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 Positano

    Villa Positano

    Positano, SA

    Luxury villa with private pool near Positano and overlooking the sea Villa Positano is a luxury semi-detached villa with views over the sea and the coast. The villa has been completely restored and is located in a picturesque area near the town of...

    Pool

    EUR1,700 to EUR3,068/night

  2. VILLA
    Villa Dominick

    Villa Dominick

    Positano, SA

    Villa with jacuzzi, pool and garden in Positano, beautiful view Villa Dominick is a beautiful holiday home on the Amalfi coast in Positano. The villa is a 10-minute walk from Piazza dei Mulini and from the main beach in Positano. Opposite the villa...

    Pool

    EUR1,514 to EUR2,964/night

  3. VILLA
    Villa Sky meets Sea

    Villa Sky meets Sea

    Nocelle, SA

    Luxury villa with infinity pool, breathtaking views, a very special place If you are looking for a panoramic villa in Positano, furnished with great taste, and able to let you enjoy the beauty of the Amalfi Coast, choose Villa Sky Meets Sea. This...

    Pool

    EUR1,444 to EUR1,953/night

  4. HOUSE
    Villa Amagioia

    Villa Amagioia

    Varignana, BO

    Beautiful villa in the hills of Bologna, with large garden and swimming pool. This fine and astonishingly beautiful Villa, lies surrounded by five hectares of lush private garden, where peace and privacy are guaranteed. Among olive trees and...

    Pool

    EUR1,398 to EUR2,098/night

  5. 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

  6. 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

  7. VILLA
    Villa Sole

    Villa Sole

    Macerata, MC

    Exclusive villa with pool and panoramic location on the hills of the Marche Villa Sole is a luxury property located a few kilometers from Macerata, in the heart of the Marche region. The villa has a unique location on top of a hill surrounded by...

    Pool

    EUR1,086 to EUR1,760/night

  8. VILLA
    Boheme

    Boheme

    Taormina, ME

    Villa with sea view and private pool very near to the center of Taormina Exclusive villa with private swimming pool in Taormina. Refined and prestigious, this splendid property is situated in close proximity to the Greek Theatre and to Corso...

    Pool

    EUR970 to EUR1,676/night

  9. HOUSE
    Villa Celeste 14

    Villa Celeste 14

    Fiumana, FC

    Beautiful villa with annex and private swimming pool the Emilia Romagna area Villa Celeste is a beautiful and luxurious villa in the Emilia Romagna region. The villa is surrounded by a beautiful vineyard and consists of a villa and an annex with a...

    Pool

    EUR931 to EUR1,945/night

  10. 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

  11. VILLA
    Villa Mezzeria

    Villa Mezzeria

    Guardea, TR

    Luxurious villa, near Orvieto, with heated pool and private spa Villa Mezzeria is in the open countryside in southern Umbria, on a hill with panoramic views over the oasis of Alviano below, a few kilometers from the Umbrian towns such as Orvieto,...

    Pool

    EUR871 to EUR1,171/night

  12. HOUSE
    Villa Gioia

    Villa Gioia

    Filottrano, AN

    Luxurious villa in the countryside, close to the beaches of the Conero Villa Gioia is a beautiful and luxurious villa for an exclusive holiday with excellent privacy. It is located in the surroundings of the beautiful beaches of the Conero. The...

    Pool

    EUR816 to EUR1,356/night

  13. VILLA
    Villa Limonaia

    Villa Limonaia

    Sinalunga, SI

    Villa with private pool, tennis court and shared swimming pool in the Tuscan hills In the hills between San Gimignano and Torrita di Siena and close to Sinalunga is a special estate among olive trees, vineyards and cypress trees. The estate is...

    Pool

    EUR814 to EUR973/night

  14. VILLA
    Gualtierottivilla

    Gualtierottivilla

    Pistoia, PT

    Exclusive villa in the countryside of Pistoia with private pool and jacuzzi The Villa is an enchanting destination in the heart of unspoiled nature, a place where time has stopped and it is easy to appreciate the charm and tranquility, perhaps...

    Pool

    EUR747 to EUR1,094/night

  15. 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

  16. ESTATE
    Castello

    Castello

    Sarteano, SI

    Sleeping in a beautiful castle, private pool, beautiful garden Castello is a castle from 1465 on an estate in an idyllic part of Tuscany with elms, pines, vineyards and olive groves between the Val di Chiana and Val d'Orcia. The exterior of the...

    Pool

    EUR730 to EUR826/night

  17. VILLA
    Villa delle Rose

    Villa delle Rose

    Mondavio, PU

    Beautiful villa with swimming pool and hot tub, near the beach of Fano Villa delle Rose is located near Mondavio in the province of Pesaro-Urbino. It is a beautiful villa. You have a fantastic view over the surrounding countryside and the village of...

    Pool

    EUR702 to EUR1,104/night

  18. VILLA
    Villa Metauro

    Villa Metauro

    Montemaggiore al Metauro, PU

    Villa between vineyards and stunning views Midway between the sea and the hinterland, surrounded by breathtaking countryside: this is the setting for Villa Tombolina, old summer residence of the Archbishops of Urbino, a picturesque relais with...

    Pool

    EUR699 to EUR1,070/night

  19. VILLA
    Villa L'Oasi

    Villa L'Oasi

    Massa Lubrense, NA

    Beautiful villa with pool and fantastic sea view in the enchanting Amalfi Coast Villa L'Oasi offers stunning views of the sea and is a little paradise. An exclusive villa with lots of privacy, situated in Nerano on the Sorrento peninsula. Nerano is...

    Pool

    EUR686 to EUR1,091/night

  20. HOUSE
    Paternone

    Paternone

    Chianni, PI

    Two beautifully restored farmhouses with swimming pool in the hills of Pisa Casale PATERNONE is a combination of two farmhouses, built 30 m apart and offering the perfect solution for a large group wishing to spend time together without necessarily...

    Pool

    EUR677 to EUR1,236/night

  21. VILLA
    Monte Amiata

    Monte Amiata

    Selva Santa Fiora, GR

    A beautiful villa in the Maremma area. Villa Monte Amiata is a 150 year old farmhouse. It is in the heart of the Maremma area in southern Tuscany. This beautiful, hilly region has a rich artistic heritage. The villa has been carefully renovated....

    Pool

    EUR657 to EUR856/night

  22. VILLA
    Villa Acropolis

    Villa Acropolis

    Anzio, RM

    Spacious villa with pool and jacuzzi with disco and games room ideal for groups Villa Acropolis is a very special villa with pool in classical style located in the Anzio countryside and its well known seaside resort located in the south of Rome....

    Pool

    EUR650 to EUR1,011/night

  23. 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

  24. 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

  25. 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

  26. HOUSE
    Villa Albizia

    Villa Albizia

    Ossuccio, CO

    Exclusive villa with swimming pool, terrace and fenced garden Beautiful detached villa, located in a quiet residential area, 300 meters from the lake. The villa features a large landscaped garden with lawn and flowers completely enclosed, while it...

    Pool

    EUR605 to EUR937/night

  27. COTTAGE
    Trulli Oleandro

    Trulli Oleandro

    Martina Franca, TA

    Private pool surrounded by greenery, the outside area is great for relaxing The trullo is a luxury holiday mansion in Puglia. These authentic trulli are conservatively restructured in full consideration of their old charm and have been beautifully...

    Pool

    EUR605 to EUR1,146/night

  28. VILLA
    Villa Agello

    Villa Agello

    Agello, PG

    Beautiful villa with private pool Rustic Villa Agello, near the Trasimeno Lake, is situated at the border between Tuscan and Umbria, the two Italian regions mostly visited. The villa is a beautiful independent stone house with rectangular shape and...

    Pool

    EUR597 to EUR936/night

  29. 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

  30. HOUSE
    Villa Celeste 8

    Villa Celeste 8

    Fiumana, FC

    Beautiful villa with annex and private swimming pool the Emilia Romagna area Villa Celeste is a beautiful and luxurious villa in the Emilia Romagna region. The villa is surrounded by a beautiful vineyard and consists of a villa and an annex with a...

    Pool

    EUR592 to EUR1,269/night