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
    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

    EUR742 to EUR1,583/night

  2. VILLA
    Morena

    Morena

    Marsala, TP

    Detached villa just steps from one of the most beautiful beaches of Marsala Beautiful, Mediterranean style villa situated just a just a stone's throw away from one of the most popular sandy beaches south of Marsala, an ancient small town located 30...

    EUR675/night

  3. 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

    EUR654 to EUR1,054/night

  4. 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

    EUR574 to EUR704/night

  5. 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

    EUR543 to EUR799/night

  6. 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

    EUR505 to EUR733/night

  7. 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

    EUR486 to EUR596/night

  8. 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

  9. 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

    EUR464 to EUR973/night

  10. 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

    EUR450 to EUR773/night

  11. 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

    EUR435 to EUR712/night

  12. 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

    EUR399 to EUR808/night

  13. VILLA
    Villa Luminosa

    Villa Luminosa

    Cortona, AR

    Villa at 300-m altitude, with private swimming pool and views of Cortona Villa Luminosa is a beautiful villa in the hills near Cortona. The villa enjoys a picturesque location and is surrounded by olive groves and vineyards, typical of the Tuscan...

    Pool

    EUR395 to EUR684/night

  14. VILLA
    Villa Berta

    Villa Berta

    Cortona, AR

    Villa with private swimming pool and stunning views across hilly surroundings Villa Berta with private pool is located at 350 meters altitude in the hills north of the Etruscan town of Cortona. The villa is surrounded by 800 olive trees of the...

    Pool

    EUR382 to EUR603/night

  15. HOUSE
    Santo Vento

    Santo Vento

    San Fratello, ME

    Organic farmhouse with private pool and Spa with view of the Aeolian Islands The family had the dream to revive their old houses from 1820. They built this farm at the foot of the mountain, an oasis of calm and relaxation. It is situated on the...

    Pool

    EUR370 to EUR507/night

  16. VILLA
    Villa Mimosa 2

    Villa Mimosa 2

    Corlaga, MS

    Magnificent villa with piano, private pool and enclosed garden with terrace Meet this beautiful stately villa with its fresh, modern and attractive interior. Beautiful details like the wonderful mosaic floor on the upper level and French doors...

    Pool

    EUR349 to EUR539/night

  17. HOUSE
    Villa Rita

    Villa Rita

    Monopoli, BA

    Gated villa with private pool in the hills of Monopoli and Castellana Grotte It is a bright and spacious villa with a private pool of 10x5 meters. It is located in the countryside along the hills between Monopoli and Castellana Grotte only a short...

    Pool

    EUR331 to EUR460/night

  18. HOUSE
    Piccadilly Home #16636

    Piccadilly Home #16636

    Naples, FL

    Absolutely Gorgeous 4 bedroom home located in a serene community in the center of Naples. This home features 4 bedrooms & 2.5 baths. The Master bedroom and bath are on the first level while the other 3 guest rooms are upstairs with a shared bath. A...

    Pool

    $331/night

  19. VILLA
    Pignabianca

    Pignabianca

    Marusa, TP

    Exclusive villa with private pool and wellness centre, only 3km from the sea! La Pigna Bianca is a beautiful villa with pool situated near Trapani, halfway between the nature reserve of the salt pans and the Stagnone lagoon. The property, which...

    Pool

    EUR329 to EUR519/night

  20. HOUSE
    Villa Fano

    Villa Fano

    Isola di Fano, PU

    Farm with fenced private pool, rolling hills, 25 km from the sea Villa Fano is an agriturismo. The rustic house consists of three apartments and a large dining room. It is an ideal place for families but 3 are very fond of their privacy. The...

    Pool

    EUR325 to EUR597/night

  21. VILLA
    Villa Miriam

    Villa Miriam

    Cortona, AR

    Villa with private swimming pool at an altitude of 600 m, in the hills, 2 km from Cortona Villa Miriam is located about 600 meters in the hills and has a panoramic view of the Valdichiana. This Tuscan villa with annexed hayloft has been completely...

    Pool

    EUR313 to EUR496/night

  22. ESTATE
    Residence Templari Uno 6P

    Residence Templari Uno 6P

    Montebello Vicentino, VI

    Captivating and historic restored home, with ample garden, privacy Historic building dating back to the 17th century, finely restored and offering guests all necessary comforts. The property benefits from large and well cared-for outdoor spaces and...

    EUR266 to EUR284/night

  23. COTTAGE
    Trulli Santa Maria dei Grani

    Trulli Santa Maria dei Grani

    Ceglie Messapica, BR

    Luxury trulli with very panoramic terraces and a great Pool This Trulli are a unique example of ancient architecture that still survives and currently offers our guests the opportunity to experience a truly and authentic holiday in Puglia, together...

    Pool

    EUR255 to EUR444/night

  24. HOUSE
    Paneolio

    Paneolio

    Pistoia, PT

    House in the Pistoia countryside with pool and garden, ideal for outdoor lunches Ground floor villa, immersed in a beautiful Tuscan olive grove. The house has a private pool at the full disposal of guests and offers an ideal setting for enjoying...

    Pool

    EUR241 to EUR338/night

  25. HOUSE
    Pinivilla

    Pinivilla

    Custonaci (trapani), TP

    Modern villa with private swimming pool and a few hundred meters from the sea Pinivilla is a modern villa with swimming pool situated just a few hundred metres from the sea and the beautiful sandy beach of Cornino, a small fishing village halfway...

    Pool

    EUR240 to EUR483/night

  26. COTTAGE
    Trulli del Mandorlo

    Trulli del Mandorlo

    Ceglie Messapica, BR

    wood stove and barbecue are available, pool and private garden The trullo is a newly renovated charming complex of trulli with a private pool (12x6m) and outdoor barbecue. Inside the main trullo you will find a studio consisting of an alcove...

    Pool

    EUR230 to EUR524/night

  27. HOUSE
    Falcons Glen Home #12950

    Falcons Glen Home #12950

    Naples, FL

    Golf Course CommunityTee off in your own backyard! This home has it all!!! The home is on the second hole ( par 5 ) of Flamingo 150 yards out from the green with an incredible wide view of the course. Take a long walk on the nature trail, or jump in...

    Pool

    $215 to $520/night

  28. VILLA
    Villa Mimosa 1

    Villa Mimosa 1

    Corlaga, MS

    Stately villa with piano, private pool and enclosed garden with terrace Meet this beautiful stately villa with its fresh, modern and attractive interior. Beautiful details like the wonderful mosaic floor on the upper level and French doors towards...

    Pool

    EUR203 to EUR501/night

  29. ESTATE
    Residence Templari Uno 4P

    Residence Templari Uno 4P

    Montebello Vicentino, VI

    Captivating and historic restored home, with ample garden, privacy Historic building dating back to the 17th century, finely restored and offering guests all necessary comforts. The property benefits from large and well cared-for outdoor spaces and...

    EUR202 to EUR220/night

  30. ESTATE
    Residence Templari Cinque 4P

    Residence Templari Cinque 4P

    Montebello Vicentino, VI

    Captivating and historic restored home, with ample garden, privacy, pets allowed Historic building dating back to the 17th century, finely restored and offering guests all necessary comforts. The property benefits from large and well cared-for...

    EUR202 to EUR220/night