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20,814 Holiday homes

Filters applied: Cycling holidays

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

5

Province of Siena / Rocca d'Orcia

3 7 2 nights min

  • 3 bedrooms
  • Sleeps 7
  • 2 nights min
  • Child friendly
  • Ask about pets

 …see more

from £103 / night

£428 / week

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from £103 / night

(3) Very Good 

24

Province of Catania / Linguaglossa

4 12 Min stay varies

  • 4 bedrooms
  • Sleeps 12
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 12 km
  • Ski

 …see more

from £26 / night

£274 - £1898 / week

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from £26 / night

15

Province of Varese / Brenta

2 7 Min stay varies

  • 2 bedrooms
  • Sleeps 7
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 10 km
  • Child friendly

 …see more

Pricing unknown

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Featured properties

(1) Excellent 

47

Province of Reggio Calabria / Reggio Calabria

3 10 1 night min

  • 3 bedrooms
  • Sleeps 10
  • 1 night min
  • Beach / lakeside relaxation
  • Nearest beach 300 km
  • Child friendly

 …see more

from £86 / night

£217 - £1078 / week

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from £86 / night

17

Province of Perugia / Giano dell'Umbria

2 6 1 night min

  • 2 bedrooms
  • Sleeps 6
  • 1 night min
  • Child friendly
  • Ask about pets
  • Private garden

 …see more

from £56 / night

£359 / week

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from £56 / night

(3) Very Good 

31

Province of Palermo / Trappeto

3 7 Min stay varies

  • 3 bedrooms
  • Sleeps 7
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Child friendly

 …see more

from £43 / night

£300 - £718 / week

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from £43 / night

(5) Excellent 

26

Ugento / Torre San Giovanni

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Child friendly

 …see more

from £38 / night

£227 - £1409 / week

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from £38 / night

(3) Excellent 

17

Italy holiday apartment rental

Lazio / Rome

3 7 Min stay varies

  • 3 bedrooms
  • Sleeps 7
  • Min stay varies
  • Nearest beach 35 km
  • Child friendly
  • Car not necessary
“Perfect long-term stay in Rome!” Our experience with living in the Panoramic apartment for 4,5 months is very good. We were welcomed upon arrival by the owner, Flavio, who helped with useful information about the apartment, the neighborhood and other  …see more

from £77 / night

£428 - £1389 / week

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from £77 / night

17

Holiday apartment in Sicily

Province of Ragusa / Ragusa

5 5 1 night min

  • 5 bedrooms
  • Sleeps 5
  • 1 night min
  • Ask owner if suitable for children
  • Air conditioning
  • Ask about pets
Specifically, helpfulness, kindness  …see more

from £35 / night

£214 / week

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from £35 / night

(5) Very Good 

20

Holiday apartment in Italy

Alghero / Centro Storico, Alghero

1 4 3 nights min

  • 1 bedroom
  • Sleeps 4
  • 3 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.5 km
  • Child friendly
“Wonderful Apartment” The apartment is very modern, clean and safe; it is centrally located and particularly well equipped. The service provided by the owners was exceptionally nice and helpful. We felt very comfortable in the apartment and if we ev  …see more

from £60 / night

£419 - £748 / week

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from £60 / night

20

Holiday apartment with shared pool in Sicily

Province of Palermo / Cefalu

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 5 km
  • Swimming pool
The Residence Seaview offers comfortable accommodations for all your needs, ideal for families, couples and groups of friends on holiday. It is located on a hill, in a district surrounded by gardens and a spectacular sea view. Just 5 km from the city centre and the mai  …see more

from £72 / night

£754 / week

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from £72 / night

17

Apartment rental in Umbria with tennis court

Province of Perugia / Spoleto

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 150 km
  • Child friendly
Exclusive and independent apartment with private garden. Entrance from the private garden, large living room with fireplace and dining table for 8 people, fully equipped kitchen with dishwasher, double bedroom with walk-in closet, bathroom with bathtub, study with soba  …see more

from £60 / night

£385 - £795 / week

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from £60 / night

24

Province of Latina / San Felice Circeo

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
  • Air conditioning

 …see more

from £84 / night

£582 - £1710 / week

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from £84 / night

(1) Very Good 

15

Province of Lucca / Massaciuccoli

2 7 7 nights min

  • 2 bedrooms
  • Sleeps 7
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 15 km
  • Swimming pool

 …see more

from £135 / night

£941 / week

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from £135 / night

12

Province of Rome / Genzano di Roma

2 6 1 night min

  • 2 bedrooms
  • Sleeps 6
  • 1 night min
  • Beach / lakeside relaxation
  • Nearest beach 30 km
  • Suitable for children age 5+

 …see more

from £43 / night

£300 / week

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from £43 / night

(2) Excellent 

14

Province of Livorno / Castagneto Carducci

2 4 30 nights min

  • 2 bedrooms
  • Sleeps 4
  • 30 nights min
  • Beach / lakeside relaxation
  • Child friendly

 …see more

from £80 / night

£556 / week

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from £80 / night

(1) Very Good 

14

Italian Riviera / Rapallo

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0.1 km
  • Car not necessary

 …see more

from £73 / night

£496 - £941 / week

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from £73 / night

(3) Excellent 

26

Rome / San Pietro, Rome

3 8 2 nights min

  • 3 bedrooms
  • Sleeps 8
  • 2 nights min
  • Nearest beach 30 km
  • Child friendly
  • Car not necessary

 …see more

from £103 / night

£718 - £2146 / week

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from £103 / night

20

Province of Pesaro and Urbino / Piobbico

4 10 2 nights min

  • 4 bedrooms
  • Sleeps 10
  • 2 nights min
  • Nearest beach 55 km
  • Ski
  • Ask owner if suitable for children

 …see more

from £214 / night

£1026 / week

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from £214 / night

12

Alghero / Alghero Town Centre

2 3 3 nights min

  • 2 bedrooms
  • Sleeps 3
  • 3 nights min
  • Beach / lakeside relaxation
  • Nearest beach 1 km
  • Car not necessary

 …see more

from £26 / night

£154 - £334 / week

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from £26 / night

(1) Excellent 

24

Holiday home with swimming pool in Italy

Province of Arezzo / Ambra

5 12 2 nights min

  • 5 bedrooms
  • Sleeps 12
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets
Two old tuscan houses isolated in the countryside between Siena, Arezzo and Florence. In July and August we rent them only together, in the other periods they are available also separately. The houses with swimming pool at La Doccia are just 5 minutes from the town of  …see more

from £134 / night

£930 - £1026 / week

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from £134 / night

9

Province of Alessandria / Voltaggio

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Child friendly
  • Private garden

 …see more

from £39 / night

£206 / week

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from £39 / night

(1) Excellent 

5

Province of Perugia / Gubbio

5 20 Min stay varies

  • 5 bedrooms
  • Sleeps 20
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly

 …see more

Pricing unknown

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Pricing unknown

17

Alghero / Mamuntanas

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 2 km
  • Car not necessary
  • Air conditioning

 …see more

from £39 / night

£257 - £642 / week

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from £39 / night

(4) Very Good 

11

Sicily / Province of Trapani

2 6 1 night min

  • 2 bedrooms
  • Sleeps 6
  • 1 night min
  • Beach / lakeside relaxation
  • Nearest beach 5 km
  • Child friendly

 …see more

from £65 / night

£449 / week

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from £65 / night

(3) Excellent 

23

Holiday villa in Italy

Province of Arezzo / Caprese Michelangelo

1 2 1 night min

  • 1 bedroom
  • Sleeps 2
  • 1 night min
  • Beach / lakeside relaxation
  • Nearest beach 125 km
  • Swimming pool
Exclusive Villa set in a 100 acre private resort. Perfect for couples. Stunning views of castle where Michelangelo was born. Heated salt water pool, Medieval Towns to explore, great local restaurants, peace and tranquility. Cortona, Florence and La Verna nearby  …see more

from £130 / night

£790 - £890 / week

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from £130 / night

(2) Excellent 

43

Province of Sondrio / Livigno

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Suitable for children age 5+
  • Ask about pets

 …see more

from £86 / night

£599 / week

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from £86 / night

(2) Very Good 

65

Province of L'Aquila / Pacentro

5 11 1 night min

  • 5 bedrooms
  • Sleeps 11
  • 1 night min
  • Ski
  • Child friendly

 …see more

from £27 / night

£176 / week

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from £27 / night

7

Italy holiday b&b rental

Province of Siena / San Gimignano

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets
Conveniently placed between world famous hilltop towns of San Gimignano Florence and Siena. We offer 360° views from the top of a hill surrounded by vines and olive trees. Abundant buffet breakfast and home cooked evening meals are avaialble for our guests, relax b  …see more

from £82 / night

£539 - £718 / week

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from £82 / night

12

Holiday apartment in Tuscany

Province of Lucca / Viareggio

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
  • Air conditioning
Nice new apartment 50 m far from the beach of Viareggio at second floor. Perfect for 4 people .  …see more

from £86 / night

£599 - £958 / week

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from £86 / night

22

Italy holiday villa rental

Todi / Torrececcona

7 15 7 nights min

  • 7 bedrooms
  • Sleeps 15
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Only 10 minutes from Todi, and surrounded by farmland, this beautiful and just restored farmhouse is an ideal place to tour Umbria or simply relax.The property consists of a main house with 5 bedrooms and 5 bathrooms (3 en suite). A pathway down leads to a 7x17 infinity  …see more

from £855 / night

£5983 / week

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from £855 / night

(1) Excellent 

4

Holiday villa with swimming pool in Tuscany

Province of Arezzo / Cortona

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Nearest beach 15 km
  • Swimming pool
  • Child friendly
“Good large home and easy for Cortona and other Tuscany places” For our extended family vacation -,this was more than perfect! The main villa with its three bedrooms and then the private annex which our parents enjoyed - gave us complete flexibility as  …see more

from £192 / night

£1341 - £2767 / week

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from £192 / night

(2) Very Good 

19

Val Gardena / Ortisei

1 2 3 nights min

  • 1 bedroom
  • Sleeps 2
  • 3 nights min
  • Child friendly
  • Private garden

 …see more

from £82 / night

£471 / week

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from £82 / night

(1) Excellent 

12

Province of Palermo / Isola Delle Femmine

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0 km
  • Child friendly

 …see more

from £52 / night

£359 - £624 / week

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from £52 / night

(7) Excellent 

52

Province of Trapani / Castellammare del Golfo

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Nearest beach 1 km
  • Child friendly
  • Car not necessary

 …see more

from £35 / night

£240 / week

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from £35 / night

36

Italy holiday penthouse rental

Province of Rome / Tivoli

3 8 1 night min

  • 3 bedrooms
  • Sleeps 8
  • 1 night min
  • Beach / lakeside relaxation
  • Nearest beach 30 km
  • Swimming pool
ROME Golf Club Penthouse Apartment. 3 Double Bedrooms. Fully fit Kitchen, 2 Jacuzzi Toilets, Parking, Pool  …see more

from £206 / night

£1197 - £1436 / week

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from £206 / night

36

Rome / Garbatella

2 1 1 night min

  • 2 bedrooms
  • Sleeps 1
  • 1 night min
  • Nearest beach 15 km
  • Car not necessary
  • Private garden

 …see more

from £22 / night

£137 / week

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from £22 / night

7

Province of Siena / Casole d'Elsa

1 4 Min stay varies

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

 …see more

from £75 / night

£453 - £830 / week

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from £75 / night

(3) Very Good 

21

Holiday cottage with shared pool in Italy

San Romano in Garfagnana / Sillicagnana

3 7 Min stay varies

  • 3 bedrooms
  • Sleeps 7
  • Min stay varies
  • Swimming pool
  • Child friendly
“Fantastic stay with perfect hosts” Fantastic property. Wonderful hosts and spotlessly clean. The pool was wonderful but a little cold. A very spacious block with a large space for the kids to play in. Eduardo and Eugenio could not have been more accom  …see more

from £95 / night

£530 - £885 / week

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from £95 / night

9

City of Venice / Mestre

Studio 4 Min stay varies

  • Studio
  • Sleeps 4
  • Min stay varies
  • Beach / lakeside relaxation
  • Child friendly
  • Car not necessary

 …see more

Pricing unknown

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