Italy apartment or villa with a private pool area

Close

View larger map

Also consider

Europe Holidays
430742 properties
Italy Holidays
102096 properties
Coastal Cottages
222 properties
Apartments Sardinia
478 properties
Apartments Tuscany
3181 properties
Apartments Lake Garda Area
103 properties
Apartments Lake Como Area
494 properties
Apartments Sicily
634 properties
Villas Tuscany
25,478 properties
Villas Sicily
14,979 properties
Holiday rentals Lazio
11,339 properties
Villas Puglia
8,504 properties
Villas Lombardy
6,695 properties
Villas Campania
6,479 properties
Villas Sardinia
6,372 properties
Villas Veneto
4,387 properties
Villas Umbria
3,525 properties
Villas Liguria
2,638 properties
Villas Piedmont
2,307 properties
Holiday homes Marche
1,950 properties
Holiday rentals Emilia-Romagna
1,849 properties
Villas Calabria
1,539 properties

Italy

No dates Enter dates for accurate prices -

Adults, Children

Enter dates for more accurate prices

Payment Protection
To book this holiday home you need to pay through the Holiday Lettings website. We can’t protect your payment if you don’t pay through us. Learn more

9,557 Holiday homes

Filters applied: Private pool (9,557)

Travellers going to Italy are booking June dates now. Secure your holiday home today and have the perfect trip.

19

Province of Trapani / Castellammare del Golfo

4 10 5 nights min

  • 4 bedrooms
  • Sleeps 10
  • 5 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly

 …see more

from £300 / night

£2100 - £4648 / week

Book View

from £300 / night

13

Cottage accommodation in Italy with swimming pool

Province of Siena / Cetona

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Private garden
Podere Le Lame is an enchanting Tuscan Mill house, set in four hectares of olives - a house for complete peace and relaxation. All bedrooms have en suite bathrooms with power showers. There is a large hall/dining/kitchen with an open fire and French windows to a loggia  …see more

Pricing unknown

Book View

Pricing unknown

28

Holiday villa in Italy

Province of Siena / Pienza

6 13 7 nights min

  • 6 bedrooms
  • Sleeps 13
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Luxury Villa near Pienza, ideal for large families or friend's group.  …see more

from £249 / night

£1740 - £5957 / week

Book View

from £249 / night

Featured properties

39

Holiday villa with swimming pool in Italy

Amalfi Coast / Positano

8 16 Min stay varies

  • 8 bedrooms
  • Sleeps 16
  • Min stay varies
  • Swimming pool
  • Private garden
Villa Barocca is a gorgeous historic residence built in 1741 totally decorated with antic furniture and paintings so it seems as if you are living in a museum. It is located in the oldest district of Positano, overlooking the spettacular Positano Bay. The villa, spread  …see more

from £2609 / night

£18261 - £24348 / week

Book View

from £2609 / night

24

Castellammare del Golfo / Scopello

4 10 5 nights min

  • 4 bedrooms
  • Sleeps 10
  • 5 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly

 …see more

from £205 / night

£1405 - £3087 / week

Book View

from £205 / night

23

Province of Perugia / Perugia

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

Pricing unknown

Book View

Pricing unknown

(2) Average 

13

Sicily holiday villa rental

Province of Palermo / Balestrate

6 12 7 nights min

  • 6 bedrooms
  • Sleeps 12
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 3 km
  • Swimming pool
This exclusive old country house is situated on a calm and sunny knoll just over 500m away from a main road close to Balestrate, a beach resort on the north coast of the island, 40 km west of Palermo. The carefully restored estate with a wonderful panoramic view of the  …see more

from £187 / night

£1305 - £3044 / week

Enquire View

from £187 / night

23

Holiday villa in Italy

Province of Florence / Castelfiorentino

4 10 1 night min

  • 4 bedrooms
  • Sleeps 10
  • 1 night min
  • Nearest beach 80 km
  • Swimming pool
  • Child friendly
The estate is one of the few that still keeps all the traces of the ancient times and its fascination.It lies in the charming tuscan hills, sorrounded by cypresses, olive trees and vineyards.  …see more

from £374 / night

£2618 / week

Book View

from £374 / night

(10) Excellent 

18

Holiday villa with private pool in Alberobello

Alberobello / Trulli District

5 11 7 nights min

  • 5 bedrooms
  • Sleeps 11
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 25 km
  • Swimming pool
“Having stayed in many rented properties this one is outstandingly good” This villa exceeded our expectations in terms of quality and style. Immaculately presented, wonderfully peaceful and a thoroughly enjoyable place to spend time, in very gentle cou  …see more

from £215 / night

£1500 - £3200 / week

Book View

from £215 / night

(43) Excellent 

39

Holiday villa in Tuscany

Province of Siena / Siena

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Nearest beach 90 km
  • Swimming pool
  • Child friendly
“Perfect villa in perfect location” I need to start to say thank you to Jacopo and Fabio that made our holiday and stay absolutely perfect. They were both so helpful and such a pleasure to liaise with, even if we arrived later than expected! The  …see more

from £243 / night

£1696 - £4348 / week

Book View

from £243 / night

(1) Excellent 

11

Province of Lecce / Presicce

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min
  • Beach / lakeside relaxation
  • Nearest beach 7 km
  • Swimming pool

 …see more

from £91 / night

£634 / week

Book View

from £91 / night

36

Villa rental in Italy with swimming pool

Province of Trapani / Marsala

4 11 7 nights min

  • 4 bedrooms
  • Sleeps 11
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
One of the most gorgeous Sicilian villa in Marsala area, just 4 km’s away from the sea. Stylish and elegant, this villa spreads on two levels. There are 4 double bedrooms (among which 2 suites with ensuite bathrooms), 3 bathrooms, two spacious living rooms, and a  …see more

from £187 / night

£1305 / week

Book View

from £187 / night

(3) Excellent 

50

Villa rental in Tuscany with swimming pool

Province of Pisa / Montescudaio

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 10 km
  • Swimming pool
New Luxury Villa in Montescudaio, Tuscany for 8 guests with swimming pool, terraces, outdoor kitchen, internet WiFi. Ideal place for all year holiday. 10 km to wonderful beaches of Ligurian sea and only 2 km to local restaurants and shops. Bring the Kids !  …see more

from £340 / night

£1022 - £3170 / week

Book View

from £340 / night

8

Monsummano Terme / Monsummano Alto

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

Pricing unknown

Book View

Pricing unknown

(1) Excellent 

24

Holiday villa with swimming pool in Italy

Province of Perugia / Citta della Pieve

7 15 3 nights min

  • 7 bedrooms
  • Sleeps 15
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Private garden
Villa Campogrande is a delightful stone villa located in the gorgeous Umbria's country settings. On the ground floor a generous entrance leads to a great staircase. Six gorgeous double bedrooms, each adorned in a different style with unique antiques and paintings,  …see more

from £609 / night

£3044 / week

Book View

from £609 / night

20

Italy holiday villa rental

Lake Como / Menaggio

8 16 7 nights min

  • 8 bedrooms
  • Sleeps 16
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
This outstanding 19th century villa is set on five acres of private gardens with a swimming pool, a tennis court, superb lake views and, on request, a private mooring (at additional cost) at the San Siro harbor.  …see more

from £1914 / night

£13392 - £23479 / week

Enquire View

from £1914 / night

100

Villa rental in Italy with swimming pool

Province of Florence / Barberino Val d'Elsa

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Nearest beach 80 km
  • Swimming pool
  • Child friendly
Villa Lucia in Chianti is right in the heart of Tuscany, the ideal location for exploring the region and has a beautiful formal Italian garden and a private pool. A whole range of activities can be organized to make your stay extra special.  …see more

from £435 / night

£2931 - £5479 / week

Enquire View

from £435 / night

(3) Excellent 

11

Province of Palermo / Contessa Entellina

12 23 2 nights min

  • 12 bedrooms
  • Sleeps 23
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Private garden

 …see more

from £1696 / night

£11870 - £14000 / week

Book View

from £1696 / night

25

Province of Lucca / Lucca

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from £66 / night

£857 - £1344 / week

Book View

from £66 / night

(4) Excellent 

50

Holiday home with swimming pool in Tuscany

Camaiore / Pieve

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 10 km
  • Swimming pool
Charming little villa, panoramic position with stunning views, completely and lovingly restored in 2011/2012 with roof top terrace, large park and garden, car park and a private pool 12 m by 6 m. Special services: Restaurant bookings and recommandations by owner<br  …see more

from £292 / night

£2040 - £2561 / week

Book View

from £292 / night

24

Pergine Valdarno / Pieve A Presciano

6 12 7 nights min

  • 6 bedrooms
  • Sleeps 12
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Private garden

 …see more

from £540 / night

£3779 / week

Book View

from £540 / night

(1) Very Good 

100

Holiday villa with swimming pool in Puglia

Province of Brindisi / Ostuni

7 16 7 nights min

  • 7 bedrooms
  • Sleeps 16
  • 7 nights min
  • Nearest beach 15 km
  • Swimming pool
  • Child friendly
This magical and charming villa is perfect for a family or group getaway in the relaxing and tranquil region of Puglia. Spending your holiday in a Trullo will leave you with an experience that you will never forget.  …see more

from £323 / night

£2261 - £4696 / week

Enquire View

from £323 / night

34

Province of Brindisi / San Michele Salentino

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly

 …see more

from £34 / night

£566 - £609 / week

Book View

from £34 / night

29

Villa rental in Italy with swimming pool, tennis court

Scicli / Cava d'Aliga

7 14 7 nights min

  • 7 bedrooms
  • Sleeps 14
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Gorgeous villa by the sea. The stay, immersed in a lush tropical park, spreads on two levels where we can find 7 elegant and spacious suites and 9 bathrooms. At the entrance there is a gorgeous living room and a fully equipped kitche, The exterior has a huge and stylish  …see more

from £504 / night

£3522 - £6131 / week

Book View

from £504 / night

25

Italy holiday villa rental

Province of Siena / Siena

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
The villa lies in the hills of southern Tuscany (with a beautiful panorama) around 3 Kms from Radicofani. It forms an ideal starting point for enjoying the peace of the surrounding hills and on the other hand making trips by car (the highway A1 Florence-Rome is 25 Kms f  …see more

from £435 / night

£2087 - £3044 / week

Enquire View

from £435 / night

73

Villa rental in Italy with indoor pool

Province of Siena / Castelnuovo Berardenga

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 50 km
  • Swimming pool
  • Child friendly
The Piaggione of Serravalle is like a gateway entrance that protects an uncontaminated hill that seems lost in time and where nature apparently undisturbed articulates its own natural rhythms. Located on one of the highest summits of Chianti, in between Siena and Floren  …see more

from £174 / night

£1035 - £1992 / week

Book View

from £174 / night

24

Province of Pistoia / Pistoia

4 9 14 nights min

  • 4 bedrooms
  • Sleeps 9
  • 14 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from £233 / night

£1631 / week

Book View

from £233 / night

47

Amalfi Coast holiday villa rental

Amalfi Coast / Praiano

8 16 Min stay varies

  • 8 bedrooms
  • Sleeps 16
  • Min stay varies
  • Swimming pool
  • Private garden
Villa Bideri blends perfectly with the natural surroundings, the house is a true Amalfi style building all white with arched windows and columns. The property is spread over three floors, a floor, a ground floor and a tower up to the front door, which is accessed indepe  …see more

from £1758 / night

£12305 - £16261 / week

Book View

from £1758 / night

10

Province of Monza and Brianza / Monza

1 3 1 night min

  • 1 bedroom
  • Sleeps 3
  • 1 night min
  • Swimming pool
  • Ask about pets

 …see more

from £57 / night

£305 / week

Book View

from £57 / night

17

Province of Verona / Torri del Benaco

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 2 km
  • Swimming pool

 …see more

from £150 / night

£1044 / week

Book View

from £150 / night

18

Holiday villa with swimming pool in Tuscany

Province of Siena / Radicofani

7 14 7 nights min

  • 7 bedrooms
  • Sleeps 14
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
The villa lies in a hilly location with stunning panoramic views of the surrounding hills and mountains, about 8 km from the village of Radicofani. It is an ideal starting point for enjoying the tranquility of the surrounding mountainous landscape and on the other to ma  …see more

from £199 / night

£1392 - £3044 / week

Enquire View

from £199 / night

23

Syracuse / Plemmirio

4 8 Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

 …see more

from £96 / night

£670 - £1487 / week

Book View

from £96 / night

(64) Excellent 

52

Holiday villa letting

Province of Siena / Sinalunga

12 26 Min stay varies

  • 12 bedrooms
  • Sleeps 26
  • Min stay varies
  • Nearest beach 170 km
  • Swimming pool
  • Child friendly
Villa Scopetello is the perfect holiday home for large groups and families who wish to spend their holidays together. (Between September and May it is also possible to rent just a portion of the Villa or even one bedroom) The 1000 square meter large Villa with 12 bedro  …see more

from £522 / night

£3653 - £7827 / week

Book View

from £522 / night

19

Campania holiday villa rental

Province of Naples / Massa Lubrense

5 10 Min stay varies

  • 5 bedrooms
  • Sleeps 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Villa Ivory can accommodate ten people and is equipped with all modern comforts. The structure of 600 mq in total, is divided into different levels. Just a few steps away from the villa there is the access to the poolequipped with teak sun beds, and rocking chairs.  …see more

from £385 / night

£2692 - £5035 / week

Book View

from £385 / night

19

Province of Messina / Patti

3 6 3 nights min

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Private garden

 …see more

from £174 / night

£1087 / week

Book View

from £174 / night

16

Province of Palermo / Cinisi

3 8 3 nights min

  • 3 bedrooms
  • Sleeps 8
  • 3 nights min
  • Beach / lakeside relaxation
  • Nearest beach 2 km
  • Swimming pool

 …see more

from £174 / night

£1218 / week

Book View

from £174 / night

20

Villa rental in Tuscany with swimming pool

Province of Arezzo / San Giustino Valdarno

10 20 Min stay varies

  • 10 bedrooms
  • Sleeps 20
  • Min stay varies
  • Swimming pool
  • Suitable for children age 5+
  • Air conditioning
Villa Il Borro is a wonderful luxury Tuscany villa immersed in the countryside, near the small village of San Giustino Valdarno. This magnificent villa rental, owned by the Ferragamo family sleeps up to 20 people and is not too far from Florence.  …see more

from £5286 / night

£37000 / week

Enquire View

from £5286 / night

31

Province of Lecce / Gagliano del Capo

8 16 7 nights min

  • 8 bedrooms
  • Sleeps 16
  • 7 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child friendly

 …see more

from £1119 / night

£7827 / week

Book View

from £1119 / night

29

Holiday villa with swimming pool in Italy

Orbetello / Ansedonia

7 14 Min stay varies

  • 7 bedrooms
  • Sleeps 14
  • Min stay varies
  • Swimming pool
  • Private garden
Situate on a coastal hillside in the Maremma area of Tuscany, Villa Bellevue Ansedonia is a unique property facing on the wonderful scenario of Argentario Muont and the Natural Park of Uccellina. The villa, set in a rocky ridge, as a precious gem, is focused on its fron  …see more

from £969 / night

£6783 - £12174 / week

Book View

from £969 / night

40

Villa rental in Tuscany with swimming pool

Province of Arezzo / Castiglion Fiorentino

6 12 Min stay varies

  • 6 bedrooms
  • Sleeps 12
  • Min stay varies
  • Swimming pool
  • Private garden
nestling in the heart of the world-famous chianti valley, just thirty minutes from florence, stands castello  di ginevra. This graceful country residence is located near the ancient town of castelfiorentino and is steeped in history. Traces of the original 13th-cen  …see more

from £1019 / night

£7131 - £10696 / week

Book View

from £1019 / night