59 Luxury Holiday Rentals Siena

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, Jacuzzi, Golf, Pool, Concierge

Atop of a hill, with magnificent Val d´ Orcia views, this luxury Tuscany villa rental enjoys a 3 acres garden with a private swimming pool. Siena sits around 1 h drive away, while Florence can be reached in less than 2 hours. The house is distributed on 2 floors and features 8 bedrooms. The whole...

Atop of a hill, with magnificent Val d´ Orcia views, this luxury Tuscany villa rental enjoys a 3 acres garden with a private swimming pool. Siena sits around 1 h drive away, while Florence can be reached in less than 2...

Terrace, Parking, Pool, Daily Cleaning, Concierge, Seaside

A classical Tuscany villa, this home for rent is perfect for those looking for a serene countryside vacation with five-star modern amenities. Strategically situated in Siena area, in Val d´ Orcia, a Unesco World Heritage site, this cozy villa sleeps 8. Perfect both for a family holiday...

A classical Tuscany villa, this home for rent is perfect for those looking for a serene countryside vacation with five-star modern amenities. Strategically situated in Siena area, in Val d´ Orcia, a Unesco...

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...

Terrace, Parking, Pool, Concierge

This Tuscany villa rental sits close to Siena. It enjoys total serenity and easy access to all the first-need amenities one might need including shops, cafes and restaurants. The house sleeps up to 14 people and has 2 levels. It benefits from several living areas, a private swimming pool and a...

This Tuscany villa rental sits close to Siena. It enjoys total serenity and easy access to all the first-need amenities one might need including shops, cafes and restaurants. The house sleeps up to 14 people and has 2...

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, 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...

Parking, Pool, Concierge

This beautiful Siena holiday home sits among Chianti classico vineyards and olive groves, within a short drive from Gaiole in Chianti. Some other charming villages of the area including Lecchi, San Sano and Raddi in Chianti can also be reached within less than half an hour. The villa enjoys a...

This beautiful Siena holiday home sits among Chianti classico vineyards and olive groves, within a short drive from Gaiole in Chianti. Some other charming villages of the area including Lecchi, San Sano and Raddi in...

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

Sitting on the hill and surrounded by a lush vegetation and woods, this house is a very intimate place ideal for guests that want to spend a green and quite stay. Located few kilometers away from Siena, it is a perfect place to spend vacation with your family.On the ground floor, you will find a...

Sitting on the hill and surrounded by a lush vegetation and woods, this house is a very intimate place ideal for guests that want to spend a green and quite stay. Located few kilometers away from Siena, it is a perfect...

Terrace, Parking, Pool, Daily Cleaning, Concierge

Sitting by the vineyards of the estate, the 650 m2 property is divided in three separated buildings that can accommodate up to 8 guests. Located not too far from Siena, it is a the perfect place to enjoy privacy and silence and spend a great vacation with friends and family.The Main HouseOn the...

Sitting by the vineyards of the estate, the 650 m2 property is divided in three separated buildings that can accommodate up to 8 guests. Located not too far from Siena, it is a the perfect place to enjoy privacy and...

Terrace, Parking, Pool, Daily Cleaning, Concierge

Terrace, Parking, Pool, Concierge

This Tuscany two-storey stone villa was built in 1900 and carefully restored to offer all the modern amenities to its guests. With incomparable views on Val d´Orcia, Unesco Heritage Site, it sits next to several small traditional Tuscan villages. You will find some cafes and small grocery shops...

This Tuscany two-storey stone villa was built in 1900 and carefully restored to offer all the modern amenities to its guests. With incomparable views on Val d´Orcia, Unesco Heritage Site, it sits next to several small...

Parking, Pool, Concierge

Luxury Villas Tuscany : Experience luxury rural life in this nice traditional Italian vaulted farmhouse that has seen centuries pass by. Forget about all your everyday problems, get back to the countryside, to the clean fresh air, to the green trees and grass. This holiday home sleeps 10 people....

Luxury Villas Tuscany : Experience luxury rural life in this nice traditional Italian vaulted farmhouse that has seen centuries pass by. Forget about all your everyday problems, get back to the countryside, to the clean...

Terrace, Parking, Pool, Daily Cleaning, Concierge

Sitting on the hills in val d'Orcia, this 580 m2 refurbished farmhouse can accommodate up to 18-20 guests in 9 bedrooms. Two more single bedrooms can be arranged in the lounge areas. The estate comprises of 5 separate units all offering a self catering space. With sleek interiors and modern...

Sitting on the hills in val d'Orcia, this 580 m2 refurbished farmhouse can accommodate up to 18-20 guests in 9 bedrooms. Two more single bedrooms can be arranged in the lounge areas. The estate comprises of 5 separate...

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, 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, Tennis court(s), Sauna, Pool, Fitness, Daily Cleaning, Concierge

Luxury Rental House‏ Tuscany : This elegant villa located close to Siena enjoys quiet picturesque setting overlooking the hills. The decoration, the furniture and soft furnishing of the residence create atmosphere of home. It’s a wonderful house very well situated in a village called Ville...

Luxury Rental House‏ Tuscany : This elegant villa located close to Siena enjoys quiet picturesque setting overlooking the hills. The decoration, the furniture and soft furnishing of the residence create...

Pool, Concierge

Luxury Villas Tuscany : A truly outstanding modernized Italian villa hidden away in the nature within a short drive from a small village with all the amenities that one might need. A perfect marriage of the canonical and modern elements, represented by the traditional vaulted ceilings and modern...

Luxury Villas Tuscany : A truly outstanding modernized Italian villa hidden away in the nature within a short drive from a small village with all the amenities that one might need. A perfect marriage of the canonical...