Cottages in Italy

Small is beautiful at our special collection of cosy cottages in Italy. This selection of charming places to stay includes properties in the Italian regions of Tuscany and Umbria. These Italian cottage rentals sleep 2 to 6 guests.

Our holiday cottages in Italy take no short-cuts with quality. Cottage interiors offer a modern take on traditional rural Tuscan décor. Like every Tuscany Now & More property — large and small — our cottage rentals come with a private swimming pool.

Each of our Italian country cottages has air-conditioning, in bedrooms or throughout, so you get a good night’s sleep even on the warmest summer nights. Bathrooms are typically ensuite or provided 1 per bedroom in most cases. See the individual villa descriptions for any exceptions and details of many extra features in our cottage rentals, like hot tubs, manicured gardens and panoramic terraces.

For every Tuscan cottage rental, our award-winning concierges are standing by to book you a table at the best local restaurants, arrange a private chef to cook dinner in your cottage kitchen or just to have shopping delivered to the villa in time for your arrival. This concierge service is absolutely free for all Tuscany Now & More guests.

You can browse our full collection of handpicked cottages in Italy below. The selection includes a converted barn with a terrace facing the Florence skyline; several Tuscany villas for two; small farmhouses in the Chianti winelands; and a stone-built cottage in the Maremma, with beamed ceilings, terracotta tiled floors and outdoor dining terraces.

For something larger in the rural style, we offer a collection of Italian farmhouse rentals. If you are soon to be married, you may wish to browse our honeymoon villas in Italy — which includes cottages for two and larger romantic properties.

Condé Nast Traveller 2023 Award
Showing: 16 villas
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Showing: 16 villas

Special Easter Offer

SLEEPING: 12 - BEDROOMS: 6 - BATHROOMS: 6

  • Maid included
  • Fully air-conditioned villa
  • Internet connection
  • Private pool
  • Heated pool
  • Hot tub

Prestigious Tuscan villa with private heated infinity pool & magnificent views of San Gimignano. Extra-sleek interiors with A/C in all rooms. Sumptuous bedrooms have oak flooring & ensuite marble bathrooms. Private spa & hot tub.

Weekly prices
From
To
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€ 7,880
€ 13,133
$ 8,491
$ 14,152
£ 6,793
£ 11,321

SLEEPING: 4 - BEDROOMS: 2 - BATHROOMS: 2

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

Beautiful home on the Tuscan coast with private access to the sea. Private pool & private tennis court set in the cliffs. Lots of shaded living area for relaxing & eating with ensuite bathrooms.

Weekly prices
From
To
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€ 3,583
€ 11,076
$ 3,861
$ 11,935
£ 3,089
£ 9,548

SLEEPING: 8 - BEDROOMS: 4 - BATHROOMS: 4

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

Beautiful home on the Tuscan coast with private access to the sea. Private pool & private tennis court set in the cliffs. Lots of shaded living area for relaxing & eating with ensuite bathrooms.

Weekly prices
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€ 5,512
€ 11,075
$ 5,939
$ 11,935
£ 4,751
£ 9,548

SLEEPING: 4 - BEDROOMS: 2 - BATHROOMS: 2

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

Fully air-conditioned charming stone house in Umbria, within an unspoilt hilltop town with a private heated swimming pool. Unbelievable views and very stylish interiors complete with en suite bathrooms. Short walk to shops and restaurants.

Weekly prices
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To
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€ 2,028
€ 3,372
$ 2,185
$ 3,634
£ 1,748
£ 2,907

SLEEPING: 6 - BEDROOMS: 3 - BATHROOMS: 3

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

Fully air-conditioned charming stone house in Umbria, within an unspoilt hilltop town with a private heated swimming pool. Unbelievable views and very stylish interiors complete with en suite bathrooms. Short walk to shops and restaurants.

Weekly prices
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To
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€ 2,788
€ 4,637
$ 3,005
$ 4,996
£ 2,404
£ 3,997

SLEEPING: 8 - BEDROOMS: 4 - BATHROOMS: 4

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

Fully air-conditioned charming stone house in Umbria, within an unspoilt hilltop town with a private heated swimming pool. Unbelievable views and very stylish interiors complete with en suite bathrooms. Short walk to shops and restaurants.

Weekly prices
From
To
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€ 3,485
€ 5,795
$ 3,756
$ 6,245
£ 3,005
£ 4,996

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
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€ 2,998
€ 4,916
$ 3,230
$ 5,298
£ 2,584
£ 4,238

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

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

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: 4 - BEDROOMS: 2 - BATHROOMS: 3

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

Fantastically positioned villa with a private heated swimming pool in the hills near Florence. Fully air-conditioned, with a modern kitchen and modern bathrooms and a very pretty garden.

Weekly prices
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To
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€ 3,792
€ 5,309
$ 4,087
$ 5,721
£ 3,269
£ 4,577

SLEEPING: 6 - BEDROOMS: 3 - BATHROOMS: 4

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

Fantastically positioned villa with a private heated swimming pool in the hills near Florence. Fully air-conditioned, with a modern kitchen and modern bathrooms and a very pretty garden.

Weekly prices
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€ 4,018
€ 5,625
$ 4,329
$ 6,061
£ 3,464
£ 4,849

SLEEPING: 4 - BEDROOMS: 2 - BATHROOMS: 3

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

Remodelled stone barn with private pool 20km from San Gimignano, between Florence & Siena. Interior has A/C in all rooms, luxury bathrooms, a modern kitchen & sauna. Garden with outdoor living, dining area & views of rolling hills.  

Weekly prices
From
To
-
€ 2,019
€ 3,887
$ 2,176
$ 4,188
£ 1,741
£ 3,351

SLEEPING: 6 - BEDROOMS: 3 - BATHROOMS: 4

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

Remodelled stone barn with private pool 20km from San Gimignano, between Florence & Siena. Interior has A/C in all rooms, luxury bathrooms, a modern kitchen & sauna. Garden with outdoor living, dining area & views of rolling hills.  

Weekly prices
From
To
-
€ 2,524
€ 4,858
$ 2,720
$ 5,235
£ 2,176
£ 4,188

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
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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
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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

SLEEPING: 2 - BEDROOMS: 1 - BATHROOMS: 1

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

Charming stone cottage with a beautiful private pool , fully air conditioned, set in an exceptionally peaceful setting in southern Tuscany. Spectacular views, surrounded by olives groves.

Weekly prices
From
To
-
€ 1,906
€ 3,782
$ 2,054
$ 4,075
£ 1,643
£ 3,260

SLEEPING: 4 - BEDROOMS: 2 - BATHROOMS: 2

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

Charming stone cottage with a beautiful private pool , fully air conditioned, set in an exceptionally peaceful setting in southern Tuscany. Spectacular views, surrounded by olives groves.

Weekly prices
From
To
-
€ 2,088
€ 4,186
$ 2,250
$ 4,511
£ 1,800
£ 3,609

SLEEPING: 6 - BEDROOMS: 3 - BATHROOMS: 3

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

Charming stone cottage with a beautiful private pool , fully air conditioned, set in an exceptionally peaceful setting in southern Tuscany. Spectacular views, surrounded by olives groves.

Weekly prices
From
To
-
€ 2,269
€ 4,590
$ 2,445
$ 4,946
£ 1,956
£ 3,957

SLEEPING: 2 - BEDROOMS: 2 - BATHROOMS: 1

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

17th-century stone farmhouse with A/C in all rooms, 20km from Florence. Tuscan interiors with terracotta floors, beamed ceilings & exposed stone. Private pool & hot tub. Manicured garden with outdoor dining area, olive trees & pomegranate trees.

Weekly prices
From
To
-
€ 1,463
€ 3,876
$ 1,577
$ 4,176
£ 1,261
£ 3,341

SLEEPING: 4 - BEDROOMS: 2 - BATHROOMS: 1

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

17th-century stone farmhouse with A/C in all rooms, 20km from Florence. Tuscan interiors with terracotta floors, beamed ceilings & exposed stone. Private pool & hot tub. Manicured garden with outdoor dining area, olive trees & pomegranate trees.

Weekly prices
From
To
-
€ 1,829
€ 4,446
$ 1,971
$ 4,791
£ 1,577
£ 3,833

SLEEPING: 4 - BEDROOMS: 2 - BATHROOMS: 2

  • Air-conditioned bedrooms
  • Internet connection
  • Private pool

Contemporary villa with private pool in the heart of Val d’ Orcia. Minimalist design with custom-made furnishings & awe-inspiring art. A/C bedrooms with en-suite bathrooms & large, open-plan living space. Nearly 360-degree views over the mesmerising countryside.

Weekly prices
From
To
-
€ 2,157
€ 4,186
$ 2,324
$ 4,511
£ 1,859
£ 3,609

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