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Siena, Italy: Siena, Italy: 7ºC 7ºC
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59 Luxury Holiday Rentals Siena

Known as one of the most visited tourist attractions of Italy, Siena enjoys a wide variety of high-end properties for rent. Book a luxury villa, hire a design penthouse, rent a holiday home with a private pool, your options are unlimited. Declared a World Heritage Site by UNESCO, Siena has recognized museums and art galleries, squares, palaces, churches, along with wonderful restaurants and bakeries, medieval ruins and holds the Palio, a world-known horse race.
Poggibonsi
12 Bedrooms12 Bathrooms24 People810
Siena Luxury Farmhouse

Terrace, Parking, Pool, Daily Cleaning, Concierge

This traditional Tuscany estate sits in a vast land plot lined by cypresses by Poggibonsi. The village enjoys several cafes, restaurants, shops and other first-need amenities that will make your vacation easy. The luxury house comes with a private swimming pool, AC in all the bedrooms, satellite...

This traditional Tuscany estate sits in a vast land plot lined by cypresses by Poggibonsi. The village enjoys several cafes, restaurants, shops and other first-need amenities that will make your vacation easy. The...

Price from €1,000/night
Montalcino
4 Bedrooms4 Bathrooms8 People220
Luxury House Siena

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...

Price from €400/night
Gaiole in Chianti
5 Bedrooms6 Bathrooms10 People600
Siena Chic 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...

Price from €2,357/night
Asciano
9 Bedrooms11 Bathrooms20 People580
Chic Design Siena Home

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...

Price from €1,100/night
Sinalunga
5 Bedrooms5 Bathrooms11 People
Tuscany Chic Villa

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...

Price from €1,000/night
Chianti
4 Bedrooms4 Bathrooms8 People470
Siena Retreat Farmhouse

Terrace, Parking, Pool, Daily Cleaning, Concierge

This is a cozy traditional Tuscan villa for 8 people. It benefits from a heated swimming pool, a stone fire-pit and a wood-burning oven. Featuring fine marble and ceramics finishings and Italian designer fabrics and antiques, the property offers its guests a 5-star-hotel comfort. The house has 4...

This is a cozy traditional Tuscan villa for 8 people. It benefits from a heated swimming pool, a stone fire-pit and a wood-burning oven. Featuring fine marble and ceramics finishings and Italian designer fabrics and...

Price from €1,700/night
Pienza
7 Bedrooms8 Bathrooms15 People
Deluxe Siena House

Terrace, Parking, Pool, Daily Cleaning, Concierge

Built in the XVII century, this country house sits in the unspoilt Val d´Orcia, Unesco Heritage site half-way from Florence to Rome. Benefiting from lovely views over Pienza town and Tuscany countryside, the villa for rent is a perfect marriage of the ancient decoration details and modern...

Built in the XVII century, this country house sits in the unspoilt Val d´Orcia, Unesco Heritage site half-way from Florence to Rome. Benefiting from lovely views over Pienza town and Tuscany countryside, the villa for...

Price from €1,100/night
Chianti
4 Bedrooms4 Bathrooms8 People450
Siena Retreat Luxe Home

Terrace, Parking, Pool, Daily Cleaning, Concierge

This Refurbished Tuscan Farmhouse sits on the hill and is surrounded by forests and vineyards. This 450 m2 property is divided in 3 different buildings and can accommodate up to 8 guest in its 4 en suite bedrooms. This is a perfect place to experience the green Tuscany and enjoy gastronomy,...

This Refurbished Tuscan Farmhouse sits on the hill and is surrounded by forests and vineyards. This 450 m2 property is divided in 3 different buildings and can accommodate up to 8 guest in its 4 en suite bedrooms. This...

Price from €1,700/night
Sarteano
9 Bedrooms9 Bathrooms18 People650
Luxury Rural Siena

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,...

Price from €1,500/night
Siena
4 Bedrooms5 Bathrooms8 People1
Italian Luxury Mansion

Terrace, Parking, Pool

Luxury Rental House Siena : This secluded mansion located not far from the medieval village of Celle sul Rigo dates back to XVII century. Recently renovated and tastefully furnished now it's a perfect combination of the canonical and modern elements. This splendid farmhouse enjoys fantastic views...

Luxury Rental House Siena : This secluded mansion located not far from the medieval village of Celle sul Rigo dates back to XVII century. Recently renovated and tastefully furnished now it's a perfect combination of the...

Price from €827/night
Buenconvento
7 Bedrooms6 Bathrooms14 People500
Luxury Mansion Siena

Terrace, Parking, Pool, Daily Cleaning, Concierge

Sitting in the heart of an organic farm in the Tuscany countryside, this cozy rental villa sits between Siena and Montalcino. It combines the countryside serenity with the modern facilities one might need for a carefree vacation. The house features a lift, a swimming pool, AC in the bedrooms...

Sitting in the heart of an organic farm in the Tuscany countryside, this cozy rental villa sits between Siena and Montalcino. It combines the countryside serenity with the modern facilities one might need for a carefree...

Price from €900/night
Siena
6 Bedrooms6 Bathrooms13 People250
Valley Luxury House

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...

Price from €750/night
Montalcino
9 Bedrooms9 Bathrooms18 People
Montalcino Luxury House

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...

Price from €820/night
Gaiole in Chianti
6 Bedrooms6 Bathrooms12 People
Siena Exclusive Borgo

Terrace, Parking, Pool, Daily Cleaning, Concierge

Price from €1,500/night
Siena
8 Bedrooms9 Bathrooms16 People400
Siena Exclusive Mansion

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...

Price from €2,143/night
Gaiole in Chianti
4 Bedrooms6 Bathrooms8 People200
Luxury House Chianti

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...

Price from €600/night
Sienna
7 Bedrooms7 Bathrooms13 People1
Cozy Tuscany House

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...

Price from €895/night
Montalcino
2 Bedrooms2 Bathrooms4 People140
Montalcino Luxury Home

Terrace, Parking, Pool, Daily Cleaning, Concierge

Hidden in Val d´Orcia valley in Tuscany, this cozy home for rent sits within a short drive from a small town with al the first-need facilities one might need for a vacation. Montalcino is around 20 minutes´ drive away, while Montepulciano can be reached in around 45 minutes. Some other...

Hidden in Val d´Orcia valley in Tuscany, this cozy home for rent sits within a short drive from a small town with al the first-need facilities one might need for a vacation. Montalcino is around 20 minutes´...

Price from €200/night
South of Siena
14 Bedrooms14 Bathrooms24 People1000
Luxury Monastery 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...

Price from €2,000/night
Chianti
3 Bedrooms3 Bathrooms6 People400
Siena Retreat Chic House

Terrace, Parking, Pool, Daily Cleaning, Concierge

This beautiful property is located on the Chianti hills not too far from Siena Town. the house is divided in two floor and offers a capacity of 6 people, a perfect getaway for a family or friends. On the ground floor, we find a fully equipped kitchen, a dinning room, a wine cave, a big living room...

This beautiful property is located on the Chianti hills not too far from Siena Town. the house is divided in two floor and offers a capacity of 6 people, a perfect getaway for a family or friends. On the ground floor,...

Price from €1,500/night

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