Vacation homes - vacation rentals

Close

View larger map

Also consider

Apartments Tuscany
24,827 properties
Villas Sicily
15,087 properties
Lazio
10,417 properties
Villas Puglia
9,208 properties
Campania
6,870 properties
Villas Sardinia
6,646 properties
Apartments Lombardy
6,370 properties
Apartments Veneto
4,279 properties
Apartments Umbria
3,640 properties
Villas Liguria
2,913 properties
Apartments Piedmont
2,432 properties
Holiday homes Marche
1,974 properties
Emilia-Romagna
1,922 properties
Apartments Calabria
1,555 properties
Villas Abruzzo
1,178 properties
Trentino-Alto Adige
1,138 properties
Friuli Venezia Giulia
751 properties
Basilicata
540 properties
Valle d'Aosta
449 properties
Molise
151 properties

Italy

No dates Enter dates for accurate prices -

Adults, Children

Enter dates for more accurate prices

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

20,669 Vacation rentals

Filters applied: Cycling trips

(3) Very Good 

23

Italy Vacation home rental

Cilento and Vallo di Diano National Park / Pisciotta

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
House enjoys an idyllic location, surrounded by greenery of the National Park of Cilento Pisciotta. The building has a large outdoor area, put in to prevent hazards for children. It is accessed through a driveway downhill - well lit at night with time relay - and two sh …see more

from $36 / night

$354 / week

Book View

Responds fast!
avg. 2 hours 45 minutes

from $36 / night

(16) Excellent 

16

Vacation b&b in Italy

Province of Perugia / Spoleto

4 13 1 night min

  • 4 bedrooms
  • Sleeps 13
  • 1 night min
  • Child friendly
  • Pet friendly
Typical Umbrian farmhouse of the nineteenth century, restored to its former shape with chestnut beams and stone walls, terracotta floors, view. The House is divided into 3 independent living areas and other areas. Each unit has its own entrance is from the country tha …see more

from $71 / night

$471 / week

Book View

from $71 / night

(68) Excellent 

44

Italy Vacation apartment accommodation

Province of Messina / Taormina

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.6 mi
  • Child friendly
"Borgo Borghese" guest house is located in Sant 'Alessio Siculo in the beautiful Val d' Agro just 10 km from Taormina. We are in the countryside at 600 m from the sea. Inside the property there are two buildings, one is the main house where the owners live and in the ot …see more

from $65 / night

$442 - $942 / week

Inquire View

from $65 / night

13

Vacation villa in Veneto

Province of Belluno / San Gregorio nelle Alpi

2 6 2 nights min

  • 2 bedrooms
  • Sleeps 6
  • 2 nights min
  • Child friendly
  • Pet friendly
  • Private garden
The house, with 2000sqm discovered in the grass. can accommodate up to 6 people, consists of a master bedroom, a bedroom with two bunk beds, a bathroom, a kitchen, a cozy living area, a large terrace and a large basement with washing machine and sink. It is located in a …see more

from $71 / night

$495 / week

Book View

from $71 / night

(4) Excellent 

13

Veneto ski penthouse to rent.

Province of Belluno / Auronzo di Cadore

2 5 7 nights min

  • 2 bedrooms
  • Sleeps 5
  • 7 nights min
  • Nearest beach 150 mi
  • Ski
  • Child friendly
For those who love peace and tranquility this attic on the third floor of 90 square meters. with large kitchen and separate living room decorated in a mountain style. dedicated parking space and giardino.Servizio linens included in prezzo.Situata in the country of CKING …see more

from $59 / night

$412 / week

Book View

Responds fast!
avg. 49 minutes

from $59 / night

8

Italy Vacation townhouse rental

Italian Riviera / Riva Ligure

2 7 Min stay varies

  • 2 bedrooms
  • Sleeps 7
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Pet friendly
Apartment 100 m2 Ligurian. on 2 floors to 20 mt. from the sea, renovated in June 2015 with kitchenette, large living room, large bedroom, bedroom, bathroom, laundry and storage room. The apartment is located in a characteristic Ligurian House of 1800 with vaulted ceili …see more

from $142 / night

$589 - $1,084 / week

Book View

Responds fast!
avg. 1 hour 38 minutes

from $142 / night

(36) Excellent 

12

Vacation studio rental

Province of Lecce / Porto Cesareo

Studio 2 Min stay varies

  • Studio
  • Sleeps 2
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 1 mi
  • Child friendly
In the heart of Salento, surrounded by a private garden, just minutes from the center of Porto Cesareo and renowned beaches, is Casa La Strea. Casa La Strea features an elegant mini suites, modern and stylish decor, featuring a balcony overlooking the garden. The standa …see more

from $59 / night

$412 - $1,154 / week

Book View

from $59 / night

33

Italy Vacation villa rental

Province of Florence / Florence

4 8 3 nights min

  • 4 bedrooms
  • Sleeps 8
  • 3 nights min
  • Nearest beach 120 mi
  • Swimming pool
  • Child friendly
This wonderful recently renovated 4BR/3.5BA villa sits on top of a hill and is part of a 20 hectares biological farm, immersed in the most beautiful typical Tuscan landscape. A luxury private swimming pool as well as a private lake and the most amazing direct views on …see more

from $606 / night

$4,242 / week

Book View

from $606 / night

18

Italy Vacation apartment rental

Province of Palermo / Partinico

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Ask about pets
Surrounded by a large peach orchard this well maintained country house with several apartments, each with a private terrace and plenty of privacy. From June 2017 a 7 times 13.5 meters large pool set in beautiful landscaped gardens will be available, which can be used fr …see more

from $53 / night

$365 - $1,119 / week

Book View

Responds fast!
avg. 1 hour 31 minutes

from $53 / night

(1) Excellent 

24

Italy Vacation b&b rental

Province of Turin / Cavagnolo

3 15 Min stay varies

  • 3 bedrooms
  • Sleeps 15
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly
A farm in green surroundings in the Monferrato hills where anyone who wishes can find hospitality and welcome. One space available to families, groups, organizations. The Tree of Kiri offers its guests single, double, triple rooms with bathroom, finely furnished. You ca …see more

from $107 / night

$650 - $4,492 / week

Book View

from $107 / night

(34) Very Good 

24

Vacation apartment in Italy

Province of Treviso / Treviso

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
  • Nearest beach 30 mi
  • Child friendly
  • Car not necessary
A truly Italian experience... Apartment Sile is located in a residential suburb of Treviso, often referred to as 'citta d'aque' (city of water) close to Venice and in the heart of the beautiful Veneto region. Quiet and peaceful, yet only fifteen minutes from the centre …see more

from $68 / night

$432 - $613 / week

Book View

Responds fast!
avg. 1 hour 11 minutes

from $68 / night

(6) Excellent 

17

Vacation villa in Sicily

Castelvetrano / Marinella di Selinunte

1 5 Min stay varies

  • 1 bedroom
  • Sleeps 5
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 6 mi
  • Child friendly
Sicilian house, lovingly restored, fits harmoniously into the hill that slopes towards the sea and towards Selinunte. It is 6 kilometers from the archaeological site of Selinunte and the seaside towns of the Sicilian Canal. It is located in the center of a vast area ric …see more

from $65 / night

$454 / week

Book View

from $65 / night

(1) Excellent 

7

Italy Vacation bungalow rental

Province of Ogliastra / Tortoli

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Nearest beach 0.5 mi
  • Child friendly
  • Pet friendly
This is a wooden habitat in the countryside on a plot of 2000 m 2 to 5 minutes walk from a sandy beach with clear waters. The shade of olive trees, chestnut trees, orange trees and weeping willows also ensures exceptional freshness in full summer. There is an outdoor pe …see more

from $47 / night

$330 - $495 / week

Book View

from $47 / night

(19) Very Good 

22

Vacation apartment in Tuscany

Castiglione Della Pescaia / Punta Ala

1 5 7 nights min

  • 1 bedroom
  • Sleeps 5
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.5 mi
  • Swimming pool
Suite Description: Suite (private) 50 sq. approximately inserted into the Residence Hotel (RTA) called "Golf Hotel Punta Ala" (4 stars). Two rooms with 5 beds, consisting of living area with TV and kitchenette, refrigerator, 1 sofa bed, 1 pull-out bed, double bedroom wi …see more

from $84 / night

$589 - $2,708 / week

Book View

from $84 / night

(5) Very Good 

16

Tuscany Vacation apartment rental

Radicofani / Contignano

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Nearest beach 100 mi
  • Child friendly
  • Pet friendly
Casa Franci - Andrea Apartment E 'in the historic center of Contignano, medieval village of the municipality of Radicofani, in the Val d'Orcia, UNESCO World Heritage Site, in the province of Siena Tuscany land of rare beauty where you overlook rich in history and tradi …see more

from $95 / night

$471 / week

Book View

Responds fast!
avg. 3 hours 0 minutes

from $95 / night

33

Villa rental in Campania with indoor pool, tennis court

Isola d'Ischia / Forio

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 1 mi
  • Swimming pool
Luxury Villa with descent to the sea, swimming pool, SPA, tennis, billiards wake up surrounded by nature, feel on a desert island, this is the feeling you get when you stay in. A 3000 square meters between the forest of Oaks at Punta Caruso and the sea and descend to t …see more

from $421 / night

$2,947 - $7,073 / week

Book View

from $421 / night

(10) Excellent 

Certificate of Excellence

16

B&b rental in Veneto

Province of Belluno / Santa Giustina

1 5 2 nights min

  • 1 bedroom
  • Sleeps 5
  • 2 nights min
  • Child friendly
  • Car not necessary
  • Ask about pets
The Mak family-Rizieri, Lara, Peter and Stella-will be happy to accommodate you in their small and cosy ' cottage '. We speak English. La Casetta della Pia, as it is, is a cosy apartment open to light and people meeting, styles, thoughts and experiences. There is, there …see more

Certificate of Excellence

from $76 / night

$413 / week

Book View

from $76 / night

(5) Excellent 

23

Vacation apartment with shared pool, golf nearby in Tuscany

Province of Siena / Buonconvento

2 4 4 nights min

  • 2 bedrooms
  • Sleeps 4
  • 4 nights min
  • Nearest beach 60 mi
  • Swimming pool
  • Child friendly
"Prisca House" is a wonderful first floor apartment lovingly restored to a high standard, set as a precious stone on the heart of Buonconvento Borgo. Tastefully and comfortable furnished, this apartment has a warm and friendly atmosphere and it offers guests a truly uni …see more

from $100 / night

$660 - $1,154 / week

Book View

Responds fast!
avg. 3 hours 33 minutes

from $100 / night

20

Apartment rental in Piedmont

Province of Novara / Orta San Giulio

1 4 3 nights min

  • 1 bedroom
  • Sleeps 4
  • 3 nights min
  • Beach/lakeside relaxation
  • Nearest beach 1 mi
  • Child friendly
Partial lake view from the balcony which has chairs and small table. Comfortable modern apartment situated in the historical part of Orta just 50 meters from the lake. The property comprises of a entrance with galley kitchen with all mod-cons, lounge with sofa beds on r …see more

from $88 / night

$580 - $1,051 / week

Book View

Responds fast!
avg. 3 hours 23 minutes

from $88 / night

(17) Excellent 

Certificate of Excellence

42

Vacation townhouse rental

Modica / Modica Bassa

2 6 3 nights min

  • 2 bedrooms
  • Sleeps 6
  • 3 nights min
  • Beach/lakeside relaxation
  • Air conditioning
Ideal for two couples, or a couple with adult offspring, with additional space for two more guests: a light-filled town house with its own independent guests' apartment in the fashionable Cartellone district of the Unesco preserved baroque town of MODICA, southeast Sici …see more

Certificate of Excellence

from $115 / night

$674 - $1,429 / week

Book View

from $115 / night

18

Vacation b&b in Italy

Province of Fermo / Smerillo

3 8 3 nights min

  • 3 bedrooms
  • Sleeps 8
  • 3 nights min
  • Nearest beach 45 mi
  • Child friendly
  • Pet friendly
The organic farm Amargi is situated at the foot of the Sibillini Mountains 2km from the village of Smerillo (FM). We deal with beekeeping, cultivation of medicinal plants and the production of apples. We offer hospitality at our Farm Amargiin a self-contained apartment …see more

from $153 / night

$825 / week

Book View

from $153 / night

(3) Very Good 

26

Ski villa to rent in Italy

Argegno / Sant Anna

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Beach/lakeside relaxation
  • Ski
  • Child friendly
Villa in pietra panoramica, A 6oomt slm Sempre esposta al sole, con giardino privato, box, camino. A dieci minuti dal lago di Como. Immersa nel verde, in una zona isolata, una tranquillità veramente unica ideale per passare dei giorni di completo relax …see more

from $76 / night

$530 - $707 / week

Book View

from $76 / night

(1) Very Good 

12

Vacation apartment in Italy

Italian Riviera / Levanto

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.01 mi
  • Child friendly
10 steps from the sea, mansard apartment Wonderful and comfortable mansard apartment just 10 meters from the sea and at the beginning of the historical center with sea view Centrally located just 10 steps from the sea and from the beginning of the historical center of …see more

from $69 / night

$471 / week

Book View

from $69 / night

(2) Excellent 

12

Vacation townhouse in Italy

Province of Varese / Taino

2 5 1 night min

  • 2 bedrooms
  • Sleeps 5
  • 1 night min
  • Beach/lakeside relaxation
  • Child friendly
  • Ask about pets
House of the early 900 restructured in 2013, immersed in the peace and quiet of a small town (Taino) and surrounded by a beautiful garden, a few steps from Lake Maggiore. We offer 3 apartments, each of which can be independent and accommodating two to five people. Depen …see more

from $106 / night

$589 - $1,084 / week

Book View

from $106 / night

(26) Excellent 

33

Vacation villa with swimming pool in Tuscany

Province of Arezzo / Poppi

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Nearest beach 130 mi
  • Swimming pool
  • Child friendly
Five bedrooms, 4 double bedrooms and one bedroom with two single beds, 3 full bathrooms each with a shower. Large living room with stereo, CD, SAT TV and a large fireplace. Many outdoor eating areas - overlooking the castle, overlooking the pool and overlooking the su …see more

from $236 / night

$1,178 - $3,297 / week

Inquire View

from $236 / night

(30) Excellent 

14

Vacation apartment in Sardinia

Province of Oristano / Bosa

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 2 mi
  • Child friendly
Discover Bosa and Sardinia in a new way. Our apartments are great (from 60 to 80 m2) brand new and totally equipped (living room, dining table, sofa, flat screen 42 inch Tv with satellite channels, kitchen with fridge, induction plans, tools, bathrooms with tub or showe …see more

from $137 / night

$956 / week

Book View

from $137 / night

(21) Excellent 

47

Vacation townhouse in Italy

Province of Florence / Pontassieve

2 6 2 nights min

  • 2 bedrooms
  • Sleeps 6
  • 2 nights min
  • Nearest beach 127 mi
  • Child friendly
  • Ask about pets
The agriturismo le Pialle, surrounded by greenery and quiet of the beautiful Tuscan countryside, a stone's throw from Florence is the perfect place to relax away from the bustle of the city. From here you can easily visit Florence and other cities of Tuscany with trips …see more

from $71 / night

$472 - $1,132 / week

Book View

from $71 / night

15

Vacation hotel apartment rental

Piombino / Riotorto

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.8 mi
  • Swimming pool
Small tourist complex divided into cottages, just 500 metres from the sea. The apartments are all located on the first floor, except one, all have a splendid terrace overlooking the sea or pine forest. The apartment is composed as follows: terrace, closed with wooden …see more

from $59 / night

$413 - $1,533 / week

Book View

from $59 / night

(3) Excellent 

31

Vacation chateau in Italy

Province of Udine / Strassoldo

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 18 mi
  • Child friendly
CASA RAMBALDO (90 sqm - 1 floor + loft - sleeps 4 people) This lovely medieval stone holiday home distributed on one floor plus a mezzanine is part of the Castle of Strassoldo di Sopra. It preserves the magic atmosphere of the past and has a private gard …see more

from $144 / night

$1,005 / week

Book View

from $144 / night

(3) Excellent 

29

Vacation home with swimming pool in Italy

Province of Viterbo / Bolsena

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.6 mi
  • Swimming pool
The property lies in a very quiet area, just 500 meters from the lake of Bolsena. It features a large garden of about 10.000m2 (completely fenced) and a 6x12 meter swimming pool, all for private use of the tenant. The property has been furnished with taste. It is suitab …see more

from $177 / night

$1,119 - $2,350 / week

Book View

Responds fast!
avg. 3 hours 50 minutes

from $177 / night

(7) Excellent 

45

Vacation villa with swimming pool in Italy

Province of Florence / Greve in Chianti

9 18 1 night min

  • 9 bedrooms
  • Sleeps 18
  • 1 night min
  • Nearest beach 130 mi
  • Swimming pool
  • Child friendly
Villa Benedetta is a beautiful historic residence that has been for many years the beating heart of the Folonari family, a renowned name in the Italian wine panorama. Dating back to the early 1800, the villa is located at the center of the family’s agricultural holding …see more

from $825 / night

$7,418 - $14,011 / week

Inquire View

from $825 / night

(1) Very Good 

13

Vacation apartment with shared pool in Tuscany

Province of Siena / Pievescola

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Nearest beach 70 mi
  • Swimming pool
  • Child friendly
One room apartment, very bright and with breathtaking views over the Tuscan countryside. Comfortable and functional, it is situated on the ground floor with private entrance and outdoor porch furnished for dining and enjoying the quiet and the spectacle of nature. Set …see more

from $71 / night

$472 / week

Book View

from $71 / night

(1) Excellent 

22

Tuscany Vacation apartment rental

Province of Siena / Siena

4 9 Min stay varies

  • 4 bedrooms
  • Sleeps 9
  • Min stay varies
  • Nearest beach 80 mi
  • Child friendly
  • Car not necessary
Prestigious house in the medieval heart of Siena. A beautiful house in the center of Siena, where to be pampered in the beauty of a unique city. Step into a historical building in Siena - a short walk from Piazza del Campo - and treat yourself to your holiday in a charm …see more

from $212 / night

$1,484 / week

Book View

Responds fast!
avg. 3 hours 17 minutes

from $212 / night

44

Vacation villa with swimming pool in Italy

Province of Siena / Castellina In Chianti

6 13 1 night min

  • 6 bedrooms
  • Sleeps 13
  • 1 night min
  • Nearest beach 110 mi
  • Swimming pool
  • Child friendly
Set in the heart of the magical Chianti Classico region, this wonderful 6 BD – 5 BA Villa dates back to the 15th century and is strategically located with a short distance from the lively village of Castellina in Chianti. Surrounded by an exceptionally beautiful landsc …see more

from $656 / night

$4,592 - $7,006 / week

Book View

from $656 / night

(8) Excellent 

26

Vacation apartment in Italy

Province of Carbonia-Iglesias / Buggerru

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
In the small town of Buggerru, south-west coast of Sardinia, there is the lovely apartment on the sea, with its own entrance, consists of a large veranda with sea view, kitchen, 2 bedrooms, living room, kitchen and bathroom. Equipped with all the comforts (washing machi …see more

from $59 / night

$395 - $1,013 / week

Book View

from $59 / night

(10) Excellent 

26

Vacation villa with swimming pool in Italy

Muravera / Costa Rei

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 3 mi
  • Swimming pool
A beautiful luxury Villa to rent in Sardinia, 2 miles from the best sea side in the World with the mountains all around. Tranquil yet 5 minutes drive from the shops, restaurant, "Agriturismo", Pizzerias and the Yatching Club harbour where you can hire boat or go for an …see more

from $403 / night

$2,821 - $4,707 / week

Book View

Responds fast!
avg. 2 hours 4 minutes

from $403 / night

11

Vacation townhouse with shared pool in Tuscany

Castiglion Fiorentino / Orzale

2 5 Min stay varies

  • 2 bedrooms
  • Sleeps 5
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Ask about pets
"La Fenice" is located in the lovely Valley of Chios, which with the opposite Valley of Chiana frames Castiglion Fiorentino, typical Tuscan hill country rich in architectural beauty and corners to discover. The "Phoenix" is located on a hill about 300 metres above sea l …see more

from $213 / night

$802 - $1,002 / week

Book View

from $213 / night

(3) Excellent 

12

Vacation condo in Italy

Mascali / Fondachello

2 6 1 night min

  • 2 bedrooms
  • Sleeps 6
  • 1 night min
  • Beach/lakeside relaxation
  • Child friendly
  • Pet friendly
Rent apartment in 60, 70 m from the sea, (1 minute walk), with large kitchen, bathroom, small room with two bunk beds and large double room, complete with every comfort, fully furnished (TV, washing machine, free internet wifi, parking inside the residence and in excell …see more

from $39 / night

$260 / week

Book View

from $39 / night

(2) Very Good 

15

Vacation villa in Italy

Province of Agrigento / Menfi

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Beach/lakeside relaxation
  • Child friendly
  • Pet friendly
Cosy Cottage immersed in nature, surrounded by ornamental trees with large garden and fruit trees, barbecue, veranda, 2 bedrooms, 1 double, 2 single beds, 1 bathroom, kitchen and living room, indoor and outdoor shower. place for animals. At 4 km from the sea with crysta …see more

from $47 / night

$330 / week

Book View

from $47 / night

(1) Good 

19

Ski apartment to rent in Italy

Pinzolo / Madonna Di Campiglio

1 5 4 nights min

  • 1 bedroom
  • Sleeps 5
  • 4 nights min
  • Ski
  • Child friendly
  • Car not necessary
Casa Tre Pini is a wonderful sun drenched apartment on the third floor, just a short walk from the pedestrian town centre and 200 meters from the base of the Spinale cable car which will whisk you up to Monte Spinale, at 2100 meters, the heart of Madonna di Campiglio va …see more

from $130 / night

$907 / week

Book View

Responds fast!
avg. 3 hours 34 minutes

from $130 / night