Vacation homes - vacation rentals

Close

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

Filters applied: Private pool

12,882 Vacation rentals

(10) Excellent 

26

Home rental in Italy with swimming pool

Province of Imperia / Apricale

2 5 min stay varies

  • 2 bedrooms
  • sleeps 5
  • min stay varies
  • Nearest beach 13 mi
  • Swimming pool
  • Child friendly
Perched on the upper ridge of the charming hill town of Apricale, this villa has been fully restored and equipped for the ideal Mediterranean holiday. With breathtaking poolside views of the Val Nervia and surrounding villages, the villa offers high quality living with …see more

from $228 / night

$1,595 - $1,994 / week

Book View

from $228 / night

(2) Very Good 

12

Villa rental in Veneto with swimming pool

Province of Rovigo / San Martino di Venezze

16 30 1 night min

  • 16 bedrooms
  • sleeps 30
  • 1 night min
  • Nearest beach 40 mi
  • Swimming pool
  • Child friendly
Corte Carezzabella is a big "Court" in the heart of Veneto, just a few km from the main cities of art: Venice, Padua, Ferrara and Verona, and also near the seaside resorts of the Adriatic coast. The villa has 16 rooms of different size, all with private bathroom, air co …see more

from $1,826 / night

$11,608 / week

Book View

from $1,826 / night

(7) Excellent 

39

Vacation villa in Italy

Florence / Central Florence

5 10 1 night min

  • 5 bedrooms
  • sleeps 10
  • 1 night min
  • Nearest beach 98 mi
  • Swimming pool
  • Child friendly
This fabulous 5 Bedroom - 5 Bathroom Villa dates back to the XVIIIth century and lies on the hill of "Poggio Imperiale", one of the most exclusive residential areas of the city of Florence. Being only one mile away from Porta Romana square, a renowned "gate" into the …see more

from $564 / night

$4,186 - $6,722 / week

Book View

from $564 / night

(4) Excellent 

45

Vacation villa rental

Province of Florence / San Casciano in Val di Pesa

8 16 1 night min

  • 8 bedrooms
  • sleeps 16
  • 1 night min
  • Nearest beach 90 mi
  • Swimming pool
  • Child friendly
This wonderful 8 BR – 8 BA villa is located in the beautiful village of San Casciano Val di Pesa, just about 8 miles away from the beginning of the historic district of the city of Florence. The villa traces back its origins to the early XVI century and is considered …see more

from $1,481 / night

$10,366 - $13,555 / week

Book View

from $1,481 / night

(5) Excellent 

24

Vacation villa in Italy

Province of Florence / Montelupo Fiorentino

8 17 min stay varies

  • 8 bedrooms
  • sleeps 17
  • min stay varies
  • Nearest beach 55 mi
  • Swimming pool
  • Child friendly
Bobolino is the most beautiful neighborhood of Montelupo Fiorentino near Florence, Siena, Pisa and Lucca. Villa Bobolino is located on the hills and has 8 bedrooms (up to 17 people). Each room has a TV, a beautiful private bathroom with all of the comforts (towel-warmer …see more

from $339 / night

$2,283 - $5,609 / week

Book View

from $339 / night

(5) Excellent 

47

Vacation villa rental

Province of Perugia / Tuoro sul Trasimeno

8 16 1 night min

  • 8 bedrooms
  • sleeps 16
  • 1 night min
  • Beach/lakeside relaxation
  • Nearest beach 4 mi
  • Swimming pool
Set within 2.5 acres of private land, this magnificent 8 BR - 7 ½ BA Villa is nestled on top of a hill overlooking the wonderful Trasimeno Lake and is strategically located within a short distance from the lively town of Cortona as well as several other fabulous towns i …see more

from $815 / night

$5,701 / week

Book View

from $815 / night

(11) Excellent 

25

Home rental in Puglia with swimming pool

Province of Brindisi / Ceglie Messapica

2 8 7 nights min

  • 2 bedrooms
  • sleeps 8
  • 7 nights min
  • Nearest beach 15 mi
  • Swimming pool
  • Child friendly
Holidays in Italy: Roman stone ceiling, 3 meter ceiling height and a typical Italian architecture characterize this spacious property in the heart of Puglia, which has been restored and expanded in 2014 and, 2015. The well-kept vacation home offers space for up to 8 peo …see more

from $140 / night

$977 - $2,021 / week

Book View

Responds fast!
avg. 2 hours 56 minutes

from $140 / night

(5) Excellent 

25

Vacation villa in Italy

Province of Teramo / Atri

3 8 4 nights min

  • 3 bedrooms
  • sleeps 8
  • 4 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets
Modern, spacious villa, with magnificent, open views of the Gran Sasso and Maiella mountain ranges, close by, rolling hills, plus a distant view of the Adriatic sea. The accommodation is all on one level, with 3 large bedrooms, one of which has an en-suite bathroom, …see more

from $192 / night

$1,342 - $2,356 / week

Book View

from $192 / night

(20) Very Good 

26

Home rental in Italy with swimming pool

Ostuni / Casalini

3 6 4 nights min

  • 3 bedrooms
  • sleeps 6
  • 4 nights min
  • Beach/lakeside relaxation
  • Nearest beach 8 mi
  • Swimming pool
The ideal location for your stay in the stunningly beautiful Ostuni region. The charming and ancient trullo is the integral and heart of this 3 bedroom villa which has its of your own private swimming pool set in its own private garden! You are only 5 min from the city …see more

from $143 / night

$996 / week

Book View

Responds fast!
avg. 1 hour 41 minutes

from $143 / night

(2) Excellent 

39

B&b rental in Piedmont with swimming pool

Province of Asti / Vigliano d'Asti

3 6 3 nights min

  • 3 bedrooms
  • sleeps 6
  • 3 nights min
  • Nearest beach 100 mi
  • Swimming pool
  • Air conditioning
Fantastic farmhouse in the middle of vineyards in Piedmont (we belong now to UNESCO). The villa is located on top of a hill, from which there is featuring a stupendous view over the green hill in Piedmont. We fell into the object and have the old farmhouse (1907) comple …see more

from $209 / night

$1,292 - $6,769 / week

Book View

from $209 / night

(4) Excellent 

33

Vacation villa rental

Province of Fermo / Montelparo

7 12 7 nights min

  • 7 bedrooms
  • sleeps 12
  • 7 nights min
  • Nearest beach 30 mi
  • Swimming pool
  • Child friendly
This truly distinctive, Marche stone house has been converted to a comfortable villa. It has expensive and stunning views around over countryside to mountainous backdrop. The style of the furnishing indoors, combined with the characteristic shape of the building, blend …see more

from $307 / night

$2,152 - $2,739 / week

Book View

Responds fast!
avg. 2 hours 35 minutes

from $307 / night

(3) Excellent 

17

Marche Vacation villa rental

Province of Macerata / Cingoli

4 8 1 night min

  • 4 bedrooms
  • sleeps 8
  • 1 night min
  • Swimming pool
  • Child friendly
  • Ask about pets
Whether from the "Gin O'clock" secluded patio, the extensive alfresco dining terrace or the warm natural stone surround of the pool, this secluded property offers majestic views of rolling hills and hidden valleys. The villa benefits from all mod cons as well its own tr …see more

from $400 / night

$2,314 / week

Book View

from $400 / night

29

Villa rental in Italy with swimming pool

Province of Florence / San Godenzo

6 13 min stay varies

  • 6 bedrooms
  • sleeps 13
  • min stay varies
  • Swimming pool
  • Child friendly
  • Pet friendly
If you are a big family or a large group of friends, the ideal place to spend your holidays in full relax and confort is this elegant property with exclusive swimming pool and garden that can accommodate 12+1 people, composed by an independent Villa and a nice dependan …see more

from $587 / night

$4,043 / week

Book View

Responds fast!
avg. 1 hour 27 minutes

from $587 / night

(12) 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
*** Wedding conditions: listed at the bottom of this page *** Villa Benedetta is a beautiful historic residence that has been the beating heart of the Folonari family (a renowned name in the Italian wine panorama) for many years. Dating back to the early 1800s, the vi …see more

from $792 / night

$5,980 - $13,555 / week

Inquire View

from $792 / night

22

Vacation villa with swimming pool in Italy

Province of Siena / Montisi

3 8 7 nights min

  • 3 bedrooms
  • sleeps 8
  • 7 nights min
  • Nearest beach 30 mi
  • Swimming pool
  • Child friendly
Villa Montisi has been restored over the last few years with all the modern facilities within a traditional tuscan villa this makes for a truly unique holiday experience. Located in the scenic Val d'Orcia region which was declared a world heritage site by UNESCO. …see more

from $210 / night

$1,468 - $2,987 / week

Book View

Responds fast!
avg. 2 hours 6 minutes

from $210 / night

(8) Excellent 

40

Vacation home rental

Fivizzano / Pieve San Paolo

4 9 7 nights min

  • 4 bedrooms
  • sleeps 9
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Private garden
Our large detached family villa is set in the heart of the idyllic Tuscan hamlet of Po, situated high in the hills just outside Fivizzano. With breathtaking views across the mountains it is the perfect location to relax away from it all. The newly renovated villa comp …see more

from $275 / night

$1,922 - $2,033 / week

Book View

from $275 / night

(3) Excellent 

16

Vacation villa rental

Province of Padua / Cinto Euganeo

3 6 3 nights min

  • 3 bedrooms
  • sleeps 6
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly
Lovely villa on a hill with landscape mozza, equipped with every comfort for a relaxing holiday but without sacrificing the fun. A strategic position to reach cultural attractions and sports facilities of all kinds. In the surroundings you will find restaurants for all …see more

from $183 / night

$1,239 / week

Book View

from $183 / night

(2) Very Good 

20

Italy Vacation townhouse rental

Province of Grosseto / Magliano in Toscana

4 10 min stay varies

  • 4 bedrooms
  • sleeps 10
  • min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 12 mi
  • Swimming pool
There are two indipendent apartments in the house: mine is upstairs. The downstairs one has four double rooms: of these, two rooms can become twin rooms, and one has two single beds and a bunk bed. All rooms have ensuite bathrooms with shower. You can have a meal in th …see more

from $222 / night

$1,552 / week

Book View

from $222 / night

(35) Excellent 

19

Vacation villa rental

Cefalu / Sant'Ambrogio

3 6 4 nights min

  • 3 bedrooms
  • sleeps 6
  • 4 nights min
  • Beach/lakeside relaxation
  • Nearest beach 1 mi
  • Swimming pool
This three bedroom villa is situated in Sant'Ambrogio, near Cefalu on the northern coast of Sicily. With a private swimming pool, sundeck and spectacular panoramic sea views, this is a truly breathtaking holiday location. The mature gardens, packed with palm trees, offe …see more

from $114 / night

$798 - $3,144 / week

Book View

from $114 / night

(3) Very Good 

9

Vacation villa with swimming pool in Italy

Province of Cosenza / Trebisacce

3 8 1 night min

  • 3 bedrooms
  • sleeps 8
  • 1 night min
  • Swimming pool
  • Child friendly
  • Pet friendly
Rent villa with pool immersed in the heart of orange groves of trebisacce, enjoys quiet privacy and tranquillity. Just 5 min from the town centre and just 200 m from the sea. Ideal for those who want to spend holidays in tranquillity. The villa is subdivided over two f …see more

from $261 / night

$1,826 / week

Book View

from $261 / night

(30) Excellent 

37

Vacation villa with swimming pool in Italy

Province of Lucca / Bagni di Lucca

3 6 3 nights min

  • 3 bedrooms
  • sleeps 6
  • 3 nights min
  • Nearest beach 68 mi
  • Swimming pool
  • Child friendly
Casa Zola is a comfortable and stylish place to spend some quality time in Italy. It blends a high standard of modern day comfort and functionality with the original “Stile Liberty” design of the 1930s. You will enjoy spectacular views of the Lima valley and the surroun …see more

from $183 / night

$1,139 - $1,708 / week

Book View

Responds fast!
avg. 3 hours 6 minutes

from $183 / night

48

Vacation home in Tuscany

Province of Lucca / Barga

3 6 7 nights min

  • 3 bedrooms
  • sleeps 6
  • 7 nights min
  • Swimming pool
  • Suitable for children age 5+
  • Private garden
Delightful Rustic Villa in the heart of the Garfagnana Valley, overlooking the Apuan National park, close to Lucca, Pisa and Florence. La Rocca is a beautiful old detached Tuscan farmhouse, lovingly restored to provide a comfortable holiday home for up to 6 people. …see more

from $259 / night

$1,811 - $2,846 / week

Book View

from $259 / night

(5) Excellent 

47

Emilia-Romagna Vacation castle rental

Province of Piacenza / Nibbiano

6 17 2 nights min

  • 6 bedrooms
  • sleeps 17
  • 2 nights min
  • Swimming pool
  • Child friendly
  • Private garden
Il castello di Tassara si trova sulle prime colline piacentine, a 500mt di altitudine, al limitare di un piccolo borgo antico. Dista da Milano 75km da Milano E' circondato da un vasto giardino ben accudito, con piscina a sfioro in pietra. Il panorama, bellissimo, è a pe …see more

from $1,212 / night

$8,057 / week

Book View

from $1,212 / night

12

Villa rental in Italy with swimming pool

Province of Parma / Salsomaggiore Terme

6 16 7 nights min

  • 6 bedrooms
  • sleeps 16
  • 7 nights min
  • Nearest beach 115 mi
  • Swimming pool
  • Child friendly
The estate has rooms where everyone can feel at home, including the particularly impressive, almost nave-like open loft, converted into a spacious living area. Yet all the guests can withdraw to the privacy of the six cosy bedrooms, each equipped with its own modern bat …see more

from $866 / night

$6,060 / week

Inquire View

from $866 / night

(1) Excellent 

15

Vacation apartment with swimming pool in Italy

Province of Arezzo / Monte San Savino

3 7 1 night min

  • 3 bedrooms
  • sleeps 7
  • 1 night min
  • Swimming pool
  • Air conditioning
  • Private garden
Country farm-house completely restored in the village of Monte San Savino, immersed in the Touscany country near Arezzo, Siena e Cortona, only 4 km of walk far from the castle of Gargonza. Inside simple but comfortable bedrooms with a sight beams, television and …see more

from $196 / night

$1,370 / week

Book View

from $196 / night

(4) Excellent 

32

Vacation villa in Umbria

Province of Terni / Montecchio

5 12 min stay varies

  • 5 bedrooms
  • sleeps 12
  • min stay varies
  • Nearest beach 40 mi
  • Swimming pool
  • Child friendly
The villa lies 500 meters from the charming village of Montecchio in a hilly location. From the villa you have a panoramic sight on the Tiber valley. The property has an own garden (completely fenced) with a swimming pool (10 by 3,5 meter). The whole property is for pri …see more

from $234 / night

$1,458 - $2,654 / week

Book View

Responds fast!
avg. 3 hours 35 minutes

from $234 / night

(3) Excellent 

35

Ski villa to rent in Italy

Province of Verona / San Pietro in Cariano

7 22 min stay varies

  • 7 bedrooms
  • sleeps 22
  • min stay varies
  • Nearest beach 10 mi
  • Swimming pool
  • Ski
Villa San Bonifacio is an ideal dwelling for charming holidays for groups of friends or families who wish to come together to share in a historic villa holiday enjoyment with a magical atmosphere. The villa is rented entirely and our guests are offered a discreet servic …see more

from $131 / night

$1,305 - $12,325 / week

Book View

from $131 / night

(63) Excellent 

49

Italy Vacation villa rental

Province of Arezzo / Anghiari

5 10 7 nights min

  • 5 bedrooms
  • sleeps 10
  • 7 nights min
  • Nearest beach 66 mi
  • Swimming pool
  • Child friendly
Casa Leana is over 350 years old and brimming with gorgeous original features from chunky beamed, wood ceilings and exposed stone walls to the traditional tiled kitchen. We have also lavished a whole lot of love on the interior and furnishings to transform our rambling …see more

from $446 / night

$3,120 - $4,480 / week

Book View

from $446 / night

(8) Excellent 

Certificate of Excellence

28

Abruzzo Vacation villa rental

Province of Pescara / Moscufo

4 12 7 nights min

  • 4 bedrooms
  • sleeps 12
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 11 mi
  • Swimming pool
Lovingly restored and built by a local architect and artisans, the Villa has many original features typical of the region whilst at the same time every effort has been made to provide all modern home comforts with the added advantage of both air conditioning and central …see more

Certificate of Excellence

from $253 / night

$1,767 - $2,650 / week

Book View

Responds fast!
avg. 1 hour 35 minutes

from $253 / night

33

Italy Vacation villa rental

Province of Lucca / Barga

4 12 5 nights min

  • 4 bedrooms
  • sleeps 12
  • 5 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly
The unique privacy of Chiesetta, protected by the intimate hills of the Garfagnana creates a perfect holiday destination for those looking to spend quality time in a peaceful rustic villa, cool off in a swimming pool after a day in the sun, walk through charming medieva …see more

from $222 / night

$1,479 - $2,957 / week

Book View

from $222 / night

44

Marche Vacation villa rental

Province of Macerata / San Ginesio

4 8 7 nights min

  • 4 bedrooms
  • sleeps 8
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 40 mi
  • Swimming pool
Villa Tua provides luxury self catering accomodation and is the perfect private retreat - just what you need to relax and get away from it all. The villa has breathtaking views of romantic hilltop villages, vineyards and olive groves rolling down to the Adriatic Sea w …see more

from $233 / night

$1,627 - $2,218 / week

Book View

Responds fast!
avg. 3 hours 24 minutes

from $233 / night

(3) Very Good 

99

Vacation farmhouse with swimming pool in Puglia

Province of Lecce / Carpignano Salentino

4 14 min stay varies

  • 4 bedrooms
  • sleeps 14
  • min stay varies
  • Nearest beach 12 mi
  • Swimming pool
  • Child friendly
We cannot describe the beauty, charm and exclusivity of this farm which lays beyond words. You can fully enjoy all its beauty if you should choose this exceptional home for your stay in Salento. To dive into the magical landscape and history of Puglia, with many pleasan …see more

from $292 / night

$2,044 / week

Book View

from $292 / night

(18) Very Good 

Certificate of Excellence

18

Apartment rental in Italy

Province of Siena / Siena

1 4 min stay varies

  • 1 bedroom
  • sleeps 4
  • min stay varies
  • Nearest beach 105 mi
  • Swimming pool
  • Car not necessary
This very stylish 430-square-foot apartment a few minutes walk from Piazza del Campo. You will not need anymore to walk up 66 steps to access this apartment,because now there is a new elevator to lift you on two amazing terraces and their spectacular views. The main l …see more

Certificate of Excellence

from $131 / night

$1,461 / week

Book View

Responds fast!
avg. 3 hours 46 minutes

from $131 / night

22

Vacation villa in Italy

Province of Macerata / Loro Piceno

6 12 7 nights min

  • 6 bedrooms
  • sleeps 12
  • 7 nights min
  • Nearest beach 37 mi
  • Swimming pool
  • Child friendly
Completely renovated from top to bottom, and sitting in the dramatic area of Le Marche, with an inviting swimming pool, Villa Mara is a wonderfully private and rural retreat for two or three families or group of friends. The house is in an ideal spot for those who wan …see more

from $392 / night

$2,739 - $3,652 / week

Book View

Responds fast!
avg. 2 hours 35 minutes

from $392 / night

(5) Very Good 

38

Italy Vacation home rental

Province of Arezzo / Lucignano

4 8 min stay varies

  • 4 bedrooms
  • sleeps 8
  • min stay varies
  • Nearest beach 70 mi
  • Swimming pool
  • Child friendly
The house lies in a top hill location with a beautiful panorama only 2 kms from the small charming village of Rigomagno, between Siena and Arezzo (both cities are around 30 Kms far away). It's a very quiet location. The house has a large garden with pool (13,5x5), whole …see more

from $228 / night

$1,424 - $2,279 / week

Book View

Responds fast!
avg. 3 hours 35 minutes

from $228 / night

(1) Excellent 

25

Vacation home with swimming pool in Italy

Province of Brindisi / San Vito dei Normanni

2 5 min stay varies

  • 2 bedrooms
  • sleeps 5
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
Villa Oliva, a very private charming villa with pool, set amongst ancient olive trees. A perfect blend between tradition and minamalistic mordern comfort. An ideal location to unwind and discover the best that Puglia has to offer. Villa Oliva is located less than 2 km …see more

from $188 / night

$1,315 / week

Book View

from $188 / night

(2) Excellent 

22

Italy Vacation trullo accommodation

Province of Bari / Locorotondo

4 8 7 nights min

  • 4 bedrooms
  • sleeps 8
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Trulli Mirabello is a stunning eight cone trullo residential property located just ouside the town of Locorotondo, one of the most beautiful towns in Valle d'Itria (provinces of Bari and Taranto). Not far from the Adriatic sea (only 20 minutes by car to reach Fasano and …see more

from $336 / night

$2,350 - $3,721 / week

Book View

Responds fast!
avg. 46 minutes

from $336 / night

(3) Excellent 

30

Vacation villa rental

Province of Messina / Graniti

2 7 3 nights min

  • 2 bedrooms
  • sleeps 7
  • 3 nights min
  • Nearest beach 10 mi
  • Swimming pool
  • Child friendly
Circondata da un giardino mediterraneo (vigneto, frutteto, ortaggi) con fiori profumati e piante, Villa Gaetano è sita a breve distanza dal centro di Graniti,nel territorio della valle dell'Alcantara, vicina alle Gole dell'Alcantara, Giardini Naxos, Taormina ed alCampo …see more

from $327 / night

$2,350 - $3,721 / week

Book View

Responds fast!
avg. 2 hours 28 minutes

from $327 / night

(7) Very Good 

10

Villa rental in Italy with swimming pool

Province of Perugia / Pietralunga

3 6 3 nights min

  • 3 bedrooms
  • sleeps 6
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly
Banditelle holiday villa - nothing less than enchanting. Relax by the pool and luxuriate, soak in the stunning scenery and solitude. Alternatively, venture out from your personal paradise and the very best of Italian culture, history and hospitality awaits. The town of …see more

from $185 / night

$1,257 / week

Book View

from $185 / night

(3) Excellent 

18

Italy Vacation villa rental

Province of Pescara / San Valentino in Abruzzo Citeriore

3 8 min stay varies

  • 3 bedrooms
  • sleeps 8
  • min stay varies
  • Nearest beach 30 mi
  • Swimming pool
  • Child friendly
Holiday Apartment Duepiùinsieme is in the green heart of Abruzzo, surrounded by mountains and nature, located in Majella National Park. The house, set within a forest of oaks, is composed of living room, large equipped kitchen and 3bedrooms with private entrance. …see more

from $157 / night

$1,044 - $1,631 / week

Book View

from $157 / night

Also consider