50 Best Italy Vacation rentals on Holiday Lettings - Villas

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96,755 Vacation rentals

20

Vacation villa in Italy

Greve in Chianti / Casole

7 14 7 nights min

  • 7 bedrooms
  • Sleeps 14
  • 7 nights min
  • Swimming pool
  • Pet friendly
This very attractive villa was originally built in the second half of the 19th century, and has been completely renovated throughout. The views from the property are like a picture of typical Chianti landscape, rich with gently rolling hills covered with vineyards …see more

from $850 / night

$5,947 - $10,533 / week

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from $850 / night

18

Vacation apartment in Italy

Province of Bologna / Bologna

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Ask about children
  • Air conditioning
Modern and cozy apartment of about 45 m2 on two levels and located on the ground floor of an elegant building in the historic center of Bologna. It is less than a 10-minute walk from Piazza Maggiore and very convenient to reach the Railway Station on foot. Guests have a …see more

from $145 / night

$772 - $2,602 / week

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from $145 / night

22

Vacation villa in Italy

Radda in Chianti / Volpaia

6 11 7 nights min

  • 6 bedrooms
  • Sleeps 11
  • 7 nights min
  • Swimming pool
  • Ask about pets
  • Private garden
This property is located in the fortified medieval hamlet of Volpaia, in the Chianti Classico area, in a secluded position ensuring complete privacy. It is just a 300 metre walk to the centre of the hamlet, with two restaurants, one of which managed by the Castello di V …see more

from $530 / night

$3,710 - $7,418 / week

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from $530 / night

26

Vacation apartment in Italy

Lombardy / Milan

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Ask about children
  • Air conditioning
  • Pet friendly
Modern and bright one bedroom apartment for rent in Milan with balcony, completely renovated and refurbished in 2012, located on the first floor of a building (with elevator) close to Gambara metro stop. This charming 65 sq.mt apartment, fitted with air conditioning, op …see more

from $186 / night

$860 - $2,045 / week

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from $186 / night

20

Vacation villa in Tuscany

Rignano sull'Arno / San Donato in Collina

6 12 7 nights min

  • 6 bedrooms
  • Sleeps 12
  • 7 nights min
  • Swimming pool
  • Ask about pets
This huge property, located in a very panoramic position overlooking the hills of Florence and a small lake, consists of 3 parts, the oldest of which was built in the 13th century and was used afterwards by the pilgrims who stopped there to rest. The property is l …see more

from $707 / night

$4,945 - $8,638 / week

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from $707 / night

36

Italy Vacation villa rental

Province of Arezzo / Bucine

20 20 7 nights min

  • 20 bedrooms
  • Sleeps 20
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Ask about pets
This villa is the big version of Villa Londa 10 (which sleeps 10 people) and Villa Londa 14 (which sleeps 14 people). EXTERNAL DESCRIPTION Villa Londa 20 is a beautiful historic villa, dating back to the seventeenth century, situated on the hills of Dicomano, in the Mug …see more

from $479 / night

$3,348 - $9,046 / week

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from $479 / night

20

Vacation villa in Italy

Province of Venice / Torcello

7 14 7 nights min

  • 7 bedrooms
  • Sleeps 14
  • 7 nights min
  • Swimming pool
  • Ask about pets
  • Private garden
Torcello is the real precursor of Venice. Settled between the fifth and seventh centuries, it became the most prosperous of the early lagoon communities with its own palaces and churches, shipyards and docks, its own nobility and laws. The growth of Venice brough …see more

from $1,413 / night

$9,891 - $12,364 / week

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from $1,413 / night

9

Vacation apartment in Lombardy

Lombardy / Milan

1 5 Min stay varies

  • 1 bedroom
  • Sleeps 5
  • Min stay varies
  • Ask about children
All the 16 apartments of the Farini complex have been recently refurbished and offer a comfortable, functional environment. The one bedroom apartments (two) belonging to this cathegory have floor surface of approx. 50-62 sq.mt, and they are located on either the first o …see more

from $232 / night

$998 - $3,123 / week

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from $232 / night

19

Vacation apartment in Emilia-Romagna

Province of Bologna / Bologna

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Ask about children
  • Air conditioning
  • Ask about pets
Intimate and extremely well-cared-for apartment of 50 m2, located on the second floor of an elegant palazzo in the old town, with elevator and concierge, the latter available until 12:00 noon on weekdays. The property is located in the immediate vicinity of Piazza Maggi …see more

from $165 / night

$866 - $2,456 / week

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from $165 / night

24

Vacation apartment in Lombardy

Lombardy / Milan

2 3 Min stay varies

  • 2 bedrooms
  • Sleeps 3
  • Min stay varies
  • Ask about children
  • Air conditioning
  • Ask about pets
Two-bedroom 80 m2 apartment with large terrace, completely renovated in 2017 with new furnishing, just a few steps from the Primaticcio Metro station (line MM1 - red), ideal to reach the city center within minutes. This beautiful 80 m2 apartment, which also features a 3 …see more

from $227 / night

$1,355 - $2,973 / week

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from $227 / night

20

Lake Maggiore Vacation villa rental

Lake Maggiore / Dormelletto

6 12 7 nights min

  • 6 bedrooms
  • Sleeps 12
  • 7 nights min
  • Swimming pool
  • Ask about pets
  • Private garden
This property is situated on the western side of Lake Maggiore in the beautiful park of “Lagoni di Mercurago”. From many points on the estate, especially from the large garden, it is possible to enjoy magnificent views of the lake and the medieval fortress of Ange …see more

from $881 / night

$6,167 - $8,638 / week

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from $881 / night

8

Italy Vacation apartment rental

Lombardy / Milan

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Ask about children
  • Air conditioning
The apartments belonging to this category - seven - have a floor surface comprised between 40 and 50 sq.mt, and they are located on either the first or the second floor. Carefully refurbished, they provide a cosy but functional ambience in a residential building that ha …see more

from $220 / night

$926 - $2,104 / week

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from $220 / night

14

Studio rental in Italy

Province of Florence / Florence

Studio 2 3 nights min

  • Studio
  • Sleeps 2
  • 3 nights min
  • Ask about children
  • Air conditioning
  • Ask about pets
External Description: Located on the first floor, wihtout elevator (20 steps to climb) of a building located on Via Cavour. The apartment has an ideal location to visit the city's history, culture, art, but also to reach shops, bars and all the services of a modern city …see more

from $97 / night

$625 - $687 / week

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from $97 / night

20

Italy Vacation villa rental

Province of Lucca / San Michele di Moriano

10 20 7 nights min

  • 10 bedrooms
  • Sleeps 20
  • 7 nights min
  • Swimming pool
  • Pet friendly
  • Private garden
Villa Clara is a typical 18th Century Manor villa with its own small formal park and chapel, at the centre of an estate with farmhouses where the farmers looking after the winery used to live. The owners have fully furnished it in an elegant style and have provide …see more

from $1,143 / night

$7,997 - $11,127 / week

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from $1,143 / night

17

Tuscany Vacation apartment rental

Province of Florence / Florence

1 4 3 nights min

  • 1 bedroom
  • Sleeps 4
  • 3 nights min
  • Ask about children
  • Air conditioning
  • Ask about pets
External Description: Located on the first floor, no elevator - 20 steps to climb, of a building located on Via Cavour. The apartment has an ideal location to move quickly on foot to visit the city with its history, culture, art, but also to reach shops, bars and all th …see more

from $133 / night

$894 - $969 / week

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from $133 / night

8

Italy Vacation apartment rental

Lombardy / Milan

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Ask about children
  • Air conditioning
The apartments belonging to this category - seven - have a floor surface comprised between 40 and 50 sq.mt, and they are located on either the first or the second floor. Carefully refurbished, they provide a cosy but functional ambience in a residential building that ha …see more

from $220 / night

$926 - $2,949 / week

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from $220 / night

18

Vacation apartment with swimming pool in Italy

Province of Grosseto / Roccatederighi

1 4 3 nights min

  • 1 bedroom
  • Sleeps 4
  • 3 nights min
  • Swimming pool
  • Ask about children
  • Pet friendly
Lovely one-bedroom 33 m2 apartment located on the first floor of the Residence Il Ciliegio of Roccatederighi (a hamlet of Roccastrada, in province of Grosseto), in the heart of the beautiful Maremma region. The entrance leads straight to the living room with kitchenette …see more

from $128 / night

$636 - $826 / week

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from $128 / night

20

Villa rental in Italy with swimming pool

Province of Pisa / Montelopio

5 9 7 nights min

  • 5 bedrooms
  • Sleeps 9
  • 7 nights min
  • Swimming pool
  • Ask about pets
  • Private garden
This villa, dating from the 16th century, still retains the atmosphere of a an antique Templar residence. The central part of the villa and the right wing have recently been totally restored, maintaining the cotto floors and the beamed ceilings, yet adding all mod …see more

from $673 / night

$4,711 - $8,482 / week

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from $673 / night

19

Italy Vacation apartment rental

Province of Florence / Florence

1 4 3 nights min

  • 1 bedroom
  • Sleeps 4
  • 3 nights min
  • Ask about children
  • Air conditioning
External Description: Located on the second floor, no elevator - 49 steps, of a palace located on via del Moro just a short walk from central Santa Maria Novella station. The apartment is an ideal starting point to take advantage of everything that Florence can offer, h …see more

from $137 / night

$818 - $1,301 / week

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from $137 / night

19

Vacation home rental

Aci Castello / Acitrezza

1 4 3 nights min

  • 1 bedroom
  • Sleeps 4
  • 3 nights min
  • Nearest beach 6 mi
  • Child friendly
  • Air conditioning
Willy Home is ideal for your relaxation. It consists of a large terrace with stunning views, a beautiful open plan kitchen-living room, a bedroom with double bed and cot. Bathroom with shower for your relaxing moments and washing machine. The living room is also nice wi …see more

from $40 / night

$261 - $434 / week

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from $40 / night

22

Italy Vacation apartment rental

Province of Florence / Florence

2 3 3 nights min

  • 2 bedrooms
  • Sleeps 3
  • 3 nights min
  • Ask about children
  • Air conditioning
External Description: Located between the first and second floor (without elevator), 10 steps to climb, of a lovely house located on Via San Niccolò in the historic district of Oltrarno, one of the most beautiful areas of the city, few steps from Ponte Vecchio (600mt) a …see more

from $176 / night

$1,130 - $1,237 / week

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from $176 / night

20

Tuscany Vacation villa rental

Camaiore / Orbicciano

6 12 7 nights min

  • 6 bedrooms
  • Sleeps 12
  • 7 nights min
  • Swimming pool
  • Pet friendly
  • Private garden
This very attractive property is located in an exceptionally panoramic position among olive groves, in the hills between Lucca and the Versilia coast. The house was meticulously restored from what were formerly an olive mill and a barn, now connected by a large e …see more

from $834 / night

$5,837 - $9,155 / week

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from $834 / night

31

Apartment rental in Italy with swimming pool

Province of Grosseto / Roccatederighi

1 4 3 nights min

  • 1 bedroom
  • Sleeps 4
  • 3 nights min
  • Swimming pool
  • Ask about children
  • Pet friendly
Comfortable one-bedroom 36 m2 apartment located on the first floor of the Residence Il Ciliegio of Roccatederighi (a hamlet of Roccastrada, in province of Grosseto), in the heart of the beautiful Maremma region. The entrance leads straight to the living room with kitche …see more

from $128 / night

$636 - $826 / week

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from $128 / night

31

Italy Vacation apartment rental

Province of Grosseto / Roccatederighi

1 4 3 nights min

  • 1 bedroom
  • Sleeps 4
  • 3 nights min
  • Swimming pool
  • Ask about children
  • Pet friendly
Quiet one-bedroom 33 m2 apartment located on the second floor of the Residence Il Ciliegio of Roccatederighi (a hamlet of Roccastrada, in province of Grosseto), in the heart of the beautiful Maremma region. The entrance leads straight to the living room with kitchenette …see more

from $128 / night

$636 - $826 / week

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from $128 / night

8

Vacation apartment in Lombardy

Lombardy / Milan

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Ask about children
  • Air conditioning
The apartments belonging to this category - seven - have a floor surface comprised between 40 and 50 sq.mt, and they are located on either the first or the second floor. Carefully refurbished, they provide a cosy but functional ambience in a residential building that ha …see more

from $220 / night

$926 - $2,949 / week

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from $220 / night

32

Tuscany Vacation apartment rental

Province of Grosseto / Roccatederighi

1 4 3 nights min

  • 1 bedroom
  • Sleeps 4
  • 3 nights min
  • Swimming pool
  • Ask about children
  • Pet friendly
Bright one-bedroom 36 m2 apartment located on the second floor of the Residence Il Ciliegio of Roccatederighi (a hamlet of Roccastrada, in province of Grosseto), in the heart of the beautiful Maremma region. The entrance leads straight to the living room with kitchenett …see more

from $128 / night

$636 - $826 / week

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from $128 / night

20

Vacation villa with swimming pool in Italy

Camaiore / Nocchi

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Swimming pool
  • Ask about pets
  • Private garden
La Madonnina is situated in a small hamlet in a very picturesque hillside setting near the village of Camaiore, only a few km from the wide sandy beaches and the many facilities of the Versilia coast. The architect-designed restoration sympathetically blends the cha …see more

from $351 / night

$2,457 - $6,056 / week

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from $351 / night

21

Italy Vacation studio rental

Province of Verona / Verona

Studio 2 3 nights min

  • Studio
  • Sleeps 2
  • 3 nights min
  • Ask about children
  • Air conditioning
Large and bright 66 m2 studio on the second floor of the Residence “La Vigna in Città - An authentic vineyard in the heart of Verona”, on Via XX Settembre, in the heart of the city of Verona. This studio consists of foyer, single room which serves as a living/sleeping a …see more

from $108 / night

$433 - $865 / week

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from $108 / night

28

Tuscany Vacation studio rental

Province of Grosseto / Roccatederighi

Studio 3 3 nights min

  • Studio
  • Sleeps 3
  • 3 nights min
  • Swimming pool
  • Ask about children
  • Pet friendly
Bright 28 m2 studio apartment located on the ground floor of the Residence Il Ciliegio of Roccatederighi (a hamlet of Roccastrada, in the province of Grosseto), in the heart of the beautiful Maremma region. Consisting of a unique environment with a day/night function ar …see more

from $108 / night

$413 - $668 / week

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from $108 / night

8

Italy Vacation apartment rental

Lombardy / Milan

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Ask about children
  • Air conditioning
The apartments belonging to this category - seven - have a floor surface comprised between 40 and 50 sq.mt, and they are located on either the first or the second floor. Carefully refurbished, they provide a cosy but functional ambience in a residential building that ha …see more

from $220 / night

$926 - $2,949 / week

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from $220 / night

23

Vacation apartment rental

Province of Verona / Verona

2 5 3 nights min

  • 2 bedrooms
  • Sleeps 5
  • 3 nights min
  • Ask about children
  • Air conditioning
The apartment, which is made very bright by two large windows, opens onto the living room/kitchen, which is equipped with everything you need, including induction hob, microwave oven, coffee maker, kettle and toaster. The apartment is furnished with dining table for 6, …see more

from $161 / night

$989 - $1,190 / week

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from $161 / night

8

Italy Vacation apartment rental

Lombardy / Milan

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Ask about children
  • Air conditioning
The apartments belonging to this category - seven - have a floor surface comprised between 40 and 50 sq.mt, and they are located on either the first or the second floor. Carefully refurbished, they provide a cosy but functional ambience in a residential building that ha …see more

from $220 / night

$926 - $2,949 / week

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from $220 / night

19

Italy Vacation villa rental

Florence / Settignano

4 7 3 nights min

  • 4 bedrooms
  • Sleeps 7
  • 3 nights min
  • Ask about children
  • Ask about pets
EXTERNAL DESCRIPTION Villa Al Pozzo is a property located between fields of olive trees and the woods that cover the hill of Fiesole. The villa has been renovated in 2010 and it boasts all the comforts surrounded by a charming nature. The mansion has 2 private entrances …see more

from $761 / night

$5,325 - $7,121 / week

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from $761 / night

14

Vacation studio accommodation

Province of Brescia / Toscolano-Maderno

Studio 2 Min stay varies

  • Studio
  • Sleeps 2
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
New 29 m2 studio ideal for 2 guests, located on the ground floor of the “Corte Benaco” residential complex, an eighteenth-century recently restructured villa with swimming pool and private parking in Toscolano Maderno, on the shores of Lake Garda. This studio consists o …see more

from $122 / night

$731 - $1,372 / week

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from $122 / night

(5) Excellent 

12

Vacation apartment in Italy

Province of Trento / Riva Del Garda

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Child friendly
The apartment on via Masetto is only 400 metres from the beaches of the Garda Lake and the centre of Riva. It is a three-roomed flat consisting of a large living room with kitchen that offers every comfort, two double rooms and two balconies. The apartment is very brigh …see more

from $124 / night

$744 - $1,314 / week

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Responds fast!
avg. 2 hours 21 minutes

from $124 / night

20

Vacation villa with swimming pool in Italy

Montopoli in Val d'Arno / Marti

2 3 7 nights min

  • 2 bedrooms
  • Sleeps 3
  • 7 nights min
  • Swimming pool
  • Pet friendly
  • Private garden
This charming, small house, was recently completely restored and equipped with all modern facilities, including air conditioning in the bedrooms, hi-fi system, fax machine, wi-fi connection and satellite TV. It is located in a very quiet position 3 kms away from t …see more

from $237 / night

$1,659 - $2,270 / week

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from $237 / night

9

Tuscany Vacation b&b rental

Province of Arezzo / Lucignano

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Swimming pool
  • Child friendly
On the first floor of a typical country house, a bright and spacious double room with private bathroom (with shower). The room is facing east, has an area of ​​about 20 square meters and is equipped with minibar and kettle with selection of teas and infusions. Floors of …see more

from $81 / night

$564 / week

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from $81 / night

15

Italy Vacation apartment rental

Province of Verona / Verona

2 2 3 nights min

  • 2 bedrooms
  • Sleeps 2
  • 3 nights min
  • Ask about children
  • Air conditioning
  • Ask about pets
Bright two-bedroom 91 m2 apartment on the third floor of the Residence “La Vigna in Città - An authentic vineyard in the heart of Verona”, on Via XX Settembre, in the heart of the city of Verona. Upon entering the apartment, guests access the living room/kitchen, which …see more

from $130 / night

$861 - $1,917 / week

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from $130 / night

27

Vacation apartment rental

Lombardy / Milan

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Ask about children
  • Air conditioning
Spacious one-bedroom property with view for rent in Milan, a few steps from the Istria Metro station (line MM5 - purple), in close proximity to the Village of Journalists. This 60 m2 apartment is located on the fifth floor serviced by elevator, very quiet and bright, an …see more

from $207 / night

$993 - $1,293 / week

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from $207 / night

20

Vacation villa with swimming pool in Italy

Montopoli in Val d'Arno / Marti

5 9 7 nights min

  • 5 bedrooms
  • Sleeps 9
  • 7 nights min
  • Swimming pool
  • Pet friendly
Le Rondini is a very special property located on the same estate as La Capinera, one of our most popular houses. It has been recently restored to a very high standard preserving the original Tuscan country style with beamed ceilings and original cotto floors. It is …see more

from $383 / night

$2,677 - $4,899 / week

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from $383 / night