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.
SLEEPING: 12 - BEDROOMS: 6 - BATHROOMS: 5
Serene hilltop villa 10km from Grosseto with 17m infinity pool overlooking vineyards. Seamless indoor/outdoor living between alfresco dining areas. Ideally located on organic wine estate near Tuscany’s best beaches. Complimentary wine tasting & tour.
SLEEPING: 4 - BEDROOMS: 2 - BATHROOMS: 2
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.
SLEEPING: 8 - BEDROOMS: 4 - BATHROOMS: 4
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.
SLEEPING: 4 - BEDROOMS: 2 - BATHROOMS: 2
Fully air-conditioned (except one bedroom) 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.
SLEEPING: 6 - BEDROOMS: 3 - BATHROOMS: 3
Fully air-conditioned (except one bedroom) 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.
SLEEPING: 8 - BEDROOMS: 4 - BATHROOMS: 4
Fully air-conditioned (except one bedroom) 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.
SLEEPING: 4 - BEDROOMS: 2 - BATHROOMS: 2
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.
SLEEPING: 4 - BEDROOMS: 2 - BATHROOMS: 2
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.
SLEEPING: 6 - BEDROOMS: 3 - BATHROOMS: 2
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.
SLEEPING: 6 - BEDROOMS: 3 - BATHROOMS: 2
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.
SLEEPING: 4 - BEDROOMS: 2 - BATHROOMS: 3
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.
SLEEPING: 6 - BEDROOMS: 3 - BATHROOMS: 4
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.
SLEEPING: 4 - BEDROOMS: 2 - BATHROOMS: 3
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.
SLEEPING: 6 - BEDROOMS: 3 - BATHROOMS: 4
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.
SLEEPING: 2 - BEDROOMS: 2 - BATHROOMS: 2
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.
SLEEPING: 2 - BEDROOMS: 2 - BATHROOMS: 2
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.
SLEEPING: 4 - BEDROOMS: 2 - BATHROOMS: 2
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.
SLEEPING: 4 - BEDROOMS: 2 - BATHROOMS: 2
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.
SLEEPING: 2 - BEDROOMS: 1 - BATHROOMS: 1
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.
SLEEPING: 4 - BEDROOMS: 2 - BATHROOMS: 2
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.
SLEEPING: 6 - BEDROOMS: 3 - BATHROOMS: 3
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.
SLEEPING: 2 - BEDROOMS: 2 - BATHROOMS: 1
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.
SLEEPING: 4 - BEDROOMS: 2 - BATHROOMS: 1
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.
SLEEPING: 4 - BEDROOMS: 2 - BATHROOMS: 2
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.