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 Castagni

    Villa Castagni

    Pesaro, PU

    Modern villa with sea view, 4 km from the beach, spacious garden Villa Castagni is a beautiful villa overlooking the Adriatic sea. The villa is close to Pesaro, a popular coastal town. The nearest beaches are about 4 km away and are perfect for a...

    EUR233 to EUR386/night

  2. HOUSE
    Villa il Forno

    Villa il Forno

    Cortona, AR

    Beautiful villa with private swimming pool in the Tuscan hills near Cortona A few steps from the beautiful Etruscan town of Cortona, rises Villa il Forno, a beautiful stone building surrounded by ancient olive trees, set in a strategic position from...

    Pool

    EUR298 to EUR410/night

  3. VILLA
    Villa Caracciole

    Villa Caracciole

    Fossombrone, PU

    Villa with private pool, stunning views, near sea Villa Caracciole is a cozy and carefully restored villa located in the Metauro valley near Fossombrone. The villa is situated in a panoramic position with a beautiful view over the valley with hills,...

    Pool

    EUR260 to EUR492/night

  4. HOUSE
    Portico del Tasso

    Portico del Tasso

    Foiano Della Chiana, AR

    Attractive apartment on large property with lake and Roman building This warm and charming apartment is located, together with three others, on a large estate with two fully restored houses. The apartment is tastefully furnished and finished with...

    Pool

    EUR119 to EUR173/night

  5. VILLA
    Salinella

    Salinella

    PACECO, TP

    Comfortable villa with private pool, nearby Trapani and only 450m from the sea! Salinella is a beautiful, comfortable villa with private swimming pool situated near Trapani, ancient town at the extreme western point of Sicily. The property is set on...

    Pool

    EUR565 to EUR668/night

  6. APARTMENT
    Crescenzio 1

    Crescenzio 1

    Roma, RM

    Elegant apartment in the heart of Rome, nearby the Vatican Apartment Crescenzio 1 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...

    EUR251 to EUR267/night

  7. HOUSE
    Castagno della Civetta

    Castagno della Civetta

    Foiano Della Chiana, AR

    Attractive apartment on large property with lake and Roman building This warm and cozy apartment is located on a large estate with two fully restored houses, along with five other apartments. The apartment is tastefully furnished and finished with...

    Pool

    EUR143 to EUR215/night

  8. 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

    EUR326 to EUR514/night

  9. VILLA
    Villa Stintino

    Villa Stintino

    Stintino, SS

    Villa on a hill near Stintino and only 3km from the sea Set on a hill with a private swimming pool. Elegantly furnished in a typical Sardinian style and equipped with every service for a special holiday. Comfortable and bright. Surrounded by a...

    Pool

    EUR136 to EUR550/night

  10. HOUSE
    Villa del Duca

    Villa del Duca

    Civitella San Paolo, RM

    Villa with swimming pool in Fiano Romano, ideal for a Roman holiday The Villa is situated in the green Roman countryside and enjoys an excellent panoramic position. It faces a valley from where you can see Mount Soratte and in the evenings you can...

    Pool

    EUR264 to EUR479/night

  11. HOUSE
    Iris

    Iris

    Montaione, FI

    Apartment in beautiful farmhouse with pool in the heart of Tuscany Ground floor apartment in a converted farmhouse in the beautiful Tuscan countryside, renovated and furnished with care and very comfortable. Surrounded by greenery and quiet of a...

    Pool

    EUR135 to EUR191/night

  12. VILLA
    Palazzo Antico

    Palazzo Antico

    Montepulciano, SI

    Villa surrounded by vines, on top of a hill with stunning views. This beautiful, spacious villa is surrounded by vines and is located on the top of a hill from where you can enjoy beautiful panoramas. The villa has a beautiful green garden with...

  13. HOUSE
    Mazzei in collina

    Mazzei in collina

    Montignoso, MS

    Pretty apartment immersed in the greenery, perfect for a peaceful holiday! This charming and comfortable apartment is located in Montignoso, a village immersed in the green province of Massa, Tuscany. Finely and comfortably furnished, this really...

    EUR108 to EUR199/night

  14. HOUSE
    La casa di Marta

    La casa di Marta

    Taormina Messina, ME

    House with charm close to stunning Taormina This typical Sicilian house is located on the beautiful east coast of Sicily. The house is fully equipped. The decor is simple and classic, and has a warm atmosphere thanks to the used colors. For those...

    EUR104 to EUR156/night

  15. VILLA
    Lauras

    Lauras

    Marsala, TP

    Wonderful villa with swimming pool nearby Marsala, just 5km from the sea! Lauras is a beautiful property with pool situated on the edge of Marsala, ancient town at the extreme western point of Sicily. Recently built, this splendid villa features...

    Pool

    EUR366 to EUR699/night

  16. HOUSE
    Villa Spaziosa

    Villa Spaziosa

    Valderice, TP

    Superb, luxurious, spacious villa with privatepool and spacious garden near sea. Villa Spaziosa is a fantastic place to spend your well-deserved holiday. The villa is located inside a natural pine forest, in a valley, as a result there is so much...

    Pool

    EUR347 to EUR539/night

  17. VILLA
    Villa Simona

    Villa Simona

    Meina, NO

    Exclusive villa Lake Maggiore, with private swimming pool and own small beach. This exclusive villa is situated directly at the shores of the Lake Maggiore. It has a private swimming pool and its own small beach. The modern villa is all on one...

    Pool
  18. HOUSE
    Casa Pizziddu

    Casa Pizziddu

    Acireale, CT

    Attractive sunny and cosy holiday home at the beautiful, clear, Sicilian Sea This attractive, sunny holiday home is beside the clear, azure Sicilian Sea. The spacious terrace (100m2) is perfect for enjoying delightful evenings. You can admire...

  19. 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

    EUR609 to EUR905/night

  20. HOUSE
    Villa Laura

    Villa Laura

    Cortona, AR

    Beautiful villa with infinity pool surrounded by beautiful Tuscan hills Villa Laura is the ideal place to spend an holiday in the spirit of the beauties of Tuscany. The Villa is situated in one of the hills that surround the Etruscan town of...

    Pool

    EUR377 to EUR547/night

  21. HOUSE
    Podere San Donato Due

    Podere San Donato Due

    San Donato in Fronzano (fi), FI

    Attractive apartment on estate with vineyards and olive grove, near Florence This cozy apartment is part of a large 18 acre estate. This property houses a number of restored buildings that are home to a total of 6 apartments. The apartment is...

    Pool

    EUR97 to EUR143/night

  22. APARTMENT
    Yachting Residence- Bilo Classic

    Yachting Residence- Bilo Classic

    Lavena Ponte Tresa, Lombardia

    Apartment in a newly built luxury residence, facing the lake, with swimming pool Prestigious residence, the result of the complete renovation, completed in 2017, of an old factory, overlooking Lake Lugano just a short distance from the center of...

    Pool

    EUR165 to EUR229/night

  23. CONDOMINIUM
    La Peninsula Home #40385

    La Peninsula Home #40385

    Naples, FL

    Incredible views of the from this 3rd floor spacious 2 bedroom 2 1/2 bath condo! 2140 Sq Ft. Amenities include tennis courts on site, fitness center, heated pool and spa, docks for fishing. AmenitiesElevatorSightseeingBalconyFamilyOutdoor...

    Pool

    $126 to $230/night

  24. ESTATE
    Cigliè

    Cigliè

    Bastia Mondovì, CN

    Apartment with large covered terrace, in small residence with swimming pool Old Piedmont (built circa 1470) winery, lovingly restored and furnished with care - very well equipped apartment with modern living kitchen, tasteful living room, bedroom...

    Pool

    EUR190 to EUR267/night

  25. HOUSE
    Giovanna

    Giovanna

    Gaiole in Chianti, SI

    Cosy apartment in the well known Chianti area, with swimming pool and terrace. Il Podere is a typical Tuscan colonial house, on the hills of Chianti Classico, close by Gaiole in Chianti. The property boasts an absolutely panoramic, breath taking...

    Pool

    EUR147 to EUR187/night

  26. VILLA
    Casa Perticara

    Casa Perticara

    Sant'Agata Feltria, RN

    Villa with private swimming pool, lush and large garden, beautiful area Casa Perticara is a beautiful villa with private swimming pool in Emilia Romagna. The strategic location of the villa makes it possible to go to the Adriatic Sea and to visit...

    Pool

    EUR241 to EUR362/night

  27. 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
  28. 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
  29. HOUSE
    Everhart Lane

    Everhart Lane

    Florence, AZ

    HEATED POOL! Rare Florence home find. 3 bedroom, 2 bath, 2 car garage house, located in the Oasis Sunrise subdivision, surrounded by the Oasis Golf Club. Step inside this charming contemporary home and enter a large open concept great room....

    Pool Pets OK

    $88 to $138/night

  30. VILLA
    Giuly

    Giuly

    Gallipoli, LE

    Wonderful villa with private pool near Gallipoli and the main beaches! Beautiful villa with private pool located in Gallipoli, just a few minutes drive from some of the most beautiful beaches of the Apulian Ionian coast. Ideal residence to enjoy a...

    Pool

    EUR1,191 to EUR3,090/night