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. HOUSE
    Podere San Giovanni

    Podere San Giovanni

    Chianni, PI

    A beautiful house with breathtaking view, large private pool, near Pisa "Podere S. Giovanni is an oasis of tranquility, the old farmhouse is surrounded by the hills of Pisa and offers the opportunity to relax, take long walks, to go swimming in the...

    Pool

    EUR508 to EUR742/night

  2. VILLA
    La Collina Grande Completa

    La Collina Grande Completa

    Tredozio, FC

    Villa with private swimming pool and panoramic view of the green hills This beautiful villa has two individual apartments, which can be hired as a whole, which makes this villa ideal for a family or group of friends who want to enjoy the peace in an...

    Pool

    EUR502 to EUR787/night

  3. HOUSE
    Villa Cecanibbi

    Villa Cecanibbi

    Cecanibbi (todi), PG

    Detached house with private pool in green surroundings, near Todi Close to the Umbrian town of Todi, this charming holiday home sits amidst the lush forest and offers complete privacy—including your own personal swimming pool! The location boasts...

    Pool

    EUR501 to EUR644/night

  4. HOUSE
    Villa Capo Passero

    Villa Capo Passero

    Portopalo Capo Passero, SR

    A dreamy house on top of a cliff at sea with private pool Villa Capo Passero is an exclusive cliff top villa with swimming pool located a few hundred metres from the beach and the small town centre of Portopalo di Capo Passero, Sicily's southernmost...

    Pool

    EUR500 to EUR726/night

  5. VILLA
    Dragovilla

    Dragovilla

    Donnalucata, RG

    Luxurious villa with pool and wellness area in Donnalucata, 1.4km from the sea! Dragovilla is a luxury villa with swimming pool and wellness area in Donnalucata, a popular seaside resort on the south-east of Sicily. Framed by typical dry-stone...

    Pool

    EUR495 to EUR775/night

  6. VILLA
    La Villa

    La Villa

    Cisternino, BR

    Old farmhouse, private pool and Trullis for a typical 'vacanza Pugliese' Feel the sheer pulse where an ancient rural farmhouse, sea, and olive trees collide. Built to help the local peasants with the harvest. Having changed very little in the past...

    Pool

    EUR494 to EUR697/night

  7. VILLA
    Sanciro

    Sanciro

    Salemi, TP

    Elegant villa with swimming pool and garden, in a quiet area close by Salemi San Ciro is an elegant dwelling with swimming pool set in a quiet, sunny location close to Salemi, characteristic small town in the province of Trapani. The villa is...

    Pool

    EUR490 to EUR732/night

  8. APARTMENT
    Crescenzio 3

    Crescenzio 3

    Roma, RM

    Elegant apartment in the heart of Rome, nearby the Vatican Apartment Crescenzio 3 is located in the prestigious Prati district, just a few meters from St. Peter's Square and the Vatican Museum. You can walk to main tourist attractions, such as...

    EUR488 to EUR519/night

  9. VILLA
    Villa Marcy

    Villa Marcy

    Marciano Della Chiana, AR

    Villa with private pool, beautiful view, in the Chiana Valley, wifi Villa Marcy is situated on a hill with olive trees in the heart of the Chiana Valley in Tuscany, near Marciano della Chiana, a medieval town. From the villa you have a panoramic...

    Pool

    EUR486 to EUR970/night

  10. HOUSE
    Indian Well Home #12946

    Indian Well Home #12946

    Naples, FL

    Discover the convenience and value of Lely Resort. Amenities include a clubhouse, restaurant, and proshop, community pool and spa, walking and biking trails and fishing. This Indian Wells home features a magnificent view of the golf course from the...

    Pool

    $484/night

  11. ESTATE
    Villa Angeli

    Villa Angeli

    Santa Maria Degli Angeli, PG

    Villa with private pool on an estate near Assisi Villa Angeli is a charming country house in the heart of an area of outstanding natural beauty. The villa is surrounded by land and enjoys enchanting views of the world famous city of Assisi. The city...

    Pool

    EUR481 to EUR716/night

  12. HOUSE
    Corte Dorata

    Corte Dorata

    Scicli, RG

    Beautiful villa with pool near the very charming Baroque town of Scicli Corte Dorata is a beautiful country villa with swimming pool situated on the edge of Scicli, a charming baroque town and a UNESCO world heritage site. A wonderful rural...

    Pool

    EUR481 to EUR590/night

  13. VILLA
    Villa Maremma

    Villa Maremma

    Grosseto, GR

    Beautiful villa with private pool, Jacuzzi and fitness equipment near the sea Villa Maremma is a beautiful villa in the Maremma region on a hill and is surrounded by beautiful vineyards. There is a beautiful 360 degree view of the sea to the green...

    Pool

    EUR473 to EUR1,099/night

  14. VILLA
    Villa Collina

    Villa Collina

    Castiglion Fiorentino, AR

    Villa with private swimming pool, spacious garden and magnificent views, 2km away from the town Villa Collina is an old farmhouse situated on a hill and was recently renovated. The Tuscan charm is retained by the careful renovation. The villa has...

    Pool

    EUR473 to EUR911/night

  15. HOUSE
    Villa Il Cedro

    Villa Il Cedro

    Cortona, AR

    Beautiful restored villa with private swimming pool in the Tuscan countryside A few steps from the beautiful Etruscan town of Cortona, rises Il Cedro, a beautiful stone building recently restored, set in a strategic position from which you can enjoy...

    Pool

    EUR472 to EUR845/night

  16. VILLA
    Villa Bianca

    Villa Bianca

    Ripatransone, AP

    Beautiful villa with a private swimming pool in hilly surroundings Villa Bianca is immersed in the beautiful hills of Ascoli in a panoramic position in the heart of the Marche region. The villa is surrounded by a large garden with roses, fruit trees...

    Pool

    EUR469 to EUR764/night

  17. HOUSE
    Villa Cipresso

    Villa Cipresso

    Moniga del Garda, BS

    Luxury apartment with air conditioning and private swimming pool near Lake Garda Experience this semi-detached holiday home, just 1 km from Lake Garda! The house includes an enclosed garden with a beautiful lawn. You can enjoy a lovely breakfast in...

    Pool

    EUR469 to EUR628/night

  18. VILLA
    Il Giglio 18

    Il Giglio 18

    Montefiascone, VT

    Villa with pool and jacuzzi in a panoramic position near Bolsena lake The Villa is situated on top of a green hill with a lovely view over Lake Bolsena and the valleys and surrounding hills of Tuscia, in Tuscany and Umbria, a short distance from...

    Pool

    EUR466 to EUR753/night

  19. VILLA
    Villa Core

    Villa Core

    Fabbri di Montefalco, PG

    Villa with private pool in Umbria near the town of Montefalco Villa Marica is a charming villa with a private pool in Umbria, located near the famous town of Montefalco, known for its Sagrantino wine production. The stone farmhouse has been...

    Pool

    EUR464 to EUR794/night

  20. HOUSE
    Villa America

    Villa America

    Castiglion Fiorentino, AR

    Hillside villa with swimming pool and stunning views in peaceful location Villa America is in a beautiful location on top of a hill, a few kilometers from the bustling cities of Castiglion Fiorentino and Cortona. This old Tuscan farmhouse enjoys...

    Pool

    EUR463 to EUR665/night

  21. VILLA
    Villa Celeste

    Villa Celeste

    Cortona, AR

    Villa with spacious garden and private pool, barbecue and pizza oven, near Cortona Villa Celeste is situated in open countryside between Cortona and Lake Trasimeno. The villa has a large garden with roses and other plants and is surrounded by green...

    Pool

    EUR463 to EUR645/night

  22. HOUSE
    Masseria Tarsia Incuria

    Masseria Tarsia Incuria

    Conversano, BA

    A luxurious and spacious Masseria with private pool on 1 hectare of private land The masseria is a 17th Century building of over 300 square meters with a large private pool of 10x6 meters. The Masseria has been tastefully furnished and offers 3...

    Pool

    EUR461 to EUR963/night

  23. VILLA
    Villa Sant Angiola

    Villa Sant Angiola

    Terricciola, PI

    A beautiful Tuscan farmhouse and a large swimming pool and relaxing A beautiful Tuscan farmhouse and a large swimming pool and relaxing near oak and cypress trees, lush vineyards and olive groves. Ideal for a large family or group of friends can...

    Pool

    EUR460 to EUR859/night

  24. HOUSE
    La Cumbre

    La Cumbre

    Lucca, LU

    Charming and comfortable villa near Lucca with private pool Since three generations the family owns this charming 18th century farm house on the hills of the medieval city of Lucca, just beside an 11th century small white stoned facade church. The...

    Pool

    EUR457 to EUR716/night

  25. VILLA
    Villa Graziosa

    Villa Graziosa

    Cortona, AR

    Villa with private swimming pool and spacious garden in the Valdichiana, close to Cortona Villa Graziosa is located in Valdichiana near the Etruscan city of Cortona. Here you can enjoy peace, quiet and privacy. Cortona is just 2 km away. The ground...

    Pool

    EUR457 to EUR771/night

  26. VILLA
    Villa Melina

    Villa Melina

    Desenzano del Garda, BS

    Elegant Art Nouveau villa with private pool a short distance from the lake. Liberty style villa, built in 1917, surrounded by a fenced garden with private swimming pool (6 x 10 m) with sunbeds. Central heating and air conditioning in the double...

    Pool

    EUR453 to EUR749/night

  27. VILLA
    Panchevilla

    Panchevilla

    Pistoia, PT

    Exclusive villa surrounded by peaceful Pistoia, with private pool and spa! This villa was built in 1718 as a summer residence for the Bishop of Pistoia and Prato, as evidenced by a plaque in Latin seen in the living room. The villa is located in a...

    Pool

    EUR448 to EUR938/night

  28. HOUSE
    Villa Mezzogiorno

    Villa Mezzogiorno

    Cortona, AR

    Magnificent villa, extremely panoramic position, sauna, jacuzzi and private pool Villa Mezzogiorno is the perfect place for an unforgettable experience! This magnificent property is situated in the heart of the hills of Cortona, in an extremely...

    Pool

    EUR446 to EUR727/night

  29. HOUSE
    Villa dei Fiori

    Villa dei Fiori

    Ragalna, CT

    Beautiful house with private pool and a lovely terrace with outdoor kitchen Villa dei Fiori is a beautiful dwelling with private pool in Ragalna, a characteristic village on the slopes of Mount Etna, Europe's highest and most active volcano,...

    Pool

    EUR446 to EUR766/night

  30. VILLA
    Villa Acqua

    Villa Acqua

    Castiglione D'orcia, SI

    Beautiful villa with privacy and pool This beautiful villa in the Val D'Orcia consists of 4 apartments and a spacious common living room with fireplace and kitchen of 70 square meters. The interior is cozy and typical Tuscan with hanging made tiles...

    Pool

    EUR444 to EUR769/night