Curated Luxury holiday rentals deals in Siena

With a stay at Relais Castel Bigozzi in Monteriggioni, you'll be 4.1 mi (6.5 km) from Monteriggioni Castle and 11.5 mi (18.6 km) from City Hall Castellina In Chianti. This spa hotel is 14 mi (22.6 km) from San Gimignano Communal Palace and 14.5 mi (23.3 km) from Piazza del Campo.

Agriturismo Podere Casato is located in the Chianti Classico region, in the heart of the Tuscan countryside and 15 mi from Siena. It features rooms and apartments with panoramic views, and a large swimming pool. WiFi is free.

The accommodations at the Podere is all air-conditioned and includes satellite TV. Both rooms and apartments feature original terracotta flooring, and panoramic views of the Chianti and Crete Senesi hills.

This historic country manor has a bar. The restaurant specializes in local cuisine. There is a sun terrace around the swimming pool.

Free parking is provided on site. The Colonna del Grillo exit of the Raccordo Siena-Bettolle motorway is a 4-minute drive from the property, and the center of Castelnuovo Berardenga is 2.2 mi away.

With a pool, Villa Casalecchi is a 19th-century property 1.6 mi from Castellina in Chianti. It features free Wi-Fi and a sun terrace overlooking the vineyards and olive groves.

All accommodations at the Casalecchi is en suite. The Villa offers rooms with antique furnishings and a rustic décor. Each has a TV, and some are air conditioned.

Breakfast is buffet style, with a combination of sweet and savory items.

Surrounded by a large terraced Italian garden, Villa Casalecchi also features a chapel with frescoes. Staff can help arranging tours to nearby attractions.

In the heart of the Chianti area, the property is a 30-minute drive from Siena and 45 minutes from Florence. Riding stables are available nearby.

Hotel Monteriggioni is set in the heart of Chianti, in the walled medieval town of Monteriggioni. It features a large garden with a swimming pool and olive trees.

Monteriggioni shines from the top of a hill with its stone crown. One of the oldest, most memorable and recognizable villages in all of Italy. A true mirage for those who want to dove into the Middle Ages, the Tuscan poet Dante Alighieri used the turrets of Monteriggioni to evoke the sight of the ring of giants encircling the Infernal abyss.

Each guest room has a unique design. They all come with air conditioning and TV with local channels. Breakfast is included and can be enjoyed out in the garden in warm weather.

The Monteriggioni Romantik Hotel also features a bar. There is also a private car park.

There are 4 characteristic restaurants right in front of the hotel where you can sample Tuscan cuisine.

Due to being in an old medieval village, Wifi Connection is not very fast.

Siena is a 20-minute drive away.

Offering quiet street views, Villa Sant'Alberto in Monteroni dʼArbia provides accommodations, a garden, and barbecue facilities. This property offers access to a terrace, table tennis, free private parking, and free Wifi. Guests can make use of the picnic area or the seasonal outdoor pool, or enjoy views of the garden and inner courtyard.

The units at the country house feature private entrance and soundproofing so guests can enjoy a peaceful stay. Each room comes with a kettle and a private bathroom with a bidet and bathrobes, while certain rooms will provide you with a fully equipped kitchen. At the country house, each unit comes with bed linen and towels.

À la carte and continental breakfast options with fresh pastries, fruit, and juice are available. At the property, there is an family-friendly restaurant serving Italian cuisine as well as vegetarian options.

For guests with children, the country house offers outdoor play equipment. A bicycle rental service is available at Villa Sant'Alberto.

Piazza del Campo is 11 miles from the accommodation, while Palazzo Chigi-Saracini is 11 miles away.

With a stay at Belvedere di San Leonino in Castellina in Chianti, you'll be 11.4 mi (18.4 km) from Siena Cathedral and 11.5 mi (18.5 km) from Piazza del Campo. This hotel is 11.5 mi (18.5 km) from Fonte Gaia.

Located in Castellina in Chianti, Villa Casalecchi Country Hotel is in a rural location, within a 10-minute drive of City Hall Castellina In Chianti and Walls of Monteriggioni. This hotel is 14 mi (22.5 km) from Piazza del Campo and 1.8 mi (2.9 km) from Castellina Fortress.

Set in the hills of the Chianti wine district, Borgo Argenina is in a medieval village surrounded by vineyards. It offers an outdoor swimming pool and hot tub in a traditional Tuscan wooden Loggia.

La Pieve is a traditional Tuscan house as well ith rooms available, 6.2 mi outside the town of Gaiole In Chianti. Its swimming pool offers beautiful views of Brolio Castle and green olive groves. Breakfast is available at the property.

La Pieve also offer cooking courses.

All apartments have a rustic design with original stone walls and wood-beamed ceilings. Each one has its own furnished garden and a cozy living room with fireplace.

You will find the hot tub with relaxing music and essential oils, which is open all year. The swimming pool is open from April to October and has sun loungers and a gazebo.

Located in Gaiole in Chianti, Hotel Le Pozze Di Lecchi is on a river, within a 15-minute drive of Cantalici Winery and Medieval Tower of Barbischio. This spa hotel is 4.6 mi (7.4 km) from Castle of Brolio and 5.1 mi (8.3 km) from Chianti Sculpture Park.

With a stay at Palazzo Squarcialupi in Castellina in Chianti, you'll be just steps from Castellina Fortress and Archaeological Museum of Chianti. This spa hotel is 14 mi (22.6 km) from Piazza del Campo and 0.2 mi (0.3 km) from City Hall Castellina In Chianti.

Podere Palazzolo is a country farmhouse set outside Castellina in Chianti. It has large gardens with swimming pool overlooking the Chianti Valley. Parking and Wi-Fi are free.

The rooms are elegantly decorated, and feature terracotta floors, and exposed wooden beams on the ceilings. Each comes with an iPod/iPhone docking station, and most have views of the Tuscan countryside.

Sessions in the wellness area with a 2-seater hot tub and sauna are bookable on site.

The property is family-run and staff speak Italian, French, English, and German. The restaurant is open from 12:00 to 21:30 and serves traditional food and snacks, including bruschette.

The Palazzolo is 9.3 mi from Siena and 25 mi from Florence. San Gimignano is a 30-minutes drive away.

When you stay at Relais Le Macine di Stigliano in Sovicille, you'll be next to a golf course and steps from Val di Merse. This golf hotel is 16.5 mi (26.6 km) from Piazza del Campo and 6.9 mi (11.1 km) from Ecco La Cucina.

<h2>Elegant Accommodations</h2>

Podere La Casa in Villa dʼArceno offers a country house with an infinity swimming pool, fitness center, sun terrace, and a beautiful garden. Free WiFi is available throughout the property.

<h2>Comfortable Amenities</h2>

Guests enjoy private check-in and check-out services, a fitness room, daily housekeeping, outdoor play area, and badminton equipment hire. Additional facilities include free on-site private parking, bicycle parking, and bike hire.

<h2>Stunning Views</h2>

The property features a terrace, balcony, and patio with garden and pool views. Mountain and inner courtyard views enhance the serene environment.

<h2>Convenient Location</h2>

Located 17 mi from Piazza del Campo and 28 mi from Piazza Matteotti, Podere La Casa is 50 mi from Florence Airport. Cycling enthusiasts can explore the surrounding area.

Located in Radda in Chianti, 13 miles from Piazza Matteotti, LOCANDA PODERE LE VIGNE provides accommodations with a seasonal outdoor swimming pool, free private parking, a garden and a restaurant. This 4-star hotel features free WiFi and a bar. Guests can have a drink at the snack bar.

An Italian breakfast is available at the hotel.

Piazza del Campo is 22 miles from LOCANDA PODERE LE VIGNE, while The Mall Luxury Outlet is 23 miles away. Florence Airport is 36 miles from the property.

Located on a hillside and surrounded by vineyards and cypress trees, Capanelle Wine Resort is around 500mt from Gaiole in Chianti's town center. It offers a panoramic outdoor swimming pool and free Wi-Fi throughout.

Featuring a characteristic Tuscan style, the air-conditioned rooms come with terracotta floors, wood beamed ceilings and wooden furnishings. Each has a flat-screen TV and private bathroom equipped with free toiletries and a hairdryer.

An Italian breakfast, with hot drinks, juice and pastries, is served daily. A tour of the winery, including wine tasting, is available on request.

Siena is 19 mi from Capanelle Wine Resort. Greve in Chianti is a 40-minute drive away.

15 miles from Piazza del Campo in Murlo, La Serra offers accommodations with access to a hot tub, spa facilities, and beauty services. This property offers a private pool, free Wifi, and free private parking. The country house features an outdoor fireplace and a 24-hour front desk.

The air-conditioned country house consists of 1 bedroom, a living room, a fully equipped kitchen with a dishwasher and a coffee machine, and 1 bathroom with a walk-in shower and bathrobes. A private entrance leads guests into the country house, where they can enjoy some wine or champagne and fruit. The country house offers bed linen, towels, and laundry service.

There is a coffee shop, and a mini-market is also available.

For guests with children, the country house provides an indoor play area and outdoor play equipment. There is a garden with a barbecue at this property, and guests can go cycling nearby.

National Picture Gallery Siena is 15 miles from La Serra, while Palazzo Chigi-Saracini is 15 miles from the property.

10 miles from Piazza del Campo in Castellina in Chianti, Luxury Serviced Cottage in a Historical Chianti Borgo offers accommodations with access to an open-air bath. This property offers access to a terrace, tennis at the tennis court, free private parking, and free Wifi. The country house features a pool with garden views, hot tub, and bicycle parking.

The air-conditioned country house consists of 2 bedrooms, a living room, a fully equipped kitchen with a dishwasher and a coffee machine, and 2 bathrooms with a walk-in shower and a hot tub. A private entrance leads guests into the country house, where they can enjoy some wine or champagne and fruit. The country house offers bed linen, towels, and daily room service.

During warmer months, you can make use of the barbecue facilities and eat on the private patio.

Guests at the country house can enjoy cycling and hiking nearby, or make the most of the garden.

Piazza Matteotti is 18 miles from Luxury Serviced Cottage in a Historical Chianti Borgo. Florence Airport is 37 miles from the property.

Castello di Leonina Relais - Adults Only was once a noble residence. This 13th-century castle is set in Asciano and has beautiful views of the hills. It features a wellness corner, a Finnish sauna and a swimming pool with hydromassage area.

Guest rooms are spacious and elegantly decorated. They come with satellite TV and a mini-bar. This 4-star hotel also features meeting facilities and a fine restaurant with terrace.

The small spa is located in one of the towers, and includes a Turkish bath, and shower with chromotherapy and aromatherapy.

The wellness corner has also a relax area where guests can enjoy a different kinds of tisanes, and a massage room offering several types of treatments.

Castello di Leonina Relais - Adults Only is located 11 mi from Siena, while Asciano is reachable by car in 20 minutes.

Surrounded by vineyards, Belvedere Di San Leonino is located in Castellina in Chianti, in the heart of the Chianti area. Set in a historic country house from the 1400s, this property offers rooms decorated in a characteristic Tuscan style.

The Belvedere features private gardens with free parking and a spacious outdoor swimming pool. The beautiful panoramic views include the vineyards, olive groves, the Elsa Valley, San Gimignano and Siena.

Each room comes with terracotta flooring, high oak-beamed ceilings, antique furniture and wrought-iron beds.

Il Cortile restaurant serves buffet breakfast, and Tuscan cuisine for dinner. In the evening, aperitif and drinks are served in the bar with lounge. During summer, dinner is serve in the garden.

Guests can enjoy free wine tasting at a nearby shop.

Florence is 28 mi from Hotel Belvedere Di San Leonino, while Siena is a 20-minute drive away.

Castello di San Fabiano offers accommodations in Monteroni dʼArbia, 8.6 miles from Piazza del Campo and 8.6 miles from National Picture Gallery Siena. The property is around 8.6 miles from Palazzo Chigi-Saracini, 10 miles from National Museum of Etruscan Archaeology, and 10 miles from Siena Train Station. The country house offers garden views, a picnic area, and free Wifi is available throughout the property.

At the country house, units include a desk. There's a private bathroom with shower and a hair dryer in each unit, along with free toiletries. At the country house, the units include bed linen and towels.

Continental and Italian breakfast options with local specialities, fresh pastries, and fruit are available.

You can play table tennis at the country house, and bike rental is available. Guests can swim in the saltwater pool, relax in the garden, or go cycling.

San Cristoforo Church is 11 miles from Castello di San Fabiano, while Bagno Vignoni is 23 miles from the property.