59 Luxury Holiday Rentals Siena

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...

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

Terrace, Pool, Concierge

Luxury Villas Tuscany : A truly outstanding modernized rental house hidden away in the nature within a short drive from Sarteano will be your perfect holiday letting. Enjoy the lovely Mediterranean sun and fantastic overviews in this fabulous property that sleeps up to ten people. There are five...

Luxury Villas Tuscany : A truly outstanding modernized rental house hidden away in the nature within a short drive from Sarteano will be your perfect holiday letting. Enjoy the lovely Mediterranean sun and fantastic...

Terrace, Parking, Pool, Daily Cleaning, Concierge

Not too far from Siena, this Tuscan palace was originally built in the 15th century. Once an hospital, it was transformed into a private majestic home hosting a famous family of Siena in 1924. The estate is surrounded by 450 hectares of land, gardens and woods. Sitting close to the famous vineyard...

Not too far from Siena, this Tuscan palace was originally built in the 15th century. Once an hospital, it was transformed into a private majestic home hosting a famous family of Siena in 1924. The estate is surrounded...

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, 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, Daily Cleaning, Concierge

Located in Tuscany countryside atop of a hill, surrounded by woods and fields, this luxury farmhouse is a perfect place for nature and serenity seekers. This large property can host up to 28 people in its 14 ensuite bedrooms. The house comprises of 3 units offering a perfect setting for a family...

Located in Tuscany countryside atop of a hill, surrounded by woods and fields, this luxury farmhouse is a perfect place for nature and serenity seekers. This large property can host up to 28 people in its 14 ensuite...

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, 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

Rental House Tuscany : This refined prestigious villa is located near San Casciano dei Bagni, a beautiful village known as a thermal land. It's an independent residence composed of a main building and an annex. The property sleeps 13 people. The principal building can accommodate 9...

Rental House Tuscany : This refined prestigious villa is located near San Casciano dei Bagni, a beautiful village known as a thermal land. It's an independent residence composed of a main building and an annex. The...

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, 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, 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, Concierge

Sitting half-way from Florence to Siena, this countryside villa enjoys lovely Tuscany views. This house is only half-an-hour drive from Florence, the cradle of Renaissance and open-air museum. All the essential facilities are situated in San Casciano Val di Pensa, just 12 minutes´ drive away. The...

Sitting half-way from Florence to Siena, this countryside villa enjoys lovely Tuscany views. This house is only half-an-hour drive from Florence, the cradle of Renaissance and open-air museum. All the essential...

Terrace, Parking, Pool, Daily Cleaning, Concierge

This authentic Tuscan farmhouse has been totally refurbished to offer its guest a truly luxurious place to spend a vacation with friends or family. This 435 m2 house is divided in two estates. It sits on the hill surrounded by a lush wood and can accommodate up to 8 guests in its 4 large en suite...

This authentic Tuscan farmhouse has been totally refurbished to offer its guest a truly luxurious place to spend a vacation with friends or family. This 435 m2 house is divided in two estates. It sits on the hill...

Terrace, Daily Cleaning, Concierge

Part of a bigger estate with organic vineyards, this Siena luxury villa rental is an ideal option for a small family or 2 couples. Located in the heart of Tuscany, this place benefits from total serenity and easy access to five-star hotels with a spa and a restaurant just steps away from the house....

Part of a bigger estate with organic vineyards, this Siena luxury villa rental is an ideal option for a small family or 2 couples. Located in the heart of Tuscany, this place benefits from total serenity and easy access...

Terrace, Parking, Pool

With a garden of 5.000 m2 and more than 1.000 m2 of indoors, this luxury Tuscany villa is a perfect vacation or wedding venue. It is a totally restored historic residence built in the XVII century within a short distance form Cortona. It boasts wonderful frescoes and vaulted ceilings. In addition,...

With a garden of 5.000 m2 and more than 1.000 m2 of indoors, this luxury Tuscany villa is a perfect vacation or wedding venue. It is a totally restored historic residence built in the XVII century within a short...

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 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...