Cycling holiday villas and apartments Italy | Holiday Lettings

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  • Basilicata (80)
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  • Emilia-Romagna (566)
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  • Liguria (773)
  • Lombardy (1,700)
  • Marche (671)
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  • Piedmont (791)
  • Puglia (2,095)
  • Sardinia (1,935)
  • Sicily (3,082)
  • Trentino-Alto Adige (381)
  • Tuscany (5,505)
  • Umbria (1,132)
  • Valle d'Aosta (151)
  • Veneto (764)

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22,852 Holiday homes

Filters applied: Cycling holidays (22,852)

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

(36) Excellent 

1 / 19

Holiday villa in Italy

Lake Como / Argegno

5 bedroomsSleeps 82 nights min stay

  • 5 bedrooms
  • Sleeps 8
  • 2 nights min stay

from $566 / night

$3396 - $5546 / week

Book Book View

from $566 / night

(14) Very Good 

1 / 34

Italy holiday apartment rental

Rome / Central Rome

4 bedroomsSleeps 82 nights min stay

  • 4 bedrooms
  • Sleeps 8
  • 2 nights min stay

from $448 / night

$0 / week

Book Book View

from $448 / night

(9) Excellent 

1 / 20

Holiday apartment in Lake Como

Lake Como / Sala Comacina

3 bedroomsSleeps 72 nights min stay

  • 3 bedrooms
  • Sleeps 7
  • 2 nights min stay

from $169 / night

$1292 - $2258 / week

Book Book View

from $169 / night

Featured properties

(19) Excellent 

1 / 24

Holiday condo in Italy

Rome / Rione Monti

3 bedroomsSleeps 6Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies

from $226 / night

$1697 - $5477 / week

Book Book View

from $226 / night

(21) Excellent 

1 / 109

Italy holiday villa rental

Province of Modena / Modena

3 bedroomsSleeps 7Min stay varies

  • 3 bedrooms
  • Sleeps 7
  • Min stay varies

from $159 / night

$1110 / week

Book Book View

from $159 / night

(3) Excellent 

1 / 39

Holiday apartment in Lake Maggiore

Lake Maggiore / Verbania

2 bedroomsSleeps 62 nights min stay

  • 2 bedrooms
  • Sleeps 6
  • 2 nights min stay

from $113 / night

$882 / week

Book Book View

from $113 / night

(7) Excellent 

1 / 17

Holiday apartment with swimming pool in Italy

Province of Palermo / Cefalu

2 bedroomsSleeps 4Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies

from $130 / night

$905 - $2187 / week

Book Book View

from $130 / night

(3) Excellent 

1 / 16

Holiday apartment with shared pool in Italy

San Siro / Acquaseria

4 bedroomsSleeps 83 nights min stay

  • 4 bedrooms
  • Sleeps 8
  • 3 nights min stay

from $374 / night

$2604 - $3849 / week

Book Book View

from $374 / night

(3) Very Good 

1 / 50

Holiday townhouse in Italy

Oliveto Lario / Onno

4 bedroomsSleeps 10Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies

from $283 / night

$2219 - $4437 / week

Book Book View

from $283 / night

(8) Very Good 

1 / 53

Apartment rental in Tuscany

Florence / Central Florence

2 bedroomsSleeps 64 nights min stay

  • 2 bedrooms
  • Sleeps 6
  • 4 nights min stay

from $128 / night

$802 - $1271 / week

Book Book View

from $128 / night

(6) Excellent 

1 / 33

Lazio holiday apartment rental

Lazio / Rome

3 bedroomsSleeps 63 nights min stay

  • 3 bedrooms
  • Sleeps 6
  • 3 nights min stay

from $337 / night

$2359 - $2977 / week

Book Book View

from $337 / night

(7) Very Good 

1 / 16

Holiday home letting

Lake Como / Menaggio

2 bedroomsSleeps 53 nights min stay

  • 2 bedrooms
  • Sleeps 5
  • 3 nights min stay

from $136 / night

$906 - $1019 / week

Book Book View

from $136 / night

(10) Very Good 

1 / 37

Holiday apartment in Italy

Florence / Central Florence

3 bedroomsSleeps 71 night min stay

  • 3 bedrooms
  • Sleeps 7
  • 1 night min stay

from $394 / night

$0 / week

Book Book View

from $394 / night

(26) Excellent 

1 / 67

Lake Como holiday apartment rental

Lake Como / Como

3 bedroomsSleeps 6Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies

from $261 / night

$1642 - $2490 / week

Book Book View

from $261 / night

(7) Very Good 

1 / 29

Holiday apartment in Italy

Amalfi Coast / Positano

3 bedroomsSleeps 51 night min stay

  • 3 bedrooms
  • Sleeps 5
  • 1 night min stay

from $283 / night

$1755 - $2190 / week

Book Book View

from $283 / night

(9) Excellent 

1 / 33

Holiday apartment with shared pool in Tuscany

Greve in Chianti / San Polo in Chianti

2 bedroomsSleeps 55 nights min stay

  • 2 bedrooms
  • Sleeps 5
  • 5 nights min stay

from $113 / night

$787 - $944 / week

Book Book View

from $113 / night

(20) Excellent 

1 / 14

Holiday apartment in Lazio

Rome / San Pietro, Rome

3 bedroomsSleeps 93 nights min stay

  • 3 bedrooms
  • Sleeps 9
  • 3 nights min stay

from $272 / night

$1902 - $3843 / week

Book Book View

from $272 / night

(1) Excellent 

1 / 37

Cottage rental in Italy

Lake Como / Cadenabbia di Griante

3 bedroomsSleeps 61 night min stay

  • 3 bedrooms
  • Sleeps 6
  • 1 night min stay

from $397 / night

$2377 - $3169 / week

Book Book View

from $397 / night

(15) Excellent 

1 / 20

Ski condo to rent in Trentino-Alto Adige

Valdaora / Sorafurcia

2 bedroomsSleeps 5Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies

from $68 / night

$453 - $736 / week

Book Book View

from $68 / night

(12) Excellent 

1 / 24

Villa rental in Italy

Italian Riviera / Chiavari

4 bedroomsSleeps 8Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies

from $146 / night

$1011 - $2241 / week

Book Book View

from $146 / night

(5) Very Good 

1 / 35

Holiday b&b in Lake Como

Lake Como / Mandello del Lario

2 bedroomsSleeps 64 nights min stay

  • 2 bedrooms
  • Sleeps 6
  • 4 nights min stay

from $91 / night

$634 - $951 / week

Book Book View

from $91 / night

(7) Excellent 

1 / 20

Italy holiday apartment rental

Italian Riviera / Lerici

2 bedroomsSleeps 41 night min stay

  • 2 bedrooms
  • Sleeps 4
  • 1 night min stay

from $66 / night

$566 - $3169 / week

Book Book View

from $66 / night

(1) Excellent 

1 / 46

Lombardy holiday villa rental

Province of Brescia / Salo

4 bedroomsSleeps 9Min stay varies

  • 4 bedrooms
  • Sleeps 9
  • Min stay varies

from $272 / night

$1902 - $3849 / week

Book Book View

from $272 / night

(3) Very Good 

1 / 22

Holiday apartment rental

Florence / Ponte Vecchio

3 bedroomsSleeps 53 nights min stay

  • 3 bedrooms
  • Sleeps 5
  • 3 nights min stay

from $247 / night

$1558 - $2986 / week

Book Book View

from $247 / night

(7) Very Good 

1 / 24

Campania holiday villa rental

Province of Naples / Sorrento

2 bedroomsSleeps 8Min stay varies

  • 2 bedrooms
  • Sleeps 8
  • Min stay varies

from $146 / night

$848 - $3996 / week

Book Book View

from $146 / night

(10) Excellent 

1 / 34

Holiday apartment in Lake Como

Lake Como / Como

2 bedroomsSleeps 6Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies

from $159 / night

$951 - $1755 / week

Book Book View

from $159 / night

(5) Excellent 

1 / 23

Holiday apartment rental

Florence / Piazzale Michelangelo

3 bedroomsSleeps 8Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies

from $317 / night

$2026 - $3169 / week

Book Book View

from $317 / night

(10) Excellent 

1 / 24

Holiday villa in Tuscany

Elba Island / Capoliveri

1 bedroomSleeps 5Min stay varies

  • 1 bedroom
  • Sleeps 5
  • Min stay varies

from $114 / night

$431 - $1608 / week

Book Book View

from $114 / night

(11) Excellent 

1 / 25

Holiday home in Italy

Florence / Central Florence

2 bedroomsSleeps 62 nights min stay

  • 2 bedrooms
  • Sleeps 6
  • 2 nights min stay

from $125 / night

$849 - $1664 / week

Book Book View

from $125 / night

(4) Excellent 

1 / 126

Holiday apartment rental

Florence / Central Florence

3 bedroomsSleeps 71 night min stay

  • 3 bedrooms
  • Sleeps 7
  • 1 night min stay

from $203 / night

$1348 - $1545 / week

Book Book View

from $203 / night

(1) Very Good 

1 / 24

Apartment rental in Italy

Florence / Tornabuoni

2 bedroomsSleeps 4Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies

from $283 / night

$0 / week

Book Book View

from $283 / night

(12) Excellent 

1 / 90

Holiday condo rental

Florence / Santa Croce, Florence

3 bedroomsSleeps 62 nights min stay

  • 3 bedrooms
  • Sleeps 6
  • 2 nights min stay

from $169 / night

$1011 - $1129 / week

Book Book View

from $169 / night

(10) Excellent 

1 / 21

Italy holiday apartment let

Province of Florence / Figline Valdarno

2 bedroomsSleeps 4Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies

from $90 / night

$550 - $775 / week

Book Book View

from $90 / night

(3) Excellent 

1 / 66

Holiday villa with golf nearby in Italy

Province of Florence / Fiesole

3 bedroomsSleeps 6Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies

from $142 / night

$963 - $5659 / week

Book Book View

from $142 / night

(12) Very Good 

1 / 22

Italy holiday apartment rental

Rome / San Giovanni

4 bedroomsSleeps 8Min stay varies

  • 4 bedrooms
  • Sleeps 8
  • Min stay varies

from $165 / night

$1036 - $2411 / week

Book Book View

from $165 / night

(5) Excellent 

1 / 26

Lazio holiday farmhouse rental

Province of Rome / Nemi

4 bedroomsSleeps 81 night min stay

  • 4 bedrooms
  • Sleeps 8
  • 1 night min stay

from $91 / night

$623 - $2287 / week

Book Book View

from $91 / night

(8) Excellent 

1 / 24

Piedmont holiday penthouse rental

Province of Turin / Turin

2 bedroomsSleeps 62 nights min stay

  • 2 bedrooms
  • Sleeps 6
  • 2 nights min stay

from $340 / night

$1811 - $3396 / week

Book Book View

from $340 / night

(2) Excellent 

1 / 25

Tuscany holiday home rental

Cortona / Mercatale di Cortona

3 bedroomsSleeps 6Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies

from $190 / night

$1201 - $2173 / week

Book Book View

from $190 / night

(40) Excellent 

1 / 32

Apartment rental in Lombardy

Milan / Duomo

1 bedroomSleeps 32 nights min stay

  • 1 bedroom
  • Sleeps 3
  • 2 nights min stay

from $102 / night

$0 / week

Book Book View

from $102 / night

(1) Excellent 

1 / 41

Apartment rental in Tuscany

Province of Florence / Florence

3 bedroomsSleeps 71 night min stay

  • 3 bedrooms
  • Sleeps 7
  • 1 night min stay

from $334 / night

$1811 - $2263 / week

Book Book View

from $334 / night

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