Italy Vacation Rentals - 2312 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 over 2000 vacation homes, villas, apartments and condos in Italy, all ready to rent with a simple, hotel-style reservation process.

Search results

  1. Sleeps 10, $765 to $1200/night

    City : Tuscany
    Bedrooms : 4
    Bathrooms : 4.5
    Pool Hot Tub

    "After extensive renovation, this medieval building, part of which...

  2. Sleeps 11, $945 to $1515/night

    City : Crespina
    Bedrooms : 6
    Bathrooms : 3

    Bellavista is an elegant Tuscan villa with its antique tower dates...

  3. Sleeps 12, $950 to $1640/night

    City : Capannori
    Bedrooms : 6
    Bathrooms : 5

    Just minutes away from the town of Lappato, Casa Luciana is one of...

  4. Sleeps 17, $2055 to $3315/night

    City : Radicofani
    Bedrooms : 9
    Bathrooms : 9
    Pool

    Faggeto offers every convenience: from the pool and the...

  5. Sleeps 10, $520 to $1140/night

    City : Pescaglia
    Bedrooms : 5
    Bathrooms : 3

    "Macennere is a lovely stone-built farmhouse located in a very...

  6. Sleeps 8, $650 to $1290/night

    City : Lastra a Signa
    Bedrooms : 4
    Bathrooms : 4
    Pool

    "This beautiful villa is situated a few kilometres from the ancient...

  7. Sleeps 8, $650 to $1140/night

    City : San Gimignano
    Bedrooms : 4
    Bathrooms : 3

    "This lovely property is located in the countryside, only 5 kms from...

  8. Sleeps 8, $610 to $1075/night

    City : Camaiore
    Bedrooms : 4
    Bathrooms : 4

    This property is located in a valley only 2kms from the center of...

  9. Sleeps 6, $4315 to $7975/night

    City : Montalcino
    Bedrooms : 3
    Bathrooms : 3.5

    Originally home to the estate's olive oil press, Villa Oliviera is...

  10. Sleeps 2, $635 to $1165/night

    City : Sorrento
    Bedroom : 1
    Bathroom : 1

    Situated between Massa Lubrense and Sorrento, Perla, a romantic...

  11. Sleeps 14, $1475 to $3715/night

    City : Tuscany
    Bedrooms : 7
    Bathrooms : 7
    Hot Tub

    Beautiful and stylish villa on the coastal region of Maremma....

  12. Sleeps 30, $2530 to $3940/night

    City : Gubbio
    Bedrooms : 15
    Bathrooms : 14

    This magnificent castle dates back to the early Middle Ages (1200...

  13. Sleeps 16, $2185 to $3125/night

    City : Tuscany
    Bedrooms : 8
    Bathrooms : 7
    Pool

    "Castello dei Canonici is situated in a hamlet of Camaiore in the...

  14. Sleeps 12, $1570 to $2150/night

    City : Umbertide
    Bedrooms : 6
    Bathrooms : 6
    Pool

    "This toddler friendly Umbrian villa for 12 people is situated on...

  15. Sleeps 17, $2875 to $6100/night

    City : Todi
    Bedrooms : 8
    Bathrooms : 9.5
    Pool

    "Casale Cerfoglio is an exceptional villa, created for those with...

  16. Sleeps 8, $740 to $1350/night

    City : Tuscany
    Bedrooms : 3
    Bathrooms : 4
    Pool Hot Tub

    "1213 La Residenza is perfectly situated in the tiny but charming...

  17. Sleeps 10, $1295 to $2190/night

    City : Tuscany
    Bedrooms : 5
    Bathrooms : 5
    Pool

    "This wonderful farmhouse is located in the very peaceful area of...

  18. Sleeps 8, $1850 to $4515/night

    City : Sardinia
    Bedrooms : 4
    Bathrooms : 4
    Pool

    "Alice stands on a promontory, which dominates the magnificent Bay...

  19. Sleeps 10, $945 to $2530/night

    City : Umbertide
    Bedrooms : 4
    Bathrooms : 4

    Arriving at the summit of this beautiful, private 280 acre estate,...

  20. Sleeps 12, $785 to $1625/night

    City : Vicchio
    Bedrooms : 6
    Bathrooms : 4

    Giotto is a historic farmhouse converted into a private villa,...

  21. Sleeps 10, $700 to $1370/night

    City : Montalto di Castro
    Bedrooms : 5
    Bathrooms : 4
    Pool

    Duna Grande is a unique venue in Italy. In Tuscany you will rarely...

  22. Sleeps 10, $1045 to $1770/night

    City : Ravello
    Bedrooms : 5
    Bathrooms : 3
    Pool

    Villa Gioia is set only 1.5 kilometers away from the charming town...

  23. Sleeps 14, $1240 to $1640/night

    City : Siena
    Bedrooms : 7
    Bathrooms : 6.5
    Pool

    When you dream about a Villa in Tuscany, this is the house you dream...

  24. Sleeps 10, $685 to $820/night

    City : Monte San Savino
    Bedrooms : 6
    Bathrooms : 5
    Pool

    Mulino in Italian means Mill and this house used to be the mill of...

  25. Sleeps 6, $450 to $640/night

    City : Lucignano
    Bedrooms : 3
    Bathrooms : 3
    Pool

    Small villas (this one sleeps 4 to 6 guests) with private pools are...

  26. Sleeps 8, $1445 to $2890/night

    City : Ravello
    Bedrooms : 6
    Bathrooms : 6.5
    Pool

    The sun and the nature, Italian traditions and exclusivity- these...

  27. Sleeps 4, $600 to $655/night

    City : Castelvetrano
    Bedrooms : 2
    Bathrooms : 2
    Pool

    Set in a private large estate of about 10 hectares of olive trees...

  28. Sleeps 12, $2100 to $3610/night

    City : Pienza
    Bedrooms : 6
    Bathrooms : 7
    Pool

    Situated in the heart of Val d'Orcia- an ancient corner of Tuscany,...

  29. Sleeps 12, $1270 to $2540/night

    City : Massa Lubrense
    Bedrooms : 6
    Bathrooms : 9
    Pool

    Located in a quiet and private area, surrounded by 14.000 sqm of...

  30. Sleeps 12, $600 to $940/night

    City : Vicenza
    Bedrooms : 7
    Bathrooms : 6
    Pool

    Villa San Bastiano has a superb location. It lies up in the hills a...