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. VILLA
    Villa Cherry

    Villa Cherry

    Cortona, AR

    Elegant villa at an altitude of 500 m in the hills, with a private swimming pool Villa Cherry is a charming cottage situated in a unique location. It is immersed in the hills of Cortona with stunning views and total privacy. The villa is about 500...

    Pool

    EUR1,239 to EUR1,431/night

  2. VILLA
    Moon

    Moon

    Fontane Bianche, SR

    Exclusive villa with private swimming pool that enjoys a splendid seafront view Exclusive villa with private swimming pool that enjoys a splendid seafront position in Fontane Bianche, a popular seaside resort south of Syracuse. Surrounded by a well...

    Pool

    EUR1,169 to EUR1,947/night

  3. VILLA
    Cuoricino

    Cuoricino

    Siracusa, SR

    Villa with private swimming pool and large equipped terrace for dining al fresco Beautiful villa with private swimming pool situated on the Maddalena peninsula, just a little bit south of Syracuse. The villa is the ideal property for those seeking a...

    Pool

    EUR896 to EUR1,664/night

  4. VILLA
    Agora

    Agora

    Agrigento, AG

    Exclusive luxury villa in Agrigento with private pool, Jacuzzi and BBQ Exclusive villa with private swimming pool near Agrigento and the Valley of the Temples, majestic archaeological area listed as a World Heritage site. Ideal property for those...

    Pool

    EUR735 to EUR1,567/night

  5. VILLA
    Villanovia

    Villanovia

    Volterra, PI

    Roomy and comfortable house with beautiful views and pool for refreshment Villanovia is a fully renovated country property, inside a natural park, with a 360° amazing panorama. It overlooks the cities of Volterra and Pomarance, the Metallic Hills...

    Pool

    EUR691 to EUR988/night

  6. COTTAGE
    Trulli Tra Pietre

    Trulli Tra Pietre

    Ceglie Messapica, BR

    The terrace is ideal for outside dining, the great pool is surrounded by lawn It is a large complex of luxury Trulli (more than 200m²) with a stunning natural rock carved pool. All the rooms of the villa are equipped with individually controlled...

    Pool

    EUR648 to EUR1,045/night

  7. COTTAGE
    Trulli Country Golf

    Trulli Country Golf

    Gioia del Colle, BA

    Golf course, swimming pool and jacuzzi ideal for stays with family and friends Wonderful complex made up by 11 rural ancient trulli with a big swimming pool (14x7 mt) and a Pitch & Putt nine-holes amateur golf course, fully illuminated also for the...

    Pool

    EUR643 to EUR1,037/night

  8. VILLA
    Azzurro marino

    Azzurro marino

    Marina di Modica, RG

    Villa with private swimming pool and jacuzzi in a splendid sea front position Exclusive villa with private swimming pool situated in a splendid sea front position in Marina di Modica, a small seaside resort on the southern coast of Sicily. This...

    Pool

    EUR630 to EUR1,719/night

  9. VILLA
    Terranova

    Terranova

    Modica, RG

    luxury villa with private pool in Modica! For a relaxing holiday in Sicily Terranova is a luxury villa with pool located on the edge of Modica, ancient, charming, baroque town on the south-east of Sicily. Majestic and elegant, this splendid...

    Pool

    EUR596 to EUR1,111/night

  10. 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

    EUR569 to EUR697/night

  11. HOUSE
    Le Edicole

    Le Edicole

    Ragusa, RG

    Beautiful villa with swimming pool surrounded by nature near Ragusa and the sea Le Edicole is a splendid villa with pool immersed in beautiful countryside, near the Donnafugata Castle, on the road that from the baroque town of Ragusa leads to the...

    Pool

    EUR537 to EUR1,019/night

  12. HOUSE
    Villa Milivita

    Villa Milivita

    Monopoli, BA

    Renovated villa with private pool and huge garden with equipped terrace Itis a luxury mansion with four large bedrooms, featuring a saltwater swimming pool of 14x7m. The villa is sized 250m² on two levels and is situated in the peaceful...

    Pool

    EUR537 to EUR791/night

  13. 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 EUR862/night

  14. APARTMENT
    Ninfea

    Ninfea

    Gratillon Saint Nicolas, AO

    Magnificent apartment with private sauna in a historic village near Aosta Beautiful apartment in a chalet located in a historic village a few kilometers from Aosta.Spacious,elegant and refined. Furnished with style and care of every detail.Charming...

    EUR488 to EUR504/night

  15. 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
  16. 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 EUR631/night

  17. 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

  18. 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

    EUR448 to EUR665/night

  19. VILLA
    Villa Valentina

    Villa Valentina

    Cortona, AR

    Villa in the hills of Cortona, with private swimming pool and stunning views Villa Valentina is a beautiful house from the seventeenth century on a hill with beautiful views over the Tuscan countryside. The villa has been completely renovated and...

    Pool

    EUR448 to EUR658/night

  20. 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 EUR735/night

  21. VILLA
    Villa Torre

    Villa Torre

    Pietranico, PE

    Villa with tower between olive trees with private swimming pool, nice view Near the tiny village Pietranico in Abruzzo is situated vacation home Torre. The oldest part of the house dates from 1709 and was rebuilt in 2014. The entire house has wifi...

    Pool

    EUR440 to EUR713/night

  22. HOUSE
    Villa Bottoni

    Villa Bottoni

    Ripabottoni, CB

    House with pool, garden and wifi in medieval village, with panoramic views. The house has been renovated and carefully furnished by the owner which paid special attention to the ancient details trying to keep them alive in the whole apartment. The...

    Pool
  23. VILLA
    Villa Isabella

    Villa Isabella

    Cortona, AR

    Charming villa in idyllic surroundings, with private swimming pool and spacious garden Villa Isabella is situated in an enchanting landscape of vineyards and extensive olive groves. The villa has been carefully restored and the Tuscan charm has been...

    Pool

    EUR420 to EUR816/night

  24. VILLA
    Villa Passignano

    Villa Passignano

    Passignano sul Trasimeno, PG

    Luxurious villa with private pool and panoramic views over Lake Trasimeno Villa Passignano is located 350 meters high in the hills overlooking the Trasimeno lake. The luxury villa is set in a beautiful panoramic location and has a spacious terrace,...

    Pool

    EUR417 to EUR706/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

    EUR416 to EUR771/night

  26. VILLA
    Villa Tuoro

    Villa Tuoro

    Tuoro sul Trasimeno, PG

    Villa with pool and garden, beautiful view over Lake Trasimeno Villa Tuoro is 700 meters high on the border between Tuscany and Umbria. The villa is set in the hills and has beautiful views over Trasimeno lake. It is a pristine place just minutes...

    Pool

    EUR416 to EUR981/night

  27. HOUSE
    Casasellate

    Casasellate

    Volterra, PI

    Your own piece of Tuscany in an oasis of calm with a lovely private pool Casa Sellate is a country house located in Volterra's countryside in Etruria's heart, at the edge of the Nature Reserve Berignone. The estate, over 200 hectare of woods,...

    Pool

    EUR409 to EUR747/night

  28. VILLA
    Arangea

    Arangea

    Marsala, TP

    Beautiful villa with pool situated near Marsala, town by the sea Beautiful villa with pool situated near Marsala, ancient town by the sea at the extreme western point of Sicily. This splendid villa features spacious, well kept interior spaces and...

    Pool

    EUR407 to EUR812/night

  29. VILLA
    Villa Vista

    Villa Vista

    Castiglion Fiorentino, AR

    Villa with private swimming pool and garden, panoramic view over the valley Villa Vista is located in the hills at about 600 meters altitude, between the historic cities of Cortona and Castiglion Fiorentino, It is a fully independent villa with...

    Pool

    EUR397 to EUR608/night

  30. ESTATE
    Casa Dieci

    Casa Dieci

    Poppi, AR

    Luxury hamlet in exclusive use with private pool and beautiful garden Casa Dieci consists of two luxurious holiday homes in a small borgo. You will therefore have access to two deluxe villas with heated swimming pool, air conditioning and Wi-fi in...

    Pool

    EUR396 to EUR801/night