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 2021 Award
Showing: 16 villas
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Showing: 16 villas

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
-
€ 2,500
€ 4,100
$ 3,523
$ 5,778
£ 2,404
£ 3,943
No reviews for this villa

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. Breakfast included in the price. 

Weekly prices
From
To
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€ 3,400
€ 5,000
$ 4,792
$ 7,047
£ 3,270
£ 4,808
No reviews for this villa

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
-
€ 2,800
€ 4,640
$ 3,946
$ 6,539
£ 2,693
£ 4,462
No reviews for this villa

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. Breakfast included in the price. 

Weekly prices
From
To
-
€ 3,700
€ 5,540
$ 5,215
$ 7,808
£ 3,558
£ 5,328
No reviews for this villa

SLEEPING: 4 - BEDROOMS: 2 - BATHROOMS: 3

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

Newly restored stone barn with private pool 20km from San Gimignano, between Florence & Siena. Interior has A/C in all rooms, luxury bathrooms & modern kitchen. Garden with outdoor living & dining area, hot tub & sauna.

Weekly prices
From
To
-
€ 1,680
€ 3,234
$ 2,368
$ 4,558
£ 1,616
£ 3,110

SLEEPING: 6 - BEDROOMS: 3 - BATHROOMS: 4

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

Newly restored stone barn with private pool 20km from San Gimignano, between Florence & Siena. Interior has A/C in all rooms, luxury bathrooms & modern kitchen. Garden with outdoor living & dining area, hot tub & sauna.

Weekly prices
From
To
-
€ 2,100
€ 4,042
$ 2,960
$ 5,697
£ 2,020
£ 3,888

SLEEPING: 2 - BEDROOMS: 1 - BATHROOMS: 1

  • 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
-
€ 1,125
€ 2,730
$ 1,586
$ 3,848
£ 1,082
£ 2,626

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
From
To
-
€ 1,688
€ 2,806
$ 2,378
$ 3,955
£ 1,623
£ 2,699

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
From
To
-
€ 2,321
€ 3,859
$ 3,270
$ 5,438
£ 2,232
£ 3,711

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
-
€ 1,586
€ 3,147
$ 2,235
$ 4,436
£ 1,525
£ 3,027

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
-
€ 1,738
€ 3,484
$ 2,449
$ 4,910
£ 1,671
£ 3,350

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
-
€ 1,888
€ 3,820
$ 2,661
$ 5,384
£ 1,816
£ 3,674

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. Rental option with all-inclusive wine available. 

Weekly prices
From
To
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€ 1,240
€ 3,285
$ 1,748
$ 4,630
£ 1,193
£ 3,159

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. Rental option with all-inclusive wine available. 

Weekly prices
From
To
-
€ 1,550
€ 3,769
$ 2,185
$ 5,312
£ 1,491
£ 3,625

SLEEPING: 4 - BEDROOMS: 2 - BATHROOMS: 1

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

This rental option for Colli Fiorentini includes an everflowing supply of DOC Tuscan red, white & rosé wine for your stay in this 17th-century stone farmhouse, 20km from Florence

Weekly prices
From
To
-
€ 2,155
€ 4,374
$ 3,037
$ 6,164
£ 2,072
£ 4,206

SLEEPING: 4 - BEDROOMS: 2 - BATHROOMS: 2

  • Air Conditioned Bedrooms
  • Internet Connection
  • Private Pool
  • Heated Pool

Pretty stone farmhouse with a private heated swimming pool and air-conditioned bedrooms within walking distance to a village, near the coast. Lots of shaded outdoor living areas

Weekly prices
From
To
-
€ 1,581
€ 3,374
$ 2,229
$ 4,755
£ 1,521
£ 3,244

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
-
€ 1,713
€ 3,326
$ 2,414
$ 4,687
£ 1,648
£ 3,198
No reviews for this villa

SLEEPING: 2 - BEDROOMS: 1 - BATHROOMS: 1

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

A peaceful, romantic stone farmhouse with a private pool on the Tuscan coast. Whitewashed interior, loft-style master bedroom & ensuite bathroom. Fully air-conditioned. Walk to pebble beach.

Weekly prices
From
To
-
€ 1,496
€ 3,197
$ 2,109
$ 4,506
£ 1,439
£ 3,075
Rental options (size of party):

SLEEPING: 4 - BEDROOMS: 2 - BATHROOMS: 2

  • Air Conditioned Bedrooms
  • Internet Connection
  • Private Pool

Tranquil farmhouse with eco-sustainable biopool 3km from Arezzo. Interior has stone walls, terracotta floors & modern kitchen. Flagstoned portico with outdoor dining & garden with olive groves & oak trees. Ideal location to explore Tuscany & Umbria.

Weekly prices
From
To
-
€ 1,792
€ 3,163
$ 2,526
$ 4,457
£ 1,724
£ 3,042
No reviews for this villa

SLEEPING: 6 - BEDROOMS: 3 - BATHROOMS: 4

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

Charming property near Grossetto on the Tuscany Coast.  Fully air-conditioned with ensuite modern bathrooms. Contemporary furnishings and fitting with lots of shade and a shared swimming pool. 

Weekly prices
From
To
-
€ 1,746
€ 3,055
$ 2,461
$ 4,306
£ 1,679
£ 2,938

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