59 Luxury Holiday Rentals Siena

Terrace, Parking, Pool, Fitness

This charming villa for rent by Siena sits around 4 km from a small village of Gaiole in Chianti. It houses several grocery shops, cafes, a pharmacy and some other facilities. Perfect for families, the villa is a great base for travelling around - to Florence, Siena, Arezzo and Montepulciano - and...

This charming villa for rent by Siena sits around 4 km from a small village of Gaiole in Chianti. It houses several grocery shops, cafes, a pharmacy and some other facilities. Perfect for families, the villa is a great...

Terrace, Parking, Pool, Concierge

Luxury Villas Tuscany : This secluded self-catering holiday home is set in the heart of Italy, Tuscany. It offers accommodation for 10 people and benefits from fantastic views of the region. Surrounded by astonishing nature (30 acres of the forest) and meticulously landscaped gardens, this luxury...

Luxury Villas Tuscany : This secluded self-catering holiday home is set in the heart of Italy, Tuscany. It offers accommodation for 10 people and benefits from fantastic views of the region. Surrounded by astonishing...

Terrace, Parking, Pool, Daily Cleaning, Concierge

Not too far from Siena and Chianti vineyards this traditional Tuscan house is a great place to spend your vacation with friends or family. Sitting on the hill, the guest will enjoy the fantastic views over the valley. This 420 m2 property can accommodate up to 8 guests in its 4 en suite...

Not too far from Siena and Chianti vineyards this traditional Tuscan house is a great place to spend your vacation with friends or family. Sitting on the hill, the guest will enjoy the fantastic views over the valley....

Terrace, Parking, Jacuzzi, Pool, Daily Cleaning, Concierge

Set a small village of the inimitable Tuscany, in Siena area, this charming historic house for rent sits within an easy access to many other beautiful villages. Built in the middle ages, this place has a lot of stories to tell. With its stunning frescoes, beamed and stucco ceilings, the property...

Set a small village of the inimitable Tuscany, in Siena area, this charming historic house for rent sits within an easy access to many other beautiful villages. Built in the middle ages, this place has a lot of stories...

Terrace, Parking, Jacuzzi, Pool, Daily Cleaning, Concierge

This Traditional Tuscan Property is surrounded by 26 acres of Vineyards and 7 acres of Olives trees. Divided in two different estates, this large property can accommodate big groups of friends or family.The main HouseOn the ground floor, you will find a fully equipped kitchen, a dinning room, two...

This Traditional Tuscan Property is surrounded by 26 acres of Vineyards and 7 acres of Olives trees. Divided in two different estates, this large property can accommodate big groups of friends or family.The main HouseOn...

Parking, Sauna, Golf, Pool, Fitness, Concierge

Rental House Tuscany : Situated in the province of Siena, in a beautiful village called Cetona, this fantastic holiday house is the perfect place for you to have a great and relaxing time. Carefully decorated, this luxury place offers accommodation for nine people. There is a living and dining...

Rental House Tuscany : Situated in the province of Siena, in a beautiful village called Cetona, this fantastic holiday house is the perfect place for you to have a great and relaxing time. Carefully decorated, this...

Terrace, Parking, Pool, Daily Cleaning, Concierge

Located not too far from Siena, the property sits on the hill and is surrounded by vineyards and olive trees. The house with private infinity heated pool can accommodate up to 10 people. It is the perfect place to host big group or family whom want to spend vacation in the green Tuscany. The estate...

Located not too far from Siena, the property sits on the hill and is surrounded by vineyards and olive trees. The house with private infinity heated pool can accommodate up to 10 people. It is the perfect place to host...

Terrace, Parking, Jacuzzi, Pool, Daily Cleaning, Concierge

This cozy traditional Tuscany house rental sits in the Val d´ Orcia. It is a part of a 300 ha organic farm that promises you will have a serene vacation though within a short drive to restaurants, cafes and shops. The property enjoys a billiard and table tennis, a petanque court, a wooden...

This cozy traditional Tuscany house rental sits in the Val d´ Orcia. It is a part of a 300 ha organic farm that promises you will have a serene vacation though within a short drive to restaurants, cafes and...

Terrace, Parking, Pool, Daily Cleaning, Concierge

This elegant villa rental sits in Montepulciano area, just 8 minutes´ drive form the town. Once a watchtower, now it benefits form sleek interior and five-star amenities - all for a perfect vacation in Tuscany. Home to some of the finest Italian wines, the area also offers gorgeous landscapes and...

This elegant villa rental sits in Montepulciano area, just 8 minutes´ drive form the town. Once a watchtower, now it benefits form sleek interior and five-star amenities - all for a perfect vacation in Tuscany. Home to...

Terrace, Parking, Pool, Daily Cleaning, Concierge

Hilltop, this property sits amidst ancient medieval villages, olives trees and vineyards. Once a monastery, the property has been fully refurbished to offer its guests an utmost vacation experience in Tuscany. The house consists of the main building and a cottage. There is a beautiful private...

Hilltop, this property sits amidst ancient medieval villages, olives trees and vineyards. Once a monastery, the property has been fully refurbished to offer its guests an utmost vacation experience in Tuscany. The house...

Terrace, Parking, Pool, Concierge

This is a charming rehabilitated Siena farmhouse featuring unbelievable views on Tuscany countryside. Ideal for a family or a group of friends, the house enjoys several comfortable outdoor areas, a private swimming pool with a sunbathing area and a manicured garden with local plants and...

This is a charming rehabilitated Siena farmhouse featuring unbelievable views on Tuscany countryside. Ideal for a family or a group of friends, the house enjoys several comfortable outdoor areas, a private swimming pool...

Terrace, Parking, Pool, Concierge

This cozy countryside home sits in the heart of Tuscany, in Montalcino area, Val d´ Orcia, a famous Unesco Heritage Site. Part of a bigger estate of organic farming, the house benefits from total privacy. Renewed in 2019, the property consists of two wings - the north and the south ones -...

This cozy countryside home sits in the heart of Tuscany, in Montalcino area, Val d´ Orcia, a famous Unesco Heritage Site. Part of a bigger estate of organic farming, the house benefits from total privacy. Renewed in...

Terrace, Parking, Pool, Concierge

Originally a farmhouse, this Siena villa rental has been renovated using the local natural materials. The villa sleeps up to 14 people. It features a garden with several outdoor chill-out areas and a private swimming pool. The property is distributed over 3 floors.Ground floorThis level enjoys 5...

Originally a farmhouse, this Siena villa rental has been renovated using the local natural materials. The villa sleeps up to 14 people. It features a garden with several outdoor chill-out areas and a private swimming...

Terrace, Parking, Tennis court(s), Pool, Fitness, Daily Cleaning, Concierge

This wonderful historic property is a part of a bigger estate housing an organic farm. Benefiting from proximity to Siena, the house is perfect for Tuscany exploration and wine tourism. It features a wellness - spa area with a sauna, a gym, a private swimming pool and a tennis court. Ideal both for...

This wonderful historic property is a part of a bigger estate housing an organic farm. Benefiting from proximity to Siena, the house is perfect for Tuscany exploration and wine tourism. It features a wellness - spa area...

Terrace, Parking, Jacuzzi, Pool, Fitness, Concierge

This beautifully renovated house sits in the area of Siena. It is close to several charming villages of the area including Radda in Chianti, Lecchi, San Sano and Gaiole in Chianti. The house boasts lovely countryside views and is framed by vineyards and olive groves. The property comprises of 3...

This beautifully renovated house sits in the area of Siena. It is close to several charming villages of the area including Radda in Chianti, Lecchi, San Sano and Gaiole in Chianti. The house boasts lovely countryside...

Terrace, Parking, Pool, Daily Cleaning, Concierge

Luxury Rentals Tuscany : Are you looking for quiet and tranquil vacation? You are in the right place. This wonderful villa will allow you to relax and enjoy the large garden and the forest. Projected as farmhouse it sleeps up to 13 people. On the ground floor there is a large living room, a games...

Luxury Rentals Tuscany : Are you looking for quiet and tranquil vacation? You are in the right place. This wonderful villa will allow you to relax and enjoy the large garden and the forest. Projected as farmhouse it...

Terrace, Parking, Jacuzzi, Pool, Fitness, Concierge

This stylish Siena house rental sits in the heart of Val d´ Orcia within a short drive from two small villages offering first-need facilities to the travellers. Siena itself is a bit more than one hour drive away, while Florence can be reached in around two hours. Authentic yet refurbished, the...

This stylish Siena house rental sits in the heart of Val d´ Orcia within a short drive from two small villages offering first-need facilities to the travellers. Siena itself is a bit more than one hour drive away,...

Terrace, Parking, Pool, Daily Cleaning, Concierge

The estate enjoys a fantastic view of San Gimignano town and the valley surrounding. This large refurbished farmhouse is divided in two buildings and can accommodate up to 8 guests in 4 en suite bedrooms. A large garden and a heated infinity pool will offer the guest a perfect place to spend a...

The estate enjoys a fantastic view of San Gimignano town and the valley surrounding. This large refurbished farmhouse is divided in two buildings and can accommodate up to 8 guests in 4 en suite bedrooms. A large garden...

Terrace, Parking, Pool, Concierge

This fine villa for rent sits in Siena area, by the town of Montepulciano. Boasting sleek interiors, a manicured garden and gorgeous views on the Tuscany countryside, this property is perfect for a laid-back vacation. The property enjoys about 1.000 m2 and a garden of 2.500 m2. There is a private...

This fine villa for rent sits in Siena area, by the town of Montepulciano. Boasting sleek interiors, a manicured garden and gorgeous views on the Tuscany countryside, this property is perfect for a laid-back vacation....

Terrace, Parking, Pool, Daily Cleaning, Concierge

Hidden in the countryside of Tuscany, within the province of Siena, yet close to Umbria, the luxury rental home is an ideal base for the area exploration. Perfect both for family vacation and a getaway with friends, the property enjoys sophisticated design, manicured gardens and wonderful chill-out...

Hidden in the countryside of Tuscany, within the province of Siena, yet close to Umbria, the luxury rental home is an ideal base for the area exploration. Perfect both for family vacation and a getaway with friends, the...