59 Luxury Holiday Rentals Siena

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...

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

Located in the Chianti hills, this Tuscany luxury villa can host up to 16 people in its 8 en-suite bedrooms. The property comprises of 2 separate buildings connected with a glass corridor. They are the tower and the barn. Recently refurbished and benefiting form sleek interiors, it offers a perfect...

Located in the Chianti hills, this Tuscany luxury villa can host up to 16 people in its 8 en-suite bedrooms. The property comprises of 2 separate buildings connected with a glass corridor. They are the tower and the...

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...

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

This impeccable Siena villa rental was built in the XVII century in Roman Baroque style. With superb manicured gardens, the house is perfect for a big family or several couples. Within a short drive from Siena and Florence, the place is an ideal base for the Tuscany exploration.The house enjoy 13...

This impeccable Siena villa rental was built in the XVII century in Roman Baroque style. With superb manicured gardens, the house is perfect for a big family or several couples. Within a short drive from Siena and...

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

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, 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, Fitness, Concierge

This totally refurbished Tuscany villa rental enjoys sleek interiors and perfect modern amenities along with traditional architectural elements. Ideal both for families and friends, the house enjoys a private swimming pool with a sunbathing area, a gym, a steam room and a children playground. Just...

This totally refurbished Tuscany villa rental enjoys sleek interiors and perfect modern amenities along with traditional architectural elements. Ideal both for families and friends, the house enjoys a private swimming...

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

This cozy Tuscan villa sits in Siena province. It is within 6 minutes' drive from a small village housing several cafes and restaurants, a couple of shops and some other essential amenities. The famous town with hot springs of Bagno Vignoni are about 17 minutes away as well as some other charming...

This cozy Tuscan villa sits in Siena province. It is within 6 minutes' drive from a small village housing several cafes and restaurants, a couple of shops and some other essential amenities. The famous town with hot...

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, 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 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, Fitness, Daily Cleaning, Concierge

Sitting in the hills of Tuscany, in the province of Siena, this totally-refurbished house for rent enjoys sleek interiors and perfect modern amenities. Just 13 minutes´ drive form Radda in Chainti and other charming villages of the area, it is Ideal both for families and friends. The house is set...

Sitting in the hills of Tuscany, in the province of Siena, this totally-refurbished house for rent enjoys sleek interiors and perfect modern amenities. Just 13 minutes´ drive form Radda in Chainti and other charming...

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, Tennis court(s), Pool, Fitness, Concierge

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...

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...