Villas with large swimming pools in Italy

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Whether you’re an avid swimmer, travelling with a large group or with children, you will understand the importance of having a larger swimming pool. Many of our hand-picked villas have swimming pools to perfectly complement the warm Tuscan sunshine, but for some occasions only a big pool will do.

Condé Nast Traveller 2023 Award
Showing: 30 villas
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Showing: 30 villas

SLEEPING: 16 - BEDROOMS: 8 - BATHROOMS: 8

  • Cook included
  • Air-conditioned bedrooms
  • Internet connection
  • Private pool

Elegant 17th-century villa with a private pool surrounded by a stunning park which includes an amphitheatre. Air-conditioned bedrooms with en suite bathrooms. Breakfast service [ingredients excluded] and maid service included.

Weekly prices
From
To
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€ 8,829
€ 13,856
$ 9,514
$ 14,932
£ 7,611
£ 11,945

SLEEPING: 16 - BEDROOMS: 8 - BATHROOMS: 8

  • Cook included
  • Air-conditioned bedrooms
  • Internet connection
  • Private pool

For an Umbrian wedding with up to 50 guests (up to 90 with an extra fee) in a 17th-century villa with private pool, surrounded by 10-acre park with formal gardens, fountains & amphitheatre. A/C bedrooms with ensuite bathrooms. Breakfast service [ingredients excluded] and maid service included.

Weekly prices
From
To
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€ 11,036
€ 17,321
$ 11,892
$ 18,664
£ 9,514
£ 14,932

SLEEPING: 16 - BEDROOMS: 8 - BATHROOMS: 8

  • Cook included
  • Maid included
  • Fully air-conditioned villa
  • Internet connection
  • Heated pool

Stylish 16th-century luxury villa in Chianti with staff & cook. Terraced garden with outdoor living & dining areas. Private heated pool, gym & wellness area with treatment room and sauna [wellness area services available to those purchasing treatments]. Elegant interiors, internal lift & A/C in all rooms. On-site concierge. Breakfast & dinner included in the rental price.

Weekly prices
From
To
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€ 11,446
€ 17,223
$ 12,334
$ 18,559
£ 9,867
£ 14,848

SLEEPING: 10 - BEDROOMS: 5 - BATHROOMS: 5

  • Maid included
  • Air-conditioned bedrooms
  • Internet connection
  • Private pool
  • Hot tub

Charming country villa with private infinity pool & hot tub 18km from San Gimignano. A/C bedrooms & ensuite bathrooms. Wealth of alfresco living areas. On-site attentive staff can prepare meals & offer cooking lessons.

Weekly prices
From
To
-
€ 4,593
€ 9,608
$ 4,949
$ 10,354
£ 3,959
£ 8,283

SLEEPING: 10 - BEDROOMS: 5 - BATHROOMS: 5

  • Maid included
  • Air-conditioned bedrooms
  • Internet connection
  • Private pool
  • Hot tub

A food lover’s paradise complete with chef services for breakfast & dinner, plus one cooking class. A/C bedrooms & ensuite bathrooms. Private infinity pool & hot tub. On-site attentive concierge. 18km from San Gimignano. 

Weekly prices
From
To
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€ 8,505
€ 13,520
$ 9,165
$ 14,569
£ 7,332
£ 11,655

SLEEPING: 14 - BEDROOMS: 7 - BATHROOMS: 5

  • Maid included
  • Air-conditioned bedrooms
  • Internet connection
  • Private pool
  • Hot tub

Charming country villa with private infinity pool & hot tub 18km from San Gimignano. A/C bedrooms with two family suites, perfect for younger families. Wealth of alfresco living areas. On-site attentive staff can prepare meals & offer cooking lessons.

Weekly prices
From
To
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€ 5,511
€ 11,530
$ 5,939
$ 12,424
£ 4,751
£ 9,939

SLEEPING: 14 - BEDROOMS: 7 - BATHROOMS: 5

  • Maid included
  • Air-conditioned bedrooms
  • Internet connection
  • Private pool
  • Hot tub

A food lover’s paradise complete with chef services for breakfast & dinner, plus one cooking class. A/C bedrooms with two family suites, perfect for younger families. Private infinity pool & hot tub. On-site concierge. 18km from San Gimignano.

Weekly prices
From
To
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€ 9,423
€ 15,442
$ 10,155
$ 16,640
£ 8,124
£ 13,312

SLEEPING: 10 - BEDROOMS: 5 - BATHROOMS: 5

  • Maid included
  • Air-conditioned bedrooms
  • Internet connection
  • Private pool
  • Tennis court

Luxury villa with stunning views overlooking San Gimignano with an oversized private swimming pool and full size tennis court. Air conditioned bedrooms with en suite bathrooms.  

Weekly prices
From
To
-
€ 7,913
€ 11,444
$ 8,527
$ 12,332
£ 6,821
£ 9,865

SLEEPING: 10 - BEDROOMS: 5 - BATHROOMS: 5

  • Maid included
  • Air-conditioned bedrooms
  • Internet connection
  • Private pool
  • Tennis court

This rental option for Diaspero includes services of a professional chef for breakfast 6 days a week and dinner upon arrival. The cost of food is included, but drinks are not included. Additional meals can be arranged as an extra.

Weekly prices
From
To
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€ 10,242
€ 13,773
$ 11,036
$ 14,841
£ 8,829
£ 11,873

SLEEPING: 8 - BEDROOMS: 4 - BATHROOMS: 5

  • Cook included
  • Maid included
  • Air-conditioned bedrooms
  • Internet connection
  • Private pool

Luxury hilltop villa 18km from Orvieto with staff & cook. A/C interiors, antique painting collection & internal lift. Modern en-suite bathrooms & professional kitchen. 25-acre park with formal gardens & private mosaic-paved pool. Breakfast & dinner service included in the price.

Weekly prices
From
To
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€ 6,354
€ 8,810
$ 6,847
$ 9,493
£ 5,478
£ 7,594

SLEEPING: 14 - BEDROOMS: 7 - BATHROOMS: 9

  • Cook included
  • Maid included
  • Air-conditioned bedrooms
  • Internet connection
  • Private pool

Luxury hilltop villa 18km from Orvieto with staff & cook. A/C interiors, antique painting collection & internal lift. Modern en-suite bathrooms & professional kitchen. 25-acre park with formal gardens & private mosaic-paved pool. Breakfast & dinner service included in the price.

Weekly prices
From
To
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€ 9,776
€ 13,553
$ 10,535
$ 14,605
£ 8,428
£ 11,684

SLEEPING: 12 - BEDROOMS: 7 - BATHROOMS: 6

  • Air-conditioned bedrooms
  • Internet connection
  • Private pool

Elegant 17th-century farmhouse & guesthouse on a hilltop 5km from Greve in Chianti. Private pool & Chianti views. Interior has beamed ceilings, terracotta floors, A/C bedrooms & modern bathrooms. Ideal location to explore Tuscany.

Weekly prices
From
To
-
€ 4,768
€ 9,535
$ 5,138
$ 10,275
£ 4,110
£ 8,220

SLEEPING: 16 - BEDROOMS: 11 - BATHROOMS: 9

  • Air-conditioned bedrooms
  • Internet connection
  • Private pool

Elegant 17th-century farmhouse & guesthouse on a hilltop 5km from Greve in Chianti. Private pool & Chianti views. Interior has beamed ceilings, terracotta floors, A/C bedrooms & modern bathrooms. Ideal location to explore Tuscany.

Weekly prices
From
To
-
€ 6,756
€ 13,508
$ 7,280
$ 14,556
£ 5,824
£ 11,645

SLEEPING: 12 - BEDROOMS: 6 - BATHROOMS: 6

  • Fully air-conditioned villa
  • Internet connection
  • Private pool

Newly restored Renaissance-style villa with private pool & Italianate gardens 15km from Florence. Immaculate interiors with classic Tuscan decor & contemporary art collection. A/C in all rooms, ensuite bathrooms & modern kitchen. Large shaded loggia with outdoor living & dining areas.

Weekly prices
From
To
-
€ 8,359
€ 12,872
$ 9,007
$ 13,871
£ 7,206
£ 11,097
Rental options (size of party):

SLEEPING: 10 - BEDROOMS: 5 - BATHROOMS: 5

  • Air-conditioned bedrooms
  • Internet connection
  • Private pool
  • Heated pool

Luxury stone farmhouse with A/C bedrooms, luxurious en-suite bathrooms & private heated swimming pool. Bright contemporary interiors and well-equipped kitchen Lush, planted garden on a hilltop with unforgettable views 20km from Siena

Weekly prices
From
To
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€ 6,839
€ 11,448
$ 7,370
$ 12,336
£ 5,896
£ 9,869

SLEEPING: 10 - BEDROOMS: 5 - BATHROOMS: 5

  • Maid included
  • Air-conditioned bedrooms
  • Internet connection
  • Private pool

Multi-generational family farmhouse with air-conditioned bedrooms, lots of en suite bathrooms and a private swimming pool with plenty of shaded outdoor living areas near the beautiful town of Massa Martana.

Weekly prices
From
To
-
€ 3,535
€ 5,331
$ 3,809
$ 5,745
£ 3,047
£ 4,596

SLEEPING: 18 - BEDROOMS: 9 - BATHROOMS: 9

  • Maid included
  • Air-conditioned bedrooms
  • Internet connection
  • Private pool

Multi-generational family farmhouse with air-conditioned bedrooms, lots of en suite bathrooms and a private swimming pool with plenty of shaded outdoor living areas near the beautiful town of Massa Martana.

Weekly prices
From
To
-
€ 5,050
€ 7,616
$ 5,442
$ 8,207
£ 4,353
£ 6,565

SLEEPING: 18 - BEDROOMS: 9 - BATHROOMS: 9

  • Maid included
  • Air-conditioned bedrooms
  • Internet connection
  • Private pool

This rental option at Solomonio includes a breakfast buffet and a chef that shall prepare three evening meals, to be enjoyed at the villa in one of the any dining areas available at the villa.   

Weekly prices
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To
-
€ 8,193
€ 10,950
$ 8,828
$ 11,800
£ 7,063
£ 9,440

SLEEPING: 10 - BEDROOMS: 5 - BATHROOMS: 5

  • Cook included
  • Maid included
  • Fully air-conditioned villa
  • Internet connection
  • Hot tub

Classic stone farmhouse in the Val d’Orcia with panoramic views of Pienza. Fully A/C, spacious open-plan living areas with ensuite bathrooms. 12m infinity pool, hot tub & dining terrace.

Weekly prices
From
To
-
€ 7,384
€ 10,548
$ 7,957
$ 11,367
£ 6,365
£ 9,093

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