List your home
Apply filters
£ to

Price

£10 - 500+

Price per night

£ to per night

Location

  • Italy Clear
  • Tuscany Clear
  • Province of Siena Clear

Location

Province of Siena

  • Show all locations
  • Abbadia San Salvatore (2)
  • Asciano (11)
  • Bagno Vignoni (1)
  • Buonconvento (12)
  • Casole d'Elsa (20)
  • Castellina In Chianti (21)
  • Castelmuzio (8)
  • Castelnuovo Berardenga (24)
  • Castiglione D'Orcia (5)
  • Cetona (22)
  • Chianciano Terme (3)
  • Chiusdino (2)
  • Chiusi (6)
  • Colle di Val d'Elsa (11)
  • Gaiole in Chianti (33)
  • La Piazza (1)
  • Montalcino (12)
  • Montepulciano (25)
  • Monteriggioni (11)
  • Monteroni d'Arbia (7)
  • Monticiano (4)
  • Montisi (2)
  • Murlo (2)
  • Palazzone (3)
  • Pienza (26)
  • Pievasciata (1)
  • Poggibonsi (18)
  • Radda in Chianti (11)
  • Radicofani (8)
  • Radicondoli (34)
  • Rapolano Terme (4)
  • Rosia (1)
  • San Casciano dei Bagni (3)
  • San Gimignano (53)
  • San Giovanni d'Asso (10)
  • San Quirico d'Orcia (1)
  • Sarteano (7)
  • Siena (51)
  • Sinalunga (18)
  • Sovicille (8)
  • Torre A Castello (1)
  • Torrita di Siena (2)
  • Trequanda (4)
  • Ville di Corsano (4)

more +

less -

Bedrooms

Show all

  • Show all
  • Studio
  • 1 Bedroom
  • 2 Bedrooms
  • 3 Bedrooms
  • 4 Bedrooms
  • 5 Bedrooms
  • 6 Bedrooms
  • 7 Bedrooms
  • 8 Bedrooms
  • 9 Bedrooms
  • 10 Bedrooms
  • 11 Bedrooms
  • 12 Bedrooms
  • 13 Bedrooms
  • 14 Bedrooms
  • 15+ Bedrooms

more +

less -

To book this holiday home you need to pay through the Holiday Lettings website. We can’t protect your payment if you don’t pay through us. Learn more

Filters applied: DVD player (514)

32 of 514 Results

Sort by: Default

  • Default
  • Price low to high
  • Price high to low
  • Reviews

from £206 / night

£1439 - £1947 / week

View

(3) Excellent 5/5 

1 / 24

Holiday farmhouse rental

Farmhouse / 2 Bedrooms / sleeps 5

  • Nearest beach 80 km
  • Swimming pool
  • Great for children of all ages
  • Car advised

Excellent 5/5 

Add to shortlist

from £206 / night

£1439 - £1947 / week

View

A typical stone barn immersed in the Tuscan countryside of San Gimignano. A large garden overlooks the hills and surrounding countryside. Up to 7 people in a both modern and rustic atmosphere.  …see more

from £258 / night

£1802 - £2574 / week

View

(1) Excellent 5/5 

1 / 24

Holiday villa with swimming pool in Montepulciano

Villa / 6 Bedrooms / sleeps 12

  • Nearest beach 120 km
  • Swimming pool
  • Great for children of all ages
  • Car essential

Excellent 5/5 

Add to shortlist

from £258 / night

£1802 - £2574 / week

View

The place is peaceful, outside in the garden; you have the possibility to relax under the trees or to eat under the stars. Beautiful structure for a relaxing holiday in the tuscany area . ask for availability we have several solution for you. also self catering apartments with breakfast service.  …see more

from £452 / night

£3162 - £4265 / week

View

(1) Excellent 5/5 

1 / 16

Holiday farmhouse with swimming pool in San Fabiano

Farmhouse / 6 Bedrooms / sleeps 20

  • Nearest beach 80 km
  • Swimming pool
  • Great for children of all ages
  • Car not necessary

Excellent 5/5 

Add to shortlist

from £452 / night

£3162 - £4265 / week

View

Climatized villa with swimming pool, wi-fi,and TV with Sky channels, offers relax and fun at only 7 miles from Siena. The Count Filippo Fiorentini, English speaking will welcome you with a good glass of wine, in his villa.  …see more

Featured properties

from £147 / night

£1023 - £2023 / week

View

(3) Excellent 5/5 

1 / 24

Holiday guest house in Siena

Guest house / 2 Bedrooms / sleeps 4

  • Great for children of all ages
  • Car advised
  • Air conditioning
  • Some pets are welcome - please contact the owner

Excellent 5/5 

Add to shortlist

from £147 / night

£1023 - £2023 / week

View

Villa di Geggiano - home and winery of the Bianchi Bandinelli family since 1527. Just 5 kilometres from Siena, in the hills of Chianti Classico. Originally built in 14th century, the the Villa has now been complemented by the recent addition of two luxury guest suites. The Villa and its gardens are a National Heritage property and there is a great deal to see and enjoy!  …see more

from £209 / night

£1460 - £3395 / week

View

(3) Excellent 5/5 

1 / 24

Villa rental in Siena with swimming pool

Villa / 9 Bedrooms / sleeps 18

  • Nearest beach 95 km
  • Swimming pool
  • Great for children of all ages
  • Car essential

Excellent 5/5 

Add to shortlist

from £209 / night

£1460 - £3395 / week

View

Beautiful Tuscan detached villa with swimming pool near Siena to rent for sleeps up to-10-16-20-It is an ideal place for families to spend a relaxing holiday far from town noises among the peace of the country. A heaven of peace in the heart of Montagnola Senese at a stone's throw from Siena.  …see more

from £179 / night

£1250 - £2519 / week

View

(2) Very Good 4.5/5 

1 / 24

Holiday farmhouse with swimming pool in Montepulciano

Farmhouse / 5 Bedrooms / sleeps 10

  • Nearest beach 200 km
  • Swimming pool
  • Great for children of all ages
  • Car advised

Very Good 4.5/5 

Add to shortlist

from £179 / night

£1250 - £2519 / week

View

Due to the central geographical position of Villa Pietra del Diavolo you can spend a day touring famous cities rich in history, culture, architecture and artistic works such as Siena (km 45), Arezzo (km 50), Firenze (km 110), Perugia (km 70), Roma (km 150). Croce di Febo take care of our land according to the traditions of organic agricolture respecting the soil.  …see more

from £177 / night

£1236 - £1633 / week

View

(1) Excellent 5/5 

1 / 21

Holiday villa with swimming pool in San Giovanni d'Asso

Villa / 3 Bedrooms / sleeps 5

  • Nearest beach 120 km
  • Swimming pool
  • Great for children of all ages
  • Car essential

Excellent 5/5 

Add to shortlist

from £177 / night

£1236 - £1633 / week

View

3 BDR cosy house with patio,small pool,AC,Wifi, in the heart of Siena countryside, nestled in a village. Private parking. Please,ALWAYS enquiry about prices.  …see more

from £171 / night

£1192 - £2170 / week

View

(3) Excellent 5/5 

1 / 31

Holiday lodge in Pienza

Lodge / 3 Bedrooms / sleeps 8

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Some pets are welcome - please contact the owner

Excellent 5/5 

Add to shortlist

from £171 / night

£1192 - £2170 / week

View

Modern and tastefully decorated cottages with an infinity swimming pool where you can totally relaxed surrounded by the typical tuscany landscape: a fantastic view. Perfect for families, couples or groups of friends to enjoy cultural, art, good wine and italian food.  …see more

from £96 / night

£666 - £1500 / week

View

(9) Excellent 5/5 

1 / 15

Holiday apartment in Siena

Apartment / 2 Bedrooms / sleeps 4

  • Great for children of all ages
  • Car not necessary
  • No pets allowed

Excellent 5/5 

Add to shortlist

from £96 / night

£666 - £1500 / week

View

In the very center of Siena, Historic Residence Palazzo Bichi Ruspoli is the best choice to visit the city. Just a few steps from the famous Piazza del Campo, you'll live in an ancient medieval building in a newly remodeled apartment.  …see more

from £103 / night

£716 - £920 / week

View

(1) Excellent 5/5 

1 / 22

Radicondoli holiday home rental

House / 3 Bedrooms / sleeps 6

  • Beach / lakeside relaxation
  • Nearest beach 60 km
  • Great for children of all ages
  • Car advised

Excellent 5/5 

Add to shortlist

from £103 / night

£716 - £920 / week

View

Podere la Fonte is situated in a most spectacular position just below the ancient castellated village of Radicondoli. It has magnificent uninterrupted views over the Cecina valley and the surrounding hills.At night you can see the lights of Volterra.  …see more

from £375 / night

£2625 - £4203 / week

View

(4) Excellent 5/5 

1 / 26

Holiday villa rental

Villa / 8 Bedrooms / sleeps 16

  • Nearest beach 120 km
  • Swimming pool
  • Great for children of all ages
  • Car essential

Excellent 5/5 

Add to shortlist

from £375 / night

£2625 - £4203 / week

View

8 BDR luxury historical villa with garden and pool in the heart of Siena countryside nestled in a village.AC, WiFi,Private parking Please,ALWAYS,enquiry about prices.The house can be rented just in part (4BDR).  …see more

from £72 / night

£500 - £890 / week

View

(6) Excellent 5/5 

1 / 23

Holiday farmhouse with shared pool in Montepulciano

Farmhouse / 2 Bedrooms / sleeps 6

  • Nearest beach 0 km
  • Swimming pool
  • Great for children of all ages
  • Car advised

Excellent 5/5 

Add to shortlist

from £72 / night

£500 - £890 / week

View

2 bedroom beautiful 500 year old restored farmhouse. 7km outside of Montepulciano. Pool, terrace, garden area, patio, and BBQ. 5 minute drive to nearest supermarket, shops, bars and restaurants.  …see more

from £95 / night

£662 / week

View

(13) Excellent 5/5 

1 / 19

Holiday apartment in Montisi

Apartment / 1 Bedroom / sleeps 4

  • Suitable for children over 5
  • No pets allowed

Excellent 5/5 

Add to shortlist

from £95 / night

£662 / week

View

The apartment is ideal if you want to experience life in a Medieval town in Tuscany; your host is a professional Siena tourist guide, an official cheese taster and wine expert and the apartment is elegantly decorated with antiques but has all of the modern comforts.  …see more

from £100 / night

£699 - £1177 / week

View

(16) Excellent 5/5 

1 / 23

Holiday farmhouse rental

Farmhouse / 3 Bedrooms / sleeps 8

  • Nearest beach 99 km
  • Great for children of all ages
  • Car advised
  • Some pets are welcome - please contact the owner

Excellent 5/5 

Add to shortlist

from £100 / night

£699 - £1177 / week

View

Gorgeous views from this spacious restored farmhouse on artisanal working farm . Priv. balcony and patios, huge kitchen, Wi-Fi, Sat TV. Help in finding cooking classes, baby-sitting, horseback riding, motorcycle, winery, bike & walking tours  …see more

from £137 / night

£956 - £1250 / week

View

(2) Excellent 5/5 

1 / 17

Monteriggioni holiday villa rental

Villa / 2 Bedrooms / sleeps 6

  • Nearest beach 80 km
  • Swimming pool
  • Great for children of all ages
  • Car advised

Excellent 5/5 

Add to shortlist

from £137 / night

£956 - £1250 / week

View

Wonderful Villa with private pool overlooking the castle of Monteriggioni  …see more

from £184 / night

£1287 - £1655 / week

View

(4) Excellent 5/5 

1 / 24

Val d'Orcia holiday villa rental

Villa / 4 Bedrooms / sleeps 9

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Some pets are welcome - please contact the owner

Excellent 5/5 

Add to shortlist

from £184 / night

£1287 - £1655 / week

View

A really charming and full of style apartment in a XVI th century stone villa near Montalcino, Pienza, Siena, Montichiello. An enchanted garden and an amazing swimming pool with view on Montalcino for an unforgettable holiday: good food and wine, art, sport and relax..  …see more

from £144 / night

£1004 - £1236 / week

View

(5) Excellent 5/5 

1 / 20

Radicondoli holiday apartment rental

Apartment / 3 Bedrooms / sleeps 9

  • Nearest beach 60 km
  • Swimming pool
  • Great for children of all ages
  • Car advised

Excellent 5/5 

Add to shortlist

from £144 / night

£1004 - £1236 / week

View

Enjoy the view, meanwhile swimming in the pool, dine in the outside garden watching the beautiful sunset vew,in front of the chimney during the winter in the comfort of the heated pavements.  …see more

from £103 / night

£721 - £993 / week

View

(3) Very Good 4.5/5 

1 / 24

Farmhouse rental in Caprera

Farmhouse / 3 Bedrooms / sleeps 6

  • Nearest beach 100 km
  • Great for children of all ages
  • Car advised
  • Air conditioning

Very Good 4.5/5 

Add to shortlist

from £103 / night

£721 - £993 / week

View

Elegant Liberty farmhouse on the hills, in a quite village just ten minutes from Siena city centre. Stunning view toward the city steeples across the countryside. Olive groves and fields for walking and horse riding. Garden and farm yard for outdoor dining.  …see more

from £43 / night

£295 - £405 / week

View

(2) Excellent 5/5 

1 / 17

Holiday home in Cetona

House / 2 Bedrooms / sleeps 4

  • Not suitable for children
  • Car advised
  • Some pets are welcome - please contact the owner

Excellent 5/5 

Add to shortlist

from £43 / night

£295 - £405 / week

View

Opportunity awaits you to experience your Italian holiday in this unique home. The history and character of the home, neighborhood and Cetona will make you feel immersed in the lifestyle and truly feel like a local. We specialize in bike tours,rental and itineraries A short stroll from the home will take you to the piazza where you find restaurants, cafes, and shops  …see more

from £164 / night

£1148 - £1324 / week

View

(1) Excellent 5/5 

1 / 21

Colle di Val d'Elsa holiday villa accommodation

Villa / 3 Bedrooms / sleeps 8

  • Nearest beach 90 km
  • Swimming pool
  • Great for children of all ages
  • Car essential

Excellent 5/5 

Add to shortlist

from £164 / night

£1148 - £1324 / week

View

In the heart of Tuscany, the Antica Canonica is a historical residence, excellently located for exploring the area and discovering the delights of Tuscany. Ideal for families seeking relaxation. Swimming-pool, hydro massage, exclusive garden. The original characteristics keep the old glamour and suggest the idea that the time has stopped.  …see more

from £526 / night

£3677 - £5148 / week

View

(3) Very Good 4.5/5 

1 / 20

Holiday villa rental

Villa / 12 Bedrooms / sleeps 24

  • Nearest beach 50 km
  • Swimming pool
  • Great for children of all ages
  • Car advised

Very Good 4.5/5 

Add to shortlist

from £526 / night

£3677 - £5148 / week

View

Tuscan private luxurious Villa, stone built, private pool, jacuzzi, 12 bedrooms, 12 bathrooms, up to 24 people private park, organic olive oil , garden, terrace. Ideal for big family or big group of friends, weddings, meetings  …see more

from £65 / night

£450 - £800 / week

View

(5) Excellent 5/5 

1 / 20

Apartment accommodation in Gaiole in Chianti with shared pool

Apartment / 2 Bedrooms / sleeps 6

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning

Excellent 5/5 

Add to shortlist

from £65 / night

£450 - £800 / week

View

With beautiful views over the village, this ground floor, comfortable apartment is the perfect spot! Modern facilities including a Swimming pool a gym, and table tennis. The apartment has 2 bedrooms, a well equipped kitchen, a dining terrace, and underground parking. The multinational users are generally quiet and friendly, respectful of the natural ambience of the Borgo.  …see more

from £162 / night

£1132 - £1825 / week

View

(3) Excellent 5/5 

1 / 16

Radicondoli holiday villa rental

Villa / 5 Bedrooms / sleeps 12

  • Nearest beach 40 km
  • Swimming pool
  • Great for children of all ages
  • Car advised

Excellent 5/5 

Add to shortlist

from £162 / night

£1132 - £1825 / week

View

Charming independent villa in the heart of Tuscany with pool garden parking wonderful panorama, near siena and san gimignano.  …see more

from £69 / night

£478 - £736 / week

View

(1) Excellent 5/5 

1 / 13

Holiday cottage with shared pool in Crete Senesi

Cottage / 1 Bedroom / sleeps 2

  • Swimming pool
  • Great for children of all ages
  • Car advised
  • No pets allowed

Excellent 5/5 

Add to shortlist

from £69 / night

£478 - £736 / week

View

Agriturismo Podernuovo is an excellent place for a relaxing vacation. Independent and quiet, next to the owner's residence, has a wonderful 360° panorama looking the Crete Senesi hills with view over Siena in one side and Montalcino and Trequanda in the other side. Agriturismo Podernuovo is 10 km from the hot springs of Rapolano Terme, while Siena is 30 km away.  …see more

from £73 / night

£508 - £688 / week

View

(1) Excellent 5/5 

1 / 24

Holiday castle with shared pool in Monteroni d'Arbia

Castle / 2 Bedrooms / sleeps 4

  • Beach / lakeside relaxation
  • Nearest beach 50 km
  • Swimming pool
  • Great for children of all ages

Excellent 5/5 

Add to shortlist

from £73 / night

£508 - £688 / week

View

A country hideaway with traditional comforts. Excellent equestrian, golfing and spa activities, hiking and biking. Kids Club. Excellent for touring art cities and Chianti and Brunello wine countries. For nature lovers, artists and photographers. Full concierge services. Please request for Formignano B&B, Horse Riding & Golf, Spa Days, Art City & Local Tours, Weddings & Events.  …see more

from £59 / night

£410 - £505 / week

View

(3) Very Good 4.5/5 

1 / 16

Holiday farmhouse with shared pool in San Gimignano

Farmhouse / 1 Bedroom / sleeps 4

  • Nearest beach 80 km
  • Swimming pool
  • Great for children of all ages
  • Car essential

Very Good 4.5/5 

Add to shortlist

from £59 / night

£410 - £505 / week

View

Romantic one bedroom apartment in a converted traditional Tuscan farmhouse between San Gimignano and Volterra. Beautifully renovated farm building, Terraces with fantastic views, pool, ideal for rest and relaxation! Easy access Siena , Pisa and Florence.  …see more

from £127 / night

£883 - £1398 / week

View

(3) Excellent 5/5 

1 / 22

Villa rental in Chiusi

Villa / 5 Bedrooms / sleeps 12

  • Beach / lakeside relaxation
  • Great for children of all ages
  • Car advised
  • Pets welcome

Excellent 5/5 

Add to shortlist

from £127 / night

£883 - £1398 / week

View

Self-catering Tuscan villa with stunning rolling hill views, just 2mins from supermarket, restaurants. Private garden and balcony for al-fresco dining. In the middle way from Florence to Rome. Many tourist places to visit in as Chiusi, Montepulciano, Pienza.  …see more

from £53 / night

£368 - £3015 / week

View

(6) Excellent 5/5 

1 / 23

Holiday villa with swimming pool in Castelnuovo Berardenga

Villa / 6 Bedrooms / sleeps 11

  • Nearest beach 60 km
  • Swimming pool
  • Great for children of all ages
  • Car essential

Excellent 5/5 

Add to shortlist

from £53 / night

£368 - £3015 / week

View

Villa in Chianti/Siena, Tuscany, Italy On top of a Hill with Private Pool and Large Terrace A Haven of Peace and Quietness, 20 Minutes from Siena Sleeps 11 (6 Bedrooms with en suite bathrooms) For parties of 2 or 4 people the villa will be shared , unless the guests are willing to pay an exta  …see more

from £43 / night

£295 - £442 / week

View

(4) Very Good 4.5/5 

1 / 24

Poggibonsi holiday apartment rental

Apartment / 1 Bedroom / sleeps 3

  • Nearest beach 80 km
  • Swimming pool
  • Great for children of all ages
  • Car advised

Very Good 4.5/5 

Add to shortlist

from £43 / night

£295 - £442 / week

View

Five apartments in a pretty, rural location in Chianti. Within very easy access of routes to Florence and Siena, Podere Oliveta is a good choice for exploring the area , a relaxing holiday with a beautiful swimming pool and stunning views. While staying in this peaceful property you may enjoy wine tasting from the producers or cooking lessons.  …see more

from £70 / night

£490 - £665 / week

View

(3) Excellent 5/5 

1 / 23

San Gimignano holiday apartment rental

Apartment / 1 Bedroom / sleeps 3

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • No pets allowed

Excellent 5/5 

Add to shortlist

from £70 / night

£490 - £665 / week

View

Lovely apartment set inside a renovated farmstead dating back to the XVII century, featuring large common spaces and a wonderful pool with breathtaking views over the sloping Tuscan hills and the ancient town of Volterra. Private garden and veranda for alfresco dining.  …see more

from £94 / night

£657 - £1752 / week

View

(9) Very Good 4/5 

1 / 24

Holiday villa with swimming pool, tennis court in Radda in Chianti

Villa / 3 Bedrooms / sleeps 7

  • Nearest beach 110 km
  • Swimming pool
  • Great for children of all ages
  • Car essential

Very Good 4/5 

Add to shortlist

from £94 / night

£657 - £1752 / week

View

What makes a holiday at LisiDor an unforgettable memory? the people you will meet ... * our Chef * our lovely housekeeper * our professional tennis teacher * our local guide * our 'PERSONAL DAILY HOLIDAY PLANNER' !! ... EXPERIENCE REAL TUSCANY ... Self-catering villa stunning view over hills Private pool. tennis court wifi  …see more

from £37 / night

£254 - £291 / week

View

(1) Excellent 5/5 

1 / 14

Holiday apartment with shared pool in Cetona

Apartment / 1 Bedroom / sleeps 4

  • Swimming pool
  • Great for children of all ages
  • No pets allowed

Excellent 5/5 

Add to shortlist

from £37 / night

£254 - £291 / week

View

Cetona is the perfect small Tuscan village offering ambiance, tranquility, and character. Cetona has all the services you will need also; restaurants, bars and cafes, shops, and services, right in the piazza, just a short walk from the apartment.  …see more
first

Also consider

Don’t let an old browser slow down your holiday

Your browser is out of date and might not work well with our website. Download the latest version to speed up your hunt for the perfect holiday home.

Just click on the icons to get to the download page