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: Swimming pool

29,533 Vacation rentals

(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

$978 - $2,023 / week

Book View

Responds fast!
avg. 2 hours 56 minutes

from $140 / 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 $816 / night

$5,707 / week

Book View

from $816 / night

17

Vacation home rental

Impruneta / Falciani

4 11 5 nights min

  • 4 bedrooms
  • sleeps 11
  • 5 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly
Our farmhouse is very old, once it was the seat of the farmers who were responsible for the care of the vines. It has been renovated but respecting its nature, the fireplace is the original one and all the ceilings have wooden beams. Windows and doors have been moderniz …see more

from $237 / night

$1,313 / week

Book View

Responds fast!
avg. 3 hours 39 minutes

from $237 / night

(3) Excellent 

18

Vacation villa with shared pool, golf nearby in Italy

City of Venice / Venice

12 28 2 nights min

  • 12 bedrooms
  • sleeps 28
  • 2 nights min
  • Nearest beach 30 mi
  • Swimming pool
  • Child friendly
Castel Venezze is a delicious countryside relais obtained in a Venetian Villa of the fifteenth-century. The beautiful and original antiques furniture and ornaments of the apartments and rooms reflect the elegant style of its age. It is the ideal destination for a pleasa …see more

from $2,611 / night

$18,277 / week

Book View

from $2,611 / night

(2) Excellent 

12

Italy Vacation townhouse rental

Province of Grosseto / Montemassi

2 5 2 nights min

  • 2 bedrooms
  • sleeps 5
  • 2 nights min
  • Nearest beach 20 mi
  • Swimming pool
  • Child friendly
La rosa dei venti is located within the grounds of the farm, cultivated mainly Ristella vineyards and olive groves and is located at the foot of the medieval village of Montemassi in about 200 meters above sea level, in a setting of olive trees, typical of the Maremma g …see more

from $112 / night

$782 / week

Book View

from $112 / night

40

Vacation farmhouse in Italy

Province of Pesaro and Urbino / Cagli

4 10 min stay varies

  • 4 bedrooms
  • sleeps 10
  • min stay varies
  • Nearest beach 40 mi
  • Swimming pool
  • Child friendly
The house is located in a fantastic property of 12 acres of and with fantastic view on all Montefeltro's Valley. Poll with stratgic position. In the area of Cagli, at 2 km from Acqualagna famous Capital of the Precious Truffle,s Fair, all the year At 20 mn from Urbino, …see more

from $158 / night

$1,101 / week

Book View

from $158 / night

(1)  

27

Italy Vacation farmhouse rental

Magione / Sant'Arcangelo

1 4 2 nights min

  • 1 bedroom
  • sleeps 4
  • 2 nights min
  • Beach/lakeside relaxation
  • Nearest beach 10 mi
  • Swimming pool
Agriturismo in tiny village close to the most famous cities of art of both Tuscany and Umbria 2 Room, living room with divan beds, kitchenette corner, balcony, bathroom with shower, double bedroom and divan bed 50 mq. Country House - Trattoria Enoteca. In a sm …see more

from $63 / night

$434 / week

Book View

from $63 / night

12

Apartment rental in Italy with shared pool

Province of Siena / Radicondoli

1 2 3 nights min

  • 1 bedroom
  • sleeps 2
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Pet friendly
This lovely apartment is placed inside the beautiful Borghetto Poggio Bianco, a peaceful place, surrounded by nature where our guest can relax, enjoy a swim, looking at the sunset inside the Jacuzzi, take a walk in the wood or just take the car and enjoying good food, w …see more

from $144 / night

$1,006 / week

Book View

from $144 / night

30

Vacation apartment with swimming pool, golf nearby in Emilia-Romagna

Emilia-Romagna / Province of Parma

2 10 1 night min

  • 2 bedrooms
  • sleeps 10
  • 1 night min
  • Beach/lakeside relaxation
  • Nearest beach 125 mi
  • Swimming pool
The cottage of 1600, Alleluja Country House, is located in pristine mountains of Parma. The views over the beautiful valley Stirone, all around the fields and forests are part of our farm. The interior style ranges from the classic 70s and all rooms have bathroom, are s …see more

from $144 / night

$1,048 - $4,349 / week

Book View

from $144 / night

(3) Excellent 

25

Apartment rental in Italy with shared pool

Province of South Tyrol / Lana

1 4 7 nights min

  • 1 bedroom
  • sleeps 4
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Car not necessary
Many beautiful moments together to create a whole: luck! Whether sports enthusiasts or connoisseurs - here everyone gets their Kosten.Ob you are lounging by the sun's rays, dip your feet in the pool, or jogging breathe fresh clean air - through our unique location best …see more

from $125 / night

$874 / week

Book View

from $125 / 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 $274 / night

$1,914 - $2,024 / week

Book View

from $274 / 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

$1,293 - $6,776 / week

Book View

from $209 / 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 $588 / night

$4,047 / week

Book View

Responds fast!
avg. 1 hour 26 minutes

from $588 / night

(29) 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 $229 / night

$1,373 - $3,318 / week

Inquire View

from $229 / night

13

Vacation apartment in Italy

Province of Ascoli Piceno / Ripatransone

1 4 3 nights min

  • 1 bedroom
  • sleeps 4
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Private garden
Our Apartments 3 comfortable apartments each with its own terrace overlooking the sea or panoramic mountain views. Just a few hundred meters from the Rotweinstrasse the brands The wellness oasis Nestled in 5,000 square meters Mediterranean, partly subtropical garden "Il …see more

from $92 / night

$644 / week

Book View

from $92 / night

(18) Excellent 

32

Italy Vacation villa rental

Italian Riviera / Chiavari

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 2 mi
  • Swimming pool
The Olive Press Lodge, as its name suggests, is a renovated farm house where olive oil used to be made. The villa is situated on a gentle hill, about a 15-minute walk from the sea and the town centre. It is ideal for a relaxing holiday and offers a great opportunity to …see more

from $225 / night

$1,572 / week

Book View

from $225 / 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 $398 / night

$2,303 / week

Book View

from $398 / night

(7) Excellent 

25

Villa accommodation in Italy with swimming pool

Province of Ascoli Piceno / Carassai

4 9 1 night min

  • 4 bedrooms
  • sleeps 9
  • 1 night min
  • Nearest beach 5 mi
  • Swimming pool
  • Child friendly
A well furnished villa with a private swimming pool and stunning views. Peaceful and relaxing surroundings where you can while away the hours around the pool or from the beautiful terrace, eating and drinking the local produce whilst admiring the wonderful surroundings …see more

from $265 / night

$1,854 / week

Book View

from $265 / night

(13) Excellent 

62

Vacation apartment in Italy

Province of Olbia-Tempio / Trinita d'Agultu e Vignola

1 4 min stay varies

  • 1 bedroom
  • sleeps 4
  • min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 5 mi
  • Swimming pool
The residence Pala Stiddata is set on the outskirts of the tranquil traditional village Trinita D'Agultu. It is located in two building complexes of twenty apartments on the top of a hill. All the apartments are situated in the new part of residence under of the swimmin …see more

from $40 / night

$460 / week

Book View

from $40 / 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 $308 / night

$2,162 - $2,751 / week

Book View

Responds fast!
avg. 2 hours 35 minutes

from $308 / night

(4) Excellent 

27

Italy Vacation home rental

Castiglione di Sicilia / Solicchiata

1 4 3 nights min

  • 1 bedroom
  • sleeps 4
  • 3 nights min
  • Nearest beach 25 mi
  • Swimming pool
  • Child friendly
Typical Sicilian house renovated with stone oven and fireplace. Close to the beaches of Taormina and the slopes of Mount Etna. The house is located next to that of the owners and close to the town of Solicchiata, renowned production of Etna wines. The property has a swi …see more

from $79 / night

$549 / week

Book View

Responds fast!
avg. 28 minutes

from $79 / night

(12) Excellent 

22

Vacation villa with swimming pool in Italy

Province of Terni / Morre

3 6 7 nights min

  • 3 bedrooms
  • sleeps 6
  • 7 nights min
  • Nearest beach 110 mi
  • Swimming pool
  • Child friendly
The lovely Villa Cipresso has been constructed in a sublime spot, where locals had a refuge for many centuries already. Facing the south it is now a private villa, fully restored and transformed into a comfortable and welcoming accommodation. Originally an olive oil mil …see more

from $245 / night

$1,708 - $3,415 / week

Book View

from $245 / night

(1) Excellent 

48

Italy Vacation villa rental

Cilento and Vallo di Diano National Park / Santa Lucia, Cilento

2 7 3 nights min

  • 2 bedrooms
  • sleeps 7
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Ask about pets
Villa Angelina is surrounded by the green hills of the beautiful Cilento region. The villa is in a quiet area and enjoys plenty of privacy. The only sound you will hear in the evenings is flowing water and a grasshopper or two. The 19th century villa has been renovated …see more

from $190 / night

$1,325 / week

Book View

from $190 / night

16

Vacation villa in Italy

Province of Bologna / Granarolo dell'Emilia

7 12 5 nights min

  • 7 bedrooms
  • sleeps 12
  • 5 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Farmhouse close to Bolonia city (20 minutes by car) Safe place for family with childreen. The perfect place where you can relax at the owner's swimming pool, or spend a day to visit one of the monumental towns: Florence, Venezia, Modena, Reggio Emilia, Ferrara, Ravenna …see more

from $276 / night

$1,931 / week

Book View

Responds fast!
avg. 1 hour 19 minutes

from $276 / night

(2) Very Good 

33

Home accommodation in Italy with swimming pool

Province of Vibo Valentia / Zambrone

2 6 1 night min

  • 2 bedrooms
  • sleeps 6
  • 1 night min
  • Beach/lakeside relaxation
  • Nearest beach 3 mi
  • Swimming pool
This is a beautiful 2 bedroom townhouse nestling high on the hillside with BREATHTAKING VIEWS of Zambrone Beach, the Tyrrhenian Sea, Tropea and the iconic island of Stromboli. Zambrone village is an easy 20 minute stroll and here you can enjoy the weekly market and the …see more

from $119 / night

$1,117 / week

Book View

Responds fast!
avg. 2 hours 41 minutes

from $119 / night

(15) Excellent 

Certificate of Excellence

10

Vacation townhouse with swimming pool in Italy

Province of Siena / Sovicille

2 5 2 nights min

  • 2 bedrooms
  • sleeps 5
  • 2 nights min
  • Nearest beach 72 mi
  • Swimming pool
  • Child friendly
The farm, in the organic farm, is located in San Giusto a Balli in the heart of Montagnola, a hilly area west of the city of Siena in Tuscany, wooded and full of springs, and for its historic natural features and art is a Site of Community Interest. The farm is in an ex …see more

Certificate of Excellence

from $144 / night

$1,009 / week

Book View

Responds fast!
avg. 3 hours 57 minutes

from $144 / night

(19) Very Good 

29

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 $142 / night

$991 / week

Book View

Responds fast!
avg. 1 hour 12 minutes

from $142 / night

18

Vacation condo rental

Province of Teramo / Pineto

1 4 7 nights min

  • 1 bedroom
  • sleeps 4
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Swimming pool
Offers for rent summer apartment in Pineto (2014 blue flag), in the central area, in a residence with pool, place for car and bike, at 50 mt from the pine forest and the sea. The apartment is on the 2nd floor with lift, has a bedroom with double bed, in which enters a c …see more

from $118 / night

$852 / week

Book View

from $118 / night

(3) Good 

15

Vacation apartment with shared pool in Italy

Lignano Sabbiadoro / Lignano Pineta

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Residence in excellent position, surrounded by the pine wood, with swimming pool (open approximately from the beginning of June to the middle of September) and reserved parking places, at about 100m from the beach, in Lignano Pineta. Type C: on the garden level living-d …see more

from $58 / night

$401 - $1,427 / week

Book View

from $58 / night

(38) Excellent 

Certificate of Excellence

25

Vacation villa with swimming pool in Sardinia

Province of Olbia-Tempio / Santa Teresa Gallura

3 7 min stay varies

  • 3 bedrooms
  • sleeps 7
  • min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.1 mi
  • Swimming pool
Villa Carina is perfect for a relaxing holiday in this beautiful part of Sardinia, with stunning views over the islands of Maddalena. Situated in a lovely private residential area enjoying the luxury of a private swimming pool (open from May until November) with views …see more

Certificate of Excellence

from $183 / night

$1,175 - $2,376 / week

Book View

from $183 / night

(3) Excellent 

9

Tuscany Vacation farmhouse rental

Province of Massa Carrara / Mulazzo

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 20 mi
  • Swimming pool
The property is in the medieval village of Mulazzo, in the heart of Lunigiana reason in the north of Tuscany, far away from the touristic crowd, nestled on the hills overlooking the Magra river valley. Lunigiana is well known for its middle age castles, many of them ope …see more

from $210 / night

$1,103 - $1,379 / week

Book View

from $210 / night

(2) Very Good 

17

Italy Vacation farmhouse rental

Magione / Agello

2 8 4 nights min

  • 2 bedrooms
  • sleeps 8
  • 4 nights min
  • Nearest beach 1 mi
  • Swimming pool
  • Child friendly
An ancient farmhouse nestled between farmland and rolling hills. The Lake Trasimeno accompanying sweet harmony with the beauty of the Umbrian countryside. A lovely place to rediscover nature, enjoy moments of comfort and pleasure, stopping time and estranged from the ro …see more

from $177 / night

$980 / week

Book View

from $177 / 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 $258 / night

$1,805 - $2,836 / week

Book View

from $258 / night

(3) Excellent 

24

Vacation apartment with shared pool in Italy

Province of Florence / Tavarnelle Val di Pesa

2 7 5 nights min

  • 2 bedrooms
  • sleeps 7
  • 5 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
Peace and tranquility in the Chianti, in the heart of Tuscany between Florence and Siena, near Badia a Passignano and the medieval villages of San Donato, Panzano and Greve in Chianti. The apartment, recently renovated, is part of an old farmhouse complex located on a h …see more

from $184 / night

$1,245 / week

Book View

Responds fast!
avg. 1 hour 47 minutes

from $184 / night

18

Italy Vacation hotel apartment rental

Province of Taranto / Torricella

1 3 7 nights min

  • 1 bedroom
  • sleeps 3
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Swimming pool
Solar Residence 10 meters from the beach !! Classic Studio - mezzanine - no sea view for a low cost holiday without sacrificing comfort. These apartments consist of a double bed (with the possibility of single or cot bed) kitchen and bathroom. Also available is a shared …see more

from $57 / night

$396 / week

Book View

Responds fast!
avg. 3 hours 55 minutes

from $57 / night

9

Italy Vacation apartment rental

Province of Lecce / Muro Leccese

1 3 2 nights min

  • 1 bedroom
  • sleeps 3
  • 2 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
Elegant 30 sqm Studio with a fireplace in leccese stone! Guests have access to a small garden for the exclusive use (great outdoor space for their four-legged friends). This apartment was born in the area until the summer of 2014 was destined to horses. During the reali …see more

from $125 / night

$871 / week

Book View

from $125 / night

24

Vacation farmhouse in Tuscany

Province of Arezzo / Monterchi

3 11 3 nights min

  • 3 bedrooms
  • sleeps 11
  • 3 nights min
  • Nearest beach 130 mi
  • Swimming pool
  • Child friendly
The Fienile is part of Montemiliano Farmhouse, which is described in detail below. Formerly a hay barn, it is disposed on two floors both large apr. 50 square meters and with independent access. The upper one (not interconnected with the lower apt) has two bedrooms and …see more

from $262 / night

$1,965 / week

Book View

from $262 / night

(31) Excellent 

22

Vacation b&b with shared pool in Italy

Province of Olbia-Tempio / Olbia

1 3 2 nights min

  • 1 bedroom
  • sleeps 3
  • 2 nights min
  • Beach/lakeside relaxation
  • Nearest beach 18 mi
  • Swimming pool
THE PRICE SHOWED IS FOR TWO ADULTS Hidden inside a huge area, surrounded by Mediterranean plants and granitic rocks, Isole di Pietra, welcomes its guests for a relaxing holiday and encounter with nature. Only 15 kms from Olbia and the beautiful beaches is ideal for fami …see more

from $105 / night

$736 / week

Book View

from $105 / 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 $1,834 / night

$11,658 / week

Book View

from $1,834 / 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

Also consider