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.

Filter by Region:


Filter by Amenities:


Filter by Entertainment:


Close Filters
  1. 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

  2. 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

  3. HOUSE
    Castagneto 7

    Castagneto 7

    Castagneto Carducci, LI

    Magnificent apartment located on the private beach of Marina di Castagneto Carducci This beautiful apartment is located in a modern four-storey building, right on the beach of Marina di Castagneto Carducci. You reach this tastefully decorated...

    EUR125 to EUR312/night

  4. HOUSE
    Sassetta 2

    Sassetta 2

    Sassetta, LI

    Detached house with pool 12 km from the private beach This beautiful detached holiday home with shared pool is situated in a hilly area near Sassetta, at an altitude of 500 meters. The holiday home is tastefully decorated and fully equipped. In...

    Pool

    EUR176 to EUR369/night

  5. HOUSE
    Castagneto 4

    Castagneto 4

    Castagneto Carducci, LI

    Nice apartment in a wooded area 300 meters from the private beach This lovely apartment is situated in a sixties villa in a wooded area, just 300 meters from the beach of Marina Castagneto Carducci. The apartment is on the ground floor and is...

    EUR87 to EUR236/night

  6. HOUSE
    Pino

    Pino

    Cortona, AR

    Beautiful holiday home with view over Cortona in beautiful surroundings Cortona The beautiful view of Cortona, your comfortable apartment and engaging hospitality of the owner will determine the success of your holiday in Agriturismo Rodolfo! You...

    Pool

    EUR67 to EUR170/night

  7. HOUSE
    Antico Borgo i Cancelli 1

    Antico Borgo i Cancelli 1

    Palazzuolo sul Senio, FI

    Beautiful apartment in an old farmhouse with pool, surrounded by nature Antico Borgo i Cancelli is made up of 80 holiday homes. They are spread across the estate in rows of 4 or 6 link-detached houses. The holiday homes are furnished in a neat and...

    Pool

    EUR73 to EUR150/night

  8. VILLA
    Fontana Tutto

    Fontana Tutto

    Monteverdi Marittimo, PI

    Luxury air conditioned villa with private pool on large grounds with terrace You are bound to enjoy yourself in this pleasant, spacious villa situated up in the hills by Monteverdi Marittimo. Enjoy the enclosed private swimming pool with outdoor...

    Pool

    EUR310 to EUR378/night

  9. VILLA
    Fontana Sei

    Fontana Sei

    Monteverdi Marittimo, PI

    Luxury air conditioned villa with private pool on large grounds with terrace You are bound to enjoy yourself in this pleasant, spacious villa situated up in the hills by Monteverdi Marittimo. Enjoy the enclosed private swimming pool with outdoor...

    Pool

    EUR167 to EUR212/night

  10. HOUSE
    Sassetta 3

    Sassetta 3

    Sassetta, LI

    Nice apartment in the Tuscan hills, 12 km from the private beach This beautiful apartment with shared pool is situated in a sixties villa in a hilly area near Sassetta, at an altitude of 500 meters. There are three apartments in the villa. This...

    Pool

    EUR82 to EUR175/night

  11. COTTAGE
    Olivi Giallo

    Olivi Giallo

    San Quirico - Pescia, PT

    Authentic Tuscan country home situated between Pistoia and Lucca Authentic Tuscan country home situated between Pistoia and Lucca. This holiday home is the result of the skilful renovation of an old country property. The original characteristics and...

    Pool

    EUR91 to EUR139/night

  12. FARMHOUSE
    Portico

    Portico

    Montepulciano, SI

    Farm holiday with swimming pool, 500 m from Montepulciano, beautiful surroundings Portico is a charming apartment in an agritourism area. This old stone farmhouse has been completely renovated and there are 4 apartments in total. The agritourism...

    Pool

    EUR100 to EUR136/night

  13. HOUSE
    Girasole

    Girasole

    Marina di Massa, MS

    Cozy appartment in Marina di Massa, just 500m from the sea and from the beach Apartment on the first and top floor of a lovely, peaceful building, with a very well-kept garden. As well as having a spacious lounge, it also has a furnished terrace...

    EUR93 to EUR256/night

  14. COTTAGE
    Casale Castiglione

    Casale Castiglione

    Castiglione di Garfagnana, LU

    Cozy house with private pool and breathtaking views of the Garfagnana area The farmhouse is entirely handmade in stone and dates back to the late 1700. The structure faces South so you have the sun all for yourselves from 07.00 in the morning. You...

    Pool

    EUR219 to EUR334/night

  15. 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

    EUR401 to EUR615/night

  16. VILLA
    Angels House

    Angels House

    Tabiano Castello, PR

    Magnificent old country house with garden and private pool, with wifi This beautiful villa has a fantastic view on the countryside of the Emilian Apennines and the castle of Tabiano that you can reach in a few minutes by car or otherwise on foot, a...

    Pool

    EUR397 to EUR699/night

  17. HOUSE
    Poggiolino

    Poggiolino

    Castiglion Fiorentino, AR

    Home with shared pool, surrounded by nature in Castiglion Fiorentino This home is part of a property in the hills of Castiglione Fiorentino. The cottage is built in the last century, renovated respecting the original style and perfect for a number...

    Pool

    EUR102 to EUR129/night

  18. HOUSE
    Antico Borgo i Cancelli 2

    Antico Borgo i Cancelli 2

    Palazzuolo sul Senio, FI

    Beautiful apartment in an old farmhouse with pool, surrounded by nature Antico Borgo i Cancelli is made up of 80 holiday homes. They are spread across the estate in rows of 4 or 6 link-detached houses. The holiday homes are furnished in a neat and...

    Pool

    EUR79 to EUR163/night

  19. HOUSE
    Pinuccia

    Pinuccia

    Marina di Massa, MS

    Atmospheric apartment with a garden and balcony, 600 m from the beach Life is good in Tuscany! The sea with a nice sandy beach is at just 600 meters from this apartment in Marina di Massa! The apartment has a small garden at the back. At the front...

    EUR105 to EUR278/night

  20. HOUSE
    Sassetta 1

    Sassetta 1

    Sassetta, LI

    Beautiful apartment in the Tuscan hills, 12 km from the private beach This beautiful apartment with shared pool is situated in a sixties villa in a hilly area near Sassetta, at 500 meters altitude. There are three apartments in the villa. You...

    Pool

    EUR98 to EUR278/night

  21. APARTMENT
    Negritella Quadri sr

    Negritella Quadri sr

    Cavalese, TN

    Apartment in Cavalese center, 900m from the ski slopes Apartment in Cavalese center, at a few steps from the shops and restaurants. The apartment is close to the ice skating rink, the swimming pool and the lifts to the Cermis ski slopes. The...

    EUR121 to EUR226/night

  22. VILLA
    Fontana Otto

    Fontana Otto

    Monteverdi Marittimo, PI

    Luxury air conditioned villa with private pool on large grounds with terrace You are bound to enjoy yourself in this pleasant, spacious villa situated up in the hills by Monteverdi Marittimo. Enjoy the enclosed private swimming pool with outdoor...

    Pool

    EUR227 to EUR272/night

  23. 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

  24. VILLA
    Villa Terra

    Villa Terra

    Cortona, AR

    Villa with private swimming pool, garden and nice views, nearby Cortona Villa Terra is a completely renovated villa with stunning views over the valley and the nearby town of Cortona. The villa is a former farm and is surrounded by a beautiful...

    Pool

    EUR305 to EUR606/night

  25. 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

    EUR551 to EUR824/night

  26. COTTAGE
    Casa Rondò

    Casa Rondò

    Montecatini Terme, PT

    Charming and well kept holiday home Charming and well kept holiday home, (ground floor, 80 m) newly built in period style - traditional, wooden beamed ceilings and Tuscan terracotta tiles. It is nestled in the breathtaking Tuscan hills and...

    Pool

    EUR141 to EUR252/night

  27. HOUSE
    Capo Nord Maisonettes Trilo

    Capo Nord Maisonettes Trilo

    Albarella, RO

    Apartment with airconditioning on a vacation island in the Gulf of Venice These well-kept apartments are located in the northernmost part of the island and close to the beautiful sandy beach. You can choose a 4 person apartment with 2 bedrooms...

    Pool

    EUR170 to EUR295/night

  28. APARTMENT
    Residenza Cervinia Pt

    Residenza Cervinia Pt

    Breuil-Cervinia, AO

    Just 30m from the ski lifts This accommodation is for the true ski lovers who would like to try something new. In fact it is located in the Aosta Valley in the northwest of Italy, where in direct comparison to many ski resorts in Tirol you still...

    EUR121 to EUR364/night

  29. HOUSE
    Castagneto 2

    Castagneto 2

    Castagneto Carducci, LI

    Large apartment located in a wooded area 300 meters from the private beach This spacious apartment is located in a sixties villa in a wooded area, just 300 meters from the beach of Marina Castagneto Carducci. Three steps lead to the ground floor...

    EUR139 to EUR369/night

  30. APARTMENT
    Residenza Cervinia 2P

    Residenza Cervinia 2P

    Breuil-Cervinia, AO

    Just 30m from the ski lifts This accommodation is for the true ski lovers who would like to try something new. In fact it is located in the Aosta Valley in the northwest of Italy, where in direct comparison to many ski resorts in Tirol you still...

    EUR121 to EUR364/night