Naples
    Bedrooms : 5
    Bathrooms : 3
    Pool Pets OK

    Outstanding Five Bedroom home that has been recently renovated with...

  27. Sleeps 6, $189 to $482/night

    City : Naples
    Bedrooms : 3
    Bathrooms : 2
    Pool Pets OK

    Wonderful 3 bedroom/ 2 bathroom home in a lovely neighborhood....

  28. Sleeps 6, ~$172/night

    City : Naples
    Bedrooms : 3
    Bathrooms : 2
    Pool

    Discover the convenience and value of Lely Resort. Amenities include...

  29. Sleeps 6, ~$172/night

    City : Naples
    Bedrooms : 3
    Bathrooms : 2
    Pool

    Discover the convenience and value of Lely Resort. Amenities include...

  30. Sleeps 8, ~$151/night

    City : Naples
    Bedrooms : 4
    Bathrooms : 3
    Pool

    Verona Walk is a quiet, tucked away neighborhood in an affluent...