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
    Villanovia

    Villanovia

    Volterra, PI

    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 of Larderello and untouched forest and farm scenarios. The house has...

    Pool

    $765 to $1,093/night

  2. HOUSE
    Sanciro

    Sanciro

    Salemi, TP

    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 surrounded by a well-tended Mediterranean garden with a splendid pool and boasts...

    Pool

    $543 to $1,005/night

  3. 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
  4. HOUSE
    Casasellate

    Casasellate

    Volterra, PI

    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, meadows and organically planted fields, is bordered by three rivers: an oasis...

    Pool Pets OK

    $452 to $826/night

  5. HOUSE
    Arangea

    Arangea

    Marsala, TP

    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 outdoor areas. On the ground floor are a large living room with...

    Pool

    $445 to $793/night

  6. HOUSE
    Pignabianca

    Pignabianca

    Marusa, TP

    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 overlooks its lovely garden, offers - besides the swimming pool - large, panoramic...

    Pool

    $360 to $700/night

  7. 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
  8. HOUSE
    Antigua Home #34084

    Antigua Home #34084

    Naples, FL

    Whether it’s watching the sunset from your private pool, hosting a game night in the family room or creating a meal for the family in the gourmet kitchen, relaxation is the name of the game in this stunning Marco Island vacation home. Elegance and...

    Pool

    $269 to $664/night

  9. 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

  10. HOUSE
    Sunbury Home #34752

    Sunbury Home #34752

    Naples, FL

    Wonderful 3 bedroom/ 2 bathroom home in a lovely neighborhood. Unwind in your very own private swimming pool or take a walk on the winding trails provided. The gated community of Briarwood is located close to Naples beaches, Fifth Ave South & the...

    Pool Pets OK

    $197 to $502/night

  11. HOUSE
    Giovanna

    Giovanna

    Gaiole in Chianti, SI

    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 view on the woods and hills, till Siena. The accommodation consists of 7 finely...

    Pool Pets OK

    $181 to $207/night

  12. HOUSE
    Lavanda

    Lavanda

    Pennabili, AR

    The rugged countryside in this part of the Apennine Mountains is indescribably beautiful. At 650 metres above sea-level, there's a retreat where your mind can totally relax; and all 100% "Made in Italy". Pennabilli is located in the Val Marecchia...

    $169 to $202/night

  13. HOUSE
    Mazzei in collina

    Mazzei in collina

    Montignoso, MS

    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 bright flat features a large, equipped terrace where you can enjoy the...

    Pets OK

    $136 to $219/night

  14. 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

  15. 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

    $94 to $149/night