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: 29 villas
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Showing: 29 villas

New for 2024

SLEEPING: 12 - BEDROOMS: 6 - BATHROOMS: 6

  • Fully air-conditioned villa
  • Air-conditioned bedrooms
  • Internet connection
  • Private pool
  • Tennis court

A luxury contemporary villa in the Tuscan hills near San Gimignano. A/C throughout with precious marble finishes. 15m private gated pool, immaculate grounds, sauna & tennis court. 

Weekly prices
From
To
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€ 6,452
€ 9,332
$ 6,952
$ 10,056
£ 5,562
£ 8,045

SLEEPING: 8 - BEDROOMS: 6 - BATHROOMS: 5

  • Air-conditioned bedrooms
  • Internet connection
  • Private pool

Elegant 17C country villa with a private pool near Venice. Air-con bedrooms, modern bathrooms. Stunning gardens with gated pool, small lake. Walk to bus stop for venice, shops, restaurants, tennis.

Weekly prices
From
To
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€ 4,133
€ 7,973
$ 4,454
$ 8,592
£ 3,563
£ 6,874

SLEEPING: 11 - BEDROOMS: 6 - BATHROOMS: 5

  • Air-conditioned bedrooms
  • Internet connection
  • Private pool

Elegant 17C country villa with a private pool near Venice. Air-con bedrooms, modern bathrooms. Stunning gardens with gated pool, small lake. Walk to bus stop for venice, shops, restaurants, tennis.

Weekly prices
From
To
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€ 4,807
€ 8,596
$ 5,180
$ 9,263
£ 4,144
£ 7,410

SLEEPING: 6 - BEDROOMS: 3 - BATHROOMS: 3

  • Air-conditioned bedrooms
  • Internet connection
  • Private pool

Luxury fully air-conditioned private home near the city of Orvieto. Private twenty meter saltwater swimming pool with stunning views. Lots of outdoor shaded living space. Large bedrooms with en suite bathrooms.

Weekly prices
From
To
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€ 4,741
€ 6,954
$ 5,109
$ 7,493
£ 4,087
£ 5,994

SLEEPING: 10 - BEDROOMS: 5 - BATHROOMS: 5

  • Air-conditioned bedrooms
  • Internet connection
  • Private pool

Luxury fully air-conditioned private home near the city of Orvieto. Private twenty meter saltwater swimming pool with stunning views. Lots of outdoor shaded living space. Large bedrooms with en suite bathrooms.

Weekly prices
From
To
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€ 5,176
€ 7,591
$ 5,577
$ 8,180
£ 4,462
£ 6,544

SLEEPING: 10 - BEDROOMS: 5 - BATHROOMS: 5

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

Brick farmhouse & stylish barn conversion in the Valdichiana with mesmerising views of nearby Cortona. Bright open-plan interiors with original features & open brick fireplaces, A/C bedrooms with en-suite shower rooms & a large heated private pool.

Weekly prices
From
To
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€ 5,228
€ 7,469
$ 5,634
$ 8,048
£ 4,507
£ 6,438
Rental options (size of party):

SLEEPING: 6 - BEDROOMS: 3 - BATHROOMS: 4

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

Stone-built Tuscan villa once home to Mona Lisa & Gherardi family. Classic Tuscan decor with A/C bedrooms. 5-acres of luxuriant gated grounds with a private gated pool & views over Chianti. Short walk to iconic Villa Vignamaggio winery.

Weekly prices
From
To
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€ 5,079
€ 6,983
$ 5,473
$ 7,525
£ 4,378
£ 6,020

SLEEPING: 10 - BEDROOMS: 6 - BATHROOMS: 5

  • Air-conditioned bedrooms
  • Internet connection
  • Private pool

Beautifully set farmhouse & guest house with a large private pool enjoying beautiful views of the countryside near the pretty town of Cetona with air-con bedrooms, en suite bathrooms & a fantastic kitchen.

Weekly prices
From
To
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€ 4,456
€ 6,723
$ 4,802
$ 7,245
£ 3,841
£ 5,796

SLEEPING: 8 - BEDROOMS: 5 - BATHROOMS: 5

  • Air-conditioned bedrooms
  • Internet connection
  • Private pool

Charming hill top farmhouse with a beautiful garden & large private pool. Air-con bedrooms, games room, great kitchen, loggia for dining with terrific views & sunsets. Pool has a paddling area.

Weekly prices
From
To
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€ 2,698
€ 5,146
$ 2,908
$ 5,545
£ 2,326
£ 4,436

SLEEPING: 10 - BEDROOMS: 5 - BATHROOMS: 5

  • Air-conditioned bedrooms
  • Internet connection
  • Private pool

Charming hill top farmhouse with a beautiful garden & large private pool. Air-con bedrooms, games room, great kitchen, loggia for dining with terrific views & sunsets. Pool has a paddling area.

Weekly prices
From
To
-
€ 3,175
€ 5,996
$ 3,422
$ 6,461
£ 2,737
£ 5,169

Special rates for May and June

SLEEPING: 4 - BEDROOMS: 2 - BATHROOMS: 2

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

Hilltop stone villa with private heated pool, 10km from one of Tuscany’s prettiest medieval towns. Tuscan interiors with A/C bedrooms. Panoramic terrace with multiple outdoor seating & dining areas. Memorable sunsets over rural Tuscany.

Weekly prices
From
To
-
€ 2,998
€ 4,916
$ 3,230
$ 5,298
£ 2,584
£ 4,238

Special rates for May and June

SLEEPING: 4 - BEDROOMS: 2 - BATHROOMS: 2

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

Hilltop stone villa with staff & cook, 10km from one of Tuscany’s prettiest medieval towns. Tuscan interiors with A/C bedrooms. Private heated pool & panoramic terrace with multiple outdoor seating & dining areas. Memorable sunsets over rural Tuscany.

Weekly prices
From
To
-
€ 3,195
€ 5,114
$ 3,443
$ 5,510
£ 2,754
£ 4,408

Special rates for May and June

SLEEPING: 6 - BEDROOMS: 3 - BATHROOMS: 2

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

Hilltop stone villa with private heated pool, 10km from one of Tuscany’s prettiest medieval towns. Tuscan interiors with A/C bedrooms. Panoramic terrace with multiple outdoor seating & dining areas. Memorable sunsets over rural Tuscany.

Weekly prices
From
To
-
€ 3,357
€ 5,563
$ 3,618
$ 5,995
£ 2,894
£ 4,796

Special rates for May and June

SLEEPING: 6 - BEDROOMS: 3 - BATHROOMS: 2

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

Hilltop stone villa with staff & cook, 10km from one of Tuscany’s prettiest medieval towns. Tuscan interiors with A/C bedrooms. Private heated pool & panoramic terrace with multiple outdoor seating & dining areas. Memorable sunsets over rural Tuscany. 

Weekly prices
From
To
-
€ 3,555
€ 5,761
$ 3,831
$ 6,208
£ 3,065
£ 4,967

SLEEPING: 2 - BEDROOMS: 2 - BATHROOMS: 2

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

Very comfortable villa with a private pool, near San Gemini. Tastefully decorated. Air-conditioned bedrooms. Ensuite bathrooms. Beautiful garden, loggias, views. Large pool, Hike to village.

Weekly prices
From
To
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€ 1,318
€ 2,812
$ 1,420
$ 3,030
£ 1,136
£ 2,424

SLEEPING: 2 - BEDROOMS: 2 - BATHROOMS: 2

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

This rental option at l’Olmo includes a talented local cook that shall prepare your evening meals. Breakfast is also included and prepared by the maid. Please note that food & wine are not included.

Weekly prices
From
To
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€ 2,793
€ 4,288
$ 3,010
$ 4,620
£ 2,408
£ 3,696

SLEEPING: 4 - BEDROOMS: 2 - BATHROOMS: 2

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

Very comfortable villa with a private pool, near San Gemini. Tastefully decorated. Air-conditioned bedrooms. Ensuite bathrooms. Beautiful garden, loggias, views. Large pool, Hike to village.

Weekly prices
From
To
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€ 1,465
€ 3,124
$ 1,579
$ 3,367
£ 1,263
£ 2,693

SLEEPING: 4 - BEDROOMS: 2 - BATHROOMS: 2

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

This rental option at l’Olmo includes a talented local cook that shall prepare your evening meals. Breakfast is also included and prepared by the maid. Please note that food & wine are not included.

Weekly prices
From
To
-
€ 2,941
€ 4,600
$ 3,169
$ 4,956
£ 2,535
£ 3,965

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