List your home
Apply filters
£ to

Holiday homes 32

Reset search

Show results on map

Filter your search

Price per night

Price per night

£ to per night

Bedrooms

Location

  • Italy Clear
  • Tuscany Clear
  • Province of Siena Clear
  • Poggibonsi Clear

Location

  • All locations
  • (4)
  • (2)
  • (2)

more +

less -

Property type

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
Staggia Senese
11 properties
Cedda
10 properties
Staggia
5 properties

Filters applied: Air conditioning (32)

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
32 Results   |  
24 Photos

Province of Siena / Poggibonsi

Villa / 7 Bedrooms / sleeps 18

7 Nights min stay

Add to shortlist

from £178 / night

£1241 - £3869 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Air conditioning
  • Some pets are welcome - please contact the owner
  • Private garden
Splendid villa with breathtaking view over the Castle of Strozzavolta, in the Chianti, between Florence and Siena.  …see more

Excellent 5/5 

28 Photos

Province of Siena / Poggibonsi

Villa / 6 Bedrooms / sleeps 12

Excellent 5/5 

7 Nights min stay

Add to shortlist

from £546 / night

£3819 - £5092 / week

View

Key info:

  • Swimming pool
  • Ask owner if suitable for children
  • Air conditioning
  • Some pets are welcome - please contact the owner
This hilltop villa in the Tuscan countryside is located near the charming village of Monteriggioni and offers close proximity to Siena, San Gimignano, and Florence as well as the Chianti Classico. With panoramic views, a private pool, and a peaceful atmosphere, a family  …see more


13 Jul 2013

5/5

"Gail's review of Chianti Villa near a Charming Village - Prima C"

We were a family of 10 with teenagers and younger children. (8 and10) All of us were simply in awe when we drove into the villa and saw the accomodations. It is like a feature property in Travel and L… More


16 Jun 2012

5/5

"Donna's review of Chianti Villa near a Charming Village - Prima"

Fabulous! Beautiful views, so many different places to take it all in. The Villa is centrally located for travel to Siena, Florence and of course Monteriggioni. The Villa has elegant furnishings. We h… More


26 Jul 2008

5/5

"Alan's review of Chianti Villa near a Charming Village - Prima C"

Wonderful location. Beautiful house and property. Extremely helpful owner and caretaker. The 18th century house is a pleasure to inhabit. The location is perfect for access to cities and hill towns, … More

See all reviews Continue

Very Good 4.5/5 

24 Photos

Province of Siena / Poggibonsi

Apartment / 1 Bedroom / sleeps 3

Very Good 4.5/5 

Min stay varies

Add to shortlist

Pricing unknown

View

Key info:

  • Nearest beach 80 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
  • Private garden
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 p  …see more


19 Nov 2013

5/5

"Bliss"

Beautifully quaint apartments surrounded by amazing views of the Tuscan countryside. Lovely pool and we were the only ones in it for most of our stay. Fabio the owner was very helpful and recommended … More


20 Jun 2013

5/5

"A Wonderful Place to Begin a Chianti Vacation"

For 3 weeks we rented the Falco apt from our gracious host, Fabio. The apt was one of the best furnished that we stayed in over the yrs. It had 2 bedrooms, a living space/ and dining area. The kitchen… More


12 Sep 2014

4/5

"Lovely base in Tuscany, rustic apartment with shared pool"

Had a great stay in Falco recently. The apartment is rustic and comfortable. Lovely old furniture and a small TV with only news channels in English. Wifi is good but charged as an extra. Good bathr… More

See all reviews Continue

Featured properties

16 Photos

Province of Siena / Poggibonsi

Villa / 6 Bedrooms / sleeps 12

3 Nights min stay

Add to shortlist

from £1000 / night

£7000 - £9400 / week

View

Key info:

  • Not suitable for children
  • Air conditioning
  • No pets allowed
  • Private garden
Luxury Villa in Chianti panoramic view, private swimming pool, 6 bedrooms, ensuite bathrooms, air cond, heating, wine tasting and visit to cellar included. Half an hour from Florence and Siena, 15 minutes drive from San Gimignano  …see more

Excellent 5/5 

25 Photos

Province of Siena / Poggibonsi

B&B / 5 Bedrooms / sleeps 11

Excellent 5/5 

2 Nights min stay

Add to shortlist

from £37 / night

£256 / week

View

Key info:

  • Nearest beach 76 km
  • Not suitable for children
  • Car essential
  • Air conditioning
  • No pets allowed
  • Private garden
Sangimignano, ospedale Le Scotte, ospedale di Poggibonsi, Chianti, Siena, Firenze, Volterra, Monteriggioni  …see more


19 Aug 2015

5/5

"Nel cuore del Chianti"

Il podere si affaccia su splendide colline da cui si può godere il tramonto, e all'orizzonte si può ammirare il colle dove si erge la splendida San Gimignano. Un mattino siamo stati piacevolmente sv… More


27 Jun 2015

5/5

"Tutto è Meraviglia!!....."

Cercavamo relax e lo abbiamo trovato! Luogo incantevole, camere curate e spaziose, colazione molto varia e abbondante, cordialità meravigliosa. Luogo dove si può rimanere ad ascoltare la bellezza de… More


4 Jun 2015

5/5

"Incanto e pace"

Cercavamo un'oasi di pace immersi nei colli del Chianti e l'abbiamo trovata! Le foto non rendono l'atmosfera che regala questo luogo ... Ci siamo goduti un tramonto mozzafiato sull'amaca, il posto era… More

See all reviews Continue

Excellent 5/5 

24 Photos

Poggibonsi / Staggia Senese

Villa / 6 Bedrooms / sleeps 12

Excellent 5/5 

7 Nights min stay

Add to shortlist

from £418 / night

£2920 - £3892 / week

View

Key info:

  • Nearest beach 70 km
  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Air conditioning
  • Some pets are welcome - please contact the owner
  • Private garden
Ancient and noble mansion of the XVIII century overlooking Chianti hills, for a luxury and leisure stay in the hearth of Tuscany... Its location in the centre of Tuscany, a few km from the highway Firenze-Siena.  …see more


15 May 2015

5/5

"Fantastic villa with amazing views!"

The villa itself is a couple hundred years old and is in amazing shape. And it's huge! Great place to visit the Siena area of Tuscany! The owners Chiara and Tommaso are very nice. Chiara is an amazing… More

See all reviews Continue

Excellent 5/5 

15 Photos

Poggibonsi / Staggia Senese

Apartment / 1 Bedroom / sleeps 3

Excellent 5/5 

1 night min stay

Add to shortlist

from £66 / night

£460 / week

View

Key info:

  • Great for children of all ages
  • Car advised
  • Air conditioning
  • Pets welcome
  • Private garden
The apartment is located in Staggia Senese, a cosy and historical village in the borough of Siena, nearby La Rocca, an extraordinary example of architecture dated 1300. The area surrounding La Casina has many attractions and offers opportunities. The place is available  …see more


8 Sep 2014

5/5

"Posto delizioso!Lo consiglio vivamente!"

Sono stata alla Casina di Anna un paio di settimane fa con degli amici e mi sono trovata benissimo. Location meravigliosa, posto pulito. Elda è una persona splendida e molto disponibile! Lo consigl… More


29 Apr 2015

5/5

"Che magnifica esperienza!!!"

Siamo stati ospiti della "Casina di Anna"per alcuni giorni ma avremmo voluto prolungare il nostro soggiorno!! L'appartamento, funzionale e dotato di ogni confort, fa rivivere l'atmosfera di altri temp… More

See all reviews Continue

13 Photos

Province of Siena / Poggibonsi

B&B / 25 Bedrooms / sleeps 44

1 night min stay

Add to shortlist

from £47 / night

£329 / week

View

Key info:

  • Not suitable for children
  • Air conditioning
  • No pets allowed
La position statégique,au centre de la Toscane facilite des nombreuses excursions A strategic position, in the heart of Tuscany, offers you countless excursions possibilities Parking and Wi-Fi are Free  …see more

13 Photos

Province of Siena / Poggibonsi

B&B / 1 Bedroom / sleeps 2

2 Nights min stay

Add to shortlist

from £33 / night

£230 / week

View

Key info:

  • Great for children of all ages
  • Air conditioning
  • No pets allowed
  • Private garden
Sangimignano, ospedale Le Scotte, ospedale di Poggibonsi, Chianti, Siena, Firenze, Volterra, Monteriggioni  …see more

22 Photos

Province of Siena / Poggibonsi

Apartment / 3 Bedrooms / sleeps 4

4 Nights min stay

Add to shortlist

from £95 / night

£665 - £1168 / week

View

Key info:

  • Nearest beach 75 km
  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Air conditioning
  • Some pets are welcome - please contact the owner
  • Private garden
"Casa Serena" is located in a panoramic position, blessed with mesmerising views over the Chianti vineyards and enchanting hamlets. Quiet location but not isolated. Local assistant 24 H in case of need - english speaking  …see more

8 Photos

Province of Siena / Poggibonsi

Apartment / 2 Bedrooms / sleeps 5

2 Nights min stay

Add to shortlist

from £52 / night

£363 - £435 / week

View

Key info:

  • Swimming pool
  • Not suitable for children
  • Car essential
  • Air conditioning
  • No pets allowed
  • Private garden
Firenze (35km), Siena (25km), San Gimignano (13km), Monteriggioni 15(km), Pienza (40km). Nonchè le più importanti città storiche del chianti come Castellina in Chianti, Radda, Gaiole, Greve in Chianti, Panzano.  …see more

24 Photos

Poggibonsi / Staggia Senese

Villa / 6 Bedrooms / sleeps 12

7 Nights min stay

Add to shortlist

from £409 / night

£2862 - £3431 / week

View

Key info:

  • Nearest beach 110 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
  • Private garden
Villa Senese is an ancient mansion dating back to the eighteenth century, located in the heart of Chianti Senese, just 17 km away from Siena and 45 Km from Florence.  …see more

11 Photos

Province of Siena / Poggibonsi

Apartment / 2 Bedrooms / sleeps 4

7 Nights min stay

Add to shortlist

from £84 / night

£584 - £701 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • No pets allowed
  • Private garden
Casale Oliveta is located in a little hamlet with a few houses up in the hills.  …see more

21 Photos

Province of Siena / Poggibonsi

Apartment / 3 Bedrooms / sleeps 4

4 Nights min stay

Add to shortlist

from £95 / night

£660 - £1015 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Air conditioning
  • No pets allowed
La Terrazza sul Chianti Apartment for rent with swimming pool in Poggibonsi  …see more

30 Photos

Province of Siena / Poggibonsi

Villa / 6 Bedrooms / sleeps 12

7 Nights min stay

Add to shortlist

from £426 / night

£2978 - £5139 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Air conditioning
  • No pets allowed
Villa Belvedere Villa for rent with swimming pool in Poggibonsi  …see more

30 Photos

Poggibonsi / Staggia

Villa / 6 Bedrooms / sleeps 12

7 Nights min stay

Add to shortlist

from £435 / night

£3044 - £4058 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Air conditioning
  • Pets welcome
  • Private garden
Villa Staggia Villa for rent with swimming pool in Poggibonsi  …see more

30 Photos

Province of Siena / Poggibonsi

Villa / 6 Bedrooms / sleeps 12

7 Nights min stay

Add to shortlist

from £429 / night

£3000 - £5176 / week

View

Key info:

  • Swimming pool
  • Not suitable for children
  • Air conditioning
  • No pets allowed
This beautiful villa rental is located in the Chianti hills and is part of a large farm where excellent wine is produced. It has been recently renovated with great care, elegantly combining the ancient Tuscan farmhouse structure with new materials and light colors. The  …see more

12 Photos

Poggibonsi / Cedda

Apartment / 2 Bedrooms / sleeps 4

7 Nights min stay

Add to shortlist

from £62 / night

£429 - £537 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • No pets allowed
1 Double room with a double bed, 1 double room, living room in the little tower, kitchen, bathroom, over two floors.  …see more

11 Photos

Poggibonsi / Cedda

Apartment / 2 Bedrooms / sleeps 4

7 Nights min stay

Add to shortlist

from £62 / night

£429 - £537 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • No pets allowed
  • Private garden
1 double room with a double bed, 1 double room, living room with double sofa bed, kitchen, bathroom. First floor. No heating system. 112 sqm.  …see more

14 Photos

Province of Siena / Poggibonsi

B&B / 1 Bedroom / sleeps 3

1 night min stay

Add to shortlist

from £44 / night

£307 / week

View

Key info:

  • Great for children of all ages
  • Air conditioning
  • No pets allowed
  • Private garden
Sangimignano, ospedale Le Scotte, ospedale di Poggibonsi, Chianti, Siena, Firenze, Volterra, Monteriggioni  …see more

14 Photos

Province of Siena / Poggibonsi

B&B / 1 Bedroom / sleeps 2

2 Nights min stay

Add to shortlist

from £33 / night

£230 / week

View

Key info:

  • Nearest beach 76 km
  • Great for children of all ages
  • Car essential
  • Air conditioning
  • No pets allowed
  • Private garden
Sangimignano, ospedale Le Scotte, ospedale di Poggibonsi, Chianti, Siena, Firenze, Volterra, Monteriggioni  …see more

15 Photos

Province of Siena / Poggibonsi

B&B / 1 Bedroom / sleeps 2

1 night min stay

Add to shortlist

from £33 / night

£230 / week

View

Key info:

  • Great for children of all ages
  • Air conditioning
  • No pets allowed
  • Private garden
Sangimignano, ospedale Le Scotte, ospedale di Poggibonsi, Chianti, Siena, Firenze, Volterra, Monteriggioni  …see more

15 Photos

Province of Siena / Poggibonsi

B&B / 1 Bedroom / sleeps 2

1 night min stay

Add to shortlist

from £33 / night

£230 / week

View

Key info:

  • Nearest beach 76 km
  • Not suitable for children
  • Car essential
  • Air conditioning
  • No pets allowed
  • Private garden
Sangimignano, ospedale Le Scotte, ospedale di Poggibonsi, Chianti, Siena, Firenze, Volterra, Monteriggioni  …see more

18 Photos

Province of Siena / Poggibonsi

House / 6 Bedrooms / sleeps 12

7 Nights min stay

Add to shortlist

from £11 / night

£73 - £4058 / week

View

Key info:

  • Swimming pool
  • Not suitable for children
  • Air conditioning
  • Some pets are welcome - please contact the owner
Six Bedroom Private Villa Chianti Villa Vincent is a beautiful 18th Century country villa perched elegantly on the hillside in wonderful elevated position overlooking beautiful Chianti countryside. Now carefully restored to its' former splendour the villa is beautifull  …see more

31 Photos

Province of Siena / Poggibonsi

House / 4 Bedrooms / sleeps 10

3 Nights min stay

Add to shortlist

from £156 / night

£1086 - £1811 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Air conditioning
  • Pets welcome
  • Private garden
Anticopozzo Independent house for rent with swimming pool in Poggibonsi  …see more

35 Photos

Province of Siena / Poggibonsi

House / 3 Bedrooms / sleeps 8

3 Nights min stay

Add to shortlist

from £169 / night

£1182 - £1608 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Car essential
  • Air conditioning
  • No pets allowed
  • Private garden
Villa Linari Independent house for rent in Barberino Val d'Elsa  …see more

31 Photos

Province of Siena / Poggibonsi

House / 4 Bedrooms / sleeps 10

3 Nights min stay

Add to shortlist

from £157 / night

£1094 - £2279 / week

View

Key info:

  • Swimming pool
  • Not suitable for children
  • Air conditioning
  • Pets welcome
In a panoramic position in the hills of the Chianti Classico stand two typical barns that have been recently restored with great care and equipped with every comfort and every convenience in order to allow their guests to enjoy the most of this splendid corner of Tusca  …see more

21 Photos

Province of Siena / Poggibonsi

Apartment / 3 Bedrooms / sleeps 4

4 Nights min stay

Add to shortlist

from £95 / night

£665 - £1171 / week

View

Key info:

  • Swimming pool
  • Not suitable for children
  • Air conditioning
  • No pets allowed
Modern apartment in a small residential complex built in Tuscan style, near Poggibonsi, a town bordering the provinces of Florence and Siena. Situated at the foot of the Chianti hills, the countryside is typical of this part of Tuscany with vineyards and olive groves su  …see more

24 Photos

Poggibonsi / Staggia

Villa / 6 Bedrooms / sleeps 12

7 Nights min stay

Add to shortlist

from £439 / night

£3073 - £4325 / week

View

Key info:

  • Nearest beach 0 km
  • Swimming pool
  • Great for children of all ages
  • Car advised
  • Air conditioning
  • No pets allowed
This villa is an elegant 18th century mansion near Siena in the Chianti wine region, perfect for visiting Tuscany and relaxing by the pool during your holiday in Italy. The villa has a vantage point on a hill above the old town of Staggia Senese. From the terr...  …see more

20 Photos

Province of Siena / Poggibonsi

House / 6 Bedrooms / sleeps 11

7 Nights min stay

Add to shortlist

from £557 / night

£3897 - £5484 / week

View

Key info:

  • Swimming pool
  • Ask owner if suitable for children
  • Air conditioning
  • No pets allowed
(Minimum of one week rental required) Villa Chianti Rosa is located in the heart of Chianti Senese, just 19 ​​km away from Siena and 55 Km from Florence. It is located in an advantageous position on a hill above the old town of Staggia Senese. Dating back to the 18t  …see more

20 Photos

Poggibonsi / Staggia Senese

House / 6 Bedrooms / sleeps 12

7 Nights min stay

Add to shortlist

from £600 / night

£4200 - £5600 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • No pets allowed
  • Private garden
Villa Cherubina is a splendid sixteenth-century three-story villa located on top of a small hill. It sleeps 12 people. From Villa Cherubina you will enjoy a wonderful view of the Senesi hills. Villa Cherubina is 500 square meters (5380 square feet)  …see more

49 Photos

Province of Siena / Poggibonsi

Villa / 3 Bedrooms / sleeps 8

7 Nights min stay

Add to shortlist

from £518 / night

£3623 - £5105 / week

View

Key info:

  • Swimming pool
  • Great for children of all ages
  • Air conditioning
  • No pets allowed
Located in Tuscany Italy, this beautiful villa is the perfect place for your holidays. The villa features: a swimming Pool, air Conditioning, an internet Connection .  …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