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Siena, Italy: Siena, Italy: 19ºC 19ºC
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60 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.
Pienza
14 Bedrooms13 Bathrooms28 People1000
Chic Siena Retreat

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...

Price from €5,000/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
Pienza
8 Bedrooms8 Bathrooms16 People560
Valley Luxury Villa

Terrace, Parking, Pool, Concierge

This chic countryside villa sits in Siena province, within a short drive from a small town with a couple of shops and other first-need facilities. The place belongs to the Unesco heritage site of Val d´Orcia known for its stunning landscapes. Finished in a traditional yet sleek Tuscany style, the...

This chic countryside villa sits in Siena province, within a short drive from a small town with a couple of shops and other first-need facilities. The place belongs to the Unesco heritage site of Val d´Orcia known for...

Price from €1,200/night
San Casciano dei Bagni
7 Bedrooms6 Bathrooms12 People350
Orcia Luxury House

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...

Price from €1,800/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
Siena
9 Bedrooms9 Bathrooms17 People800
Tuscany Deluxe House

Parking, Tennis court(s), Sauna, Pool, Concierge

Luxury Villas Tuscany : This incredible rental house located near beautiful village Radicofani sleeps 17 people. On the ground floor there is a hall, a meeting room with satellite TV, two computers with fax and printer and a large lounge with central fireplace and home theatre system....

Luxury Villas Tuscany : This incredible rental house located near beautiful village Radicofani sleeps 17 people. On the ground floor there is a hall, a meeting room with satellite TV, two computers with fax...

Price from €181/night
Poggibonsi
7 Bedrooms6 Bathrooms14 People1000
Luxury Palace Siena

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...

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
Siena
13 Bedrooms13 Bathrooms26 People
Siena Luxury Palazzo

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...

Price from €6,000/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
Chianti
8 Bedrooms9 Bathrooms16 People400
Chianti Luxury House

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...

Price from €1,500/night
Montalcino
9 Bedrooms8 Bathrooms18 People450
Montalcino Country House

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...

Price from €1,300/night
San Casciano
5 Bedrooms4 Bathrooms10 People318
Siena Luxe House

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...

Price from €450/night
Montefollonico
6 Bedrooms6 Bathrooms12 People
Design Home Siena

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

With fantastic views over the Tuscany countryside, this charming house rental sits in Siena area, within a short drive from Montefollonico village. The villa benefits from exceptional interior design entwined with traditional Tuscan architecture elements. There are several outdoor chill-out areas...

With fantastic views over the Tuscany countryside, this charming house rental sits in Siena area, within a short drive from Montefollonico village. The villa benefits from exceptional interior design entwined with...

Price from €1,200/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
Chianti
6 Bedrooms5 Bathrooms12 People165
Chianti Luxe Home

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

Price from €400/night
Gaiole in Chianti
6 Bedrooms6 Bathrooms12 People
Siena Exclusive Borgo

Terrace, Parking, Pool, Daily Cleaning, Concierge

Price from €1,500/night
Radda in Chianti
7 Bedrooms7 Bathrooms14 People
Design Siena Farmhouse

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...

Price from €2,000/night
Siena
8 Bedrooms8 Bathrooms14 People1
Design Luxury House Tuscany

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...

Price from €394/night
Chianti
2 Bedrooms2 Bathrooms4 People175
Siena Retreat Luxury Villa

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...

Price from €1,100/night

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