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
Rental options (size of party):

SLEEPING: 4 - BEDROOMS: 2 - BATHROOMS: 2

  • Air Conditioned Bedrooms
  • Internet Connection
  • Private Pool

Charming, peaceful stone farmhouse with with a private pool & stunning views in Chianti near Siena. Air-conditioned bedrooms. En suite bathrooms. Excellent walking and biking.

Weekly prices
From
To
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€ 1,588
€ 3,046
$ 2,238
$ 4,293
£ 1,527
£ 2,929

SLEEPING: 2 - BEDROOMS: 2 - BATHROOMS: 2

  • Air Conditioned Bedrooms
  • Internet Connection
  • Private Pool

Stone farmhouse in the peaceful hills near Pisa & Lucca with private swimming pool. Classic Tuscan interiors with A/C bedrooms & en-suite bathrooms. Garden with olive grove & panoramic views. Short walk to village square with shops, bars & restaurants. Rental option with all-inclusive wine available.

Weekly prices
From
To
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€ 1,339
€ 2,572
$ 1,888
$ 3,625
£ 1,288
£ 2,474

SLEEPING: 4 - BEDROOMS: 2 - BATHROOMS: 2

  • Air Conditioned Bedrooms
  • Internet Connection
  • Private Pool

Stone farmhouse in the peaceful hills near Pisa & Lucca with private swimming pool. Classic Tuscan interiors with A/C bedrooms & en-suite bathrooms. Garden with olive grove & panoramic views. Short walk to village square with shops, bars & restaurants. Rental option with all-inclusive wine available.

Weekly prices
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To
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€ 1,488
€ 2,861
$ 2,097
$ 4,032
£ 1,431
£ 2,751

SLEEPING: 4 - BEDROOMS: 2 - BATHROOMS: 2

  • Air Conditioned Bedrooms
  • Internet Connection
  • Private Pool

This rental option for Montaspro includes an endless supply of DOC Colli Pisani red wine for your stay in this stone farmhouse in the peaceful hills near Pisa & Lucca. 

Weekly prices
From
To
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€ 1,717
€ 2,964
$ 2,419
$ 4,177
£ 1,651
£ 2,850

SLEEPING: 4 - BEDROOMS: 2 - BATHROOMS: 2

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

Peaceful Maremma farmhouse. Beautifully updated interiors, with an air-conditioned open-plan living room with fireplace. Air-con bedrooms & ensuite bathrooms. Lovely views. Large sunny terrace.

Weekly prices
From
To
-
€ 1,416
€ 2,716
$ 1,995
$ 3,828
£ 1,361
£ 2,612

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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€ 1,097
€ 2,340
$ 1,546
$ 3,298
£ 1,055
£ 2,251

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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€ 2,324
€ 3,568
$ 3,276
$ 5,029
£ 2,235
£ 3,432

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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€ 1,220
€ 2,600
$ 1,719
$ 3,664
£ 1,173
£ 2,500

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
-
€ 2,447
€ 3,828
$ 3,449
$ 5,395
£ 2,354
£ 3,681

SLEEPING: 2 - BEDROOMS: 2 - BATHROOMS: 2

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

Utterly charming stone house in an unspoilt hill town. Walk to shops and restaurants. Unbelievable views. Rooms open to very private terraces with tiny garden and a dining terrace. Fireplace. Air-conditioned bedrooms. Internet. Ensuite bathrooms. No pool. Private and cosy . Hot tub

Weekly prices
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To
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€ 1,606
€ 2,871
$ 2,264
$ 4,047
£ 1,545
£ 2,761

SLEEPING: 2 - BEDROOMS: 2 - BATHROOMS: 2

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

Utterly unique fully air-con stone house with hot tub set in an unspoilt hilltop town. En suite bathrooms & unbelievable views of the Umbria valley. Walk to shops & restaurants. Private terraces with small garden. No pool.

Weekly prices
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To
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€ 1,290
€ 2,058
$ 1,818
$ 2,901
£ 1,241
£ 1,979

SLEEPING: 4 - BEDROOMS: 2 - BATHROOMS: 2

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

Utterly unique fully air-con stone house with hot tub set in an unspoilt hilltop town. En suite bathrooms & unbelievable views of the Umbria valley. Walk to shops & restaurants. Private terraces with small garden. No pool.

Weekly prices
From
To
-
€ 1,613
€ 2,282
$ 2,273
$ 3,215
£ 1,551
£ 2,194

SLEEPING: 2 - BEDROOMS: 2 - BATHROOMS: 2

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

Very comfortable house with a beautiful garden, a private heated pool just minutes from the charming village of San Gemini. Satellite TV with DVD. Air-con. Wireless internet.

Weekly prices
From
To
-
€ 1,097
€ 1,823
$ 1,545
$ 2,569
£ 1,055
£ 1,753

SLEEPING: 2 - BEDROOMS: 2 - BATHROOMS: 2

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

This rental option at Il Cerro includes a talented local cook that shall prepare your evening meals. Breakfast is also included prepared by the maid. Please note that Food & winne is not included.

Weekly prices
From
To
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€ 2,324
€ 3,051
$ 3,276
$ 4,299
£ 2,235
£ 2,934

SLEEPING: 5 - BEDROOMS: 2 - BATHROOMS: 2

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

Very comfortable house with a beautiful garden, a private heated pool just minutes from the charming village of San Gemini. Satellite TV with DVD. Air-con. Wireless internet.

Weekly prices
From
To
-
€ 1,219
€ 2,100
$ 1,719
$ 2,960
£ 1,173
£ 2,019

SLEEPING: 5 - BEDROOMS: 2 - BATHROOMS: 2

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

This rental option at Il Cerro includes a talented local cook that shall prepare your evening meals. Breakfast is also included prepared by the maid. Please note that Food & winne is not included.

Weekly prices
From
To
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€ 2,447
€ 3,328
$ 3,449
$ 4,690
£ 2,354
£ 3,200

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