Villas with large swimming pools in Italy

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 2020 Award
Showing: 26 villas
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Showing: 26 villas

Sleeping: 10 - Bedrooms: 5 - Bathrooms: 5

  • Maid included
  • Air Conditioned Bedrooms
  • Internet Connection
  • Private Pool
  • Hot Tub
  • Tennis Court

Luxury stone farmhouse set on a large estate amid vineyards & olive groves near Florence. Fantastic kitchen, air-con bedrooms, en suite bathrooms. Large private fenced pool, hot tub, sauna, spa, yoga deck and yoga studio with gym. Access to the Estate's private tennis court.

Weekly prices
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To
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€ 5,815
€ 8,308
$ 7,884
$ 11,264
£ 5,592
£ 7,990

Sleeping: 14 - Bedrooms: 7 - Bathrooms: 7

  • Maid included
  • Air Conditioned Bedrooms
  • Internet Connection
  • Private Pool
  • Hot Tub
  • Tennis Court

Luxury stone farmhouse set on a large estate amid vineyards & olive groves near Florence. Fantastic kitchen, air-con bedrooms, en suite bathrooms. Large private fenced pool, hot tub, sauna, spa, yoga deck and yoga studio with gym. Access to the Estate's private tennis court.

Weekly prices
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€ 7,107
€ 10,153
$ 9,636
$ 13,766
£ 6,835
£ 9,764

Sleeping: 12 - Bedrooms: 8 - Bathrooms: 7

  • Maid included
  • Air Conditioned Bedrooms
  • Internet Connection
  • Private Pool

Beautiful stone farmhouse on the edge of the Chianti near Florence. Large infinity edge pool & air con bedrooms. Large stylish outdoor seating area & stunning views. Rental option including a cook avail.

Weekly prices
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€ 4,610
€ 7,549
$ 6,250
$ 10,235
£ 4,433
£ 7,260

Sleeping: 15 - Bedrooms: 8 - Bathrooms: 7

  • Maid included
  • Air Conditioned Bedrooms
  • Internet Connection
  • Private Pool

Beautiful stone farmhouse on the edge of the Chianti near Florence. Large infinity edge pool & air con bedrooms. Large stylish outdoor seating area & stunning views. Rental option including a cook avail.

Weekly prices
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€ 5,327
€ 8,623
$ 7,222
$ 11,691
£ 5,122
£ 8,293

Sleeping: 15 - Bedrooms: 8 - Bathrooms: 7

  • Maid included
  • Air Conditioned Bedrooms
  • Internet Connection
  • Private Pool

This staffed rental option at Il Cortile includes a professional chef that shall prepare 6 fantastic evening meals and  breakfast. Please note that food and wine is not included and that cookings lessons can be arranged. 

Weekly prices
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To
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€ 7,870
€ 11,659
$ 10,670
$ 15,808
£ 7,568
£ 11,212

Sleeping: 15 - Bedrooms: 8 - Bathrooms: 7

  • Maid included
  • Air Conditioned Bedrooms
  • Internet Connection
  • Private Pool

This rental option new for 2019 at Il Cortile Pratolino includes traditional or vegetarian cooking lessons & food experiences, alongside the chef & staff who will prepare breakfast and evening meals included in the rental price.

Weekly prices
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€ 11,829
€ 15,619
$ 16,038
$ 21,176
£ 11,376
£ 15,020

Sleeping: 16 - Bedrooms: 9 - Bathrooms: 9

  • Maid included
  • Air Conditioned Bedrooms
  • Internet Connection
  • Private Pool

Glorious stone villa with a magical garden and private pool facing Lake Trasimeno. Beautifully decorated, air conditioned bedrooms, huge sitting rooms, huge loggia for dining & seating, Billiard room.

Weekly prices
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€ 5,074
€ 7,249
$ 6,879
$ 9,828
£ 4,879
£ 6,971

Sleeping: 18 - Bedrooms: 9 - Bathrooms: 9

  • Maid included
  • Air Conditioned Bedrooms
  • Internet Connection
  • Private Pool

Glorious stone villa with a magical garden and private pool facing Lake Trasimeno. Beautifully decorated, air conditioned bedrooms, huge sitting rooms, huge loggia for dining & seating, Billiard room.

Weekly prices
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€ 5,637
€ 8,054
$ 7,643
$ 10,919
£ 5,421
£ 7,745

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
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€ 5,531
€ 7,999
$ 7,499
$ 10,845
£ 5,319
£ 7,692

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 and drinks is not included. Additional meals can be arranged as an extra.

Weekly prices
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To
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€ 7,159
€ 9,627
$ 9,706
$ 13,052
£ 6,884
£ 9,258

Sleeping: 10 - Bedrooms: 5 - Bathrooms: 5

  • Maid included
  • Air Conditioned Bedrooms
  • Internet Connection
  • Private Pool
  • Tennis Court

This staffed rental option for Diaspero includes an unlimited supply of DOCG Vernaccia di San Gimignano & the services of a professional chef for breakfast 6 days a week & dinner upon arrival.

Weekly prices
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To
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€ 7,446
€ 10,433
$ 10,096
$ 14,145
£ 7,161
£ 10,033
Rental options (size of party):

Sleeping: 12 - Bedrooms: 11 - Bathrooms: 11

  • 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
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To
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€ 3,795
€ 7,591
$ 5,146
$ 10,292
£ 3,650
£ 7,300
Rental options (size of party):

Sleeping: 14 - Bedrooms: 7 - Bathrooms: 7

  • Air Conditioned Bedrooms
  • Internet Connection
  • Private Pool

Beautiful 14th century stone farmhouse & guest house with air-conditioned bedrooms and a gated private infinity pool. Beautiful location and wonderful views on a private wine estate just minutes from Castellina in Chianti.  

Weekly prices
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€ 5,500
€ 7,500
$ 7,457
$ 10,169
£ 5,289
£ 7,213

Sleeping: 8 - Bedrooms: 4 - Bathrooms: 4

  • Maid included
  • Air Conditioned Bedrooms
  • Internet Connection
  • Private Pool
  • Hot Tub

Charming villa near San Gimignano with a private pool, hot tub, air conditioned bedrooms and wonderful views of vineyards & olive groves. Arrival evening meal and next day breakfast included in the rental fee.

Weekly prices
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€ 2,880
€ 5,845
$ 3,905
$ 7,924
£ 2,770
£ 5,621

Sleeping: 8 - Bedrooms: 4 - Bathrooms: 4

  • Maid included
  • Air Conditioned Bedrooms
  • Internet Connection
  • Private Pool
  • Hot Tub

New rental option for 2020 which includes: chef services for breakfast & dinner, cooking classes, food & wine experiences. Interior with original terracotta & beamed ceilings. Private infinity pool & hot tub. A/C bedrooms, all except one with en-suite bathrooms. On-site concierge. Sleeps up to 14. 

Weekly prices
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€ 11,704
€ 14,670
$ 15,868
$ 19,889
£ 11,256
£ 14,108

Sleeping: 14 - Bedrooms: 7 - Bathrooms: 5

  • Maid included
  • Air Conditioned Bedrooms
  • Internet Connection
  • Private Pool
  • Hot Tub

Charming villa near San Gimignano with a private pool, hot tub, air conditioned bedrooms and wonderful views of vineyards & olive groves. Arrival evening meal and next day breakfast included in the rental fee.

Weekly prices
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€ 3,601
€ 7,306
$ 4,883
$ 9,906
£ 3,463
£ 7,027

Sleeping: 12 - Bedrooms: 6 - Bathrooms: 8

  • Fully Air-conditioned villa
  • Internet Connection
  • Private Pool

Tranquil stone farmhouse & guesthouse with private pool in Val d’Orcia valley. Interior has terracotta floors, beamed ceilings & A/C in all rooms. Panoramic outdoor living & dining areas & private Roman amphitheatre. Easy walk to village shops & restaurants.

Weekly prices
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€ 3,778
€ 6,900
$ 5,123
$ 9,355
£ 3,634
£ 6,636

Sleeping: 8 - Bedrooms: 4 - Bathrooms: 4

  • Maid included
  • Air Conditioned Bedrooms
  • Internet Connection
  • Private Pool

Large welcoming 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
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To
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€ 2,813
€ 4,242
$ 3,814
$ 5,752
£ 2,705
£ 4,080

Sleeping: 12 - Bedrooms: 6 - Bathrooms: 6

  • Maid included
  • Air Conditioned Bedrooms
  • Internet Connection
  • Private Pool

Large welcoming 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
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To
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€ 3,462
€ 5,221
$ 4,694
$ 7,079
£ 3,329
£ 5,021

Sleeping: 18 - Bedrooms: 9 - Bathrooms: 9

  • Maid included
  • Air Conditioned Bedrooms
  • Internet Connection
  • Private Pool

Large welcoming 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
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€ 4,328
€ 6,527
$ 5,868
$ 8,849
£ 4,162
£ 6,277

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 four 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
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€ 6,535
€ 8,735
$ 8,860
$ 11,843
£ 6,284
£ 8,400

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
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To
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€ 3,709
€ 5,595
$ 5,028
$ 7,586
£ 3,566
£ 5,381

Sleeping: 14 - Bedrooms: 8 - Bathrooms: 7

  • 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
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To
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€ 4,263
€ 6,432
$ 5,780
$ 8,720
£ 4,099
£ 6,185
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