Holiday homes - Holiday rentals

Close

View larger map

Price per night

to

Bedrooms

Bathrooms

Location

  • Italy
  • Tuscany
  • Province of Siena
  • All locations
  • Abbadia San Salvatore (2)
  • Asciano (30)
  • Bagni di San Filippo (1)
  • Bagno Vignoni (2)
  • Brenna (1)
  • Buonconvento (14)
  • Campiglia d'Orcia (1)
  • Casole d'Elsa (63)
  • Castellina In Chianti (32)
  • Castelmuzio (4)
  • Castelnuovo Berardenga (46)
  • Castiglioncello del Trinoro (2)
  • Castiglione D'Orcia (13)
  • Cetona (51)
  • Chianciano Terme (15)
  • Chiusdino (13)
  • Chiusi (11)
  • Colle di Val d'Elsa (22)
  • Gaiole in Chianti (56)
  • Gallina (3)
  • Le Piazze (4)
  • Montalcino (27)
  • Montecchio (5)
  • Montepulciano (83)
  • Monteriggioni (30)
  • Monteroni d'Arbia (16)
  • Monticiano (12)
  • Montisi (13)
  • Murlo (9)
  • Orgia (2)
  • Palazzone (9)
  • Piancastagnaio (1)
  • Pienza (58)
  • Pievescola (4)
  • Poggibonsi (53)
  • Radda in Chianti (28)
  • Radicofani (21)
  • Radicondoli (44)
  • Rapolano Terme (23)
  • Rosia (2)
  • San Casciano dei Bagni (20)
  • San Gimignano (155)
  • San Giovanni d'Asso (16)
  • San Quirico d'Orcia (5)
  • Sarteano (29)
  • Siena (103)
  • Sinalunga (29)
  • Sovicille (18)
  • Strove (1)
  • Torre A Castello (2)
  • Torrita di Siena (16)
  • Trequanda (4)
  • Ville di Corsano (8)
  • Vivo d'Orcia (1)
  • Volte Basse (1)

More

Less

Also consider

Coastal Cottages
222 properties
Apartments Sardinia
478 properties
Apartments Tuscany
3181 properties
Apartments Lake Garda Area
103 properties
Apartments Lake Como Area
494 properties
Apartments Sicily
634 properties
Villas Siena
512 properties
Villas San Gimignano
426 properties
Villas Montepulciano
292 properties
Casole d'Elsa
186 properties
Colle di Val d'Elsa
181 properties
Gaiole in Chianti
169 properties
Poggibonsi
165 properties
Castelnuovo Berardenga
162 properties
Sinalunga
161 properties
Villas Pienza
160 properties
Villas Montalcino
156 properties
Villas Castellina In Chianti
141 properties
Asciano
118 properties
Rapolano Terme
106 properties
Payment Protection
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

1,236 Holiday homes

Filters applied: Private garden (1,236)

(1) Excellent 

1 / 8

Province of Siena / Strove

2 4 7 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min stay
Key info: Child friendly ; No pets allowed; Private garden;
 …see more

from £43 / night

£300 / week

Book Book View

from £43 / night

1 / 17

Castelnuovo Berardenga / Pievasciata

4 13 3 nights min stay

  • 4 bedrooms
  • Sleeps 13
  • 3 nights min stay
Key info: Child friendly ; Car essential; Pet friendly;
 …see more

from £103 / night

£1026 / week

Book Book View

from £103 / night

(2) Very Good 

1 / 4

Province of Siena / Bagni di San Filippo

2 3 2 nights min stay

  • 2 bedrooms
  • Sleeps 3
  • 2 nights min stay
Key info: Child friendly ; Car essential; Pet friendly;
 …see more

from £77 / night

£428 / week

Book Book View

from £77 / night

Featured properties

1 / 4

Province of Siena / Orgia

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
Key info: Nearest beach 80 km; Not suitable for children; Car essential;
 …see more

from £12 / night

£80 / week

Book Book View

from £12 / night

1 / 24

Province of Siena / Palazzone

2 3 Min stay varies

  • 2 bedrooms
  • Sleeps 3
  • Min stay varies
Key info: Nearest beach 106 km; Swimming pool; Suitable for children age 5+;
 …see more

from £77 / night

£300 - £385 / week

Book Book View

from £77 / night

1 / 14

Province of Siena / Poggibonsi

1 2 2 nights min stay

  • 1 bedroom
  • Sleeps 2
  • 2 nights min stay
Key info: Nearest beach 76 km; Child friendly ; Car essential;
 …see more

from £39 / night

£270 / week

Book Book View

from £39 / night

(28) Excellent 

1 / 20

Amazing Tuscan holiday apartment in the historical Town centre of Colle di Val d'Elsa, sleeps 4 - Colle di Val d'Elsa apartment sleeps 4

Province of Siena / Colle di Val d'Elsa

2 4 2 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min stay
Key info: Nearest beach 50 km; Child friendly ; Car advised;
The Dietro Le Mura holiday home has been completely renovated and is located in the historical town centre of Colle di Val d'Elsa, a characteristically medieval town steeped in history. The apartment is on the first floor, has its own entrance and possible parking  …see more

from £69 / night

£462 - £573 / week

Enquire Enquire View

from £69 / night

(7) Excellent 

1 / 18

3 bedroom farmhouse in the picturesque Tuscan hills boasting private pool, terrace and garden, sleeps 6 - San Gimignano farmhouse sleeps 6

Province of Siena / San Gimignano

3 6 Min stay varies

  • 3 bedrooms
  • Sleeps 6
  • Min stay varies
Key info: Nearest beach 45 km; Swimming pool; Child friendly ;
Podere Le Monache set on a hillside dominates one of the most picturesque and spectacular landscapes in Tuscany. With distant views over hills, out to sea towards Livorno and Pisa. Originally a convent wrapped in history Le Monache has a magical and spiritual atmosphere  …see more

from £84 / night

£565 - £941 / week

Enquire Enquire View

from £84 / night

(30) Excellent 

1 / 24

SORTOIANO apartaments in historic Tuscan property - Val di Merse apartment sleeps 5

Siena / Val di Merse

2 5 1 night min stay

  • 2 bedrooms
  • Sleeps 5
  • 1 night min stay
Key info: Nearest beach 60 km; Child friendly ; Car essential;
OFFER IN JULY !!! FURTHER AVAILABILITY DESPITE THE BOOKING CALENDAR! PLEASE, LET'S CONTACT US! The property dates back to the 14th century and for generations has been part of the property Santini, once farmers. The apartments were once stables for livestock. It has  …see more

from £39 / night

£257 - £300 / week

Book Book View

from £39 / night

1 / 5

VILLA TINAIO - Monteroni d'Arbia house sleeps 10

Province of Siena / Monteroni d'Arbia

8 10 Min stay varies

  • 8 bedrooms
  • Sleeps 10
  • Min stay varies
Key info: Swimming pool; Child friendly ; No pets allowed;
Monteroni d'Arbia: Villa Tinaio was originally the estate wine cellar. Because of its size, it can accomodate families or groups of friends up to 24 people who can enjoy moments of absolute relax, on the border of the private pool, surrounded by ancient trees.On th  …see more

from £464 / night

£3248 - £3676 / week

Book Book View

from £464 / night

1 / 4

villa giulia - Monteriggioni farmhouse sleeps 2

Province of Siena / Monteriggioni

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
Key info: Nearest beach 60 km; Swimming pool; Child friendly ;
The propertyis a twelth century farmhouse, situated in the heart of Tuscany only 2km from the walled town monteriggioni. and surrounded by the siennese hills. The property is 500 meters above sea level surrounded by olive groves and magnificent woodlands,Peaceful wood  …see more

from £92 / night

£642 / week

Book Book View

from £92 / night

(30) Excellent 

1 / 25

Tuscan apartment in rural setting with easy access to nearby cities, property has private garden and shared pool - Castel San Gimignano apartment sleeps 6

San Gimignano / Castel San Gimignano

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
Key info: Nearest beach 55 km; Swimming pool; Child friendly ;
The apartment is located in the hamlet of Castel San Gimignano, very near to the best famous cities as Siena, Firenze, San Gimignano, Volterra and the sea is reachable in less than an hour by car. You can also start from here for a relaxing walk or ride through the oliv  …see more

from £86 / night

£471 - £727 / week

Book Book View

from £86 / night

(1) Excellent 

1 / 25

Province of Siena / Orgia

2 4 2 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min stay
Key info: Nearest beach 70 km; Child friendly ; Ask about pets;
 …see more

from £46 / night

£281 - £341 / week

Book Book View

from £46 / night

(1) Excellent 

1 / 14

Villa Verdepino - Rigomagno villa sleeps 10

Sinalunga / Rigomagno

5 10 7 nights min stay

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min stay
Key info: Swimming pool; Child friendly ; Car advised;
The villa sits on a hill immersed in the greenery of a peaceful oasis and surrounded by large grounds.Here, where pleasure and nature meet, it is possible to enjoy long walks through the countryside and at the same time be within easy reach of amenities which are just 5  …see more

from £191 / night

£1334 - £9112 / week

Enquire Enquire View

from £191 / night

1 / 20

house and wonderful garden of exclusive use - Torri villa sleeps 4

Sovicille / Torri

1 4 4 nights min stay

  • 1 bedroom
  • Sleeps 4
  • 4 nights min stay
Key info: Child friendly ; Air conditioning; Ask about pets;
“Il Molino" was restructured in 2011 applying great care of the particulars; entirely surrounded with a wide wonderful garden, the complex lies in a very quite and immaculate wood between the Chianti hills. It is only 25 minutes by car or by train far from the ce  …see more

from £77 / night

£428 / week

Book Book View

from £77 / night

1 / 31

San Gimignano / Castel San Gimignano

1 2 3 nights min stay

  • 1 bedroom
  • Sleeps 2
  • 3 nights min stay
Key info: Swimming pool; Child friendly ; Pet friendly;
 …see more

from £77 / night

£556 / week

Book Book View

from £77 / night

1 / 13

Traditional stone-built villa in Tuscan province of Siena with swimming pool, terrace and barbecue - Montisi villa sleeps 6

Province of Siena / Montisi

3 6 7 nights min stay

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min stay
Key info: Nearest beach 70 km; Swimming pool; Child friendly ;
Three bed stone built home with all the traditional and style of an old tuscan home yet all the modern comforts.Air Conditioning is a must in Tuscany.This property has air conditioning in all rooms and is remotly controlled in each room.Two large bathrooms one with a ba  …see more

from £122 / night

£851 - £1240 / week

Enquire Enquire View

from £122 / night

(1) Excellent 

1 / 16

Classic Tuscan farmhouse on a hilltop with brilliant views of the countryside, outdoor pool - San Gimignano farmhouse sleeps 13

Province of Siena / San Gimignano

7 13 1 night min stay

  • 7 bedrooms
  • Sleeps 13
  • 1 night min stay
Key info: Swimming pool; Child friendly ; Pet friendly;
Torreprima holidays house is 3 Km away from the historical center of San Gimignano, and is situated on top of a hill from where it is possible to delight the beautiful view over the surrounding valleys of olive groves and vineyards. It has availability of 5 apartments.  …see more

from £120 / night

£530 / week

Book Book View

from £120 / night

(3) Very Good 

1 / 21

Sovicille / Torri

1 3 1 night min stay

  • 1 bedroom
  • Sleeps 3
  • 1 night min stay
Key info: Swimming pool; Child friendly ; Car essential;
 …see more

from £77 / night

£471 / week

Book Book View

from £77 / night

(40) Excellent 

1 / 25

Lovingly restored stone-built Tuscan barn - San Gimignano house sleeps 4

Province of Siena / San Gimignano

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
Key info: Nearest beach 55 km; Swimming pool; Child friendly ;
Podere Torricchi is a small collection of beautifully renovated 16th Century farm buildings converted into houses and apartments. Set on a hill the entire site has stunning views of the rolling Tuscan countryside. I'l Granario' is a house set on two floors, tastefully r  …see more

from £90 / night

£625 - £925 / week

Book Book View

from £90 / night

1 / 14

Province of Siena / Poggibonsi

1 3 1 night min stay

  • 1 bedroom
  • Sleeps 3
  • 1 night min stay
Key info: Child friendly ; Air conditioning; No pets allowed;
 …see more

from £52 / night

£359 / week

Book Book View

from £52 / night

1 / 12

Agriturismo Terrarossa 4px - Valiano apartment sleeps 4

Montepulciano / Valiano

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
Key info: Swimming pool; Child friendly ; Ask about pets;
The Terrarossa farm holiday resort is deep in the stunning hills around Montepulciano. It is part of an ancient country estate counting 130 acrwes land, where with respect for the land and its natural balance wheat, sunflowers and, above all, the vines for Vino Nobile  …see more

from £129 / night

£513 - £761 / week

Book Book View

from £129 / night

(2) Excellent 

1 / 22

Pienza / Monticchiello

1 4 Min stay varies

  • 1 bedroom
  • Sleeps 4
  • Min stay varies
Key info: Child friendly ; Pet friendly; Private garden;
 …see more

from £43 / night

£291 - £375 / week

Book Book View

from £43 / night

(16) Excellent 

1 / 10

Sunny 1 bedroom apartment on the Podere Magione Holiday Farm in the San Gimignano region of Tuscany - San Gimignano apartment sleeps 2

Province of Siena / San Gimignano

1 2 3 nights min stay

  • 1 bedroom
  • Sleeps 2
  • 3 nights min stay
Key info: Nearest beach 72 km; Child friendly ; Car essential;
The Podere Magione Holiday Farm is capable of offering various possibilities for your stay in Tuscany, also maintaining an intimate, family atmosphere, considering its modest size.CIPRESSO APARTMENT has one bedroom with twins beds(or the possibility to have a big bed as  …see more

from £43 / night

£257 - £317 / week

Book Book View

from £43 / night

1 / 15

Castelnuovo Berardenga / Vagliagli

2 3 1 night min stay

  • 2 bedrooms
  • Sleeps 3
  • 1 night min stay
Key info: Child friendly ; Ask about pets; Private garden;
 …see more

from £52 / night

£342 / week

Book Book View

from £52 / night

1 / 17

A historic estate in the Crete Senesi, Tuscany - Trequanda house sleeps 4

Province of Siena / Trequanda

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
Key info: Swimming pool; Child friendly ; Car essential;
The property is located on the top of a hill. The apartment is equipped with heating, air conditioning and cooking, it has a separate entrance and overlooks the courtyard of the villa and the hills on the back. It is near the pool. It is located on the ground floor and  …see more

from £95 / night

£633 - £915 / week

Book Book View

from £95 / night

(3) Excellent 

1 / 24

Lovingly renovated Tuscan Farmhouse with pool and garden, sleeps 6 - Casole d'Elsa farmhouse sleeps 6

Province of Siena / Casole d'Elsa

3 6 7 nights min stay

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min stay
Key info: Nearest beach 60 km; Swimming pool; Child friendly ;
Casa Panoramica is a lovingly renovated farmhouse situated at the edge of the small hamlet of Lucciana, just 4 km from the lager hill town of Casole d’Elsa.Internally the house is attractively furnished with a practical kitchen opening onto the dining room with direct  …see more

from £80 / night

£556 - £1453 / week

Enquire Enquire View

from £80 / night

(1) Excellent 

1 / 37

Province of Siena / Monteroni d'Arbia

1 4 1 night min stay

  • 1 bedroom
  • Sleeps 4
  • 1 night min stay
Key info: Nearest beach 97 km; Child friendly ; Car advised;
 …see more

from £52 / night

£359 / week

Book Book View

from £52 / night

1 / 14

Province of Siena / Gaiole in Chianti

1 4 2 nights min stay

  • 1 bedroom
  • Sleeps 4
  • 2 nights min stay
Key info: Swimming pool; Child friendly ; Car essential;
 …see more

from £79 / night

£551 / week

Book Book View

from £79 / night

(7) Excellent 

1 / 24

Rapolano Terme / Serre di Rapolano

1 2 1 night min stay

  • 1 bedroom
  • Sleeps 2
  • 1 night min stay
Key info: Nearest beach 120 km; Swimming pool; Child friendly ;
 …see more

from £82 / night

£556 / week

Book Book View

from £82 / night

1 / 18

La Casina - San Casciano dei Bagni house sleeps 4

Province of Siena / San Casciano dei Bagni

2 4 2 nights min stay

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min stay
Key info: Child friendly ; Car not necessary; Ask about pets;
Elegant apartment in the historic center of San Casciano dei Bagni, just one kilometer from the spa Fonteverde SPA.Apartment with a private entrance, two double bedrooms, two bathrooms, a living room, kitchenette and a super terrace overlooking the Val di Chiana.The pri  …see more

from £129 / night

£428 / week

Book Book View

from £129 / night

1 / 15

Province of Siena / Poggibonsi

1 2 1 night min stay

  • 1 bedroom
  • Sleeps 2
  • 1 night min stay
Key info: Child friendly ; Air conditioning; No pets allowed;
 …see more

from £39 / night

£270 / week

Book Book View

from £39 / night

1 / 20

Tenuta la Santissima Suite Lily - Sovicille b&b sleeps 3

Province of Siena / Sovicille

3 3 2 nights min stay

  • 3 bedrooms
  • Sleeps 3
  • 2 nights min stay
Key info: Beach / lakeside relaxation; Child friendly ; Air conditioning;
Tenuta la Santissima is part of an old hamlet and first descriptions of the inn date back to the 13th century.The inn was a meeting place for pilgrims and it preserves his history of welcoming. Located a few minutes outside Siena, Tenuta la Santissima is a B&B surro  …see more

from £112 / night

£700 / week

Book Book View

from £112 / night

1 / 12

Province of Siena / Casole d'Elsa

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
Key info: Child friendly ; Pet friendly; Private garden;
 …see more

from £48 / night

£308 / week

Book Book View

from £48 / night

(1) Excellent 

1 / 21

Province of Siena / Abbadia San Salvatore

8 12 Min stay varies

  • 8 bedrooms
  • Sleeps 12
  • Min stay varies
Key info: Suitable for children age 5+; Car essential; Pet friendly;
 …see more

from £257 / night

£1539 - £1881 / week

Book Book View

from £257 / night

(4) Excellent 

1 / 13

Province of Siena / Torrita di Siena

2 3 1 night min stay

  • 2 bedrooms
  • Sleeps 3
  • 1 night min stay
Key info: Child friendly ; No pets allowed; Private garden;
 …see more

from £52 / night

£359 / week

Book Book View

from £52 / night

(32) Excellent 

1 / 24

LUXURY APARTMENT WITH PRIVATE GARDEN & VIEWS - Gaiole in Chianti apartment sleeps 2

Province of Siena / Gaiole in Chianti

1 2 Min stay varies

  • 1 bedroom
  • Sleeps 2
  • Min stay varies
Key info: Swimming pool; Not suitable for children; Car advised;
Ideal for couples looking for a relaxing romantic holiday, we provide everything you need in our fully equipped and tastefully decorated apartment, see our reviews. FREE WI-FI Walking distance to local restaurants. The large private garden for your exclusive use overlo  …see more

from £60 / night

£420 - £630 / week

Book Book View

from £60 / night

1 / 13

Province of Siena / Radicondoli

6 14 2 nights min stay

  • 6 bedrooms
  • Sleeps 14
  • 2 nights min stay
Key info: Swimming pool; Child friendly ; Pet friendly;
 …see more

from £312 / night

£1872 / week

Book Book View

from £312 / night

1 / 24

Montalcino / Val d'Orcia

2 6 1 night min stay

  • 2 bedrooms
  • Sleeps 6
  • 1 night min stay
Key info: Child friendly ; Air conditioning; No pets allowed;
 …see more

from £197 / night

£1377 / week

Book Book View

from £197 / night

(2) Excellent 

1 / 24

Province of Siena / Palazzone

4 10 Min stay varies

  • 4 bedrooms
  • Sleeps 10
  • Min stay varies
Key info: Beach / lakeside relaxation; Swimming pool; Not suitable for children;
 …see more

from £257 / night

£2137 / week

Book Book View

from £257 / night

Top Destination reviews

Casa Degli Olivi Cetona , Siena Tuscany
Italian friendliness, food, wine and culture at its best - Cetona - Tuscany

What a fantastic experience in the Italian countryside. Two weeks tucked away from tourist mayhem. Even prior to our departure from the Middle East to start our holiday, the owners answered all our enquiries quickly,efficiently with sound advice. The … see more
Tuscan apartment with pool in Cetona
Excellent, centrally located apartment in a charming village

We thoroughly enjoyed our stay in Cetona and, given half a chance, would go back tomorrow! We booked the apartment for two weeks with my husband and I spending the first week on our own, and our two sons and one girlfriend joined us for the second w … see more
Agriturismo Sammonti
Perfect week in Tuscany

All previous positive reviews reflect our experience. Beautiful, quiet location. Lovely hosts. The house was cosy and a great place to come home to after sightseeing. It was also very easy to spend a whole day in the local area or enjoying the pool … see more
Villa Galardini
Great location in heart of Tuscany; wonderful property and very friendly owners

Property is peaceful, clean and ideally located for daytrips to the many nearby villages and Sienna. Grocery stores and restaurants conveniently located in nearby Buonconvento . This was a 50th Birthday celebration vacation to Tuscany with spouse a … see more
I MELOGRANI II: 3BDR Tuscan villa,view,pool,WiFi
Perfect.

The owner was most helpful in terms of booking, meeting us, and checking in to ensure all was going well. We took advantage of her offer to arrange for a chef to cook for us our first night - delicious food and very good wines. If you arrive on a S … see more
Podere Val delle Corti
Very nice and total clean appartment

Beautiful property within a lovely environment Very nice and total clean appartment Landlady and the whole proprietor familiy are very friendly an helpful No kind of weakness has been discovered, at all … see more

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