Italy Vacation Rentals - 2336 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 12, $7220 to $11265/night

    City : Montalcino
    Bedrooms : 6
    Bathrooms : 6
    Pool

    Villa Oscar is the largest villa of an important estate in the heart...

  2. Sleeps 14, ~$6700/night

    City : Serravalle Pistoiese
    Bedrooms : 7
    Bathrooms : 7
    Pool

    Set on a high hill overlooking the scenic Tuscan landscape, this...

  3. Sleeps 14, $5250 to $9660/night

    City : Laglio
    Bedrooms : 7
    Bathrooms : 6
    Pool

    Villa Regina located just over one hour drive from Milan, is tucked...

  4. Sleeps 9, $4990 to $7615/night

    City : Montalcino
    Bedrooms : 5
    Bathrooms : 6.5
    Pool

    Dramatically perched on a ridge overlooking the Drago Golf Course...

  5. Sleeps 24, $4460 to $5360/night

    City : Amalfi
    Bedrooms : 12
    Bathrooms : 12
    Pool

    Villa Marina is a recently-restored spacious villa in Amalfi, set in...

  6. 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...

  7. Sleeps 8, $3630 to $4400/night

    City : Castellammare Di Stabia
    Bedrooms : 4
    Bathrooms : 4

    Villa Gioviale is a place where impeccable standards are matched by...

  8. Sleeps 20, $3395 to $4850/night

    City : Poggiardo
    Bedrooms : 9
    Bathrooms : 9.5
    Pool

    Situated in the center of the Salento peninsula, in the extreme...

  9. Sleeps 16, ~$3000/night

    City : Motta Sant'Anastasia
    Bedrooms : 8
    Bathrooms : 8
    Pool

    Sitting on a 120-hectare estate producing organic oranges, mandarins...

  10. Sleeps 10, $2990 to $3590/night

    City : Lisciano Niccone
    Bedrooms : 5
    Bathrooms : 6
    Pool

    Perched on Reschio's south-western ridge, at the end of its own 3 km...

  11. Sleeps 10, $2885 to $4185/night

    City : Santa Margherita Ligure
    Bedrooms : 6
    Bathrooms : 6
    Pool

    Buganville is a detached villa surrounded by a private area of over...

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

    City : Todi
    Bedrooms : 8
    Bathrooms : 9.5
    Pool

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

  13. Sleeps 12, $2805 to $5140/night

    City : Chiusi
    Bedrooms : 6
    Bathrooms : 6.5
    Pool

    Parco del Principe is an ancient residence dating back to the latter...

  14. Sleeps 16, $2735 to $4610/night

    City : Scandicci
    Bedrooms : 8
    Bathrooms : 8
    Pool

    Villa Leila is typical Tuscan patrician villa and is positioned high...

  15. Sleeps 10, $2625 to $3375/night

    City : Castellammare Di Stabia
    Bedrooms : 5
    Bathrooms : 5

    Villa Greta is an impressive two-floor villa located just few steps...

  16. Sleeps 30, $2525 to $3940/night

    City : Gubbio
    Bedrooms : 15
    Bathrooms : 14

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

  17. Sleeps 10, ~$2495/night

    City : Umbertide
    Bedrooms : 5
    Bathrooms : 5.5
    Pool

    Situated between Umbria and Tuscany, 10 min from the town of...

  18. Sleeps 12, $2310 to $3320/night

    City : San Teodoro
    Bedrooms : 6
    Bathrooms : 6
    Pool

    A large pool of 160 sqm dominates one of the most beautiful coasts...

  19. Sleeps 10, $2190 to $2500/night

    City : Andria
    Bedrooms : 5
    Bathrooms : 5
    Pool

    In the vicinity of Andria, between the ancient Appian Way and the...

  20. Sleeps 10, $2190 to $3125/night

    City : Capalbio
    Bedrooms : 5
    Bathrooms : 5
    Pool

    Only a 5 minutes drive from the beach, on the outskirts of the town...

  21. Sleeps 16, $2180 to $3125/night

    City : Tuscany
    Bedrooms : 8
    Bathrooms : 7
    Pool

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

  22. Sleeps 16, $2165 to $3895/night

    City : Noto
    Bedrooms : 7
    Bathrooms : 7
    Pool

    Immersed in an oasis of peace and tranquility, situated on an estate...

  23. Sleeps , $2160 to $2985/night

    City : Castelfiorentino
    Bedrooms : 17
    Bathrooms : 16
    Pool

    "Selva di Monte", 26-room apartment 640 m2 on 2 levels, on the...

  24. Sleeps 14, ~$2145/night

    City : Reggello
    Bedrooms : 7
    Bathrooms : 7
    Pool

    This elegant fully staffed villa is perfect for the discerning...

  25. Sleeps 14, $2140 to $2420/night

    City : Montalcino
    Bedrooms : 7
    Bathrooms : 7
    Pool

    Sitting on a spectacular 25-acre estate and boasting stunning views...

  26. Sleeps 17, $2130 to $3200/night

    City : Impruneta
    Bedrooms : 8
    Bathrooms : 8
    Hot Tub

    "Impruneta is a typical ""Casa Colonica"" of the 16th century,...

  27. 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,...

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

    City : Radicofani
    Bedrooms : 9
    Bathrooms : 9
    Pool

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

  29. Sleeps 18, $1995 to $3045/night

    City : Buonconvento
    Bedrooms : 9
    Bathrooms : 10
    Pool

    The original building was a typical Tuscan farm, and today it is a...

  30. Sleeps 14, $1970 to $2295/night

    City : Vertine
    Bedrooms : 7
    Bathrooms : 7
    Pool

    Dating from the 17th century, Villa Vistarenni suits those who want...