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Siena, Italy: Siena, Italy: 17ºC 17ºC
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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
12 Bedrooms12 Bathrooms24 People700
Exclusive Palace Siena

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...

Price from €4,000/night
Siena
9 Bedrooms7 Bathrooms18 People1
Siena Hill Deluxe House

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...

Price from €1,071/night
Chianti
4 Bedrooms4 Bathrooms8 People560
Siena Retreat Luxe House

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...

Price from €1,700/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
Chianti
6 Bedrooms6 Bathrooms12 People730
Siena Retreat Large House

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...

Price from €2,400/night
Sienna
5 Bedrooms5 Bathrooms10 People500
Pine Delux Villa

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...

Price from €257/night
Gaiole in Chianti
6 Bedrooms6 Bathrooms12 People
Siena Exclusive Borgo

Terrace, Parking, Pool, Daily Cleaning, Concierge

Price from €1,500/night
Sienna
5 Bedrooms5 Bathrooms9 People1
Delux Hill House

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...

Price from €257/night
Radda in Chianti
5 Bedrooms8 Bathrooms6 People1
Design Siena House

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...

Price from €1,908/night
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
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
Buonconvento
8 Bedrooms8 Bathrooms16 People2000
Montalcino Luxury Castle

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...

Price from €4,500/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
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
Chianti
6 Bedrooms5 Bathrooms12 People165
Chianti Luxe Home

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

Price from €400/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
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
Chianti
4 Bedrooms4 Bathrooms8 People560
Siena Retreat Luxe Villa

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

This refurbished farmhouse offers breath taking view of the countryside. The estate is surrounded by olive trees and peaceful nature. This 560 m2 property is divided in two separated houses that will accommodate up to 8 guests in its 4 en suite bedrooms and numerous common areas.The Main HouseOn...

This refurbished farmhouse offers breath taking view of the countryside. The estate is surrounded by olive trees and peaceful nature. This 560 m2 property is divided in two separated houses that will accommodate up to 8...

Price from €1,700/night
Sienna
5 Bedrooms5 Bathrooms10 People250
Bohemian Design House

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...

Price from €550/night
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

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