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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 4,

    City : Naples
    Bedrooms : 2
    Bathrooms : 2

    You won't find anything like this condo in Naples! It's ultra chic...

  2. Sleeps 6, ~$172/night

    City : Naples
    Bedrooms : 3
    Bathrooms : 2
    Pool

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

  3. Sleeps 4, ~$137/night

    City : Naples
    Bedrooms : 2
    Bathrooms : 2
    Pool

    Located within walking distance to shopping and only a short drive...

  4. Sleeps 6, ~$206/night

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

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

  5. 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...

  6. 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...

  7. Sleeps 5, ~$310/night

    City : Rome
    Bedrooms : 2
    Bathrooms : 2

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

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

    City : Cortona
    Bedroom : 1
    Bathroom : 1

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

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

    City : Siena
    Bedrooms : 2
    Bathroom : 1

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

  10. 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...

  11. Sleeps 6, ~$141/night

    City : Naples
    Bedrooms : 3
    Bathrooms : 3
    Pool

    604 La Peninsula is located on Isles of Capri just off of Marco...

  12. Sleeps 4,

    City : Naples
    Bedrooms : 2
    Bathrooms : 2

    This first floor unit has an open and airy living room, dining room,...

  13. Sleeps 6, ~$206/night

    City : Naples
    Bedrooms : 3
    Bathrooms : 2
    Pool

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

  14. 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...

  15. 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...

  16. Sleeps 8, ~$151/night

    City : Naples
    Bedrooms : 4
    Bathrooms : 3
    Pool

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

  17. 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....

  18. 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...

  19. 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...

  20. Sleeps 8, ~$705/night

    City : Elba
    Bedrooms : 4
    Bathrooms : 4
    Pets OK

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

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

    City : Rome
    Bedroom : 1
    Bathroom : 1

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

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

    City : Rome
    Bedrooms : 2
    Bathrooms : 2

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

  23. Sleeps 6, ~$141/night

    City : Naples
    Bedrooms : 3
    Bathrooms : 2
    Pool

    One of Naples' finest communities, located between Marco Island and...

  24. Sleeps 6, ~$172/night

    City : Naples
    Bedrooms : 3
    Bathrooms : 2
    Pool

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

  25. Sleeps 4, ~$121/night

    City : Naples
    Bedrooms : 2
    Bathrooms : 2
    Pool

    Incredible views of the from this 3rd floor, waterfront spacious 2...

  26. Sleeps 6, $102 to $151/night

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

    Heated Pool! Rare Florence home find. 3 bedroom, 2 bath, 2 car...

  27. 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...

  28. Sleeps 9, ~$540/night

    City : Sabaudia
    Bedrooms : 4
    Bathrooms : 4

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

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

    City : Rome
    Bedrooms : 2
    Bathroom : 1

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

  30. 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...